Inside the mind of a tinkerer

A more playful approach to work and productivity.

After lunch on a Sunday afternoon as a kid, I’d often hear my dad proclaim that he was going to ‘tinker’ in the shop. Despite the regularity of these Sunday tinkering ventures, I had no idea what he was it actually entailed. I was more focused on getting out of chores or yard work.

Now that I’m much old(er), I better understand what he meant by tinkering.

Tinkering is work, but it’s also not work.

It’s the kind of work that doesn’t require deep thinking or focus.

For me, it’s the stuff I can do slouched down on the couch with my laptop and The Office playing for the 348th time in the background.

For him, it was rearranging tools and cleaning up his workspace.

In many ways, it isn’t really work at all.

It’s neither hard nor laborious.

It’s both tedious and stimulating.

It’s unfocused and yet engaging.

It’s just…tinkering.

Tinkering—often mistaken for aimless activity—is a crucial foundation for creativity and innovation, providing the mental space necessary for ideas to gestate and evolve.

The act of tinkering is akin to wandering through a garden instead of marching down a path. It's not about deep focus or intentional outcomes. It's all tidying up vs. deep cleaning.

Tinkering is like a music playlist, blending work and life seamlessly. It's not always about striving for capital-P productivity but about activating new ideas through relaxed exploration. By giving ourselves the freedom to tinker, we create space for true creativity to flourish.

In exploring the essence of tinkering, I see found parallels in writing this piece. Like a tinkerer joyfully engages in tasks, such as rearranging pixels or sending emails, I've been tinkering with its ideas, words, and paragraphs, allowing my thoughts to evolve and take shape over time. Instead of leaving you with the final draft, I’ve opted to include them because, as any writer knows: showing always beats telling.

Though I’m sure it makes this article harder to read—maybe that’s the point. By engaging with the variations iterations of an idea and ignoring the modern tendency to only show our best work, we lose the opportunity to truly be creative. The process of experimentation, refinement, and playful productivity is what tinkering is all about.

"Creativity is allowing yourself to make mistakes. Art is knowing which ones to keep." - Scott Adams

It’s a bit unhinged, but in a world where we’re always showing the Instagram version of ourselves, we need more space to let the bad ideas fly, show behind-the-scenes shots, and iterate. Good ideas come through iteration and self-exploration, not striving for perfection.

The funny thing is that a lot of our modern work culture is digital tinkering.

So what is tinkering?

Tinkering with ideas is a playful exploration or a taking of inventory. It's about noodling and letting bad ideas fly pass by so you can discover the good ones. This light, unfocused work prepares for deeper, more meaningful creative work. Letting 1,000 flowers bloom requires some weeds to take root, the key is not to pluck a flower-looking weed or weed-looking flower too early. Creativity requires time to grow and develop.

Tinker-Core: Balancing Shallow and Deep Work

In productivity and creativity, tinkering is the connective tissue between the realm of shallow work and the domain of deep work. Tasks like organizing emails or reading documents can be the first step towards deeper work, a warming of up the creative engines so to speak. By allowing ourselves to tinker with ideas and concepts on a surface level, we create a foundation for deeper exploration. Tinkering, with its playful and exploratory nature, acts as a precursor to the focused attention and immersion required for deep work, enabling us to transition from light experimentation to substantial creativity.

Tinkering takes various forms but has consistent characteristics:

1. Multi-taskable - the work can be done with sports or a podcast on in the background.

2. Highly-variable - the task might not be clear until you’re in it the journey is the destination.

3. Optional - the work isn't critical, but it's necessary for productivity.

Tinkering is the shallow work we do to keep the hedonic productivity wheel turning. We know we’re supposed to work, so we do. In modern, Americanized work cultures, work is the only true form of fulfillment, value, and meaning—happiness is exists only for the productive. If productivity is next to godliness, the lack of productivity is the deepest a form of depravity.

Done right, tinkering is productive and therapeutic. Done wrong, tinkering is it’s nothing more than feckless wandering.

Tinkering, like a gardener pruning with care, can cultivate creativity and productivity. Yet, aimless tinkering is akin to a lost sailor adrift at sea, lacking direction and purpose.

Tinkering is the gentle stream that guides creativity toward its destination, channeling ideas into productive waters. But without a map or compass, tinkering may become a wandering cloud, drifting aimlessly in the sky.

In the words of J.R.R. Tolkien, 'Not all who wander are lost.' Just as wandering holds purpose, so does tinkering. Embracing a playful approach to productivity can lead to creative breakthroughs. Let's label our tinkering correctly and explore the value it brings to our work and lives.

Our work shapes how we think about it; it is a self-fulfilling prophecy. We often categorize tasks as 'work,' attaching a sense of importance or obligation to them. But what if we reframe these activities as tinkering as a way to decrease friction and find ways to reconnect with a more playful form of work? Emailing, reading documents, or sending Slack messages may not require deep thinking or effort, but labeling them as 'work' can make us feel productive. Are we becoming modern-day pencil pushers, engaging in activities that may not involve intense labor but still provide a sense of productivity?

The Value of Tinkering Across Contexts

For me and my dad, tinkering was a mix of playful productivity and therapy. It was a way to feel productive without the stress of actual work (aka the big, haunting tasks you’re avoiding). Tinkering offers a stress-free way to feel accomplished, and potentially enjoy yourself. And for people like me who struggle with perfectionism, anxiety, and intense ambition, finding ways to enjoy work while also feeling a sense of accomplishment is critical. When we push too hard, we end up going backward. It’s like having a fixed gear bike; you can pedal hard, but it’s better to go at the bike's pace, lest the chain comes off.

In the realm of everyday creativity tinkering lies a path to flourishing, as illuminated by a study titled "Everyday Creative Activity as a Path to Flourishing" by Tamlin S. Conner, Colin G. DeYoung, and Paul J. Silvia in The Journal of Positive Psychology. Their insightful research explored the daily lives of 658 young adults, revealing a fascinating cycle: engaging in creative endeavors led to elevated positive emotions and a heightened sense of flourishing the following day. This suggests that nurturing our creativity not only enhances our well-being but also fuels a continuous cycle of creative inspiration and fulfillment.

Whether you’re an entrepreneur or a corporate employee, modern work requires balance, but it can be hard to find. As I’ve written before, there are many ways of working. I'm most fulfilled when I alternate between work and life, combining elements like a guitarist or bassist.

While this approach works for me, others find it jarring or impractical. But it works for me because I spend time tinkering, sitting, thinking, keeping my mind and hands busy, not always worrying about a strong drive for capital P productivity, but activating nascent thoughts and ideas by taking my mind off them.

Organizing my to-do list is never my top priority. Just like organizing and labeling the tools in the shop were not my father’s priority. But this is the preparation for creative thinking and working—the clearing of mental clutter and RAM for productivity’s sake. Completing it in the quiet periods allows you to capitalize on your full creative potential when the opportunity arises.

If my work is a mess and I try to sit down to write, I feel the pull of the unmanaged work, nagging me to attend to it. But when I tinker unproductively, I create more space to think and create, even if not immediately. Gustave Flaubert reminds us that we should,

"Be regular and orderly in your life, so that you may be violent and original in your work.”

Reframing helps me avoid deciding when to work and reduces the anxiety of doing the work, allowing me to put real effort toward it when the time comes.

Maybe this won’t work for you, but it’s been helpful for me.

In a world where productivity is often measured by output and efficiency, the concept of jobs for individuals who simply enjoy tinkering 24/7 seems refreshing, albeit somewhat unrealistic in the near future. Imagine a workforce where individuals are encouraged to explore and experiment without the pressure of traditional work demands. Allowing time for more people to tinker could not only lead to innovative products and ideas, but also foster a unique sense of fulfillment for more of our workforce.

As I think about the impact what the future looks like for tinkerers like me, I imagine AI and Universal Basic Income will play an important role. But that’s an idea for another day, and another time.

Embracing our inner tinkerer allows us to revisit the joy found in unrestricted exploration, blending work and life into a harmonious rhythm that nurtures rather than drains. In this space, we don’t just work—we play, explore, and ultimately, flourish.

Requiem for an Office

What I miss about the office, and what I’m doing about it.

Acquisitions are weird.

One day, you’re doing your job and things are going well.

The next, you’re working for someone else and hearing that nothing will change.

It's akin to waking up from unconsciousness: the room spins, disorientation sets in, and you’re unsure where you are or how you got there.

In the blink of an eye, the familiar rhythms of my job were upended, ushering me into a new reality where, unbeknownst to me at the time, the seeds of my journey into the future of work were planted. That wild journey led me to a lot of interesting things; last minute international travel, 11pm conference calls, and my introduction to the always-on work culture I’d come to accept as normal.

But most interestingly, it led me to a core feature of what I’d come to see as a key component of the future of work: remote work.

I started working remotely in early 2013. It wasn’t really on purpose, nor was it in vogue. Prior to 2013, remote work wasn’t something people thought a lot about. Outside of support and call centers, or the occasional ‘telecommuter,’ it just wasn’t part of the work vernacular.

And it certainly didn’t feel natural in 2013.

If you look at this chart from We Work Remotely, you can see that the number of jobs listing for remote workers has grown by nearly 1200% in that time.

But honestly, it really didn’t feel like it.

There was no grand “welcome to the remote work party” banner. No strong cultural pulse that brought remote work to the forefront. If anything, remote work was considered a backup option, for specific circumstances like disabilities, outsourced roles, or consultants. It wasn’t mainstream or understood.

I stumbled into a world without borders by accident. At the time, I was working for Deloitte consulting. My job, at the ripe age of 25, was to lead the global expansion efforts for the new consulting line that had formed after the acquisition of my previous company, Übermind.

During this acquisition, I was lucky enough to be given the opportunity to avoid the traditional consultant paths offered by Deloitte, which may have been interesting, but likely would’ve sent me down a completely different career trajectory—a career with more suits, planes, and hotels next to the airport. Instead, I was lucky to be offered a global expansion role, which kept me out of client-specific consulting, and made me an internal operator, tasked with launching and growing the newly-formed Deloitte Digital Studio Model. My role in global expansion had some interesting requirements, which ultimately led me to my first remote work experience. These included:

• Time zone management. As you might imagine with the word ‘global’ in the title, my job entailed working with teams and people in different countries. This meant having to manage time zones outside of my usual +/- 3 hour calculations.

• Video and conference calls. For years, most of my meetings were in person. Whether it was in the office with my studio coworkers or meeting a client to present, my time was spent literally face-to-face. And then one day, that all changed. I went from mostly in-person, to mostly virtual. I didn’t feel it immediately, but over time, it felt like my personality shifted from being a real person to a virtual person.

• Isolation. In the shift to virtual work, it meant a disconnect from my local colleagues. Even if we worked in the same office, we didn’t have the same schedule, the same work, or the same experiences anymore. I found it more and more difficult to talk with them about work, since our worlds were so far apart. Eventually, I stopped coming into the office except to socialize or for the occasional office-sponsored happy hour.

After a decade of working remotely, I’ve realized that there are things I deeply miss about working in an office. I don’t think I’m completely alone here. In fact, just the other day, a past colleague of mine told me they’ve accepted a hybrid role. They’ve been working and advocating for remote work for years, and yet, they decided to take a little break from the fully-remote world.

As someone who has spent a lot of time thinking not just about how we work, but how we are productive, how we cultivate a relationship with work, and how we set boundaries, I think there are gaps that have yet to be filled in remote work. A growing body of research underscores the profound impact of social interactions and environmental context on our work and well-being.

I want to be abundantly clear: I do not want to return to the office, not now, not ever. Further, I don’t believe in-person work is a better way to work, at least not in most cases. But more importantly, I think the remote/in-office debate leaves little room for nuance, and therefore misses the mark altogether.

I’ve realized that there are some important things I am missing when working remotely, and I plan to fix them in 2024. And no, it’s not the ‘random coffee chats’ or ‘in-person’ meetings.

• Scheduled social interactions - again, not the random chat kind. What I miss is the scheduled social interactions of office timelines. I miss the ‘let’s grab lunch/coffee’ times of the day. When we have scheduled social time, we naturally increase our productivity in order to ensure it doesn’t interfere with our social mores the scheduled social time. When our schedule becomes flexible, we lack the urgency of fixed deadlines, even if they’re for social interaction.

• Time offline - I miss the forgiveness and empathy of needing time outside of work. The ability to say, ‘hey, I’m on my way to the office, I’ll look at that when I get in.’ I miss the option to say, ‘I have to leave early to run an errand, so I won’t be able to make a 4pm meeting today.’ I find that, as a remote worker, it is incredibly difficult to share the reasons that we can’t—or won’t do things. Worse still, remote workers are often given very few options to not work. The assumption is that by giving up the commute, you have infinite time to work, and therefore should always be online.

• Thinking time - the commute is shit, but it can have benefits. First and foremost for me: time to think. One of the first things that I realized I was missing about the office was time to be alone, gather my thoughts, and think about things that were on my mind. By removing this time, I’ve found that I default to action. Instead of sitting and thinking about an idea on my commute, I choose to work. Instead of taking time to breathe, I work. Everything gets flattened to work.

• A sense of place - how we feel about what we do is incredibly important, as it shapes our self-worth and helps us orient ourselves to the world. Where we do what we do can be just as important. One of the biggest challenges of working remotely is being able to place ourselves in work mode. When you can work anywhere, we see work everywhere. But the office gives us a place to place work. It lives there. It stays there when we leave. It has a home, and it’s not our actual home.

All of these are specific to me. It doesn’t mean that they are insurmountable, or something that changes the calculation of my interest in working remotely. In fact, they further cement my position on the subject, as they reinforce the idea that remote work isn’t just about where you do your best work, but how you do your best work. If we want better ways to work, we have to think outside the box and explore all ways of working and living in harmony. I want reinforce this in my own work and in the narrative at large.

Rethinking My Office

In 2024, I’m taking a different approach to working remotely. I’m keeping the core components; working asynchronously, documentation-first, (mostly) virtual meetings, etc. But I’m also making some pivotal adjustments that I think will have a major benefit for me, my work, and my family.

• Be a 9-5er - I’m a huge fan of work-life harmony, no matter how you come by it. Historically, I’ve leaned into my natural rhythms of being a cycler, but over time, I find it wears on me. Instead of working when inspiration strikes or I feel ready to tackle something, I just end up grinding through work, all day, with micro-breaks. For 2024, I’m taking a stronger stance on remote work boundaries, and trying a 9-5 schedule—or as close to that as reasonable.

• Co-work - with our recent move back to Seattle, I’ve decided to pick up an office at a co-working space. Luckily, it’s right next to our home, so the commute is the time it takes to ride the elevator down, walk 50 yards through our garage, and ride a second elevator back up two floors. This setup allows my wife to have her own space at home, and helps me enforce my goal of being a 9-5er.

• Go analog - one of my challenges with remote work is the fact that everything goes through my screens—from my phone to my laptop to my desktop, it’s all screens. Passing thoughts, ideas, and chats through this glass box filled with pixels isn’t the way I want to exist, and it’s not how I’ll do my best work. To combat this, I’m integrating analog tools into my workflow, including a whiteboard, notebook(s), and a separate, analog desk.

• Walk it off - I need to walk more. When I was in the office, I’d walk a lot more. I’d go to lunch, get coffee, or just do a walking meeting with people from the office. While most of the time those walks happened with close colleagues and friends, that wasn’t always the case. Sometimes I’d join a random group of designers or engineers, just to get out. It’s hard to do that on your own, but I want walking to be a part of my life. So every day, I take my dog across the street for a walk. Some days, I walk my wife to work. Others, I walk to meet someone for coffee, lunch, or drinks. My goal is to walk as much as possible.

Zooming Out

Depending on your stance, these changes may sound mundane or revolutionary. Remote purists may even take issue with some of these. But that misses the point. The point of remote work has never actually been about working at home, on your couch, or on a beach in Fiji. Remote work is about flexibility. It’s about a way of working that not only helps us do our best work, but bring work and life into harmony. And the harmony of work and life can only be heard when we listen and adjust our tone.

It’s easy to look at what we don’t have and assume it’s better.

We have the Honda, but we want the Tesla.

We have the big house, but we want the boat.

The grass, perpetually seems greener, no matter the context.

In reality, the grass isn’t always greener. Sometimes, the grass is greener in a few spots, and dead everywhere else. We might only see the small patch, and assume the rest looks the same. The map is, in fact, not the territory.

Our workspace choice shouldn’t be binary.

We shouldn’t have to choose between a sub-par home office (aka kitchen table) or a high-rise office.

We shouldn’t have to choose between working a job we like, and spending necessary time with our family.

We shouldn’t have to be forced into these polarities—there exists space for convergence.

When it comes to remote work, it’s easy to feel like we need to pick sides; you’re either with us, or you’re against us. Like anything else in life, we should admit and embrace the need for better options, both in work and at home.

The Delphic oracle might have been speaking to workers when she famously said, "know thyself.” I, for one, plan to do so.

You Don’t Need Moderation

Work, Creativity, and the Fallacy of Restraint

Every Monday morning, I sit down at my desk, turn on any Tycho album, pull out my trusty notebook, and plan my week.

This little daily ritual keeps me focused and grounded.

It’s something I try to stick with every weekday, because it helps me avoid overcommitting to too many meetings, too many to-dos, too many agreements.

But recently I realized something: it doesn’t actually work.

Well, it works, but not as intended.

I know this, because I finally sat down and looked at the data.

As one of those OCD people who tracks their time, manages an overly-complex Notion workspace, and uses best-in-class productivity tools like Sunsama and Rize, I have the data.

At the beginning of each new year, I reflect on what I’ve accomplished in the last twelve months and what I’d like to tackle in the coming year. During this practice, I evaluate not just how much I completed, but how I felt about what I completed, and how much effort it took to complete everything.

This year, when I looked at my stats, they were pretty staggering. I’d worked an average of 50-60 hours each week, taken 2-3 weeks off, and only completed 60% of the goals I’d set out to accomplish at the beginning of the year. All in all, it didn’t look great. And yet, my feelings told a different story.

I felt accomplished.

I felt energized.

I felt ready for more, not less.

