Path Nine
As newsletter to help high-achievers chart new paths to earn more, work less, and live better.
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Buffett's 5/25 Rule
How to increase focus and minimize burnout
I sat down to write this article five different times. Not because I didn’t have enough to write about, but instead because I have too much to write about. Counterintuitively, I rarely suffer from the dreaded writer’s block. Instead, I’m often overwhelmed by my interest in too many topics.
Despite the overwhelming number of articles I could write each week, I find it increasingly difficult to narrow down the topics I wish to share. Many writers have a narrow niche through which they can quickly get a binary answer about whether or not the topic follows their selected niche. I’ve committed to being a multi-sport athlete in a world filled with specialization. This creates a particularly challenging problem for me: the paradox of choice.
The Paradox of Choice is as simple as it sounds; the more options you have, the easier it is to feel overwhelmed and unhappy. We often seek more, when we really need less.
In a recent article, I wrote about Work as a Sport (aka WaaS). When we think of work as a sport, we approach the world in a different way. Sports have defined constraints called rules. These rules actually help players and coaches make intelligent choices by narrowing the options in a given situation.
For example, when a football team is 35 yards from the end zone with two minutes left and one down remaining, they have the following choices:
Run the ball
Throw the ball
Kick the field goal
Punt
That’s it.
Nothing more.
Whether it’s the coach, the quarterback, or the team, they have to make a game-time decision as to which option has the highest probability of meeting their shared goals. In this case, their goal is to score and defeat the other team. Sadly, life doesn’t operate by the same rules and logic, so we have to learn to enforce our own constraints.
If we’re going to learn, let’s learn from decision-making legends.
Learning From Legends
Warren Buffett and Charlie Munger are two of the most famous investors in history.
In Silicon Valley circles, they’ve developed a cultish following, which I suspect stems not just from their overwhelming financial wealth, but also due to their rigorous and consistent decision-making abilities.
In a world filled with uncertainty, we’ve learned to fetishize decision-making because it provides a feeling of control. It gives us a toolset to use when we feel like the world around us isn’t going our way. It protects us from failure, allowing us to build our own logic-moat.
I know all too well. In fact, one of my all-time favorite books is Seeking Wisdom - a book about decision-making and the secrets of Charlie Munger.
Of the many decision-making frameworks these legendary investors used, one, in particular, stands out — the 5/25 rule.
The 5/25 rule is simple: make a list of 25 goals and then narrow it down to the 5 most important.
Here is an example of the 5/25 rule in action:
Goal: Build your business
List of 25: find 10 new customers next month, increase revenue by 25%, hire 3 engineers, build a compelling brand, find new investors, add two new product features, start a new service line, lead in your category, etc.
Top 5: find 10 new customers next month, increase revenue by 25%, build a compelling brand, find new investors, lead in your category.
Sounds too simple, right? That’s the beauty of it.
The best decision frameworks are simple, and the 5/25 rule is about as simple as it gets. Instead of forcing you to think about all the variables of each potential option, the 5/25 rule asks you to only focus on what you actually want.
When you’re the head coach faced with a game-time decision that could completely change the trajectory for your team — and yourself — you need value-adding constraints that build on your gut. And the 5/25 (aka 80/20) is all about gut. You write what you feel and select what you believe in. There is no middle ground.
No matter what your specific goals, the 5/25 rule will help you:
Avoid FOMO. It’s easy to let fear drive us to do things we don’t actually want to. Instead of letting fear make the decision, take control, and own who you are and what you want. The easiest way to erase the fear of missing out is with deep conviction about why you’re choosing to miss out.
Reduce Analysis Paralysis. With many options in front of us, it’s easy to feel like we might be missing out on something really important. The reality is, the missing out happens while we’re deciding. Sometimes we need to jump in to know what matters. Creating a list like this can help you quickly kick yourself into gear and start moving towards achieving your goals.
Increase Your Output. The more distracted you are, the easier it is to be busy without increasing your output. As we narrow in on our goals and increase our focus, our output increases along with it.
How to Use The 5/25 Rule to Defeat the Paradox of Choice
The Paradox of Choice is as simple as it sounds; the more options you have, the easier it is to feel overwhelmed and unhappy. We often seek more, when really what we need is less. This is especially true today; we need to start adding constraints to our world.
Here’s how to get started.
First, use this free tool I set up for you:
Write 25 Goals
Make a list of 25 things that would make you successful in your life. These must be individually defined. Don’t look to others, decide what YOU care about, and write it down. In fact, go with as many as 50.
During this time, just write, don’t think. Thinking is what gets in the way of us actually doing what we love and truly care about. We’re classic overthinkers, to our detriment.
Edit Down to 5
Now that you have your list of 25 items, start prioritizing your top 5. Not sure which to select? Try focusing on goals that build on existing skills or goals. While most people tend to correct weaknesses, many studies show that we’re better off focusing on our strengths.
Regret is a powerful tool that helps guide our priorities. Select ideas for regret minimization. (Ex: Will you regret spending more time at work? Probably. Will you regret spending more time with your kids or your wife? Unlikely.)
Review and Share
Last, review the goals you’ve selected and share them with someone. This can be one friend or your entire Twitter following. The goal is to keep yourself accountable and focused. Sharing your goals and objectives puts you on a pedestal. It signals to other people that you want someone to keep an eye on your work. It’s the good and the bad of social media combined.
The decisions we make teach us who we are. The journey shows us what we like. The results tell us how we did. The goals we have today will almost certainly not be the goals we have in 10 years. We are, by definition, flawed forecasters. This is what’s known as the End of History Illusion.
Get Started with 5/25
I know it’s hard to get started, so I’ve created a spreadsheet that walks you through the expanded 5/25 rule process. Simply create a copy and start using it for each of your goals and priorities.
If you’d like to read more articles on decision-making frameworks and tools, and also get free access to the tools I’ve created, click here to upvote the topic so I know.
Learning to Block
The tools and techniques remote workers can leverage to block time and avoid burnout.
American football is a brutal contact sport that leaves many with severe damage, including traumatic brain and spine injuries. It has been said:
“There is no better experimental and research laboratory for human trauma in the world than the football fields of our nation.”
Well, there is no better experimental and research laboratory for human burnout than the modern, remote workplace.
We need to rethink how we work so we can prevent injuries.
Even as work goes remote, people are experiencing burnout at record rates. A recent study by Monster found that 69% of employees are experiencing burnout symptoms while working from home in 2020.