For most, the outcome of a process like this leads to a goal of working less, scaling back, or finding ways to optimize. And I’ll admit that, for most, this is the right outcome. I’ll play along with the typical work-life balance narratives that even I espouse on a regular basis. Yet, when it comes down to it, my ambition won’t rest. The list of objectives for the coming year just gets longer and longer. And before you tell me about the 80/20 rule, Buffett’s 5/25 rule, or any other prioritization framework, know that I both know these and still find myself in the same situation.

Because, the truth is:

I willingly overstretch myself.

On any given day, I find myself toggling between:

• two monitors

• three books in progress

• dozens of article or newsletter drafts

• hundreds of open browser tabs

• thousands of ideas

For me, chaos breathes life into an otherwise mundane existence.

In fact, managing the chaos often feels like a dance does.

You can learn to dance by following step-by-step instructions; right hand on your partners shoulder, step forward with your left foot, slide your right foot across…and so on. Or, you can watch someone dance and find your own groove. Instead of resisting your natural flow, you can learn to embrace it and move with it.

If you are resisting something, you are feeding it. Any energy you fight, you are feeding. If you are pushing something away, you are inviting it to stay.
— Michael Singer

My fragmented, overworked, chaotic existence goes against all conventional productivity advice and breaks all norms. Most people simply cannot understand how—or why—someone would be a willing participant in such circumstances, especially when it comes to work. We’re willing to accept and embrace a lack of moderation when it comes to particular hobbies, passions, religion, and so many other aspects of modern life.

And yet, when it comes to work, the modern narrative tells us to cut out as much as we can.

Like sugar, work is best consumed in small doses, only when necessary.

While work might produce a nice, temporary high, enjoy too much and you’ll crash.

Or at least that’s what we’re told.

But creative work is different. And makers of all kinds — painters, artists, musicians, etc. — often find that creativity blurs the line between what is considered work, and everything else. Putting artificial constraints on your creative brain, telling it to turn off, rarely works.

Constraints are incredibly powerful tools for creativity. But creativity and innovation aren’t always about limitations. In fact, creativity and innovation often come from connecting disparate ideas or concepts. As David Epstein points out,

Modern work demands knowledge transfer: the ability to apply knowledge to new situations and different domains.

The transfer of knowledge and the ability to apply it across different domains requires expansion, not contraction. The constraints of typical productivity advice turn moderation into frustration. Which is exactly why I choose to accept life without moderation.

Where you see chaos, I see creativity.

Where you see obstacles, I see opportunities.

And, when it comes to work, my brain wants more.

As I wrote in 2020, I think this is crucial for most people to find ways to do the minimum amount necessary to get the most monetary value for themselves. It’s the most logical way to approach anything so transactional: maximize ROI.

But the I in ROI isn’t the same for everyone.

I’ve come to realize that moderation just isn’t for me. And it’s not easy, but nothing in life is easy. Instead of fighting it, I’ve learned to harness it and use it to my advantage.

Accepting and integrating chaos might be the fastest way to find the signal of creative inspiration. Whether it’s work, a hobby, a book, or a creative endeavor, keeping your momentum is the key. If you let doubt or fear stop you, it just might bring all other creative outlets to a screaming halt. Take on more than you think you can handle, and see where each permutation takes you.

Munger's Laws

10 Basic Rules Charlie Taught Me About Legacy

Charlie changed my life.

I felt I knew him, even though I didn’t.

With words alone, people have the power to engrave.

At 25, I discovered Seeking Wisdom in 2015, and it was all I needed to be a lifelong Munger follower.

I devoured every book, interview, and speech that featured him. I left no stone unturned when it came to studying the works of this great thinker, spending countless hours writing his quotes and ideas into my notes. I guess I hoped that capturing them would someone embed them so deep in my subconscious that I’d slowly become a little like Charlie.

And in some ways, they did.

I learned to sit with my thoughts long enough to realize how bad they were.

I learned to keep things simple, even when it didn’t feel right.

I learned that nobody is learning from the greats—like Munger—is an art.

Though I learned a lot about finance, investing, and mental models, something quite different stuck with me as I got older.

It wasn’t the reflections and insights that stayed with me, but Munger’s inevitable legacy.

When I was younger, I didn’t think about legacy. I focused my thoughts and energy on the now, trying to do as much as possible with what I had before me.

As time passed, I started to think more about legacy. I saw how great leaders, thinkers, artists, and creators reshaped the world, and left a mark. Even after death, the legacy lives on.

Munger’s legacy became more apparent and essential after passing away in 2023 because the insight machine that is the mind of a great man had been discontinued. We couldn’t get just one more quote or idea. That was it, the end.

But that’s what makes a rich, profound legacy like Munger’s so unique—we can relive it and continue to build on it. We can continue to learn and grow alongside his work, as I did when I was 25, devouring every word and idea he shared with the world.

My fascination with legacy stems from the dialogue it creates with the past, present, and future versions of me. Thinking about your legacy can be self-absorbed, or it can be motivating. I find when I think about it, it’s not with the lens of trying to do something to impress anyone. Instead, I remind myself that everything I do will be part of my legacy, for good or bad. In that way, it is up to me to decide what to do with my time.

Do I choose to contribute in a way that cements a legacy I would be proud of?

Munger’s work was the early inspiration for Path Nine, which became my humble attempt to build and cement a legacy of my design and thinking. Munger’s unwavering character, intelligence, honesty, humility, and professional success fueled my imagination and motivated me not just to work but also to think better.

The Munger Legacy

Great thinkers are rare.

Charlie Munger was the rarest of the rare.

He was the black swan of modern thinkers.

As I wrote in Eat a Bit of Candy,

Munger saw life with a lot of clarity. He’s a thousand-yard stare in human form; focused, precise, resolute.

Munger was the right-hand advisor to the infamous and equally brilliant Warren Buffett. Where Buffett was best known for his financial success and avuncular attitude, Munger was known for his worldly wisdom and insight. No matter your experience or background, you'll likely gain something from the insights he shared across his 99 years of calculated, thoughtful, and intellectual rigor. Unfortunately, we lost this great thinker in 2023. Upon passing, countless writers, thinkers, influencers, business leaders, tech bros, and finance execs posted their thoughts, noting Munger's impact on their lives. And before the dust settled on the digital obituary, the listicles and roundups came flying in. If you're so inclined, here are a few:

• 6 longevity tips Charlie Munger believed in for a long and happy life

• 17 Charlie Munger quotes that teach us invaluable lessons about investing and life

• ‘Diworsification’ and lifelong learning: 3 quotes from Charlie Munger that will make you a better investor

Most of the memoriam posts about Munger focus on some of his most influential insights and quotes, partly because it's the easiest way to pump out an article that gets clicks (we all love an easy win, especially if it requires minimal thought and work, for that matter). Yet, for everyone I read, I grew more and more disconnected from the richness of this thinking. A series of quotes can be interesting, but it robs us of the depth we long for and associate with great thinkers. Ironically, most of what was written and shared was antithetical to Munger's belief that everyone isn't just handed cheap, easy wins.

I believe in the discipline of mastering the best that other people have ever figured out.

He was a man who somehow existed inside and outside of time's bounds. His wisdom wasn't some cheap tweet or cursory thought pulled together for a soundbite. His thoughts were deep, nuanced, and colorful. His advice wasn't meant to be advice but to communicate a more profound truth. Munger's currency of choice wasn't advice; it was wisdom.

And that made him different—a constant pursuit of capital-T truth.

He wasn't overly concerned with being well-known despite his massive success.

Despite having millions of devotees, he focused his time and energy on something other than showmanship.

He focused on mastering the best of what other people already figured out.

And his pursuit of mastering the best rings loud in my ears.

So, instead of regurgitating Munger's thoughts, I decided to go deep and summarize his thinking into a précis, or a summary of the anthology of Munger.

This piece is my attempt to curate and synthesize 99 years of next-level thinking to serve as a pairing-down of a seminal body of work. It's not meant to be a comprehensive breakdown of Munger's work—there are books for that, after all (Poor Charlie's Almanac, etc.)—but rather a dilation of the lens with which we view and embody his work.

In the process of endlessly digesting Seeking Wisdom and Poor Charlie's Almanack, watching "The Psychology of Human Misjudgment", and devouring every article I could find on Munger, I stumbled upon natural groupings that define this anthology. These are what I call "Munger's Laws."

Laws that uphold his wisdom.

Laws that remind us of his character, intellect, and generosity.

Laws that, above all else, cement his legacy.

Law 1: Avoid stupidity

It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.

We recognized early on that very smart people do very dumb things, and we wanted to know why and who, so that we could avoid them.

In life, our primary law should be geared toward the idea of avoiding stupidity. It’s an evolutionary concept that goes back to the earliest days of every living being. You must avoid what could take you out of the game to survive. As Munger once said,

All I want to know is where I'm going to die, so I'll never go there.

At work, most of what we aim to do is to look smart, when in reality, we’d be better off if we tried to avoid stupidity. If you look at some of the most successful people, they’re rarely the smartest or even the most qualified, at least in a traditional sense. During his commencement speech at USC law school in 2007, Munger stated:

I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. They go to bed every night a little wiser than they were when they got up, and boy, does that help, particularly when you have a long run ahead of you.

Dropouts like Thomas Edison, Mark Twain, and Steve Jobs all found success via non-traditional pathways, by simply putting their head down and focusing on getting a little better each day. Reflecting early and often is one of the best ways to avoid stupidity. Though some things are complicated, only some things should be.

Law 2: Embrace the power of compound interest

Everything starts small. But compound interest turns small things into massive things; it just takes time. Compound interest is a powerful concept that can bring immense benefits to our lives. It helps us earn not only on the initial amount invested, but also on the accumulated interest. Munger knew this like the back of his hand, and he saw how it impacted everything around him, from investing to the growth of every living organism—he saw it everywhere.

Understanding both the power of compound interest and the difficulty of getting it is the heart and soul of understanding a lot of things.

But, as he points out, our ability to comprehend the power of compound interest holds us back from making better decisions. Whether it's in finance or other areas of life, we can leverage this power law to achieve greater growth and success. By continuously learning and combining our skills, we can accelerate our progress and achieve remarkable results. Just remember what Charlie said,

I think that a life properly lived is just learn, learn, learn all the time.

Law 3: Allocate time to think

We pride ourselves on our ability to do. We use phrases like “bias for action” and “be proactive” to describe and encourage people to dive headfirst into something, putting thinking aside. As someone who studied architecture and spent the early days of my consulting career thinking, I’ve always found this to be counterintuitive and, at times, counterproductive. You can’t just start building a house and figure it out as you go. You need plans, details, drawings, annotations, and coordination—all things that require thinking.

Neither Warren nor I is smart enough to make the decisions with no time to think.

In his article “In Defense of Strategy,” Packy McCormick does a fantastic job articulating the value of strategy and thinking. The art of clear thinking doesn’t come from the unpracticed; it comes from those obsessed with exploring the depths of their mind, expanding boundaries, pushing limits, testing ideas, and, most importantly, creating space. Only once we have opened up space and time for thinking can we roam the land without restriction.

If you want to be a good thinker, you must develop a mind that can jump the jurisdictional boundaries.

Law 4: Stay grounded

When starting my first company, one phone call left a lasting impact on me. I met with a fellow founder who had just sold their software company to a mid-sized tech firm in Seattle. What struck me was not the shared insights or advice but the arrogance I felt dripping off every curt and cryptic reply. Though I was still a young entrepreneur, I swore that no amount of money would ever change me, or my ability to be kind and helpful. And it goes to precisely what Munger would say,

Remember that reputation and integrity are your most valuable assets and can be lost in a heartbeat.

Success shouldn’t change you. Find a way to stay grounded.

Law 5: Create systems for success

Munger is both a complex and a simple thinker. Like Buffett, he embraces the simplicity of checklists, and also the complexity of a lattice work of mental models.

No wise pilot, no matter how great his talent and experience, fails to use his checklist.

It's so easy to get so busy you no longer have time to think. The price of not thinking clearly is relatively high, albeit sometimes delayed. But when it comes to designing a life and a career, it’s important to remember that we need systems to help keep us accountable. Or, as the infamous James Clear puts it, “You do not rise to the level of your goals. You fall to the level of your systems.”

I think about this a lot. Every day, I look at what I’ve accomplished and try to find one optimization—one way to turn a manual process into something scalable, repeatable, and easy to follow. I don’t do this to simplify work, but to maximize space for creativity and deep thinking. It’s my way of looking for patterns that keep me on track and push me toward a more successful version of myself.

You’ve got to have models in your head. And you’ve got to array your experience—both vicarious and direct—on this latticework of models.

Law 6: Stick with what works

Every week, I read a post on Reddit or Blind asking, "What is the highest-paying job in tech?" Inevitably, these questions are commonplace on platforms that promote financial success as the critical metric for a well-crafted life and career. We should expect no less from a society that cares little about the creative, alternative forms of success that often create the most fulfilling lives and careers. But we certainly shouldn't embrace it.

The problem with these types of questions is that they rarely lead to a successful career. Say you decide to be a doctor because it pays the highest salary, what happens when your passion dies out or you lose the motivation to keep moving?

What happens when lifestyle creep catches up to you, and you get stuck in a system you hate?

What happens if it causes everything else in life falls apart, and your family leaves you?

You’ll do better if you have passion for something in which you have aptitude. If Warren had gone into ballet, no one would have heard of him.

The realities of a life and career well-crafted are that they require the delicate intertwining of passion and aptitude; your interests need to meet your skills. It doesn’t need to be a 50/50 split but involves integration. The sooner you realize that moving interests and skills closer together in the Venn diagram of life, the sooner you’ll find yourself in a place that few can replicate, but many will attempt to emulate.

Law 7: Choose a path, and accept it

Starting a new business, building a new career, or doing something people don’t understand well or that doesn’t fit into a nice, neat box are all high-risk, high-reward paths in life. But they’re filled with triggers for self-doubt, imposter syndrome, and frustration. All paths are hard, it’s a question of what kind of hard you choose.

Whenever you think something or some person is ruining your life, it's you. A victimization mentality is so debilitating.

At some point, we have to chin up and move forward. Life gets hard, fast. As I look back on the adversity I’ve faced in starting, growing, and building companies, it’s easy to be overwhelmed by the challenges and frustrations faced along the journey. Yet, at the end of the day, each has made me better, and therefore made me stronger. For every mistake I made, I found two news ways to improve on that in the future. No matter how bad things seem, there is always a way through it, and a victimization mentality isn’t a solution.

Law 8: Avoid mediocrity

Most creative people are cursed with a distinct kind of pain: the pain of optionality.

Being creative often leads to multiple ideas, at times in rapid succession. It’s easy to get excited and distracted all at the same time. There are many things to pursue, and the creative brain sees opportunity everywhere. But without limitation, we risk sending ourselves into a death spiral of projects and ideas that never exceed 10% completion. As Ned Rorem once said, “It isn’t evil that is ruining the earth, but mediocrity. The crime is not that Nero played while Rome burned, but that he played badly.”

And Munger reminds us of the same pains and pitfalls of mediocrity, saying:

It takes character to sit there with all that cash and do nothing. I didn't get to where I am by going after mediocre opportunities.

In Thriving with Limitation, I shared the creative limitation that artist Pierre Soulages, "the painter of black and light," was known for creating some of the most fascinating, minimalist, abstract art in the 20th century. He often felt overwhelmed by choice — materials, colors, subjects, it was all too much. In 1979, he made the radically divergent choice to reduce his palette to one hue: black. We can learn a lot from Soulages. Whether you’re thinking about starting something, building something, or continuing something, constraints are a way to keep you grounded—they allow for and breed creativity.

Law 9: Learn to rise

Those who keep learning, will keep rising in life.

The first step to rising is realizing we can evolve—we're capable of change and maturation. Munger saw mistakes as the leavening agent in human maturation, providing the necessary conditions to encourage and facilitate intellectual expansion.

I like people admitting they were complete stupid horses’ asses. I know I’ll perform better if I rub my nose in my mistakes. This is a wonderful trick to learn.

We must first face ourselves, before we can really face the world.

Forgetting your mistakes is a terrible error if you’re trying to improve your cognition. Reality doesn’t remind you. Why not celebrate stupidities in both categories?

Mistakes are part of growth. Learn from them. Don't forget them. Instead, reflect and move on.

Law 10: Keep life simple, and minimal

One of the greatest ways to avoid trouble is to keep it simple. When you make it vastly complicated—and only a few high priests in each department can pretend to understand it—what you’re going to find all too often is that those high priests don’t really understand it at all…. The system often goes out of control.

We have a passion for keeping things simple.

We have three baskets: in, out, and too tough… We have to have a special insight, or we’ll put it in the too tough basket.

Simplicity is something I just recently understood. When studying architecture in college, I remember a long and detailed discussion with a professor about the differences between simplicity and minimalism and their relative importance in architecture. To the best of my recollection, the argument went like this:

• Simplicity = bad.

• Minimalism = good.

And from that point forward, I only referred to anything in architecture as minimal, never simple. But as I recall, the point was slightly more nuanced and focused on minimalism as a stripping down of elements. Conversely, simplicity resulted from an underdeveloped idea requiring more analysis and study, leading to a less considerate design.

Architecture lessons aside, simplicity is my north star when it comes to decision-making. My gut usually knows the answer, and my brain tries to convince my gut that it knows nothing. Of course, I’m always an advocate for Second-Order Thinking and in-depth critique, but sometimes, they can stand in the way of what would ultimately be a straightforward decision.

If something is too hard, we move on to something else. What could be simpler than that?

Learning as a Pathway to Leaving an Everlasting Legacy

For all his profound wisdom, Munger was nothing more than a man.

He sweat, bled, cried, laughed—and ate a bit of candy.

His wisdom lifted me and kept me planted firmly on the ground.

His fingerprints are all over my work and my life.

He left a mark.

Though imperfect, Munger’s laws provide foundational principles that can be passed down from generation to generation. These laws are a great place to start if we wish to think, work, and live better in the next 99 years. He was incredibly thoughtful, successful, and yet entirely grounded—and that’s exactly how I want to be remembered.

"Do not seek to follow in the footsteps of the wise, instead, seek what they sought." —Matsuo Bashō

That’s how he beat the market, outlasted the competition, and built a legacy.

Had he not been a billionaire, he’d still be successful.

Because the man, his morality, and his modus operandi surpassed the heights of his fortune.