With burnout on the rise, companies are starting to examine their internal practices to help employees cope with the circumstances.
But it’s not just about learning to cope with the world around us. Sometimes we need to build strategies that protect us. Employees need to learn the offensive and defensive skills to ensure they don’t get crushed by work.
Let’s start with blocking.
Why We Need Better Blocking
The goal of a good blocking technique is to provide your team—organizations, managers, and employees—with protection and create space for them to drive forward.
We know what it’s like when our blockers miss — we’re exposed and attacked from all angles. Our managers want more, our spouse needs more help around the house, and our kids look to us for education, entertainment, and sustenance.
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.
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.
Mental & Physical Well-being. If you’re getting hit every day, sooner or later, you start to get tired of what you’re doing.
We want to build a generation of blockers; people who understand what it means to use the tools and techniques available to create the space they need to be productive, happy, and healthy.
Employers should do this, but some simply won’t. It’s up to all of us to retrain ourselves to think about good blocking strategies.
Blocking Basics for Employees
Let’s start by establishing a goal: to safely improve our position against the competition.
Okay, now that we’ve established a goal where we can get tactical. Since we started with football, we’ll continue using it as our metaphorical guidepost.
In football, blocking is one of the most important components of a team’s strategy. Good blocking enables quarterbacks to execute a great pass, running backs to drive into the open field, and any play to optimize a path to a successful touchdown. While linemen are often considered the primary blockers, every player on the field needs to be able to block.
How can we build teams that know and understand how to block? Here’s a breakdown.
The Stance
The easiest way to get flattened by burnout is to be caught flat-footed. If you want to avoid getting flattened, you need the appropriate stance.
In football, there are two primary positions that players use for blocking: the two-point and three-point stance. Each stance is designed to help the blocker use their athleticism to their advantage, gaining leverage over their opponent and protecting a teammate along the way.
The modern, remote work environment tends to favor collaboration and cooperation at all costs. We co-locate and cram ourselves into open offices under the guise of “collaboration.” We use tools like Slack and Zoom to cooperate and keep lines of communication open. But each of these practices and tools can slowly leave us more exposed than ever.
If we want to get better at blocking and creating space for ourselves, we need to start with the right stance. The best stance for remote work is:
Agile. It keeps you on your toes and allows you to move swiftly in all directions. If you need to step up and block an incoming request, you can. If you need to drop back and protect someone else, you can.
Strong. It keeps you firmly planted, even under the most challenging circumstances. You’re ready for anything.
Repeatable. Remote work moves faster than normal work, so you have to be ready to get into a protective stance at any moment. You need to be able to move fast, with confidence.
How to Get Yourself Into the Right Stance
Plant your feet. Start by blocking off your calendar. This allows you to create space for the work. I recommend using tools like Clockwise or Reclaim to help you create space on your calendar.
Know your numbers. Consistency creates strength and confidence. You’ll build up strength and knowledge as you do more reps. Track your time with tools like Clockwise (again) or Timely to gain better insight into you could be more effective.
Keep your head up. If you can’t see it coming, you can’t block it. Burnout doesn’t just happen, it piles up over time and then suddenly crushes us. Keep yourself constantly in check and recognize when it’s time to take a break (mentally and physically). Start with this list of 10 Ways to Get Away.
Types of Blocking
Not all blocks are designed to do the same thing. Sometimes we need people to help us block. Other times, we are running out ahead to do the blocking for a teammate. We should learn how to think about these techniques and do our best to apply the right method in each situation.
Run blocking
In football, the idea of run blocking is to drive the defender away from an area or player. This may be straight ahead or off to the side in order to create a hole for the running back to come through.
At work, we can think about run blocking as a strategic and coordinated effort to create openings or protective barriers for coworkers (or ourselves).
Pass blocking
Similarly, passing situations in football require offensive blockers to protect the quarterback. They form a pocket around the quarterback and keep the defenders from getting through. Each lineman should have an assigned defender to block. Sometimes two linemen will be assigned to one player in a double-team block.
At work, we can assign blockers to a specific defender and work to effectively give ourselves and our teammates the room to run, pass, or handoff.
How to Improve Blocking
Whether we’re blocking as a group or as an individual, we can utilize the same principles to improve our blocking. The principles include:
Block offensively. In every situation, do what you can to be ahead of the blocking needs. If you use a communication app like Slack, start your day by signaling to your team what you’re working on and how they could help.
Know when to block. Don’t assume that blocking is always necessary. Unwelcome blocking can create unnecessary boundaries for those who prefer to integrate or cycle in their boundary management. If you or one of your coworkers is showing signs of burnout—additional fatigue, forgetfulness, anxiety, etc.—it’s likely time to start blocking. Not sure if you’re about to burnout? MindTools has a great little tool to help you assess your situation. Try it here.
Communication: Understanding the Snap Count
Great teams have great communication. It can seem second-nature — as if they’re reading each other’s minds.
In football, the snap count is a critical offensive and defensive communication point. Concentrating on the snap count gives offensive teams an advantage over their defensive counterparts. Instead of reacting, they’re acting at exactly the right moment, wasting no time moving too early or too late. They can start their block the second the ball is snapped, providing valuable seconds for themselves and their teammates. This takes a lot of concentration and coordination.
Most people talk about the need for remote workers to communicate, communicate, communicate. But not all communication is the same. And it’s especially difficult to notice the difference when your communication channels are digital—Zoom, Slack, and email obfuscate the underlying tone that helps us parse emotions and subtext.
In order to work well with our teams, we need to understand the snap count.
Learn About Your Coworkers
Do your coworkers have kids, a sick family member, or an outside commitment? The more we know about what other people need, the easier it is to help them block a time or even find ways to work around their schedule so we can block time for ourselves.
Recommendation: schedule regular 1:1s and check-ins using Navigator.
Schedule Other Activities
If you’re just sitting there, it’s easy to default to work. When we’re not surrounded by our work, it’s easier to avoid it. We can’t sit in the pocket all day and just assume we’ll never get sacked. Sooner or later, a defender shows up to plant us on our back. Recommendation: schedule virtual social events, pick up a new hobby or book, or pick one of the 10 Ways to Get Away.
Be Explicit With Your Goals and Actions
People can’t read your mind, so you need to tell them what you’re planning to do. In time, they’ll learn your patterns and find ways to improve together.