His legacy lives on.

Things You'll Never Regret

Loss as a Reminder of the Depths of Life

Nature's palette on full display, vibrant colors adorning the Amalfi coast after a magnificent storm.

“If today was the last day of my life, would I want to do what I’m about to do today?”

— Steve Jobs

It's difficult to fathom the pain outside our limited existence. We are the thinking, feeling, and suffering centers of our universe. Pain, pleasure, gratitude, pride, anxiety, fear, loneliness, regret; each constitutes the best and worst parts of being a human.

In times of struggle, it's helpful to remember that we all feel the same.

Recently, I lost a friend in a tragic accident. He wasn't a close friend, but proximate loss is a tragedy regardless of relationship. The loss—and my processing of it—forced me to evaluate what matters most to me and how I can live a life that honors my values. This isn't a tribute to our friend—he deserves much more than I can write about him. This is a reflection for those of us who wish to live and explore a life without regrets.

Losing anything can serve as a catalyst for change. I personally felt challenged to think critically about where and who I spend my time with. So I asked myself, "What experiences and activities can I do that I will never regret?"

The answer that's beaten into our heads over and over is that, on your deathbed, you'll never wish you'd worked more. But if regrets are simply answers to the question, "What did I want for myself that I didn't allow myself to have?" work might make the list. While there are clearly many things that should make the list, work shouldn't be exiled because that's what we're taught to think—that work is unimportant.

Who we are is a complex tapestry of seemingly innocuous acts that propel us through the universe. Work is a thread that weaves its way into the tapestry, adding color, complexity, nuance, and strength. Frequently, it's a mechanism for meaning and self-esteem. Like it or not, the thing you spend more than 50% of your life doing and focused on (i.e. work), is important.

In both work and life, we're faced with challenges. But worse still, we're handed invisible scripts that we're expected to follow mindlessly. These scripts come from our friends, parents, teachers, colleagues, neighbors— everyone and everywhere. Scripts that tell us to:

• take the well-paying job (even if you hate it)

• buy the house in the suburbs (even if you don’t want to)

• climb the corporate ladder (even if it destroys your family)

• have a few kids (even if you’re not meant to)

And on and on…

For some, they help usher us onto a path of prosperity; they lift, motivate, and encourage.

For others, they hold us back; they oppress, infuriate, and repress.

For my friend, and for many, work isn't the top priority. But I bet if asked, many people would say that work plays a significant role in their lives because it partially enshrines their legacy. Work contributes to self-worth because what we do is often conflated with who we are. While my friend may have regretted certain elements that centered around work, I suspect he wouldn't change it, for it gave him and his family the life they enjoyed together. It built a foundation for his energy. It made up or unlocked a part of him. He built a life not around work, but with work.

He owned a family business and ran it, in part, with the help of his family. Not only was he building a business, he was building a legacy, in his community, his family, and himself. His work was a part of him, not a means to an end. And this is where the confusion lies: in our ability and inability to find the genuine connection between work and living.

For me, work isn't just about laboring or making money; it's about doing something I won't regret. Writing this newsletter is work, but it's work I won't regret. While work may or may not fill the same space in your life — maybe it's your kids, your family, your hobbies, your pets — these things add up to the sum we all want: a life worth living.

Our work may not be the ultimate representation of our existence, but for many, it represents us in ways that are often indescribable: our ambition, energy, ideas, motivations, and legacy. It can open the door to new relationships. It can help you find balance and safety when things go wrong. And, if nothing else, it can be one way to live a life without regret.

“Has this world been so kind to you that you should leave with regret? There are better things ahead than any we leave behind.”

— C.S. Lewis

Like Mr. Lewis, I won't presume your like is devoid of regret. No one should. Life isn't about living without regret; it's about minimizing the regrets that you have control over. Failure is not allowing yourself to experience the thin line between a well-lived life and a life without regret. A life well-lived inevitably leads to the potential for regret, but at the end of the day, it comes down to the type of regret you're willing to accept.

Here is a list of fifteen things that you won’t regret:

• Staying out too late laughing with close friends

• Dropping whatever you’re doing to help a friend in need

• Spending a little extra on the activities that bring you joy

• Sitting down to watch the sun set

• Holding the hand of someone you love

• Standing up to injustice or oppressive forces

• Pushing physical limits and doing just one more rep at the gym

• Taking five minutes to meditate and breathe

• Stopping to give extra cash or change to a person in need on the street

• Putting every ounce of energy you have into that project at work

• Sending a “just checking in” text to a friend or family member

• Saying “no” to another meeting or request for your time

• Waking up early to go for a sunrise walk/hike/ride/swim

• Taking that ‘once in a lifetime’ trip with people you love

• Taking a leap and betting on yourself

Like it or not, we're all faced with the realities of a finite existence. And while many details in our lives are unknowable and unchangeable, we're sometimes presented with opportunities to turn mundanity into miracles. Life simply cannot be lived without regret. Instead, the essence of life lies in minimizing regret by seizing opportunities, learning, growing, and embracing the depths that life has to offer. We have the power to make choices that we will never regret—and I hope, like me, you find a way to make that happen.

So, what is it that you should do?

What actions, experiences, and contributions will bring you everlasting fulfillment and leave behind a legacy?

Like me, you may find that your work and life endeavors answer the question, "What experiences and activities can I do that I will never regret?"

And if they don't, it's time to re-evaluate.

Thriving with Limitation

The value of self-imposed constraints in a limitless world

Pierre Soulages didn’t care about earning a living. For him, life was about living—and that meant painting. As an artist, he saw possibility where others saw problems. And we can all learn a little from him.

Soulages, known as "the painter of black and light," is a world-renowned French artist known for creating some of the most fascinating, minimalist, abstract art in the 20th century. Soulages's work, associated with the "Art Informal" movement, has garnered comparisons to esteemed artists like Rothko and Morellet. His artwork commands prices ranging from millions to tens of millions of dollars. He's well known for the monochromatic palettes he uses to evoke a sense of depth, energy, and mystery in his artwork. But what's most impressive is not his education, background, or early work — it's his approach.

As a young artist, Soulages found the business of art quite complex. He often felt overwhelmed by choice — materials, colors, subjects, it was all too much. In 1979, he made the radically divergent choice to reduce his palette to one hue: black. He coined this style "outrenoir" or "beyond black" to simplify his work and set him on a path as a renowned artist.

His extreme discipline gave him endless freedom.

Harry Cooper, the director of modern art at the National Gallery of Art in Washington, once said that Soulages "thrived with limitation," by deliberately limiting his color palette. Instead, he directed his attention to the remaining elements: "Light, texture, scale, shape, direction of stroke."

He became a master of self-imposed limitations.

Rather than overwhelming his canvas with countless possibilities, he adhered to constraints that enhanced his creative focus and discipline. These limitations challenge him to push the boundaries of his chosen elements and techniques, resulting in his work's distinctive and influential aesthetic. The limits didn’t hold him back; they set him free.

We can learn a lot from Soulages. Whether you’re thinking about starting something, building something, or continuing something, constraints are a way to keep you grounded—they allow us to thrive with limitations.

The Value of Constraints

At work, school, and in life, we’re told to push boundaries and think outside the box. But creative thinking requires a certain amount of practicality, or at least a connection to reality. We need the box to think outside of it.

This was one of the first lessons I learned while studying architecture.

When receiving prompts for architectural projects, designing something interesting, unique, or fun was easy. But without constraints, the design was nothing more than a concept. Building codes, budget requirements, zoning, etc., all interfere with the creative process. But over time, I learned that the constraints forced me to think more, be better, and push myself.

We’re all working with constraints, and the most creative leaders and creators understand that constraints are a helpful hurdle, not a burden. Constraints help us in many ways, including:

1. Focus: constraints act like bumpers on a bowling alley lane; they keep you from going off track. By defining boundaries, you eliminate distractions and are forced to find solutions within your constraints instead of wandering aimlessly.

2. Creativity: paradoxically, constraints fuel creativity. Constraints require us to stretch our minds to find creative solutions or unconventional approaches to break through our limitations. Further, they force us to be more resourceful and inspire innovation.

3. Consistency: not only do constraints drive creativity, they also enforce a certain amount of consistency and efficiency. Limiting your palette reduces the potential distractions that inhibit your ability to focus on what's important.

4. Uniqueness: it's harder to stand out when everyone uses the same tools. Creative expression is enhanced by the limited factors in colors, materials, techniques, voice, etc. Constraints help shape identity.

5. Growth: constraints—those dauntless companions—beckon us to embrace new skills, capabilities, and mindsets. In their audacious grip, our minds stretch to unfathomable horizons, enabling us to ascend to loftier summits of accomplishment. Thus, through these very constraints, our potential for growth blossoms, vibrant and profound.

Overall, constraints create opportunities for us to thrive in new ways, even if we don't initially see the benefit. They encourage exploration, ideation, focus, and efficiency, ultimately leading to better outcomes.

Optionality Limits and the Art of Self-Editing

Life's most difficult challenge is embracing our limitations without suppressing our creative capacity. Extraordinary results are forged in fire.

But learning to limit ourselves is challenging. As children, we strive for the freedom that we believe adults have; the “do what I want, when I want it” mentality. Without discipline, life succumbs to chaos. It is through discipline that freedom is found. To reshape your life, embrace the power of setting and creating limits. Here are a few lessons I've learned in embracing constraints:

Reframe Constraints to Challenges - the good ol’ "Do More with Less."

Instead of perceiving our constraints as blockers, embrace them as challenges. Leverage your ambition and determination to find creative, resourceful ways to do more with less. Maximize your effectiveness, and increase your leverage. You'll soon realize that the challenge is the goal; the outcomes will follow.

Define Hard and Soft Constraints - barriers are not boundaries.

I’ve learned to differentiate between “hard” and “soft” constraints. Hard constraints refer to fixed limitations that must be strictly adhered to, leaving no room for deviation. For example, in architecture, these are building codes and zoning requirements. These limitations define the boundaries that creators must operate within.

In contrast, soft constraints are more flexible and allow for a certain degree of adaptability and interpretation. Soft constraints are boundaries that sit outside the hard constraints, acting as a second layer of creative constraints. In architecture, these might be material and/or color palettes. If you need to, soft constraints may require some flexibility, but the goal is to keep the soft constraints in place by default.

Experiment with Lots of Ideas - not every combination works; keep trying.

Experimentation is crucial for the creative process, and artists often explore numerous ideas to uncover new possibilities. Soulages was a master of experimentation. His ability to hold onto his work loosely was unmatched. If a canvas wasn't working, he rolled it up and set it on fire in the garden. He didn’t continue with bad work or work he didn’t enjoy.

“It’s what I do that teaches me what I’m looking for.”

— Pierre Soulages

Soulages understood that creative exploration involves embracing both successes and failures. Creativity often thrives in an environment that encourages risk-taking. Step outside your comfort zone and be willing to take calculated risks within the constraints. Embrace the opportunity to push boundaries, challenge conventions, and explore uncharted territory.

Explore Collaboration and Diverse Perspectives - get out of your own head.

Engage with others and seek diverse perspectives when faced with constraints. Collaborating with different individuals encourages fresh ideas, unconventional thinking, and varied skill sets that help overcome limitations and stimulate creativity.

Remember, creativity flourishes when we have to navigate within limitations rather than having complete freedom. By reframing constraints as catalysts for innovation, you can harness your creative potential and transform limitations into a springboard for original and imaginative solutions.

Whether you're running a business, creating content, managing a team, or just trying to live a more fulfilling life, constraints are the filtering mechanisms in a chaotic world. There's always too much information. We're constantly bombarded with content, data, and ideas — life is a flood of information. We lament the abundance of choice and loathe the lack of focus. Our job, if you will, is to learn to limit—to limit:

what we pay attention to,

what we spend time on,

what we absorb,

what we worry about,

what we need.

Soulages realized that where some see black as the absence of color, he saw a way to focus, innovate, and challenge. The color black represented the absence of the unnecessary, reducing the unnecessary. The color black presented an opportunity to be an empty vessel, lacking the hues that imbue specific meaning or direction. It's untainted and undisturbed. It is the work that gives it color.

How can you find ways to give your work color?

How can you use constraints to illuminate the work of your life?

How can you find the light within the darkness of a clouded mind?

If you could only paint three strokes, what would you paint?

Pierre Soulages, Walnut shell on paper, 1949

Searching for Places of Possibility

Threads and the Promise and Peril of Online Networks

This week Meta, the parent company of Facebook and Instagram, released a new app called Threads.

It’s just like Twitter, except it’s Meta.

So that’s clever (I guess).

But here's the thing: people are enamored by it.

Meta Threads App

Meta Threads App

Here are a few quick stats to reiterate that highlight this point:

• 70 million sign ups just 24 hours after launch

• Threads becomes the most rapidly downloaded app in history

• Instagram's new app was downloaded more than 30 million times in 16 hours

How'd it get so big, so fast? The simple answer is that they leveraged the 500M daily active users from Instagram (shocker!). Not to take anything away from the stats, but it's like getting called on stage at a concert and then telling everyone that 30,000 people came to see you on stage.

All that said, the hype made me wonder why so many people are so eager to try it?

What separates it from other attempted copies like Mastodon, Bluesky, and Substack Notes?

Now, this won't be a post about the features that each offers, their strategic value, or a detailed analysis of their market position. If that's what you're looking for, talk to the greats like Packy McCormick or Ben Thompson — I bet they have thoughts, and they'll be much better than mine.

No, this post is about (digital) networks and how we simultaneously shape and are shaped by the networks and the spaces we inhabit, online and offline. It's about the role online networks like Twitter and Threads play in modern personal and professional culture.

Before we get into all that, let’s take a step back and look at Threads.

What is Threads?

Threads is a new app, built by the Instagram team, for sharing text updates and joining public conversations. At its core, Threads is a text-based social network. Like many networks before it, Threads allows users to post text updates and content to a network of followers. Users log in with their Instagram account and post 500-character updates that can include links, photos, and videos up to 5 minutes in length.

But that's not all it offers.

Threads offers users a fresh start.

The UI is simple, clean, and, if anything, understated.

It presents the feeling of a clean room; everything in it's right place.

For the time being, it’s free from contamination. And given how toxic most networks appear, a sense of cleanliness is invigorating.

Threads offer hope and the possibility of a new future, a future that is free from the tainted, mutated, and often cringe content that we've come to relate with most other social media platforms.

Even though Threads is nearly identical to Twitter, it's unclear what Threads wants to be. When we look at the mission statements of the major social media networks, it isn't easy to see where Threads fits:

• Twitter: “to promote and protect the public conversation--to be the town square of the internet.”

• LinkedIn: “connect the world's professionals to make them more productive and successful.”

• Instagram: “to capture and share the world's moments.”

• Threads: ¯\_(ツ)_/¯. While Meta has stated that Threads is meant to be less political than Twitter, it hasn’t provided a specific mission statement.

While I planned to avoid statements and predictions about the future of Threads, I suspect it will have a strong start and may ultimately pull a subset of users away from Twitter but will eventually suffer the same fate. Early success rarely guarantees future success.

The lack of mission clarity is most concerning. Without a clear mission to guide engagement, feature development, and network development, there is only one thing left to shape the platform: people.

People shape their behavior to the norms of the people around them. Waiting to see how people act is a recipe for disaster, and a regression to the mean within the current discourse. Further, given that Threads is easier to use, I suspect the race to the bottom will happen in record time, as the adoption curve goes both ways.

For a great example of how platform can reshape discourse, peruse the content on your LinkedIn feed. Or, for those of you who wish to avoid LinkedIn at all costs, check out the curated examples found on r/linkedinlunatics to see how quickly social networks devolve cringe-worthy content factories.

As Trung Phan pointed out in his excellent essay titled Why is LinkedIn so cringe?, every social network has issues:

Facebook (misinformation), Twitter (trolls), Instagram (fake) etc. Compared to these other platforms, "cringe" is probably not the most pressing concern."

And while I'm hopeful that Threads can avoid the gravitational pull of this type of content, the lack of a clear mission statement leaves me feeling concerned, especially considering the role that online networks play in binding us, personally and professionally.

What’s clear is that Threads is subconsciously tapping into something we're all searching for: a place for possibility. Threads feels like the first day back to school; all your friends are already there, and it’s exciting to be together again.

The Ties that (un)Bind Us

The rise of remote work has morphed the way that online interactions shape our work, our lives, and our minds. Since social networks have become a place for personal and professional connections, our online presence—and our point of connection—is more important than ever.

Sociologist Mark Granovetter studied how functioning societies are underpinned by what he called "strong" and "weak" ties. Strong ties refer to our close relationships with friends, family, and even colleagues. As you might expect, weak ties refer to the more casual ties that form within our network.

A recent study found that email data among MIT's faculty showed a 38% decrease in weak ties during the pandemic, which resulted in 5100 net-new weak ties lost within 18 months. This indicates that, while social media has brought us more online, it has a larger impact on our overall social connection. We’re more online, but less connected.

The future of work will be distributed across these online networks, and so these connections play an increasingly important role in our personal and professional lives.

I can’t pretend to offer advice on how to use social media. I ghosted all social media for the better part of the pandemic, which was fantastic. I'm back now, but not everywhere, and not all at once.

But we need networks built for actual connection, not just another clone of the online networks built a decade ago.

We The People…Matter

For me and many, Twitter started as a place to meet great people, share things with people you know, and keep up with news and current trends. But those days are long gone, and here we are, fighting to stay alive as we navigate each new tool and platform that comes our way. That's just the reality of social platforms; they start out pure, and slowly erode into divisive, corrosive, punitive discussions among strangers.

“We shape our tools and thereafter our tools shape us”

— Marshall McLuhan

Like everything, software products and platforms can be corrupted. New products rarely change old behaviors. If I were a betting man, I'd bet that Threads would fall into the same traps that Twitter fell into.

Since Elon Musk took over Twitter, I've read countless tweets about people leaving Twitter for Bluesky and Mastadon, all in protest of Musk. (Don't get me started on the irony of using the platform you're leaving to announce your righteous departure to the latest and greatest.) And the same pattern is repeating itself with Threads.

The factions that arose during the transition seemed eager, enthusiastic, but potentially senseless. While many users did leave, others doubled down on the platform.

Those who did leave likely ported their Twitter behaviors to their new platform. And who's to say we will see a different pattern with those switching to Threads. If the behaviors are the same across platforms, at the end of the day, is there any meaningful difference between these networks? Further, what would it take to drive meaningful change?

The only way to change: if people change.

What is created on these platforms is determined not only by the UI and features, but also by the people. We, as users, have an opportunity to reshape what we want from our online social connections. The longing for something new is less about the disdain for figureheads like Elon Musk, and more about the appetite for personal social networks. Networks that mimic our real-life interactions without the posturing and cringe discourse found on Twitter and LinkedIn.

The Path to Rebuilding Personal Networks

So, is Threads the future? I have no idea. And honestly, it's not what I care about. I care about how we work and live in a world where online social networks are a core part of our existence. I care about keeping our minds sharp, building stronger relationships, and finding ways to lift each other up.

Reflecting on the social networks I've used and my experience with each, I realize they all follow a similar path: honest communication > genuine interactions > professional posturing > branding, building, and selling > trolling. That is, except for one of the OG networks: Path.

If you're not familiar with Path, let me explain.

Path was a mobile app launched in 2010 and allowed users to share personal updates with a maximum of 50 contacts. Though it eventually shut down, the ideas it embodied were way ahead of their time. Instead of asking users to follow everyone and be "friends" with thousands of people, it used constraints to its advantage, allowing users a max of 50 connections and a host of features that shared content out to other platforms, keeping you from the dreaded doom-scrolling that plagues all modern social networks.

This quote from Dave Morin says a lot about the philosophy behind Path:

“What would you expect in your home? What would you expect in your personal life? A lot of the types of content we allow people to share has direct impact on people’s personal lives.”

— Dave Morin, Founder of Path Social

Path was really more about ego networks than social networks. If you're unfamiliar with ego networks, they're a type of network that specifically maps the connections of and from a single person's perspective.

We don't often think about it, but we each have a mini-universe. We have friends and family that connect to and through us. We know the level of connection we have with each of them. We have a mental model of how we're linked and the strong or weak ties, frequent and infrequent contact.

This is what Path understood. And this is what we need from our online networks.

So how might we rebuild personal networks with the goals of having a direct impact on people's personal lives?

I'm not going to claim to know the answer to our social media puzzle, but it's in our best interests to rethink the ways we interact with each other online.

Here are the principles I'm going to follow:

1. Build relationships, not followings. Our goal is to be social, which implies we should build relationships. Followings are great, but they can be shallow and fickle. Relationships grow, change, and evolve. Instead of authenticity, followings encourage the personification of personalities.

2. Connect, don't capture. Social media has conditioned us to focus on capturing our audience and sharing content that builds a brand. Instead, if we aim to exist and develop genuine connections through authentic content, we may find that the actual connection doesn't require such posturing.

3. Live, don't lie. Our ability to build relations and connections hinges on being ourselves. Too many social platforms encourage maintaining a persona or brand. It's time to ditch the lies of the persona and embrace honesty in our personal and professional communication.

If you agree, feel free to steal these. If not, drop me a comment with suggestions.

If you're enjoying Threads—and I hope you are—then keep at it. If, like me, you feel uncomfortable looking in the funhouse mirror that Meta created, I hope you feel encouraged to step away from the pressure to join yet another network. Until I feel more confident that Threads will improve the current social media traps, I plan to remain a Threads lurker.

Regardless of your feelings on the leaders, features, and culture of these products, if you're going to use them, I have one recommendation: use them to build an authentic personal network, not a social network.

It’s time our tools help us develop places for possibility, not just profit.

Paths to Prosperity

MVF as a Tool to Achieving Financial Freedom

Recently, a friend of mine quit her job. She left with:

• No backup plan.

• No safety net.

• No plan to return.

No, this wasn't some impulsive reaction to a subpar meeting with a manager or something mundane. The roots of the quitting had been building for years. Her fast-paced startup employer pushed her in every way possible — working insane hours, decreasing headcount, and promising titles and promotions that never came. The list of bad experiences was long. All this left her burnt out, overworked, under-appreciated, and underpaid, and I can fully relate.

However, these instances of burnout and disillusionment are not isolated incidents. According to a recent report by Deloitte, 60% of employees are thinking about leaving their job for one that better supports their mental well-being. A recent LinkedIn study found that almost 70% of Gen Z and millennial Americans plan to leave their jobs in 2023. If it's not clear, workers are not having it.

The Dependent vs Independent Mindset

When I first left my salaried position in 2015, I thought I knew what I was doing. Once the money started coming in, I thought everything would be simple.

I had a salaried mindset, and a dependent mindset.

Meaning: I was looking at my potential earnings and comparing them to my compensation as a salaried employee because that's all I understood then. I figured, okay, if I made $X/year as an employee, I need to get my business(es) to make that much, and it will work. Forget taxes, business expenses, etc. — that was all I needed.

Surprisingly, as most entrepreneurs find out, I realized that I needed both more and less than I thought; because money is different for entrepreneurs. You need more, because the government wants a lot more of it. You need less, because your life changes. Your needs change. Your wants change. Your drive changes.

A salary is a tradeoff for part of your soul. It's not just money, it's potential. Your potential to find joy, value, and a satisfaction on your own path. Potential is hard to quantify, but it's safe to assume it's worth much more than your salary.

For years, I had the wrong mindset. I associated money with success, and therefore I always wanted more. To this day, I still struggle with it.

What changed?

I changed my definition of enough by defining my MVF.

What is MVF?

After realizing that just replacing my salary was not a reasonable calculation for my work or the goals that represented a life well-lived, I decided to make a new calculation. A calculation that would capture the financial thresholds that I wanted to reach, keeping me from the hedonic pursuit of 'more.'

As a product leader, I decided to build on one of the most familiar and popular models: the MVP, defined as a Minimum Viable Product. In the startup world, your MVP is not an end state but a starting point. The MVP is the minimum set of product features or functionality that a startup can build to validate its product/solution.

Similarly, MVF is the minimum financials required to help creatives and entrepreneurs validate and build their path.

• M = minimum income

• V = viable income

• F = f*** it income

Saucy, I know! Every creator or entrepreneur should know these three numbers by heart. Until you know those, you’ll always want more. Let’s dig into them a bit more.

(M)inimum Income

Definition: what you need to pay your basic expenses.

Minimum can easily sound like you're underestimating yourself or aiming too low, but it's quite the opposite. In the salaried world, where your worth correlates to compensation, we're conditioned to believe that anything less than max compensation is a sign of failure. Once you start making money independently, the money doesn't represent your worth or value; it's a proxy for building the life you want. The goal isn't to kill yourself to get to the next level; it's to keep yourself happy and motivated. Setting a lower threshold helps keep your efforts in check and ensures you're not putting yourself or your family at risk more than necessary. Too often, entrepreneurs and creators are optimistic and stick it out longer than necessary — I've certainly been guilty of this myself. Having a lower threshold gives you flexibility, which is the goal.

Sample Calculation: {current basic expenses} * 1.1
Example: {rent, utilities, etc.} * 1.25

(V)iable income

Definition: what you need to pay expenses and up-level your lifestyle.

Viable is the goal that people think about most when they think about starting a business. It’s the number we instinctively calculate because we intuitively strive to keep our lifestyle intact. For me, this calculation has changed over the years, but it’s been the most useful. Setting this number is critical because it’s the number that keeps you accountable and meets the threshold of why you would set out on your own — to build a sustainable income that you enjoy and have full authority and autonomy over. Don’t try to cheat on this one; it should be the most accurate.

Sample Calculation: {average TTM basic expenses} * 1.25
Example: {rent, utilities, etc. * 12} * 1.25

(F)*** it Income

Definition: what you need to do, whatever you want, indefinitely.

Alright, here's where the numbers get fun: they are incredibly high but not high enough to be impossible. The key is to use expenses instead of earnings to calculate the target because it encourages you to keep your expenses in check if you want to hit your goal. Every time you increase your costs, you increase the change you won't hit your target. If you're okay with that, then great. Life is about tradeoffs, so choose carefully.

While I have yet to reach this number personally, I like to know what it is to keep it in mind so I continue making the right tradeoffs. Setting the goal before you have a taste of the riches can help remind you that you've reached your goal but achieved more than you ever imagined. It's not just an important financial reminder; it's an important reminder for your mental health.

Sample Calculation: {10 year annual expenses} * 10x
Example: {rent, utilities, etc. * 12 * 10} * 1.25

Setting Your MVF

Look, everyone's numbers are going to be different. Some people live a more frugal existence. Others love to enjoy the fruits of their labor.

1. Match Your MVF to Your Business. Aligning your MVF calculations with the type of business is important. If you’re a consultant, ensure you calculate for slowdowns. If you’re a creator, think about how your expenses scale as you create and publish more. Ensure your assumptions stay consistent because things will change, and you must act fast. 

2. Create a Plan and Timeline. The biggest challenge isn't generating income; it's generating consistent income. People often return to a salaried position because their revenue dips or stops altogether, and they suddenly feel the pressure to return to the perceived safety of a paycheck. You don't want to restart the engine, so create backup plans that prepare you for the instabilities that are sure to come. Remember: solid, consistent revenue always beats amazing one-time revenue.

3. Define it. Track it. Iterate. Alright, so now you have your numbers set. Don't just calculate them; track them. Be sure to look over them quarterly and re-assess your expenses and assumptions. The goal isn't to set it and forget it — it's to set it and strive for it.

Here's a calculator that you can use to define your MVF:

Challenges of Hitting Your MVF

You're good to go now that you have your numbers, right? Well, sort of.

When I started on my own, I did many things wrong. As you step off the dependent/salary train, life hits you in the face. You realize that these calculations are just that, calculations. I promise that the numbers will change once you're in the thick of it. The biggest challenges I see for people trying to set MVF milestones are:

• Rejecting uncertainty - Removing uncertainty isn't possible, so at some point, we all have to accept that we can't control everything. Accepting uncertainty allows you to pivot, iterate, and take things as they come.

• Lifestyle creep - When you're on the salary train, it's easy to slowly and steadily increase your lifestyle requirements; it's called Lifestyle Creep. And when you leave the dependent mindset, resetting your lifestyle to match your goals is critical. One of the hardest things people experience is a perceived downgrade in anything, so the earlier you start adjusting, the easier it will be.

• Conflating ambition with earnings - More than anything else, unhooking your brain from the idea that money = happiness {or insert feeling}. Money is a tool. It helps us do things, but it will not give us anything more than that. Anyone who's earned a lot or become wealthy knows it's true.

• Setting MVF too low - We all know the stories of the founder that ate ramen, slept in their car, leveraged their mortgage, etc. And we repeatedly glorify these stories. But honestly, it's toxic. People need to eat. The pursuit of greatness has destroyed people and broken families. Setting realistic targets ensures that you don't damage every aspect of your life and potentially spend years trying to recapture what you missed out on.

• Aiming too high, too fast - Aiming too high seems like a silly problem to have. We all want to be billionaires, right? Sure. But we won't all be, and it's critical to realize that building anything takes time and a lot of patience. And people without money can't have either. Yes, some people quit their job and make 3x their old salary within six months — but it's rare. According to an Influencer Market Hub survey, 35% of the creators surveyed have built an audience for over four years and currently earn over $50k annually. Clearly, it's possible to reach a livable wage, but be realistic about what your business can — and should — make and in what timeframe.

“Your money doesn’t determine how rich you are, your desires do”

— Nick Maggiulli

Unlocking Exponential Optionality

Before you put in your notice or take that next giant leap, it's crucial to have a plan and a path to creating exponential optionality. The plan isn't meant to be a perfect map of how you'll reach one specific place but rather a way to permit yourself to try things. When you know what you need, finding what you want is easy.

MVF is critical for anyone looking to carve their path and remove their reliance on a standard employer income stream. Whether you want to be a creator, an entrepreneur, a solopreneur, or explore your curiosity, financials are the biggest hurdle to breaking free. By setting these goals early, you'll be able to:

• Reduce financial stress

• Gain freedom and flexibility

• Take risks and invest in business or career

So often, we get enamored with the idea of creating that we miss out on the things in life. Money doesn't buy happiness, but sometimes it can be a helpful signal as to whether you're living a life that meets your needs.

It's important to remember that these numbers are meant to help you, not define you. Even more importantly, a plan is just that — it is not set in stone. Part of the journey to finding your path may mean returning to the employment train. And that is okay. You can always get a job. It's not the end. Life is long. You may need to take a few runs at it. Your work is meant to set you up to do what you love.

Setting your MVF reduces the financial cravings you'll experience along the path forward. We deserve to want what we have and not feel pressured to want more. When we define our MVF, we're telling the world and, more importantly, ourselves that there is a definition of enough. And, as any ambitious person knows, this is the hardest thing to do.

Working with Worry

Strategies for Coping and Thriving in Uncertain Circumstances

This past Sunday, nearly 3 million people watched as Succession, the highly acclaimed HBO series of the decade, reached its finale. While there were many shocking and disturbing moments that shook the audience to the core, one moment in particular really hit me on a personal level. In the midst of a typically uncomfortable conversation between the quirky midwestern mercenary Tom Wambsgans and eccentric, often creepy, billionaire Lukas Mattson, Tom unexpectedly revealed a vulnerable insight into who he really is:

I’m a grinder. I grind cause I worry. I worry all night about everything, all the threats to me and to my division and my physical body. I have an excess of vigilance. I have a very high tolerance for pain and physical discomfort.

And, as insane as most of this dialogue is, wow, can I relate.

I spend a considerable portion of my life worrying. I’ve always been a worrier. It’s not a conscious choice, it just happens. I worry. A lot.

I imagine that to most people, I appear completely normal and well-adjusted. Or, at least that’s what I tell myself every morning when I look in the mirror. And yet, the worry and anxiety persists. But it’s not universal.

Interestingly, I primarily focus my worries on one thing: work.

I find myself worrying that I’m not producing enough, that my work isn’t up to my own increasingly high standard, that I’m not prioritizing the right tasks, and that I’m not ‘grinding’ enough. You know, typical hustle culture nonsense.

The more that work seeps into my brain, the harder it is to force it out. It’s like the door to work-life balance just won’t close, no matter how many locks I install. But, over time, I've realized that the worry and anxiety that I experience, along with individuals like Tom, are quite similar.

Like Tom, I come from humble beginnings. No, I was not, and am not, poor. I was squarely middle class. I have great parents and a stable family. That’s a lot more than many people have in their life. But that has never stopped the worrying. And I know many incredibly successful people who have the same feeling, whether they’re willing to share it or not.

So what causes people with stable jobs, stable lives, and good careers to stress so much? And at the end of the day, is there any benefit to worrying about work? To address it, we must first understand it.

Why We Worry.

As we’ve seen over the last few years, work has become increasingly unpredictable. Jobs that used to look safe no longer do. Career paths that were stable and consistent are falling by the wayside. Companies seem to care less and less about their employees. DEI efforts seem primarily performative. Companies that went remote during the pandemic and saw productivity increase are now reversing course.

Everything is about shareholder value. People are replaceable, so don’t get too comfortable. That’s the message, so it’s unsurprising that we’re worried.

A study found that people who have a hard time dealing with uncertainty and emotions are more likely to worry. So, as the world of work continues the path to instability, those of us who are poised for anxious thoughts and preferences of certainty will be faced with increasingly uncomfortable situations in the workplace.

This is the new reality. As much as we wish it wasn’t true, it seems to be the case. But what is worry? Is there anything we can learn about worry that may help us cope with it in the uncertain workplace?

What Is Worry?

Worrying is a direct result of fear, which can be a highly rational or irrational response to something we experience. Fear is an adaptive quality that keeps us safe, and a real or perceived threat often triggers it.

Workplace anxiety can be due to a number of issues, but it’s most likely you don’t feel safe. You’re experiencing fear for a reason. Your boss might be signaling your position is at risk. Your team may be underperforming or the market may be impacting your ability to deliver the results leadership seeks. You may have coworker conflicts that impact your work. You might not get along with someone at work. Or maybe you’re being forced back to the office after making a major life decision.

No matter your reasons for worrying, it’s important to realize that not only is it normal, it’s completely expected during such a tumultuous period of modern work.

When Worry Weighs You Down.

Last week, I wrote about a phenomenon called the Tetris Effect; basically, when you focus on something for long enough, you start to see it everywhere. As you might imagine, this can be incredibly powerful, or completely paralyzing. Worrying so much has serious consequences. Bad sleep, unhealthy eating habits, maladaptive coping strategies, grouchiness. Yep, I can be a real grump.

For others, it can cause panic attacks, stomach issues, concentration issues, procrastination, memory issues, headaches, and more. It’s truly debilitating.

The most common fears I see at work:

• becoming irrelevant

• having financial stability

• starting over

• making the wrong choice

• being viewed as a failure

• wasting time

Yep, those are all of my worst fears. And I suspect others are dealing with the same or even more issues. So, given all our fears, what can we actually do? Should we curl up into a ball, avoid the hard decisions, and let worry consume us? Obviously not. (Imagine if I wrote an article like that.)

How Worrying Can Propel You Forward.

Worrying can have positive effects at work. We worry because we have fears. The fears create a hyper-vigilance that aims to predict and control the future. In many ways, this hyper-vigilance propels us forward. We work the long hours. We take the extra meetings. We do what has to be done. Further, this additional motivation (if you want to call it that) can create positive behaviors. Research shows that worrying actually produces positive benefits and behaviors for many, including:

Increased Intelligence

Overthinking, analyzing, and evaluating; these are all the ways in which your constant worrying helps you see the world and, subsequently, likely increases your intelligence.

The positives: you’re intelligent and motivated. You have a problem solving mindset.

Heightened Awareness

The increased anxiety causes many people to have a superhero level of awareness, particularly with other people and in social situations. Being hyper-aware makes you more in tune with how other people might feel or perceive a problem.

The positives: you’re more conscious of other people’s feelings, because you care what they think. You have higher compassion and empathy.

Problem Anticipation

Worrying is a state of hyper-vigilance, which means you’re naturally a second-order thinker.

The positives: threat response is heightened. You see around corners and anticipate.

Turning Worry into Winning.

Ok, so what now? Are you doomed to be a pain sponge like Tom? Is there anything you can do to manage it? Well, yes and no.