Recommendation: use a tool like Sunsama to collaboratively track your workload. This enables managers, teammates, and even family members to see the commitments on your plate.
Learning to Block: A Work-as-a-Sport Lesson for Organizations and Managers
Overworking can decrease employee engagement, reduce well-being, increase conflict, and exacerbate collaboration issues and turnover. Employees should not be alone in this battle. Managers and organizations can help remote employees by providing more accommodation and boundary protection. Each level of the workforce plays a critical role in blocking:
Organizations = governing bodies. They can enforce rules and regulations.
Managers = coaches. They can enforce behaviors and standards for the team.
Employees = players. They train and play hard, but need to know their limits.
Culture comes from above, so these policies say a lot about what companies value. And having a little extra support every now and then can save much more than time and money — it can save a life.
Blocking As An Organization
In a recent study, about two-thirds of remote work ready companies plan to make some of their new policies permanent. As more companies go remote, organizations will need to collaborate with employees and leaders to ensure employees are learning to block for themselves and keep their team on track.
Here are five emerging practices that organizations are exploring:
Sabbaticals and mandatory vacation. Every quarterback has an off-season. Even if that means you’re still practicing and gaining new skills, you can’t go at 100% all year. Sabbaticals and vacations provide a much-needed break from the day-to-day of modern work.
Provide a minimum time off. It’s one thing to rest in the offseason. It’s an entirely different thing to play every minute of every game. Companies may need to start enforcing a minimum time off to prevent burnout and keep employees healthy, even if it’s just one day a month. Trust me, they’ll play better when they’re rested.
Spread out the work. Some players may be best suited to call the plays, move the ball, and keep the team going, but that doesn’t mean they’re alone. If an employee is going out of town, create mechanisms that allow others to step in and fill the gaps. Just like a team that relies on an all-star, you’re not doing your job if their absence is truly detrimental.
Learn Boundary Management Styles. Educate others on social differences in boundary management when team building. Embrace diversity of boundary management styles without stigma. Review your style here.
Focus on Results. Develop a culture that is results-oriented work rather than activity-oriented. Running in place is about the least productive thing a player could do, but sadly, we all know plenty of players who do this. When we change to a results-oriented culture, employees feel more open to taking breaks.
Blocking As A Manager
Too many managers ask employees to tell them where to draw the boundaries. This is insanity. Seriously.
Employees, by definition, are working for someone. Therefore, the responsibility falls to the employer, not the employee. Managers need to embrace the psychological impact of their actions and take responsibility. If you’re a manager, here’s are a few tips to help block for your employees:
Model good behavior. Don’t be the a**hole who sends emails at 11pm. Whether it’s intentional or not, you’re communicating a lack of boundary control and creating mixed signals for your employees. Many employees feel compelled to check their email or respond during non-work hours, which often leads to increased stress and anxiety.
Learn about employee values and needs. Not just surface level stuff. Try to understand where they value their time and work to meet their needs. Some employees are better at sharing their preferences proactively, so don’t be afraid to ask.
Focus on results, not activity. Managers and organizations already put enough pressure on remote worker productivity; we don’t need to overemphasize activity. Instead, let your employees know that output is what matters.
Communicate your expectations. We all lose when we’re silent. Be clear about your expectations and allow employees to know that you’re doing this so you can collaboratively reach your goals.
Be a blocker. Don’t force employees to be the only blockers on the team. Step in, and step up.
Conclusion
Boundaries are much easier to manage in a physical environment. We’ve grown accustomed to just accepting them as they are, but in the modern workforce we’re forced to face a new reality: we must protect our assets.
The habits we create at work have long-lasting consequences that take years to manifest. Whether it’s attention, energy, well-being, relationships, or communication, we need to redesign our work and our lives to create a healthy environment where we can all thrive and advance.
Organizations, managers, and employees need to work in concert to build the future of work. Why not start with blocking?
Work as a Sport (WAAS)
What sport psychology teaches us about mental health, productivity, and the future of work.
I grew up playing a variety of team and individual sports; soccer, basketball, tennis, baseball, swimming, and football.
Over time, I naturally drifted away from team sports and toward individual sports like swimming and tennis. At the time, I didn’t realize the impact my natural tendencies would have on my future career aspirations, but now I see the way sports trained me for the future of work.
Allow me to explain.
Whether you consider yourself an athlete or not, the fundamentals of work and sport are the same — both are competitive, rule-based, and require collaboration and planning. Similarly, genetics, talent, and mental grit play a large role in our overall performance in sports and work.
While athletic abilities may be honed over time, the psychological preferences are a bit harder to adjust as they’re hardwired into our personality. We like to believe we consciously choose every action we take — the partner we choose, the clothes we like, the TV shows we binge — but we’re really just advanced primates with excellent post-hoc rationalization skills.
In other words, we’re exceptionally good at reasoning our way to rationality. And, if nothing else, modern work favors rationality.
The work we choose to do is not a simple choice made at a single point in time. Instead, it’s a series of complex decisions, that compound and combines over time to create what we later define as our career.
Whether you believe you should work for a FAANG company or start your own business is largely dependent on the experience that led you to this point in time.
Where we start this journey is important, but so are the little alterations we make along the way. We are path-dependent creatures destined for an unknowable future. Many are led astray by past experiences or undue pressure to conform.
If you’re not careful, you’ll end up doing the wrong work and wondering why you’re unhappy.
But we’re not all destined for such a grim future. Instead, we can choose to look inward, learn our preferences, and use our skills to create a better path forward.
First, we need to start by going beyond the binary division of in-group/out-group behaviors of the team and individual work. The world isn’t binary, and neither is work. We can explore a third modality that comprises the Work as a Sport model:
Individual
Team
Assimilator (NEW)
Before we explore this third modality, let’s take a look at the existing paths and dimensions for exploring work as a sport.
The Four Dimensions of Work as a Sport
There are multiple dimensions to this model, but we should explore this via the following dimensions: collaboration and coordination.
Individual — a minimal degree of collaboration
Team — a high degree of collaboration
Informal — a minimal degree of coordination
Organization — a high degree of coordination
Each of these dimensions stands on its own but has specific variants. For example, swimming may be an individual sport, but you may also swim on a team or with a group. Basketball is a team sport but can also be cobbled together for ad-hoc pickup games in any neighborhood.
So how might we analyze the difference between individual and team sports as they apply to modern work?
First, let’s look at the psychological characteristics for each classification.
Individual Athlete Characteristics
When we talk about sports, we’re quick to assume we’re referring to “team sports” like football, soccer, or volleyball. Most of our entertainment is derived from team sports because, by their very nature, they’re inclusive.
But of course, just like there are many jobs that work in isolation, there are many sports that compete individually. The athletes that gravitate towards individual sports often share similar traits that align well with those who prefer individual work:
Goals-oriented. Many people who gravitate towards individual work tend to be quite ambitious. They want to go both far and fast. And they’re likely to believe they can do it alone.
Rapidly-evolving. Individual athletes have a unique advantage when it comes to learning and growing: feedback loops. When you’re an employee, you have the ability to learn from those around you, but you can also lean on them as needed. In order to be competitive, individual players must rapidly expand and improve their skillset.
Responsible. Individual sports cultivate important psychological skills. When you’re forced to practice alone, you increase the capacity for internal motivation and mental fortitude. There’s no one around to keep you focused or tell you to get to work. You are that person. Where team sports encourage social interaction, individual sports require self-reliance and responsibility. Lacking people to fall back on, individual athletes often spend more time preparing and training.
Isolated. While working alone can be nice, it can also increase anxiety. In response, individuals can quickly look to control their environment in an effort to help them reach their ambitious goals.
Vulnerable. Loss during individual sports can feel far more depressing. There is no one to blame or share in the loss.
Many draw distinctions between management-types and “individual contributors”. This is typically shorthand for people who do individual work; it can easily be confused with “team member.” As technology flattens the economic opportunities for workers, many people are wondering which type of work best suites them. This is a very new phenomenon that is creating a new opportunity. More on that in a bit.
Team Athlete Characteristics
The same way individual sports and work preferences define the optimal path for certain “athletes”, team sports need players who are of a certain mold.
Collaborative. Psychological studies have shown that people who prefer team sports are often more agreeable and collaborative. They seek to please others and look for validation, engagement, and attention.
Emotional Development. Team sports can also help with emotional development. Research published by the Canadian Fitness and Lifestyle Research Institute states that exercise can lead to a unique state of short-term relaxation which promotes increased concentration, better memory, enhanced creativity, more effective problem solving, and an improved mood — all benefits that will extend into the workplace.
Adaptable. By nature, good teammates need to fit in with their coworkers. Organizations have limited tolerance for outliers and typically push for a homogenous culture.
Trustworthy. Teammates are expected to be trustworthy. This isn’t the same level of trust that you’d expect from a significant other, but a baseline level of trust is required for true collaboration.
Teams aren’t just the people you share a business card with. A team can be two people in a video conference. A team can be a group of friends. A team can be an intimate relationship. Not to get too meta, but a team could be an athletic team.
Assimilator Athlete Characteristics
In the past, jobs were a way to create financial security and fulfillment. Now, we’re finding new ways for individuals to make money. Gig workers and the passion economy are rebalancing our expected norms when it comes to collaboration and connection.
Creators like Jack Butcher and Daniel Vassalo are finding ways to productize their work, make a solid living, and break free of the 9 to 5 while creating sustainable value. Their work is largely digital; meaning, they sell things online. Their value exists in multiple dimensions. They could continue working on their own, but they maintain optionality to rejoin an organization or partner as-needed. They are “Assimilators.”
Assimilators are a new class of workers that exists as a hybrid, combining the key characteristics of an individual player and teammate. They evolved under different circumstances and are required to fit in both worlds, although they belong in neither.
They are likely to have some professional experience in both individual and team environments, although they likely have a preference for one over the other. Additionally, they tend to combine many of the characteristics of individual and team athletes. They are:
Adaptable.
(Semi)-Collaborative.
Responsible.
Rapidly-evolving.
Not everyone can — or should — become an Assimilator. But those who can, should. The workforce is more flexible than ever before, but that may not last.
How to Decide Which Sport Is Best for You.
With the rise in contractors, consultants, freelancers, and gig workers, the line between the individual and team players is not shrinking, it’s growing wider. Those who spend too much time as team players attached to a specific team will find it difficult to switch to individual work in the future.
Know Yourself
The athletic world acknowledges that some sports are best played alone. Don’t be afraid to give yourself permission to do the same. There’s a reason we don’t see many professional athletes switching from tennis to football.
Whether you regard yourself as a teammate, an individualist, or an assimilator, it’s important to realize that your abilities and aptitudes can be applied to the future of work. If you love spending hours on calls or engaging in lively debates with colleagues, it should be obvious that teamwork is meant for you. If you’d prefer to quietly sit while you solve a problem or create a new design, maybe individual work is right for you.
While personality tests are a poor proxy for skills and certainly should not be used for major life decisions, they are a great foundation for understanding natural tendencies. I recommend starting with the 16personalities, Golden Personality Profiler, or Enneagram Type Test.
What’s important is knowing yourself and being true. There is only one you, so pick the path that’s best for you. Be unapologetic about it. By acknowledging your preferences — the good and the bad — you can quickly and easily identify your professional opportunities.
Assess Your Skills
Once you’ve assessed your preferences, do a deep dive into your skills. Do you have the skills required to work in the right sport?
Individual work forces you to sharpen your hard skills since most of your work is judged on output instead of engagement. Conversely, team-based work is better at improving soft skills like collaboration, communication, and mental/emotional flexibility. Depending on where you are looking to improve, here are a few recommended next steps:
Hard Skills (individual): try a few courses on accounting, marketing, and design.
Soft Skill (team): try a career-advancing program like re:forge, or hire an executive coach to train your communication skills.
Manage Your Time
Last, be sure to understand the boundary management style you prefer, as it will inform how you work. What you do outside of work might be a good indication of what you should do at work. For those working parents who need time to adapt their work-life balance, consider whether teamwork is best suited for you, as it may be prohibitive.
No matter your preferred working style, there is something out there that suits your needs. Remember: only when you embrace who you are, can you reach your full potential.
Remote Boundary Management Styles
Four methods for creating your optimal work-life balance
Eighteen inches — that’s the distance between my “office” and my couch.
Finding work-life balance is uncharacteristically difficult when there isn’t a natural physical distance between work and life. But boundary management is no longer optional.
Work and life are magnetic — they’re attracted and repelled by movement. And right now, our world is experiencing a strong attraction.