Yes, there is something you can do to turn your worrying nature into something positive. No, if you’re a worrier, it likely won’t ever go away. But reframing this as a positive can actually help you thrive at work (and elsewhere). Instead of letting worry dominate your life in a negative way, you can harness the energy it generates to move on, and move up.

Here are a few ways that you can improve your relationship with worry and work:

1. Audit it. Conduct a work relationship audit. To understand our relationship with work, we must review it. Put it under the microscope and examine its individual components. The easiest place to start is with a self-reflective audit.

2. Accept and activate it. You can’t change it. Embrace the uncertainty. Use the anxious energy your body feels to propel you into action. Work on things that move you closer to your goals, whether that’s in work or at home. Learn something new. Take back the control.

3. Diversify. Build a multi-hyphenate, anti-fragile career. Don’t just invest in one company. Find ways to reduce your fragility. Even if you only have one job, passion, or profession. Orient yourself to be ready for change at any moment.

Worry can be so overwhelming. But once we understand it, we can find ways to work with it. Work is such a major part of our lives that we simply can’t ignore it. We must find ways to live within the confines of a changing world, and adapt. Instead of spending our time or energy on the negative behaviors of worry, let’s turn them into positives to help propel us toward the future. It isn’t easy, but it is worth it.

How to Improve Your Relationship with Work

Plus: A Tool to Decrease Burnout and Increase Engagement

Do you:

Feel bad for not working? 

Feel guilty for having a life outside of work? 

Feel guilty when you aren’t at your desk? 

Feel like everyone around you is working more or less than you? 

If you found yourself nodding along, these are all signs that your relationship with work is fractured and in need of repair. And these are all feelings that I’ve experienced myself. 

The time when we could just simply turn work mode on and off is gone. Remote work, combined with constant connectivity, has eliminated the concept of disconnection. Work has gone from a thing we do to who we are. And, if you’re anything like me, you know the challenge — and often pain — that comes with a fractured relationship with work.

But, like any challenge, avoiding it won’t make it go away. Over the last 10 years, I’ve dealt with this challenge and struggled to find ways to strike the right balance in my relationship with work. For me, the first step is acknowledging that something isn’t working. 

What an Unhealthy Relationship With Work Looks Like

It’s not always easy to notice the signs that your relationship with work isn’t healthy. As the relationship evolves, the subtle changes that impact our day-to-day life become commonplace. But soon, these anomalies become the norm and reset our expectations within the relationship.

While certain professionals have always struggled with burnout and overworking, for many, this is a recent phenomenon. When the office existed, it was easier to spot an unhealthy relationship with work. It involved — too many hours at the office, missed events with family and friends, and just a general sense of a single priority: work.

But those days are gone.

In the modern era of work, an unhealthy relationship looks completely different. Work is increasingly done in digital environments — Slack, docs, email, virtual meetings — where the signals can quickly and easily get buried or swept under the rug. The signs are similar to those in an abusive or addictive relationship — manipulation, intensity, and possessiveness.

Sadly, the abused often suffer in silence and attempt to cover up their problems in order to save face publicly. In the short term, an unhealthy relationship with work leads to anxiety, stress, and sleep deprivation. Over time, it leads to bigger, ongoing challenges in general mental and physical health, and ultimately burnout. 

A study on burnout found that the dimensions of burnout can be boiled down to three key factors: 

• Exhaustion - physical and mental depletion of energy. 

• Cynicism - lack of motivation, interest, and increased irritation. 

• Inefficacy - loss of productivity and drive to improve it. 

In the workplace, these dimensions cause a slow but steady breakdown of trust, communication, and overall satisfaction.

I’m great at noticing exhaustion or inefficacy, but cynicism often slips past my radar. When I’m burnt out, I find myself increasingly cynical toward work, saying things like “Who cares?” and “It’s not like it matters anyway, it’s just work.” This loss of meaning is one of the most prevalent signs of burnout and a sign of potential depression. 

Conduct a Work Relationship Audit

In order to understand our relationship with work, we must review it. Put it under the microscope and examine its individual components. The easiest place to start is with a self-reflective audit. To make this process easy, I’ve created a little tool that you can use to answer the following questions:

1. How many hours do you work each week?

2. How often does work make you feel stressed or anxious?

3. Do you feel like you're expected to keep working, even after a full day of work?

4. How often do you feel irritated or irritable about work?

5. How productive do you feel each day?

6. How often do you feel fulfilled with your work?

7. Which work activities give you energy?

8. Which work activities drain you?

These questions are meant to help you introspect and test the strength of your relationship with work. If you are using the tool, it will automatically assign you a rating based on your answers. If you find yourself giving high ratings or with a short list of activities that drain your energy, you’re likely at low risk of burnout and require minimal intervention. If, on the other hand, you respond with lower ratings and a laundry list of activities that drain you, it’s time to hit reset. 

🛠 Make a copy and give it a try → Work Relationship Auditor

Resetting Your Relationship with Work

Now that you’ve conducted your Work Relationship Audit, use the information to reset and redesign your work-life relationship and re-establish important boundaries and norms.

• Regulate - Regulate time spent at work to keep the relationship balanced. Any relationship will buckle on the weight of time. Spending less time with work will allow you to reset your view of work and minimize the risk of burnout. Take a vacation, even if it’s for a day or two.

• Substitute - Sometimes it’s hard to know what to do when we’re not working. For me, if I’m not busy, I feel a bit stressed. But if I fully immerse myself in something that’s not work-related, the stress subsides and my brain returns to a point of homeostasis.

• Resist - It’s too easy to just say “Oh, I’ll do a little extra work this one time.” If you don’t resist the urge to say "yes” to every opportunity to overwork or accept every request, you’ll fall into the neverending trap of Parkinson’s Law of Productivity.

A one-time relationship reset is a great way to re-energize and refocus yourself. But don’t be surprised if you find that you need to make this a regular habit. Using the tool, you can easily set a reminder to re-evaluate your relationship with work. Simply click the [Remind Me] button, provide access, and a recurring event will be added. 

Whether you decide to proceed with recurring audits or not, the goal is to increase the quality of work and life, so focus on what works best for you. You can never invest too much effort in seeking happiness or fulfillment, so make time for the work that matters — personal work.

The Law of Unwritten Expectations

Where's the "Off Switch?"

90 Slack messages, 150 emails, dozens of comments and notes in Google Slides and Docs, and a handful of voicemails and text messages. This was the ‘Welcome back’ package I received upon returning to the virtual office one Monday morning a few years ago.

Was I gone for weeks? Months? Maybe even years? Nope.

This was the result of a three-day weekend. Yep, that’s right. A Friday, a Saturday, and a Sunday.

Did I forget to plan and let people know I’d be out? Wrong again.

I spent weeks preparing my team, coordinating with other managers, and ensuring the I's and T's were appropriately marked.

Something had gone horribly wrong.

Or had it? Was this a feature, and not a bug?

Well, it’s a little bit of both.

Remote workers dodging the constant barrage of requests 👆

The Law of Unwritten Expectations

As humans, we naturally feel compelled to be busy — or at least look busy. Research shows that people always fill their time. We take on more work than we should in order to show others how busy and productive we are. We’re quick to confuse high demand with high value. And the more we push ourselves to be busy, the more we get addicted to that validation. The harder we work, the busier we are, and the less time we have.

As companies around the world shift to working remotely, they’re also working longer hours. According to data from VPN service NordVPN, U.S. employees are logging an additional three hours per day, compared to pre-COVID-19 patterns. For those of you following along at home, that’s a 40% increase. And that’s just the average. No wonder people are stressed.

Now you’re probably thinking, a large portion of that is likely due to additional meetings required by a virtual environment—and you’d be correct. The study, which analyzed anonymous email and calendar data from 21,000 companies, found that the number of meetings increased by 13%, but meeting duration fell by 11%.

In short, we’re spending a lot of time looking busy and making sure people “see” our contributions.

But why? What is it about remote work that triggers this reaction?

Remote work seems to tap into a part of our psyche that focuses on signaling value, and it can be difficult to unwind that instinct. In a world where your value is based on output alone, people are particularly aware of the risks of work. Remote work, primarily driven by COVID-19, has created a sense of urgency and a compounding need to overcompensate for external chaos. Managers, employees, consultants, and freelancers all feel the constant need to respond to message and always be “on.” The perception of competition is only increasing.

This is primarily due to what I call the law of unwritten expectations, which states that once one employee offers 24/7 availability, all employees must follow.

Managers may not directly communicate or require that employees be online/available 24/7, but the expectation is subtly implied through the communication channels within the organization. For example, when a manager that checks email late at night or sends an email on Sunday is subtly signaling their expectations to an employee.

This behavior can be particularly pernicious for a competitive employee in a competitive work environment. Not wanting to be outdone by their counterparts, many employees will step in and work as a measure to keep the upper hand or protect their position.

And, guess what—it ultimately leads to burnout.

I’ve personally struggled with this feeling many times. Many weekends where I set out to avoid work, only to find that my time away actually produces a massive dose of anxiety. That feeling of "I should be doing more," as if not working somehow diminishes the work produce during the previous work hours. No matter how many hours, the digital capacity seems limitless.

Breaking the Law

We all need time and space to unplug. Without a physical office to enter and exit, the boundaries all but disappear. A 2019 study in the Netherlands found that employees who disconnect after work—disconnect physically, emotionally, and cognitively—experienced improved energy levels, better sleep cycles, increased concentration, and more positive moods. More importantly, these benefits did not occur when an employee disconnected during a work break, meaning that true disconnection requires longer breaks of time.

In "Remote Boundary Management Styles", I examine the many reasons we need to create balance in the modern era of work:

1. A study by National statistics in the US surfaced a recent increase in work-life stress and the need to find strategies to manage our new normal.

2. Furthermore, a Families and Work Institute study reports that 75% of working parents do not have enough time for their children or each other.

3. Despite being more connected, a study by the IBM Institute for Business Value found that millennials value drawing a line between work and non-work to better enjoy a life outside the office.

Creating physical, psychological, and emotional boundaries allows remote employees and employers to co-create a more scalable and sustainable relationship. And for some, it’s critical to create pathways to fully disconnect.

Flipping The Digital “Off Switch”

In the wake of the COVID-19 pandemic, everyone is experiencing what it feels like to be part of an always-on workforce. It’s increasingly difficult to find ways to escape work. But this isn’t new. We’ve been trending this way for years.

It all started with mobile devices, which created an open line between employers and employees, destroying work-life boundaries in the process. The freedom we gained from disconnecting the cord was quickly offset by our constant connection.

With mobile devices and lightning-fast internet in hand, the digital drinking fountain suddenly became a firehose. Tools like Slack and Discord made their way into our lives and opened up more channels, pulling employees further into the digital web.

And for remote workers, technology is what ties us to work.

So what do we do when we’re experiencing the barrage of messages I experienced during my weekend vacation? Can you shut off notifications from Notion, Slack, Gmail, and Asana?

The truth is: there is no digital off switch.

And without the off switch, employees are left to develop coping strategies for managing work-life balance. If we want a break, we have to create one for ourselves.

As I wrote in Learning to Block, we need help blocking so we can improve our:

Work-life Balance. You can’t spend every minute on the field. We understand this for athletes, and it’s no different for workers. Athletes need a break for water, coaching, and a change of perspective. Our work is no different. We need outside activities and space to increase creativity and productivity.

Pro tip: use calendar blocking tools like Reclaim or Clockwise to automatically block time for non-work priorities (e.g. working out, reading).

Productivity. Working remotely has both a positive and negative impact on productivity. It’s easy to push hard for a few plays, but it’s also easy to find yourself completely worn down and exhausted. You can run plays all day, but if you have to punt every time you get the ball, you’re doomed to fail. If we want to execute more, better, faster, we need to block our way to the end zone.

Pro tip: put your devices away and explore a non-digital hobbie, like playing an instrument or doing a puzzle.

Mental & Physical Well-being. If you’re getting hit constant requests, sooner or later, you start to get tired of what you’re doing. Burnout doesn’t just happen, it develops over time, slowly and painfully.

Pro tip: leave your desk and get some fresh air. Find a way to get your mind off of work — rest and refresh.

Now that we've identified the subtle way management is laying out remote expectations, we can start to properly tackle the problem and begin the process of renegotiating what it means to work in a remote world. But so as not to burn out, I’ll save that for a follow-up article.

Process Hacking

Why "Process" Falls Apart and How to Fix It

Bright-eyed and eager to prove myself, I entered the workforce.

With a background in design, I saw every problem as an opportunity to redesign the system for maximum output. For every inefficient operation — from sales and marketing operations to project management — I blindly assumed that implementing a standardized process would dramatically improve the performance and output. I’d invest hours outside the office rethinking nearly every aspect of our business. If I saw a flawed process, it was my duty to fix it.

To this day, the designer within me thrives on turning complex, open-ended problems into streamlined, seamless solutions.

It seemed that processes could solve everything. Unfortunately, I had yet to realize that process was in fact part of the problem. And the problem wasn’t just mine or my company’s, it was true for millions of teams and organizations. Process is both the silver bullet, and a deadly weapon.

Rethinking Process

It always baffled me how easy it was to sell process over output. Companies spend a lot of time talking about, thinking about, and designing processes. In my past life as a consultant, I could walk into a room and lull a client into a sense of security simply by showing a few well-designed process slides.

It made me realize that people want the pitch more than the actual process. They don’t just want someone to trust, they want a process they can count on when all else fails — when we’re human. And therein lies the fundamental flaw with process design. Processes can be very powerful when used correctly, but they should be the last stop on a journey to maximizing efficiency.

Should You "Trust The Process?"

“If you can’t describe what you are doing as a process, you don’t know what you’re doing.”

— W. Edwards Deming

A process is little more than a checklist to guide how things are done and ensure consistency, quality, and accountability. There are two types of processes: implicit and structured.

Implicit processes are fluid and ill-defined, naturally evolving from the patterns and actions of those engaging. “That’s just the way we do it” is a perfect example of where an implicit process exists. It’s not written down, but it’s known.

Structured processes are quite the opposite of implicit processes. Where implicit processes are not pre-defined, structured processes are highly organized, structured, and explicitly defined. If it’s written down, it’s structured.

It’s easy to believe that simply creating processes will help improve overall performance. And that may be true when the conditions are well-defined, specifically when we’re looking to:

• Scale a known set of activities

• Improve simple efficiencies

• Improve output, not outcomes

But as soon as things start changing, a process quickly falls apart, or worse, actively works against us. That’s because a process creates complacency by allowing us to rely on a checklist and remove critical thinking. In essence, the process acts as a proxy for decision-making. For instance, how often have you been told to "trust the process?"

Very few processes are adaptable. We create processes based on a static framework designed to work in a stabilized system. But, as we all quickly learn, the world is highly complex and unstable.

So why not just create an adaptable process? This, almost by definition, breaks the entire concept of "process." If we want something that’s adaptable and able to fit into a complex decision-making environment, we have to get into the smaller, more elemental details.

Instead of processes, we should build patterns, plays, and playbooks. Patterns lead to plays; plays lead to playbooks, and playbooks lead to processes.

Let’s take a bottom-up approach to process creation by starting with patterns.

Start with Patterns

Since "plays" are the "smallest, simplest form of planning", it almost begs the question, why start with patterns? The answer is: in order to create something repeatable, one would first need to recognize the patterns. Therefore, the art of seeing the pattern would be the first step.

While tempting, the key is not to jump straight into a process. We must remain diligent by working our way toward a playbook. This stage is critical to ensure we remain agile and focused on the output over the process.

Patterns, a combination of activities run in succession, are the natural precursor to plays. Each pattern starts with a singular activity which is then combined to create a more complex series of activities that add up to a pattern. By creating a pattern, we’ve now simplified a series of complex actions, making it reusable and still adaptable.

Patterns are most efficient for:

• Generating rapid activity with little governance

• Short sprints and constrained workloads

• Improving consistency without losing flexibility

Some patterns can be defined in advance but, just like using a process, the early definition can reduce the efficacy. As patterns evolve and stabilize, we can capture them as a repeatable element that becomes a play.

Design Plays

Plays, a planned action taken by a player or series of players, are the smallest, simplest form of planning. They are segmented into bite-sized chunks that can quickly be swapped or adjusted on the fly.

Plays allow for improvisation. They require minimal forethought and emphasize agility. Their beauty lies in their ability to support freeform thinking with structured outputs.

Plays can be broken out into categories and recombined to fit new definitions at a moment’s notice. Furthermore, they don’t dictate the outcome, but rather the actions. This allows for maximum flexibility for the players involved.

Why plays are important in the process hierarchy:

• They’re easier to iterate and adapt

• They can be targeted at a specific issue

• They are self-generating

• can be cobbled together

• allows for autonomous play-calling (quarterbacks can call plays)

Build Your Playbook(s)

This is where most people jump straight to when creating a process — and it’s exactly where we lose the thread. Successfully designed patterns and plays get watered down into a measly checklist for someone to blindly follow. But, we can retain the structure without losing the value by designing a playbook. Like Tetris pieces, playbooks allow us to rearrange plays and patterns at will, while providing templated structures to help guide our decisions.

They are a collection of plays, with a subtle directional indication of how to use each individual play. They reflect our plans and provide predetermined actions that can easily and efficiently be executed by those without full knowledge of the specifics.

Playbooks are most efficient for:

• Providing consistent strategy

• Maintaining quality

• Decreasing time to value

• Reducing analysis paralysis

• Increasing performance

Creating Your Own Plays and Playbooks

Like everything in life, it comes down to mindset. If we assume everything is a process, we set it in stone. If we take a more agile approach, we provide ourselves and our teams with the space to reinvent at the most fundamental level. Here’s a lightweight play to create your own plays and playbooks:

1. Constantly observe. Be on the lookout for areas of inefficiency, in life and at work. Trust me, they’re everywhere.

2. Capture patterns. We can’t act if we don’t record our observations. Capturing patterns helps us decide if the pattern should become a play.

3. Don’t fall in love. The moment we fall in love, is the moment we start losing it.

Rigid thinking is a relic of a bygone era, where the world was more orderly. Don’t get caught mindlessly following the wrong path. Take the opportunity to reinvent at every step of the journey.

Training For the Unknown

Or, How to Build and Sustain an Antifragile Career

“I haven’t updated my resume in years.”