Whether you’re an individual contributor, teammate, or manager, effectively managing your personal and professional interactions is key to maintaining optimal productivity and happiness. But there are multiple ways to get at this challenge.
When you use a screen to connect, where do you go to disconnect? What happens when your sense of space is permanently invaded by the digital signal? Remote work and remote life are forever commingled.
People are tied to their computers and phones. Screens have ruled our lives for years, but when you switch to remote work, the screen becomes your 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.
But there’s still hope. For those who want to take work-life balance into your own hands, the first step is admitting there’s a problem. The second step is understanding the four types of boundary management:
Integrators
Cyclers
Separators
Role-Firsters
Before we dive into each of the styles, let’s take a step back to understand why boundary management matters and why the rules are slowly breaking.
Why Are Work-Life Boundaries Important?
When it comes to work-life balance, remote workers are struggling to create physical—and psychological—boundaries. The rapid acceleration into remote work that COVID-19 brought on has quickly blurred the line between work and life. The increased interruptions and distractions associated with working from home decrease our productivity and force us to feel as if we’re behind the eight ball. With each passing day, we work longer hours to simply “catch up.”
We’re overworking due to over accessibility, not an increased workload. A few data points to consider:
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.
Furthermore, a Families and Work Institute study reports that 75% of working parents do not have enough time for their children or each other.
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.
As employees find it increasingly difficult to manage their work-life balance, it’s easy to resort to an oversimplification: just create better boundaries. However, anyone who’s telecommuted or worked as a remote employee knows that it is, in fact, not that simple.
Boundary Composition
“Find a job you enjoy doing, and you will never have to work a day in your life.”
We hear you, Mark, but sometimes it’s hard to tell the difference.
I’ve always loved my work and have found myself deeply absorbed, often to the point of exhaustion. For me, it’s never been a question of wanting to work. It’s been a question of whether I’m making time for anything else. Turning off email or leaving the office rarely meant I was “off.” Furthermore, I realized that physical barriers were not as critical as psychological barriers.
Every person will prioritize their barriers differently. For some, the office provides the perfect physical location and barrier, simultaneously creating distance without limiting collaboration. For others, the physical office can be stifling and restrictive, creating emotional and psychological tension. Whatever your style, there are three primary elements that make up each boundary management style:
Physical Boundaries
Physical boundaries are what we’re most accustomed to — the walk to the office; the commute home; the midday break at the coffee house; the journey to the bathroom. Working from home quickly reminds us of the value the office provided: an escape. If, like me, your desk is situated next to your living room, it’s difficult to create the space needed to detach. But physical separation can also be architected by turning off your email or creating out of office reminders. The goal is to use physical and digital environments to create separation.
Psychological Boundaries
Unplugging can be one of the biggest challenges for remote workers. Even with impeccable physical barriers, the anxiety of disconnecting can outweigh our ability to feel effectively separated from work. Whether you just need time for a mental breather, quality time with friends, family, or a partner, or just space to relax — it can feel impossible.
Emotional Boundaries
Last, but certainly not least, is the emotional safety needed to experience your emotions. The office is meant to feel cold, calculated, and logical. But life simply doesn’t comply with those rationalist constraints. As work and life find themselves indefinitely intertwined, our emotions are irrevocably connected to our work environment. Maybe it’s the feeling of missing an important moment with your child or just having a difficult interaction with a coworker, emotional boundaries are a necessity for maintaining productivity and well-being in the workplace.
Boundary Management Styles
Boundary management styles are like personalities — everyone has one and they’re all a bit different. Some of us like more physical separation, while others need more protective psychological barriers. No matter your preference, boundary control is deeply important and personal. It helps you manage the space between non-work and work.
InVision—a company I previously worked with—used to call this space between non-work and work “work-life integration.” Personally, I never liked this phrase. For me, it assumes that we should integrate our work and our life. More pedantically, it places work first — sorry, but sometimes order matters.
While that style worked for InVision, it didn’t work for me. Initially, I found this disheartening, that is, until I discovered the four boundary management styles articulated in a recent paper from Kossek, E.E. In the article, they outline the strategies that I’ve attempted to employ, with varying degrees of success as a remote employee and leader.
Integrators
Integrators are the people most responsible for the always-on culture. They seek to constantly combine work and non-work activities. They’re comfortable with ongoing interruptions and draw little distinction between work and non-work time.
Cyclers
Unlike Integrators, Cyclers need periods of separation. Instead of blending work and non-work activities, they use time-blocking to temporarily separate their time. Cyclers tend to have varying patterns of boundary interruption styles, sometimes experiencing deep integration or strong separation.
Separators
Separators are the most restrictive, keeping work and non-work activities completely separate. They rarely allow interruptions and focus on time-blocking strategies to create the physical and psychological space they need.
Role-Firsters
As an extension of the Separators, Role-Firsters define a dominant priority and prioritize their time based on that priority.
Life-First. Life-firsters experience the reverse, accepting non-work interruptions during work, and experience few interruptions during non-work hours.
Work-First. Work-firsters tend to accept a significant amount of work-related communication during non-work hours but accept few non-work interruptions during work hours.
These styles deeply impact how we adjust to remote work, particularly as it pertains to the psychological experience. For example, separators typically allow few interruptions when they’re either in work or non-work modes. By contrast, Integrators consistently engage in and encourage interruptive behaviors throughout the day, creating an always-on perception.
How to Find Your Style
The more remote the work, the more important your boundary management style becomes. Employers can only help so much, so ultimately, it’s on you to find your style.
Check your stats. Take stock of the key metrics that matter. Is it important that you spend time putting your kids to bed at the end of the day? Are you most productive and satisfied when you’re working late at night? If so, does this jive with your partner or family?
Test multiple strategies. Our natural tendencies don’t always provide the right solution for our needs. Don’t be afraid to try new strategies. If you’re a natural Integrator, you may find that switching to Separator actually helps you achieve your ideal work-life balance.
Combine and create. These styles aren’t a perfect match, so don’t be afraid to combine and create new versions. Maybe you like separation during the summer and integration throughout the school year. Iterate and find what works for you.
As work and life meld together, it should be clear that creating physical, psychological, and emotional boundaries is critical for remote employees and employers. These boundaries not only impact our attention, productivity, and well-being, but also our relationships with our families, partners, and teammates. Employers and employees need to start developing competencies in work-life balance management to foster a better work environment for the future.
WhenRemoteWorks...and When It Doesn't
My remote work journey started by accident.
It was 2012 and I worked for the infamous consulting firm, Deloitte. Like many consultants, I was well-adjusted to the 4:1 schedule—four days onsite with your client, 1 day in the office. But this was different. I reported directly to the CTO of Deloitte and, while I had counterparts in other areas of the organization, I was on an island.
Suddenly my job involved international communication and leadership. Not only did I need to adjust my communication patterns, but I also had to move my entire schedule, learn new tools and systems, and lead new teams. The changes were growth opportunities for me personally and professionally. But it wasn’t all roses.
With work spread across five different time zones, I adopted the schedule of both a night owl and an early bird, starting my day around 5 am and taking my last call at 11:30 pm. While this sounds like torture to most people, I loved it. It gave me the flexibility to get five hours of work done before most of my Seattle colleagues had finished their first cup of coffee. If I wanted to get a midday workout in, I could easily make time.
The downsides crept in slowly. While I was traveling or working remotely, most of my colleagues were still in the office. This is where isolation started to take its toll.
During my infrequent trips to our physical office, I found I had lost the personal connection with my colleagues. They were interacting face-to-face every day, while I was communicating digitally. They no longer understood my role and probably wondered if I was actually working at all.
This was particularly challenging for me, as I was working incredibly long hours and working hard to make an impact. It was obvious to my international counterparts, but not to my local colleagues. The feeling of isolation set in, and I found it increasingly hard to balance the challenge of working remotely.
This would be the beginning of a longstanding relationship with the psychological challenges of remote work.
Whether it’s Zoom fatigue, the never-ending workload, or just the additional anxiety of creating and maintaining boundaries for work-life balance, I’ve experienced it all. And though these challenges can be difficult, they are addressable. And honestly, the better we understand the new challenges of remote work, the more likely we are to find meaningful, scalable solutions.
#WhenRemoteWorks
Last week I wrote about remote hierarchies, which are the three primary strategies for companies embracing remote work:
Remote Hierarchies
1. The Crusaders (aka remote-only/first)
2. The Decentralized (aka remote-plus)
3. The Entrenched (aka remote-last)
After that post, a funny thing happened. When I logged onto Twitter to engage in my usual scrolling and eye-rolling, I noticed the #WhenRemoteWorks hashtag trending. My first thought was “this seems like an interesting thread.” The thought was immediately followed by a judgment-laden inquisition into the origin and rationality of this tweet (below).
I wondered: if remote work is so much better, why then, would we need to describe the conditions of successful implementation?
Fortunately, as a longstanding remote worker, I had a hunch. It’s easy for us to forget that, prior to the COVID-19 pandemic, employers and employees waxed and waned when it came to supporting remote work. The prominent advocates of distributed and remote work were startups and individual, tech-centric employees looking for increased flexibility, autonomy, and cost-savings.
As indicated in The 2020 State of Remote Work study by Buffer, the numbers consistently favor increased support for remote work, with nearly 98 percent of respondents agreeing with the statement below.
Perhaps unsurprisingly, the key benefit of remote work has remained the same for nearly three years: flexibility.
Whether it’s the ability to have a flexible schedule, the flexibility to work from anywhere, or the ability to work from home, every benefit listed can be traced back to flexibility.
Flash forward to 2020 and the questions about the viability and scalability of remote work have all but gone away completely.
It’s official—remote work is here to stay.
But we’re still working out the kinks in the new system.
#WhenRemoteDoesn’tWork
While many of us have been fortunate enough to have the ability and option to continue working from home, a lot of people are struggling to find their rhythm.
The Big Three
Remote work comes with unprecedented side effects for employees. Researchers find that work hours blur with non-work hours, creating additional anxiety and stress for employees. Whether it’s collaboration issues, loneliness, or the inability to unplug, remote workers are bearing the burden of work. And it’s getting heavier each day.
Now, the question is: what can we do to improve mental health and productivity?
Before we start solutioning, we need a firm understanding of the problem.
Collaboration and Communication
Meetings have long been a polarizing element of the corporate culture; they’re loved by managers and despised by employees. Ashley Willis’ tweet perfectly reflects the thrilling feeling we experience when we’re magically gifted time for productive work outside of the stale setting of a corporate meeting. 👇
Most employees value collaboration and communication, but maybe we’ve finally taken it too far.
During the recent transition to remote work, companies have been forced to evaluate which meetings are truly required for maximum productivity. Because, let’s be honest, we’re all focused on productivity at the moment.
In the early days of the COVID-19 pandemic, employees attempted to replicate their existing in-office schedule, adding everything from standup to happy hours and “random chats” to their daily calendar. Most people quickly realized that video chat is not as seamless as in-person communication—wifi signals drop, timing is always delayed, lighting is distracting, and our mics are perpetually spotty. As time in quarantine expanded, many realized that this was an unsustainable and, honestly, exhausting way to exist.
Enter: text-based communication.
Just as text messaging overtook phone conversations, people are now relying on tools like Slack and Microsoft Teams to keep a running dialogue, document decisions, and mimic in-person interactions. These ‘chats’ come with their own unique set of challenges, including the decimation of all reasonable work-life boundaries. It’s impossible to be offline if your primary communication tool is always on.
Loneliness
As meetings erode their position as the primary marker of our day, people experience more time “away,” pushing communication to tools like Slack and Teams. Each of these tools is great for increasing the perception of communication, without actually helping users feel like they’re really connecting. They reduce everything to its most efficient, transactional state. A Slack conversation might look something like this:
Sam: How’s the design proposal going?
Gene: Great! I should have it ready by EOD.
Sam: Ping me when it’s done.
Gene: 👍
Imagine this conversation taking place in a physical office. There’s a good chance this could be misconstrued as unnecessarily curt. At best, it could be categorized as accurate and efficient.
The point is: we’re pushing away from each other, not coming together.
While remote workers are learning to cope with isolation, this plays into a broader trend. Studies have shown that loneliness is on the rise in young adults, many of whom are entering a workforce that is likely to be remote-dominant for the foreseeable future. The same survey noted that people who engage in frequent meaningful in-person interactions have lower scores of loneliness.
Though I believe isolation is manageable, we need to prepare for a society without in-person engagement.
Not being able to unplug
One of the most important and underrated factors of traditional office work is the ability to unplug. When you leave, it doesn’t follow you. It’s the foundation, firmly pinned in place, awaiting your return. Though you have the option to bring it home or stay online, it is just that—an option. Remote work does not provide that option. You are the office. Forever.