The number of times I’ve heard friends and colleagues say this is astounding. Not because updating your resume is important, but because it signals a certain level of comfort, or stagnation.

Staying in one place for a long time is certainly not a bad thing. Allowing an employer — or anyone — to dictate your career, growth, and intellectual development — well that, my friend, is a travesty.

As knowledge workers, often with luxurious salaries and compensation packages, we’re prone to believing we’re well-positioned in a growing economy. While this is technically accurate, we are highly susceptible to chaotic events.

Take, for example, if a new manager is brought in to manage your team. If you get along with this manager, they have the power to accelerate your career as they rise through the ranks. Conversely, should you clash with this manager, they have the power to permanently mark your record, possibly holding you back for years to come.

This is not to say that other careers are immune to such situations, but rather to note the false sense of security that exists in most modern careers.

But what can we do? Are we all supposed to just quit our jobs?

Absolutely not. Or at least not right away.

The key here is to take a different approach to your career altogether. To look inside-out, not outside-in. The goal is to become antifragile.

What Does It Mean to Be Antifragile?

Some people benefit from chaotic events. They thrive on them and grow stronger in their pursuits, and are therefore antifragile. Others are utterly incapacitated by these same events, or fragile. It’s critical for us to know and understand how vulnerable we are, especially when it relates to our careers. To better understand this dichotomy, I find it instructive to look toward athletics for inspiration.

Professional athletes spend years developing skills. In many cases, they don’t know exactly what their opponent will throw at them when they’re in the midst of competition. So instead of trying to predict every outcome or potential move, they train for adaptation. They embrace and accept randomness. They make chaos their friend.

Antifragile is a term coined by essayist, and Twitter feud instigator, Nassim Taleb. As Taleb describes it:

Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.

The antifragile gets better. I repeat: the antifragile gets better.

So how can we build careers that are antifragile? And what does an antifragile career look like?

Antifragile Career Characteristics. There is no universal definition, but there are characteristics that, when combined, have the potential to deliver antifragility.

1. Flexibility

2. Network Strength

3. Independence

4. Leverage

5. Optionality

To become antifragile, we have to train.

Training: The Antidote to Chaos

Recently, I wrote about the idea of intellectual athleticism. The main idea was that, as intellectual athletes, we need to develop ourselves in ways that will allow us to continue growing and learning, without locking us into one particular path. In short, we need to learn to adapt our intellect at a moment’s notice.

As intellectual athletes, we need to think — and train — like world-class athletes. The best athletes sustain high levels of performance over long periods of time. Many people assume that these athletes solely focus on what they’re good at and avoid adversity in training. In reality, they trained for adversity.

In fact, the greatest athletes did some of the weirdest things. They found innovative ways to deal with adversity and prepare themselves for random events. Here are a few examples of elite athletes and their extreme training:

• Michael Phelps - The highly decorated athlete puts his head in the clouds. It was reported that Phelps sleeps in an altitude chamber at night, which simulates a high-altitude environment, allowing his body to create more red blood cells since the chamber has less oxygen.

• Michael Jordan - Most people wouldn’t be surprised to know that one of the greatest athletes of all time has a few odd methods, but this one is pretty odd. According to his former trainer, Tim Grover, Jordan used strobe light glasses to mimic the bright flashes of photographers behind the hoop are a major issue in the clutch.

• Manny Pacquiao - In the ultimate act of training for the unknown, the famed boxer had members of his camp beat him with Thai sticks while training.

These athletes embrace adversity because they know it makes them better. It happens for them, not to them. They don’t view setbacks as a victim. Instead, they focus on what they can control — their training and their response to the situation. In doing so, they develop the mindset that things will continue to happen, setbacks will occur, but they’ll be prepared for them.

When we think about our work as training, we change our mindset and, therefore, our relationship with it. Instead of thinking about a continuous flow of work, we can break it up into different sessions, where we focus on one particular area. For example, writing this newsletter takes time and energy, which uses different “muscles” than other work tasks. To train for it, I write every morning, study great writers, and read content (articles, books) on how to be a better writer. This is a method I designed to help me train to be a better writer, but the same principles can be applied to anything.

Training Principles and Practices

The lessons of athletics are timeliness and should be consistently reevaluated, especially now that we treat work as a sport.

Like becoming a professional athlete, becoming an intellectual athlete is a lifelong pursuit. It requires discipline, focus, and consistency. If you want to become an intellectual athlete, you need to take steps to make it a reality. Here’s the method and approach I use to develop the mindset and training program.

Set Goals and Train with Intention.

Whether we consciously recognize it or not, we’re already training ourselves for something. The question is: for what?

The day slips by — you’ve done stuff, but not really. Maybe you checked some boxes, but did you really accomplish anything? This is the equivalent of showing up to the gym in jeans, aimlessly wandering around for an hour, then eating a burrito to celebrate.

Know that what we’re trying to accomplish is critical, otherwise, it’s not training. Don’t try to tackle it all at once, though. Instead, aim to get 1% better at something every day. Progress is (almost) always better than perfection. Approach training with intention and you’ll see progress. Don’t, and you won’t.

Find a Training Partner.

It’s easy to set goals, it’s difficult to stick to them. Finding a training partner will keep you accountable for your goals and help you stay focused on consistency.

I have people that continue to push me in healthy, personal and professional competition. They help me train for a career with antifragile characteristics (e.g. flexibility, independence) by forcing me to examine weaknesses in the categories listed above.

Get Coaching.

Coaches are ruthless. Anyone who played sports as a kid likely recalls a time when you thought “they’re trying to kill me.” While some coaches are truly sadistic, most coaches — or at least the good ones — are good at identifying weaknesses and using the tools at their disposal to reshape you.

Athletes have a coach for a reason — it’s difficult to accurately assess our performance without feedback. Coaches, mentors, and advisors help us see ourselves in new ways and continuously develop.

Pursue Practicality and Passion.

This sounds like a no-brainer, but you’d be surprised by how many people jump into something they’re not actually passionate about simply to get fame, notoriety, or money. If your athletic abilities are not directed towards your passion, you’re starting an uphill battle. But that doesn’t mean it should be your only pursuit. Sometimes, you need to pay the bills — which is a component of antifragility.

Taleb specifically advocates bimodal strategies in work:

Have one very stable gig and one volatile vocation by moonlight.

Study.

Who are the people that you admire most? Make a list of people who inspire you and make you work hard. Setting your sights high will keep you focused and remind you what you’re aiming for in your future pursuits. Learn from their habits, skills, and techniques. And then make them your own.

Inject Randomness.

If you want to be prepared for randomness, you have to experience randomness. Setting goals and tracking progress are two key elements of the process, but testing is an entirely different beast.

It’s easy to check off our goals and our progress, but proving ourselves is much harder. Athletes have big tests — games, events, etc. — that not only focus their efforts, but allow them to gauge their abilities.

Design your own or find ways to inject them into your life. Randomly apply for that job you’ve been eyeing. Live for a month without income. Try a skill you’ve never tried before and see how you fare.

Rest and Retest.

Athletes can feel when their body needs a break. It’s not so easy with intellectual work. Instead of waiting for your body to tell you, block off time during your week to ensure you’re properly rested.

Science writer Ferris Jabr summarizes the benefits of downtime in this Scientific American article:

“Downtime replenishes the brain’s stores of attention and motivation, encourages productivity and creativity, and is essential to both achieve our highest levels of performance and simply form stable memories in everyday life … moments of respite may even be necessary to keep one’s moral compass in working order and maintain a sense of self.”

Training every day isn’t good for anyone, so don’t be shy about taking a calculated rest period.

Take Control.

Jobs are replaceable, and most people are not well-positioned to define their own destiny if someone decides the job isn’t for them. To take control of your future and career, antifragility is the key that unlocks that door. But antifragility doesn’t just happen.

Want to get a promotion? Want to get a job offer? Want to start a business? These things come through focused, intentional effort.

Building an antifragile career takes time, so don’t wait. Get to work.

Intellectual Athleticism (IA)

An Important Trait for a New Era of Work

Strikeouts. Missed free-throws. Dropped passes. These were some of the hallmarks of my early athletic endeavors.

Short, mildly overweight, and sparsely graced with coordination, I lacked the trademarks of a chosen athlete. And yet, year after year, I continued my athletic pursuits.

Despite my struggles, I figured there might be a day when the road got easier. I tried new teams, changed positions, and even exercised more. Slowly, but surely, it did get better.

But it wasn’t because I stuck it out. It was because I learned how to adapt.

The path to improvement wasn’t linear. I had to try multiple different sports before I could find my strengths, and so it was in the changing of sports that I learned what the real advantage was: adaptation.

Playing multiple sports helped me improve in other sports and activities. What I learned in weight training was easy to see expressed physically in tennis. Additional leg strength made running easier. Shoulder strength my serve in tennis. Grip strength made hitting the ball and swinging a racket/bat easier.

With every physical change came a mental change as well. Testing my skills and abilities is what allowed me to know my boundaries, which is what allowed me to push through them.

For years, I imagined what it might be like to do this for my career. If I could improve my skills physically through hard work and determination, why couldn’t I do the same at work?

As I’ve previously written, there are a lot of similarities between work and sports. If we treat work as a sport, we set ourselves up for a new training regime and increase our overall athletic ability.

When we honestly assess ourselves, we quickly learn that we all have strengths and weaknesses that we can focus on. Whether it’s physical, mental, or emotional shortcomings — we’re riddled with imperfections.

Just like an athlete who wants to improve, the best way to deal with our weaknesses is to analyze, address, and train.

But becoming an elite athlete is not easy. Professional athletes train for years and years for a chance to compete with the best. They push themselves to the limit each and every day. And for what? For the chance to live out their dream and reach their potential.

So what defines athleticism?

Intellectual vs Physical Athleticism

There’s a rich, albeit debated history of athleticism and society’s attempts to accurately test and analyze it. If we simply combine the definitions, the definition would look something like this:

ath·let·i·cism: the physical qualities that are characteristic of athletes, such as strength, fitness, and agility.

To better understand and compare physical and intellectual athleticism, I’d like to break that definition into smaller parts, starting with physical qualities. 

[Physical] Qualities — The definition selectively calls attention to multiple physical qualities, which is important to note for our intellectual definition. It’s not a single measurement that only includes one physical quality or trait. Instead, it requires that an athlete be, what many would consider, “well-rounded.”

Similarly, the intellectual athlete should harness intellectual qualities across verticals and domains. Cognitive abilities are the skills that make up our general intelligence. In the past, most definitions looked at a single ability, but modern analysis looks at a combination of abilities.

Next, let’s look at the characteristics mentioned: strength, fitness, and agility. 

Strength — Strength in physical athleticism typically refers to raw power, or one’s ability to exert power. For the intellectual athlete, “power” is more about raw horsepower, or the ability to address complex problems across diverse situations.

Fitness — Athletic fitness looks at an athlete’s condition of being physically fit and healthy. Note that healthy is the operative word in this definition. For the intellectual athlete, health is just as critical as being fit. An unhealthy mind is unbalanced and cannot perform optimally.  

Agility — Athletic agility typically refers to one's ability to move across domains with ease. This is our closest correlation to intellectual athleticism, which also requires a high degree of intellectual and cognitive agility in order to move across environments with ease.

The Intellectual Athlete’s Advantage

Year after year, new innovative technologies change the competitive landscape of intellectual and physical performance. Artificial Intelligence (AI) is one particular technology that is rapidly evolving, and finally starting to make its way into our intellectual competitive field. 

Take GPT-3 for example. Last year, GPT-3 was released and it shocked the world. Part of the panic was because, for the first time in history, AI felt like it was nipping at our heels. 

Those who work in tech or AI know the limitations of the current iterations of GPT-3, but it’s clear that technology may soon eat our lunch. And if we’re simply a few steps ahead of AI, what can we do to ready ourselves for a future where work is automated? 

The answer is simple: Build intellectual athleticism. 

Not only will technology come to take our jobs, but remote work will unlock a slew of new opportunities to redefine and reinvent “work.” More work will come online, new jobs will be created, and the best jobs will not be structured. Those who fit neatly into a particular title or role may see their job automated away by a combination of machines and junior workers. 

Just like in sports, the most competitive jobs will go to the top athletes. Those who let their muscles atrophy and train in a single modality will find themselves with limited opportunities.

The Passion Economy and the future of work are ushering in new opportunities for intellectual athletes and creating a world where intellectual athleticism will be the defining factor at work. Those who wish to thrive should understand the benefits and learn to operate like an athlete.

Assessing Your Intellectual Athleticism (IA)

In the past, measuring intellect was about the overall depth of knowledge. If, for example, you spend your entire life studying biology and can speak intelligently on the subject, you could be considered intelligent.

But as technology has changed the way we access and retain information, intellect is more about adaptability, context, and time to understanding. If we want to increase our intelligence, we should expand domains in which you are able to understand and contextualize the information.

To do this, an athlete will need experience in a wide range of subjects, while also harnessing the three main areas of intellectual athleticism:

Genetics/natural abilities – natural, genetic abilities. Both at work and in sports, this is typically the easiest to articulate and measure, but the least likely to predict success. Our natural abilities act as accelerators for intellectual athleticism, but only if applied to the right subjects. This is the limiting factor for intellectual athleticism. If not paired with the right subject, an intellectual athlete may be wasting time strengthening the wrong muscle. For example, an athlete with a naturally strong throwing arm may find themselves completely out of sync if they attempt to apply these skills in soccer. The same principle applies to intellectual athleticism.

Talent/skills – ability to perform a technical skill. When we start learning anything, we lack context. We have to walk through the steps and processes to both understand and improve our understanding of the skill we’re learning. While genetics may expedite this process for some, it does not fully account for our ability to acquire a particular skill. 

“Talent hits a target no one else can hit. Genius hits a target no one else can see.”

— Arthur Schopenhauer

Mentality/grit – work ethic and ability to handle complex environments. This is the most important factor in determining success. It’s much more than work ethic; it’s adaptability and a beginner’s mindset, paired with hard work and determination. Where genetics and skills create a foundation, mentality builds the scaffolding that supports the structure. 

While these are not perfect measures, they act as a proxy for an overall assessment of skill and aptitude. An athlete that is incredibly skilled that lacks the right mentality has limited growth potential. Conversely, an athlete who has the mentality and physical qualities but lacks skill will likely also fall short of reaching their athletic potential.

Our goal as intellectual athletes is to develop ourselves in ways that will allow us to continue growing and learning, without locking us into one particular path. So, what are you doing to strengthen your IA?

The Secret to Better Decisions

A Tool to Execute Second-Order Analysis

A great decision begins with inquiry. In many ways, the results of our decisions are determined by how many questions you ask yourself throughout the process.

The act of deciding is a mapping investigation that uses present details to predict the future. Great decision-makers are not superheroes, they’re just top-notch scenario predictors.

For example, great chess players can’t actually see the future, but with an unparalleled ability to quickly explore all future possibilities, they’re able to rapidly decipher the best move under the circumstances.

I've made less than ideal — and sometimes, downright terrible — decisions in my past. And I suspect you may have as well.

My decision-making process looks like this:

• Write down my options

• Make a pros and cons list

• Over-analyze endlessly

• Optional: Finally, make a choice and move on

Seems logical, right? Well, here is where it falls apart.

Each one of the options I wrote down had a number of subsequent consequences. And each of those consequences had a series of additional possible consequences. And so on, and so forth. Every decision has many, unforeseen ripple effects.

These are known as second-order effects, and it’s what causes us to make subpar decisions.

Our lives are made up of millions (billions?) of little decisions. One bad or good decision can alter the trajectory of our lives forever. It’s the main principle of chaos theory, which effectively states that we should expect the unexpected. We are the butterfly that flaps its wings and causes a hurricane on the other side of the world.

In a world that is increasingly complex, it’s worth investing the time required to think through how our decisions impact those around us, including our future selves.

We can't know or fully predict every outcome, but like chess masters, we can look a few moves ahead and try to see how our decisions may impact the future. The goal is to make decisions that take into account past, present, and future states.

How can you start to transform the world into a series of possible outcomes? How can you use second-order thinking to make better decisions and see the future?

I’ve created a tool to help myself, and others like me, consistently make better, more deliberate decisions. I call it the Second-Order Decision Analysis Tool.

How to Use the Second-Order Analysis Tool

Let's build some intuition for the scientific method by applying its steps to a practical problem from everyday life. To illustrate the value of the tool, let’s imagine you’re facing a pivotal life decision where you’re facing the following issue:

Should I find a new career?

Let’s walk through an example to build up your intuition and learn to use the tool together.

Step 1: Capture the problem. 

Time to complete: <2 minutes

As noted above, we know that you’re trying to decide if you should find a new career. But underneath that inquiry, there’s a problem, which could be that you’re unhappy with your current career. Let’s roll with that for now.

Problem Selection

Step 2: Look for patterns. 

Time to complete: <3 minutes

Alright, now that you have the problem identified, it’s time to start imagining the future scenarios and solutions that might address this problem. These should just be the solutions that come immediately to mind, so don’t overthink anything at this stage.

In our case, the solutions might look like the following:

First-Order Analysis

Note: they’re intentionally limited to 5 initial solutions to keep you from overanalyzing or creating endless possibilities that lead to analysis paralysis.

Step 3: Analyze and assess your options. 

Time to complete: 10-20 minutes

Now the fun begins. Once we have the initial options laid out, we can start to explore the future consequences and outcomes that could happen if we pursue each option. The tool automatically generates some basic second-order thinking prompts to encourage the process. For example:

What are the biggest risks if I find a new job at a similar company?

As we do this, we should quickly note whether the outcome is positive or negative. This helps us reduce confirmation bias by forcing us to confront disparities in our problem analysis.

For our purposes, the results of this process could look like:

Second-Order Analysis

Step 4: Weigh it out. 

Time to complete: <3 minutes

Once you’ve captured all of your inputs, move to the next tab and get a full readout of your decision analysis, including a recommended option. This recommendation is calculated by analyzing the ratio of positive to negative consequences.

Decision Analysis Report

Step 5: Act. 