Being always-on is not healthy. Why do you think people are looking for meditation retreats and digital detox sessions? People will go to great lengths to escape the always-on culture we’ve created. Working longer hours was once a marker of success, grit, and productivity. Now it’s a sign: you’re headed for a cliff.
Furthermore, it’s not even productive. We trick ourselves into believing that downtime is not productive, but the data says otherwise. Periods of downtime are critical for the brain’s subconscious processes, which boost memory and problem-solving skills.
Filling The Remote Gaps
Remote work is often touted as a benefit for mental health and work-life balance. “You’ll be your own boss,” they said. “You’ll set your schedule” they claimed. “You’ll work when, where, and—for the most part—how you want.”
They were right, but not completely accurate.
As many workers have discovered, remote work can be a difficult and often depressing environment. It’s easy to start feeling isolated, stuck at your desk hours on end, without the natural cutoff point that physically leaving the office provides. While mental health means different things to different people, we all need to find ways to stay connected and create a global culture of support.
According to a recent study, about two-thirds of businesses that have adopted remote work policies plan to keep at least some of those policies permanently. With more and more companies going remote, employers and employees need to realize that the effects of remote work could have damaging effects if not appropriately addressed. Employees need to learn how to block and tackle in order to take control of their environment and maintain work-life balance.
It’s easy to assume that the shift to remote work will be better for everyone. It won’t. Many will suffer in the transition. More will be displaced. Gaps will grow wider.
We need to accept that remote work is not inherently better for everyone. It’s different, and different doesn’t always mean better.
Some workers suffer professional costs that may be difficult to recover from or require a completely new career path. Others are forced to manage psychological changes that may not support their individual preferences or needs. Some people will find remote work incredibly fulfilling, while others will face a new kind of hell.
Not everyone is ready to give up the physical office. The underlying truth is that, as inefficient as traditional offices are, some people will prefer that experience. Our ability to recreate those elements that benefit certain employees is limited, but important to the next wave of company culture. Employees have adapted to a certain lifestyle and they long for the tricked-out kitchens, the nice couches, and open collaboration spaces. More than ever, they seek separation from their home. Furthermore, employees are seeking something we all need: space.
The need for a space to collaborate and socialize with colleagues is incredibly important for many remote workers. The loss of hallway conversations and ad-hoc interactions seems trivial, but for some it’s critical. Going forward, we can expect office life to be less about productivity and more about collaboration, socialization, and escaping the day-to-day work-from-home culture.
We need empathy for those who find remote work fulfilling and a path to better work-life balance. We also need empathy for those who need a different environment. Whether it’s psychological, financial, or emotional, we need to create space to breathe. People need the freedom to cognitively detach and focus on family and friends, go relax, or separate feelings and emotions experienced during a workday, such as missing your child or dealing with a tough interaction with a coworker.
The world is hard enough, so be kind to one another—that’s #WhenRemoteWorks.
The End of History Illusion
Embracing Change and Ambiguity
At each stage of life, we’re faced with decisions that define our future. As we grapple with these decisions, we overemphasize our current preferences and underestimate the changes that we’ll experience in the future. Your favorite band today, will likely not be as important to you in ten years. This phenomenon is called the “End of History Illusion.” It states that, despite knowing that our preferences have already changed, we predict that our preferences will largely stay the same in the future.
History is littered with failed predictions. Complex environments with changing circumstances make it difficult to accurately predict future states. While the world outside is changing, we’re each changing inside — and we’re utterly incapable of predicting these changes within ourselves.
Don’t believe me? Try this little experiment.
Flawed Forecasters: Reflecting and Predicting Our Preferences
Most people believe they know themselves well enough to predict who they’ll be in the future. Before I expose the data backing this research, let’s do a little test to see how accurate we are.
To begin, take a minute or two to write a few simple sentences that describe a few details about your life. These sentences could include attributes of your job, your family, your favorite hobbies, or anything of interest. For example:
I’m an entrepreneur and product designer. I’m currently living in Seattle and designing a house in Chelan with my partner, Kelsey. We have a 2-year-old Bernese Mountain Dog and spend our days working from our apartment in downtown Seattle.
Now, reflect back to where you were ten years ago. Would you have predicted your life would turn out this way? I know it’s difficult to assess, so just do your best and try to be honest with yourself.
If you feel like you would have predicted the life and interests you currently have, congratulations, you are among the few. Want to test your skills for future-you predictions? Continue with the next exercise.
Look ahead 10 years and write a few more sentences about your future that are specific enough to prove or disprove using the following format:
I will work in [industry/job].
I will live in my [house or apartment] in [location] with [partner + kids + pets].
My favorite bands will be [top three bands].
My favorite vacation location will be [location].
[Insert your own prompts as-needed].
Write these items in a calendar event for ten years in the future. Be sure to set a reminder to review your answers and reflect on their accuracy.
This was the exact experiment that Daniel Gilbert and his colleagues ran with over 7000 participants in 2013. The research was named after Francis Fukuyama’s prediction that liberal democracy was the final form of government, or as he called it “the end of history.”
Half of the participants were asked to report their traits, values, and preferences along with what those metrics had been ten years earlier. The other half of the participants were asked to describe those metrics in their present selves and to predict how they might change in the next decade.
Researchers reported the degree of change that each participant reported or predicted. The results were overwhelmingly conclusive: participant’s predicted the bulk of their changes were already behind them.
Furthermore, this illusion was consistent across age groups. For example, a 20-year-old expected to like the same music when they were 30, but 30-year-olds no longer had the same taste as when they were 20. While older people changed less than younger people, they underestimated their capacity for change just as much.
We might believe we’re great at envisioning our future, but maybe our dreams are simply a reflection of our past. If we can’t see the future, should we even try?
Short-Term Diversification
“In most of our decisions, we are not betting against another person. Rather, we are betting against all the future versions of ourselves that we are not choosing.”
We tend to make plans based on the data that is currently available to us. If we like modern homes today, we assume that we’ll also like them in 30 years. The conventional approach is to solve our prediction problems with more data. Unfortunately, when it comes to our preferences, we’re lacking in additional data needed to predict changes.
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.
We’re bad at translating current preferences into future predictions. What’s not clear is how we should deal with this issue.
What if we instead ditched our long-term plans altogether?