Time to complete: <1 minute

It’s one thing to arrive at the decision. But if we want to practice better decision-making over time, we need to have a way to reflect on our decisions. With this tool, you can click a button and download your decision report. This allows you to:

1. Share your decision process with collaborators (team, spouse, etc.)

2. Allow others to participate and provide feedback

3. Save your decision artifacts for future reference

In addition to showing you the options analysis, the tool also provides a recommended review date, designed to encourage thoughtful reexamination of the decision. Feel free to select the cadence of the decision and the date will automatically update. Consider adding a calendar event on this date and adding the PDF to the calendar so you can see if the decision played out as expected.

Note: the ability to automatically add a calendar event is forthcoming. Stay tuned.

When to Use Second-Order Thinking

Not every decision requires this level of rigor. In fact, this can actually be counter-productive for low-impact decisions. For me, the easiest way to decide is to ask myself:

Is this decision not easily reversible? 

Will this impact anyone except me?

If yes to either: use the tool. If no to either: go with your gut.

Whether you’re looking to decide to move to a new city, create a new product, have another child, or change careers, this tool can help you way out the options and make an accurate judgment of the future outcomes.

Start Making Better Decision, Today

We want our decisions to have the greatest positive impact on our lives and the lives of those around us. If we want to be better at work and at home, it’s imperative to use the tools available for future analysis.

Make a copy and give it a try → Second-Order Decision Analysis Tool

My goal is to help everyone make better decisions, together. This tool is completely free and will remain free forever. If you like it and want to support more tools for thought, the best thing you can do is share it.

Several Moves Ahead

Learning to Think Like a Chess Master

“I don’t believe in psychology. I believe in good moves.”

— Bobby Fischer

I started playing chess in second grade. My teacher, Mrs. Courtney, had a chessboard in her room and taught us short lessons throughout the year. Like everything else at that age, it was simultaneously too complex and oversimplified.

As expected, most of my classmates found the game boring. In each game, it was most common to experience some creative rule change or completely ignore the rules altogether. But a small group of us found solace in this quiet, indoor activity, often prioritizing the game over typical outdoor activities like basketball and soccer.

As with any spirited rivalry, I required an arch-nemesis. In this case, it was a female classmate, we’ll call her Amy. Amy played with her family at home and had far more experience with the game than I did. Day after day, Amy beat me, always finding new ways to thwart my moves. It was infuriating and motivating.

The beauty of playing chess at a young age is that your brain is primed to look for patterns, in part because you have yet to build up biased views of the world.

Each time Amy played a move, I tried to capture it and store it for later, hoping to use it against her. The more we played, the more patterns I noticed. With every game, I was forming a new visual understanding of the world, which I could then use in future games.

Amy would consistently make moves that defeated me.

What separated Amy was not that she made better moves, but that she could anticipate my moves and use that to adjust her play. She was doing what all great thinkers do—thinking ahead.

And while I did eventually beat her once or twice, that was not what stuck with me. What stuck with me was the process required to beat her. It wasn’t through superior moves or increased knowledge of the game; it was in the ability to recognize the potential consequences of each move.

In time, I realized this was called second-order thinking—and chess players are incredible at it.

What is Second-Order Thinking?

There’s a ton of information on second-order thinking, so I won’t spend time recapping or rewriting all of it. For the uninitiated, here’s the TLDR version:

The term was originally coined by legendary investor and chairman/co-founder of Oaktree Capital Management, Howard Marks. Marks first introduced the idea in his book “The Most Important Thing,” in which he attempts to honestly assess his own decisions, missteps, and lessons from a career assessing risk.

First-Order Thinking. Marks describes this as “simplistic and superficial,” noting that “just about anyone can do it.” For example, “the outlook for the company is favorable, therefore the stock will go up.”

Second-Order Thinking. Marks notes that second-order thinking is “deeper, complex, and convoluted.”

💭 Takeaway: Second-order Thinking allows us to explore options in the future so that we can reduce risk today.

Second-Order Thinking: An Example

The goal of second-order Thinking is not to remove every objection or potential pitfall. Instead, it is to minimize negative future outcomes.

In chess, each move creates a series of potential moves for the opponent. What may look like the best move at first, could quickly end the game.

For example, the oldest and most common opening move in chess is the King Pawn opening, and is what famous chess master Bobby Fischer called the “best by test” approach. This move is aggressive. It attacks on the first move and immediately claims the center, freeing up the queen and bishop.

If we were to analyze it with second-order thinking, we’d see the following pros and cons of this move:

Pros:

• Gains control of the key central squares

• Engages rapid development

• Kingside castling

Cons:

• Requires planned opening moves

• Reduces long-term pressure if black defends

The results:

• Wins 38.4% of the time

• Draw 31.3% of the time

• Lose 30.3% of the time

Simply put: this is a strong position. Does it mean you’ll always win? Nope. But we never get such guarantees, unless the game is rigged in our favor. The point is to eliminate some risk, not eliminate it altogether.

Thinking Like a Chess Master

Chess masters don’t just recognize patterns, they learn to analyze and assess the risks of each potential decision. They follow this path:

1. Capture the problem. Most of us just dive straight into solutioning. But maybe the problem we first encounter isn’t actually the problem we need to solve. The wrong problem leads to the wrong solution. Start by looking for the problem.

2. Look for patterns. Once you have the problem identified, start listing out the solutions that come to mind. These are your first-order solutions. They’re the patterns your brain immediately recognizes. Try to just get them all out—your brain knows more than you think.

3. Analyze and assess your options. Alright, this is the fun part. Start looking at each of the first-order solutions, and evaluating what will happen if you take that action. Think like a chess master, “if I move a pawn to e4, they will [x], [y], [z].”

4. Weigh it out. Whether it’s for work, family, or friends, our decisions have an impact on those around us. Hiring someone may cause you to lose another employee. Skipping dinner with a friend may lead to a conflict. Second-order thinking is not done in a vacuum.

5. Act. We’re great at believing our ideas are well-formed, but there’s a reason we seek a second opinion when it comes to important decisions like a medical diagnosis: we only see part of the picture. Sharing your decision process with friends, colleagues, and family will help you see if there are any blind spots in your analysis.

The bottom line is that if you want to become a better decision-maker, you need to go beyond tactics and learn how to analyze the impact of your decisions. Learning mental models, frameworks, and heuristics is always a great place to start. But if you don’t augment your knowledge with decision analysis for your future moves, then you’ll find yourself repeating the same patterns and missing the big opportunities.

Gratia Rationale

The Taxonomies of Gratitude

After repeatedly trying — and failing — to consistently feel grateful for good things in life, it occurred to me that I may be taking the wrong approach. Instead of abandoning the approach, I decided to take a first-principles approach and analyze how and why it wasn’t working for me.

So it got me thinking:

Could gratitude actually be logical and emotional?

After digging further, I realized that there are three types of gratitude that we can focus on:

1. Logical (Logicus)

2. Emotional (Motus)

3. Rational (Rationale)

These are the different types of the same species, similar to the way we define and organize organisms, or what is commonly referred to as “taxonomies.”

Taxonomies of Gratitude

After digging into my own gratitude practices, I realized that, while there are different types of gratitude, they are still all categorized as gratitude. These are the different types of the same species, similar to the way we define and organize organisms, or what is commonly referred to as “taxonomies.”

In order to name and organize, I recommend using the binomial naming system to categorize the types of gratitude, where the first word—Gratia—represents the Latin name for “Gratitude”, and the second word—Logicus, Motus, Rationale—represents the Latin name for the specific kind of gratitude.

Now that we’ve defined the naming and organizing principles, let’s look at how logical, emotional, and rational gratitude differs.

Gratia Logicus (aka Logical Gratitude)

What is logical? I can’t tell you how many arguments I’ve had based on this simple question. Logical thinking can be a superpower, as it allows one to escape the challenges of emotional—often illogical—thinking.

The modern definition of logic is:

Reasoning conducted or assessed according to strict principles of validity.

Logic states that for something to be logical, it must also be valid, correct, or accurate. By definition, logic leaves no room for errors or inaccuracies. Feelings and emotions, which can’t logically be verified, simply can’t factor into this equation, as logical equations are designed to eliminate such inefficiencies.

What is Logical Gratitude?

Logical gratitude is the most common, formulaic way of analyzing and capturing thankfulness. It typically recounts factual statements like “I achieved x, I completed y, I have z.” For years, this was my approach to gratitude. I created a formulaic way to analyze my life and the realities of the world around me, using them as a proxy for happiness.

This works really well because I can always write a logical equation. For example:

Food + shelter + job + romantic relationship = happiness

Most techniques, from Counting Blessings to Three Good Things, coach people to look at good things, which can often result in an oversimplified, logical view of gratitude.

But gratitude isn’t logical.

We have feelings that don’t always align with our logical reality. We experience the world through our senses, and our mind attempts to make sense of these experiences. Emotion plays a critical role in our ability to be grateful.

💭 Takeaway: Logical gratitude is the easiest place to start, but may leave you unfulfilled.

Gratius Motus (aka Emotional Gratitude)

Emotions are tricky. They’re hard to pin down, difficult to describe, and deeply personal. This is reflected in the lack of consensus on the definition, which Wikipedia states as:

Biological states associated with the nervous system brought on by neurophysiological changes variously associated with thoughts, feelings, behavioral responses, and a degree of pleasure or displeasure.”

Emotions don’t need to be accurate. They don’t require consensus. They don’t need to be proven. They simply are. And that’s what makes them beautiful and terrifying.

Emotions are powerful forces that underpin how we live, interact with others, and exist within the world. As much as we think we’re logical beings, the reality is that emotions drive the choices we make, our perceptions of the world, and how we approach our environment. Our emotions often become our experience.

So, logically, if experiencing positive emotions like happiness, pleasure, and comfort will help us make positive decisions and improve our perspective. The same research shows that emotions are not siloed. The emotions we experience in one situation can bleed into another.

What is Emotional Gratitude?

Emotional gratitude is the antidote to logical gratitude. It resides on the opposite side of the gratitude spectrum, allowing us to focus on connecting with that which does not answer to logic.

Understanding and relating to emotions can have a major impact on your day-to-day actions and decision-making abilities.

Most people see logic and emotion as polar opposites on the decision-making scale. And in many ways, they’d be right. But the good news is, there’s a third option.

💭 Takeaway: Emotional gratitude may be the most difficult, but can be the most fulfilling.

Gratia Rationale (aka Rational Gratitude)

The world isn’t binary, so why should our gratitude be? Far too often, we create an artificial divide between logical and emotional thinking. But the reality is: we exist in both camps. Instead of thinking of logic and emotion as binary decisions, we should instead look at them as two points on a spectrum. 

Rationality is not about a series of formulaic constructions that provide a binary answer to our internal analysis. Rational thought differs from logic in that it cannot be objectively proven 100% of the time. Rational thoughts are not always logical, nor are they solely emotional. They often include emotion, creativity, imagination, social conventions, and biases. 

What is Rational Gratitude?

Rational gratitude dares to break the binary divide of logic and emotion. It is what allows us to hold opposing ideas that we cannot reconcile. For example, we can be grateful for something terrible that led to something great.

But what does it mean to combine logic and emotion? Let’s try an example.

If something is objectively failing, we should not be grateful for the pain it causes, right? Wrong. Rationally, we can experience the emotions of gratitude for our experiences without it logically making sense.

This is rational gratitude. 

Rational gratitude allows us to be grateful for something challenging that exposed a growth opportunity. It empowers us to be grateful for anything, as long as we accept that logic is not required.

💭 Takeaway: Rational gratitude combines the logical approach to seeing positivity, while incorporating key emotional states.

Putting Gratitude to Work

If there’s one takeaway here, it’s that each species of gratitude is unique. What works for one person may not work for everyone.

If we’re always looking for logical gratitude, we’ll rarely find it. Emotional gratitude can be finicky and tricky to connect when our brains seek out logical conclusions. But rational gratitude offers a safe space for even the most data-driven, logical thinker.

No matter your proclivities, I recommend starting a gratitude practice to keep you in touch with the positive forces that could propel you forward in work, in your relationships, and in your life. Our gratitude pulse is a great place to start, but all practices are recommended. Gratitude transcends boundaries, so use it as a force for improvement in the years to come.

The Global Gratitude Pulse

A Crowdsourced Approach to Increase Worldwide Happiness

Here we are. It’s the first workweek of 2021. Our goals are all set, our calendars repacked, and our diets dialed. Now the only thing left to do is make it a great year.

Let’s all just pretend last year didn’t happen. Right?

Well, avoidance and disassociation is one way to deal with reality. Another is to expose ourselves to the situation and work to adjust our coping mechanisms. For example, what if instead of focusing on the negative, we looked at the positive?

Just for fun, let’s give it a try. But before we do, let me tell you a short story about a journey of gratitude.

A few years back, I was flying high in my life and career. I had worked incredibly hard to accelerate my career, my life, my financial stability, and my physical fitness. Each day, I woke up with one thing on my mind: winning.

Then, one day it all changed.

I made a life-changing decision that completely upended my life and forever changed my perspective. I like to consider this my introduction to the real world.

Every minor bump in the road felt like a tectonic shift, opening up a gap in the earth that I was falling into. It was a very dark period for me.

And guess what—I was still doing pretty well by most accounts.

I tried to remind myself to be thankful for what I had, but it was hard for me to see how or why I should be grateful for anything. It felt like the world was falling down around me and I couldn’t do anything to stop it. I wanted, so very badly, to just hit reset so I could go back to “normal.”

I was clinging to a life that was dead and gone.

I desperately wanted to fix it, so I started reading all the self-help books and blogs, talking to friends and family, seeing a therapist, and keeping a journal. The most common advice I received? Be grateful.

Be grateful? For what? I couldn’t imagine how simply being grateful would really change anything. So I continued exploring, hoping the “real” answer was waiting just around the corner. Finally, after exhausting every other option, I realized that I might just have to try this gratitude thing.

I started slow, doing a weekly gratitude journal that answered three short questions:

• what made the previous day great?

• what would make the next day great?

• what was I most thankful for?

At first, I noticed nothing. But after a few days, I started to notice some major improvements in my life. I experienced:

• A more positive outlook on the world and my work

• Better, more restorative sleep

• An improved ability to let go of negativity

• An overall decrease in stress and anxiety

• Better conversations with my partner

Needless to say, the results were compelling. But for many years, I struggled to maintain the work and found that I needed new ways to extend the process, so I created a tool to help capture and share gratitude with the world.

But before we get into the “how” of it all, let’s start with what gratitude is and why it matters.

What is Gratitude?

Gratitude is not a new practice. In fact, gratitude been around for centuries, going back to the age of the stoics. Cicero famously called gratitude the ‘mother’ of all human feelings. But what exactly do we mean when we talk about gratitude?

Gratitude has been defined in a lot of ways across history. Kand defined gratitude as “honoring a person because of a kindness he has done us.” It has been said to represent a positive personal outcome. In modern parlance, it most often refers to the condition or idea of being thankful.

Over the last decade, there’s been an increased interest in gratitude and its effects. There is some debate as to what caused the resurgence, but it’s likely due to an increased awareness of positive psychology and revised social norms. Whatever the reasoning, the renewed interest should be a positive force for good in the world.

And yet, in the twenty-first century, most of us are still struggling to find things to be grateful for. It makes sense. We have more than we’ve ever had, and yet, many people are still struggling. We’ve conditioned ourselves to want (and need) more than ever, so our bar for satisfaction continues to be just out of reach.

Despite the importance of gratitude, it’s rarely thought of or mentioned in daily life. But if we want to improve the world around us, we have to start with ourselves. And gratitude requires our attention.

The Benefits of Gratitude

The benefits of gratitude are well documented, but that doesn’t mean they’re well-known or understood. Recent studies have shown that gratitude produces strong evidence of impacting individuals, including better physical and psychological health, greater happiness and life satisfaction, less materialism, and increased overall well-being.

Individual Benefits

Physical — Reduction of pain, improved blood pressure, improved sleep quality, stronger immune system, improved stress regulation, decreased anxiety and depression.

Psychological — increased self-satisfaction, improved self-awareness, increased optimism, increased self-esteem, decreased negativity.

Social — prosocial behavior that leads to stronger relationships, increased likeability, improved communication, and great empathy.

Workplace Benefits

Most of us assume that gratitude only benefits ourselves, which is part of the reason we find it difficult to maintain. Since the benefits are not immediate and we assume it can’t help us at work; we walk away. But we’re starting to learn that, not only is gratitude beneficial for work, but it may be the defining factor for high-performers.

Studies suggest that employees who express gratitude often experience:

• Increased prosocial behavior, making them more likable and allowing them to create stronger relationships.

• Increased work performance. A recent set of studies suggests that employees who experience and value concern for others and their well-being experience increased guilt and gratitude, which motivates higher performance.

• Decreased burnout. More studies have shown that gratitude is related to decreased burnout due to a higher positive association with coworkers, supervisors, clients, and job.

While we experience a complete remodel of our work environments, now is the perfect time to reimagine our workplace habits, norms, and relationships.

Getting Started with Gratitude

Despite having my own practice, I sometimes find it difficult to cultivate gratitude. And for me, this comes down to perspective. I can’t see beyond my own world. If I could look at my life from another’s perspective, I would easily be able to see what I have that is worth my gratitude. And I imagine you’re the same.

It’s easy to see others and think, “they have it all.” The truth is, they’re struggling just like you, you simply can’t see or experience their pain.

But gratitude gives us a gift. The gift of self-reflection and an ability to cultivate happiness.

Three Types of Gratitude Practices

There are many different practices that people subscribe to when they talk about gratitude. A few of the top recommendations include:

1. Counting blessings - a practice of simply adding up your blessings

2. Three good things - a practice of recalling three things that went well in your day

3. Mental subtraction - a practice that uses a first-principles approach to analyzing gratitude and the reduction of negative outcomes

I believe that each is beneficial, as long as it works for you. The key is to use whatever method helps you generate gratitude and positivity.

Introducing: Gratitude Pulse

While my gratitude journal started off very well, I quickly found myself repeating the same kind of gratitude every day. And, in short order, my habit became more and more difficult to maintain.

I knew there was much more to be thankful for, I was just running out of ideas. So I started seeking out ideas from the world around me and writing those down. This worked quite well and helped me break out of my gratitude rut. As I added more gratitude, I started adding more gratitude prompts.

When I talked to people about their gratitude process, the most common feedback I heard was very similar to my own experience. Most people struggle to keep their habit without running out of ideas and feeling repetitive.

So, I decided to help everyone find gratitude, together.

Instead of keeping a private journal for gratitude, I’ve created a tool that allows people to anonymously share gratitude to inspire others to express gratitude to the world. Who knows what this might do for our society, but if we’re lucky, we just might change the world.

Gratitude Pulse Alpha 👇

Gratitude Pulse is a little project I put together over the holiday break in response to the global outcry for positivity in 2021.

How the Project Came Together:

• The foundation: to kickstart the project, I transferred some of my previous gratitude entries to a database, where all future gratitude entries for the project will be stored.

• Crowdsourced gratitude: once I had the database in place, I wanted to seed the project with additional data, and the best place to start was Twitter. With some basic keyword searches, I was able to get 100 gratitude-related tweets, which I then anonymized and added to the database.

• The MVP: while I have a backlist of feature ideas—clustering, etc.—that I’ve started exploring, I know that each one of these features isn’t critical for launch, so I narrowed the scope down to a simple data entry form.

Try it out!

How to Use Gratitude Pulse:

1. Go to pathnine.co/gratitude

2. Read the prompt and enter your gratitude.

3. Repeat (daily/weekly/monthly)

If you don’t see a prompt you like, just refresh the page and a new one will appear at the top.

My hope is that people use this tool to increase gratitude within their own life, and also increase the overall volume of gratitude globally. If this tool helps you, please share it with friends, family, coworkers, or anyone you know.

Catalyzing Chaos

Mental Models to Think, Live, and Work Better

“What a strange year it’s been.”

“Of course [insert absurd experience here] would happen — it’s 2020.”

“I can’t even tell what day it is.”

I’ve come to find these tropes insufferable. In part, because we’ve had the same phrases on repeat for almost a year. Even more, because I can’t help but wonder when we’ll find ourselves on the other side of these challenges we’re facing, and why we can’t seem to let go of the pain and suffering.

I keep hearing “I can’t wait for 2020 to be over.” Why? What do you think is happening in 2021?

When the clock strikes 12:01 am, January 1st, 2021, do we magically transport to 2019? Does the dark cloud of 2020 fade away, taking with it our grievances and, if my wish comes true, the insufferable ‘doesn’t this suck’ phrases?

Unlikely.

Sorry, but this strikes me as just a slightly less offensive spin on the “Make America Great Again” slogan. It reads like a call to return to a time when things were better, without taking into account the downsides that many experienced during this time of supposed prosperity.

So what actually happens when we hit 2021?

Well, the honest answer is, it’s up to you. Yep, that’s right. You are the person who decides what 2021 brings. If you want a better 2021, start with the way you understand, analyze, and interpret the world around you.

Accepting Our Chaotic World

We can’t change if we don’t accept our reality. And our reality was one of enormous social, physical, and psychological discomfort. Jobs were lost, people got sick and died, American democracy was tested, racism was simultaneously exposed and confronted, work was completely upended, and our sense of physical, emotional, and psychological safety was demolished.

After such a devastating period, it can seem difficult to move forward. But if we wish to move on, we must face reality and learn from our experiences.

Going forward, I hope we all take this as a chance to learn, iterate, and grow together. Change presents a chance to bridge the emotional, political, and relational gaps that we’ve allowed to expand over the last four(+) years.

We have a responsibility to take control of what we can. Shape our future the way we want it to be. Now is the time to take control of our collective social, physical, and psychological state. Because, as it turns out, our shared consciousness was not actually shared. 2020 made it clear that our views of the world were, in fact, quite different.

Though it may be unsettling to learn that our model of the world is flawed or that our perspective is not shared by others, it’s the first step on the path to change. Now is the best time to evaluate and update our mental models, to create a happier healthier future for all of us.

What Are Mental Models?

Mental models are simply a way of understanding the world. They help us turn the chaotic, complex world around us into a more manageable system. Primo Levi said it best in The Drowned and the Saved:

“Without a profound simplification the world around us would be an infinite, undefined tangle that would defy our ability to orient ourselves and decide upon our actions… We are compelled to reduce the knowable to a schema.”

These schemas are shorthand for the complexity that our brains simply cannot keep straight. They allow us to quickly organize, reference, and act in situations where data is limited and time is of the essence (aka all of our decisions in 2020).

Why We Update Our Mental Models.

When the world around us changes too quickly, it’s jarring. The technological inventions of the last 50 years have ushered in an unprecedented acceleration of change. The last twelve months have surfaced more change than our little brains are prepared to take in. Everything we thought we knew, fell apart. Our relationships, our work, our hobbies; our entire world feels upside down.

As both a creative and analytical thinker, I ping pong between embracing and enjoying the changes of 2020 and trying to simplify and control it. The analytical realist in me seeks comfort in control, while the creative optimist sees potential in the change. Mental models serve both masters, allowing me to simplify and organize, without losing sight of the creative nuance. But each mental model requires regular updates. Revising our models is just good critical thinking hygiene.

Mental Models from 2020

Here are the mental models I’ve developed from my experience with 2020. The models fit into a few categories that, in and of themselves say a lot about our experiences:

1. Better Thinking

2. Better Living

3. Better Working

Models For Better Thinking

Change is Inevitable and Unpredictable.

Earlier this year I wrote about The End of History Illusion, which states that, despite knowing that our preferences have already changed, we predict that our preferences will largely stay the same in the future. We tend to look for patterns we recognize, which is, in part why we often fail to predict our futures. We’re only using historic data to inform our views of the future. Whether you’re 26 or 62, the “End of History Illusion” blurs your predictive abilities all the same. In reality, we’re a work-in-progress. Our greatest mistake is to assume we’re done evolving.

Think Probabilistically.

The meta-problem of mental models is that the goal is to simplify complex decisions. Inevitably, this often forces us to aim for a binary decision, omitting nuance. Instead, we should work to think probabilistically. For example: if the chances of getting COVID are only 1%, is it worth going out without a mask?

Clear Thinking Is A Superpower.

Thinking is often considered unproductive. Amazon famously popularized the “bias for action” principle, which focuses on calculated risk-taking, particularly when a decision is reversible. “Calculated” is the operative word most often overlooked. In a society that values speed, companies, groups, and individuals are quick to act for fear of getting left behind. Whether it’s ignoring science and expertise or simply acting without regard for consequences, the art and science of clear, rational thought is dramatically underrated.

Assume Ignorance (Hanlon’s Razor).

One of my favorite mental models is Hanlon’s Razor, which states that we should ‘Never attribute to malice that which can be adequately explained by neglect.’ This was probably the most important mental model of 2020. Whether it was someone who decided to have a big wedding in the middle of a pandemic or ignore the scientific findings, it was far too common to assume this was due to malice. The reality is, they weren’t trying to kill people or be intentionally obtuse. They were, unfortunately, ignorant.

Past Data Cannot Predict the Future.

“Things that have never happened before happen all the time.”

— Scott Sagan

Many assume that 2020 was really just a Black Swan—a devastating event that is impossible to predict because it lies outside of normal circumstances. But the reality is, unprecedented things happen all the time, we’re just not prepared for them. And for good reason. We can’t prepare for something we can’t predict. Just because we can’t predict it, doesn’t mean it won’t — or shouldn’t — happen. 2020 has proved that time and time again.

Mindset Matters Most.

With the right mindset, anything can go from a challenge to a change. Life presents us with windows into a new path, but if we’re too set on returning to our previous path, we’ll miss the road ahead. It’s tempting to look back on 2020 and simply wish it away, but we learn nothing from that mindset. If we take a chance to assess, learn, and iterate from our experience, we can clear a better path forward.

Models For Better Living

Seek Solitude, Not Isolation.

Quarantine is a quick way to test our understanding of solitude and isolation. Early this year, I wrote about the difference, stating that “Solitude is chosen. Loneliness and isolation are imposed.” We easily confuse solitude with loneliness. Often people use the two interchangeably. However, they are worlds apart. Ultimately, solitude is something we should seek and enjoy. It is the art of being alone without being lonely. Solitude offers the chance for introspection, concentration, and free-flowing creativity. In truth, we need solitude whether it’s five minutes or five hours. It is essential to our mental wellbeing.

The Price of Your Attention Should Be High.

With screens acting as our portal to the world, our attention is a hot, expensive commodity. Every second we spend doing something of limited value is something we can’t get back. This type of thinking is dangerous and leads back to my first model that opposes that bias for action (at all costs). The price someone pays to get your attention should be increasingly high.

Digital Disconnection Improves Physical Connection.

I used to love the fact that everything was always available and at my fingertips. The internet created open doors that allowed me to engage with the hyper-connected world around me. But this was balanced by an ability to be physically present with those around me, creating an excuse to disconnect digitally. As that disappeared in 2020, I found it more important to create space between the physical and digital worlds.

Time-off-Task Is as Important as Time-on-Task.

Remote work exposed that most of our work actually doesn’t require 8+ hours of focus time. Many people realized that our typical day might be 8+ hours, but our output reflects far less. Guess what? Employers also realized this and decided to capitalize.

The hours we used to spend chatting at lunch, going to coffee, having side conversations with our colleagues, or just hiding in the bathroom to avoid our annoying coworkers, well that time is now available for more productive output. But maybe, just maybe, we really need that time. Time-off-task rebalances our psychological needs and provides a necessary creative way to recharge.

People Need People.

From distanced learning and work to literal social distancing, we’re at peak distancing. I’ve experienced loss over the years.

Many people have come and gone, but I always accepted their passing as just a part of life. In part, because I was able to spend time with them and be there for their passing. In the last year, many people have missed out on the opportunity to see a loved one before they go. And it’s completely unfair. I can only imagine how painful it is to not be there when your mother or father passes, and I hope that I never have to experience this myself. For those who have, I hope you find solace.

Models For Better Work

Work-Life Balance Requires Boundaries.

People are tied to their computers and phones. Screens have ruled our lives for years, but now that many have switched to remote work, the screen has become our life. Remote isn’t just a different way of working, it’s a different way of living. And if you’re not careful, the only thing you’ll experience is work. Be sure to understand your boundary management style.

Always Maintain Optionality.

Diversification is a common investment strategy that is designed to reduce risk and create optionality. Instead of solely investing in a single decision with consequences associated with a future you, diversification allows for flexible goals. Diversification maintains optionality, which creates opportunity. In 2020, any plans we made were subject to disruption. Whether it’s career goals, travel plans, or big events, the best way to plan for the future is to maintain optionality by diversifying your bets.

Real Change Requires Force.

It’s easier to keep the status quo than to make a change unless that change is forced upon us. 2020 didn’t just change the work playbook, it ripped it up, burned every scrap, and urinated on the remains. And I, for one, couldn’t be happier about it. For years, work has been demanding a change that supports flexibility, freedom, and respect—and 2020 gave us permission to make it happen.

Catalyzing Chaos for Our Future

As we look forward, I hope that 2020 serves as a catalyst for unprecedented personal and societal growth and improvement. Our collective experiences have created more distance, but carved pathways to come together stronger than ever before.

We shouldn’t want to return to “normal.” Our “normal” sucked for most people. Reaching to the past is not an option, we must burn the boats and move forward. We must use this opportunity to reevaluate every system, model, and framework and redesign new versions to meet the needs of our ever-changing world.

We’re the editors of the future, so let’s get our red pens and start marking up our old mental models—2021 deserved a revised version.

Parkinson's Law of Productivity

What it is and why it matters for work-life balance

It’s a rainy Sunday evening in Seattle. I’m firmly planted in my desk chair, wine glass in hand, staring at a list of unchecked to-dos, each one nagging away at my sense of weekend productivity. These to-dos are not for the week ahead, they’re from the previous week/weekend.

It seems, no matter how hard I try, work finds a way to absorb all of my time. Any free moments are occupied by work-related emails, Slack messages, and documents. What used to be an active, segmented part of my day, is now every living moment.

Ring a bell?

A day comes, a day goes. The workday begins slightly earlier, and “ends” slightly later, slowly absorbing any time not already dedicated to working. We continue to check off tasks, and yet, our sense of productivity continues to plummet.

This drudgery seems to be stuck on a never-ending loop, aka Groundhog Day.

A recent Families and Work Institute study reports that 75% of working parents do not have enough time for their children or each other. If that doesn’t say something about the state of work, I don’t know what will.

In 2020, a large percentage of the workforce was forced to work from home. Unfamiliar with the nuances of their new environment, many started out with a slight decrease in productivity. But that wouldn’t last long. People quickly found their stride and increased productivity, optimizing their work hours to maximize output. Many thought, “Hey, maybe this ‘work from home’ thing will give me more time outside of work.”

And yet, somehow, here we sit, having flooded our task list day-in and day-out for the last 9 months without feeling more productive, balanced, or fulfilled. The work seems to be sucking the air out of our lungs, one action-item at a time.

This, my friend, may in part be due to our sinister friend, Parkinson’s Law.

What is Parkinson’s Law?

Parkinson’s Law is a term first coined by Cyril Northcote Parkinson in a fantastic essay he penned for the Economist in 1955. What has since been aptly named Parkinson’s Law refers to the maxim that work expands to fill the time allotted. In other words, the work required to complete a task automatically adjusts to fill the time we initially allocated.

For example, if I set aside 5 hours each week to write an article, I’ve practically guaranteed that the article will in fact take at least five hours. Here’s why.

Five hours each week should be enough to draft, edit, and publish an article. But, because I know that five hours is enough time, I expand the scope of my article. What starts out as a simple, straightforward point turns into a complex argument filled with unnecessary tangents and nuanced points. (See, even some sentences fall prey to Parkinson’s Law.)

Work is like a gas — it fills the vessel in which it is contained. What originally started as a project with a fixed amount of time allocated, quickly shifts to a project with a minimum of five hours and a maximum that is “to be determined”.

This is the core premise of Parkinson’s Law.

Why We’re Particularly Susceptible to Parkinson’s Law

It’s easy to assume that we’re all just losing a battle to procrastination. But it’s far more complex than that. And the complexity we experience at work is growing exponentially.

“We Shape Our Tools, and Thereafter Our Tools Shape Us”

— Marshall McLuhan

As humans, we often look to technology to reduce and manage complexity. Unfortunately, we’re really good at creating tools that actually create more work. The sad paradox is that the more we work to reduce work, the more work we actually create for ourselves.

For example, let’s say you need to manage a project. You could start by using one of the most common and easy to use tools for project management — a spreadsheet. Ok great, we’re all set, right? What if you want to see your tasks in a calendar view? Now it’s time to go look for a purpose-built app that has this feature already built in. With a new app selected, you start creating tasks. Now you need to communicate those to your team. Ah shoot, I guess we need to invite more people. Now they’re adding tasks and contributing. Before you know it, what started as a simple project with a simple set of tools is now an overburdened process.

Whether it’s productivity apps like Sunsama, calendaring apps like Clockwise, or video conference tools like mmhmm, we’re working really hard to keep working really hard.

To go back to our gas metaphor, the work we create for ourselves is what fills our time. We don’t need to constantly create and deliver as much as we do, but because we’ve allocated the time (and space?) we feel obliged to do so.

Really what we’re struggling with is a never-ending flood of this thing we call “work.”

This is a recent phenomenon, driven by our confluence of digital tools, remote work, and our knowledge worker ‘work environment.’ When we work from home, we welcome work into our lives in a way we’ve never done before. It’s a house guest that we hoped would be kind enough to leave once they had overstayed their welcome. But here we are, months later, and they’re still using our toothpaste and eating our snacks.

Every minute we let work stay in our lives is another moment we’ve lost to actually living.

How to Keep Parkinson’s Law at Bay

Knowledge is power. But being powerful and lazy is pretty useless. While it’s great to know about Parkinson’s Law, we still have to practice preventing it from battling back into our lives. Furthermore, we should aim to actively avoid and prevent it.

The best path to successfully fighting Parkinson’s Law is to have a ready-made toolkit and a plan. There’s no one-size-fits-all answer to a complex problem, but there are a few principles:

Use the 5/25 Rule to Set (and Reset) Clear Goals

When we believe we need to fill time, it’s easy to get distracted and start adding mindless, unproductive tasks to our to-do list. That’s also the most dangerous thing we can do and what allows Parkinson’s Law to take over. To fight the urge to just keep working, I recommend using Buffett’s 5/25 Rule to increase your focus. It’s a simple 3-step rule (and tool) that I walkthrough here.

Define Your Work-Life Boundaries

Finding work-life balance is uncharacteristically difficult when we lose the natural physical distance between work and life. But boundary management is no longer optional. Employers and employees need to start developing competencies in work-life balance management to foster a better work environment for the future. Click here to learn what kind of boundary management is best for you.

Learn to Block Work and Life

Most individuals fail to protect and create space for their non-work needs. And why wouldn’t we be bad at blocking?

Prior to the last two decades, the four walls of our office created a natural blocking mechanism that automatically granted us freedom from constant work. But the world has changed a lot in the last two decades. Our work is now just one quick swipe away from our favorite past time. Our boss is literally in our homes at all times, ready and eager for a “quick sync.” If we don’t want to fall victim to Parkinson’s Law, we need to start learning to block for ourselves, our team, and our family. Here’s how to get started.

Manage Scope

There’s a Parkinson’s Law within a Parkinson’s Law message here; it’s called scope creep. The same way work naturally fills a lot of our empty time, project tasks and to-dos fill the time we allot for them. If you’re on a team, you’ve likely experienced this. You start with a set of goals and deliverables for a project, and then somewhere along the way you end up with a list twice as long. The easiest way to combat this is to write it down, sign it, and make it un-editable.

Enter, and Exit, Flow

Flow is the ideal work situation. Distraction is the enemy of flow. And right now, our world is very distracting. The issue with Parkinson’s Law is that it forces us to continuously try to stay in-flow. You can’t hit a home run every time you’re at-bat. You need to ride the pine every now and then, so we should actively seek both entering and exiting flow states.

Like any other goal, breaking it into small increments makes it easier to achieve the desired results. The steps in my recent article on flow can be used in any order and under changing circumstances. Don’t try just one; experiment, learn, and adapt.

Work doesn’t have to fill every square inch of your life. But for the foreseeable future, our employers won’t all be the shepherds of work-life balance. It’s up to each of us to create air pockets that allow us to breathe.