Before you run off, let me explain! Ditching long-term plans does not mean giving up on planning. Instead, I’d suggest another approach to the traditional method of planning. A more flexible model that embraces, and is also designed for constant change.
Enter: diversification.
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.
For example, if you want to write more, instead of requiring a minimum word count each day at a specific time, you could change the plan to be just write something every day. Creating flexibility allows for a more fluid exploration of values and preferences without detracting from goal-seeking behaviors.
Diversification maintains optionality, which creates opportunity.
Many people build their entire life around a few key decisions. Who will I marry? Where will I live? What job will I take? This strategy delivered positive results when the rate of change was low. As technology accelerates, so do the complexities and rate of change.
Embrace Change
Whether you’re 26 or 62, the “End of History Illusion” blurs your predictive abilities all the same. As humans, we’re susceptible to the idea that we exist as finished products. This can lead us to overinvest in future choices based on present preferences. In reality, we’re a work-in-progress. Our greatest mistake is to assume we’re done evolving.
Changes in the work environment are a great example of our poor preference predictions. If you had asked me ten years ago if I’d be able to work from my home every day, I would have likely predicted that it would be technically possible but that I’d prefer to be in an office. That prediction would have, at the very least been partially inaccurate.
Our predictions experience a refraction, like a prism. As we experience events, we reshape our future, creating new paths and opportunities.
As we continue to experience dramatic changes in our environment, we need more optionality and diversification. For every single bet you place, consider placing another bet that creates future optionality. There are no systems (yet) that predict what our preferences will be in the future — so we must diversify, adapt, and change.
If one thing is true, it’s that the only constant is change.
Embrace it.
The Einstein Paradox
Being Awesome While Completely, and Utterly, Alone.
For some, the idea of working alone is a dream scenario. You skip the commute, avoid the pointless meetings, and are pleasantly unconcerned with the hassle of wearing pants. Furthermore, you have the opportunity to build a distraction-free work environment for yourself by setting up the ideal workspace that allows for maximum productivity.
But ideals rarely measure up to reality. Personally, as someone who has worked with distributed teams for nearly a decade, I can confirm there is a challenge to being productive in an isolated work environment. Despite the emails, Zoom calls, and the exhaustive amount of social media options, however, we are ultimately, by ourselves - alone. So how can we stay productive when isolation borders loneliness?
Find Your Tribe
Even Einstein was not immune to the emotional and mental toll of working in isolation. How did he push through? The short answer is: Einstein found his tribe.
“Although I am a typical loner in my daily life, my awareness of belonging to the invisible community of those who strive for truth, beauty, and justice has prevented me from feelings of isolation.”
As evidenced in the quote above, Einstein never denied the isolation of working alone and the pressure that came with it.
Like Einstein, we are all building invisible communities as more and more creative work moves digital. Whether it's for personal or professional reasons, creating opportunities to be with friends, family and colleagues can secure a connection to your tribe and increase mental and physical resiliency.
Find Your Sacred Space
Nikola Tesla also notoriously worked in isolation at his Experimental Station in Colorado Springs, CO. His workspace was specifically built to study the use of high-voltage, high-frequency electricity in wireless power transmission. While most of us aren't able to create such an elaborate workspace, we can learn from Tesla's approach to hyper-productivity. By creating a purpose-driven space, he was able to focus not only on his creative efforts but his time. Like Tesla, if we want to do our best, we must create purpose-driven spaces that support peak performance.
Find Your Time of Day
In 1735, Ben Franklin popularized the phrase “Early to bed and early to rise makes a man healthy, wealthy, and wise.”
But what if you’re a night owl?
Although many of us are required to work the standard 9-5 schedule, some find those hours to be the least productive. In Daniel Pink’s book “When: The Scientific Secrets of Perfect Timing” he theorizes “our cognitive abilities do not remain static over the course of the day” suggesting the “fluctuations are more extreme than we realize.” Whereas the common 9-5 demands we are productive and energetic within those hours, working alone affords us the opportunity to respond to our energetic impulses.
Rather than try to accomplish all of the work as it arises, it’s important to be aware of your energy level and match the work accordingly. If you are a “morning person” then be most productive in the morning by tackling the most taxing work.
The Bias Blind Spot
Dismantling the Deep-Rooted Prejudice Within Us
We’re terrible at evaluating ourselves. Whether it’s judging our performance at work or our perceptions of another race, we’re not particularly insightful. Why? Our cognitive biases keep us from seeing the truth that lies just below the surface of our conscious mind.
The cognitive biases that fill our mind act like a funhouse mirror, distorting and reshaping everything we see in the world. While researchers like Daniel Kahneman and Timothy Wilson have done incredible work to peel back the curtain and give us a look at the interworkings of our mind, it’s still a bit of a black box. Bias blindspots exist and cause us to make sub-optimal decisions at every turn.
The bias blind spot is a term coined by Emily Pronin, a Princeton social psychologist who, through a series of experiments, showed that people rate themselves as less vulnerable to biases than the average person. As Pronin put it,
“This “meta-bias” is rooted in our ability to spot systematic mistakes in the decisions of others—we excel at noticing the flaws of friends—and inability to spot those same mistakes in ourselves.”
The underlying hypothesis here is that we tend to evaluate ourselves differently than we do others.
In the words of Jonah Lehrer in the New Yorker:
“When considering the irrational choices of a stranger, for instance, we are forced to rely on behavioral information; we see their biases from the outside, which allows us to glimpse their systematic thinking errors. However, when assessing our own bad choices, we tend to engage in elaborate introspection. We scrutinize our motivations and search for relevant reasons; we lament our mistakes to therapists and ruminate on the beliefs that led us astray.”
The issue is that our nervous system is designed to elevate these biases. The brain’s capacity for gut reactions was developed in our evolutionary ancestors, who lived in homogenous groups and understood that anyone outside of the group could be a threat to their survival. We build mechanisms that allow us to define “us” and “them,” without any conscious awareness.
These biases have remained in our DNA for millennia, guiding how we perceive the world around us. In addition to the ancestral biases, our experiences, preferences, education, and upbringing all continue to contribute to the model of who we are. None of these biases are inherently bad on their own. The biases become problematic when we weaponized these biases as an excuse to suppress a particular group of people.
Check Your Blind Spots
If no one is immune to bias, what can we do? The first step is to recognize it. Remember, everyone is biased. Biases in isolation are designed to help us survive. These biases are not inherently negative unless we give them the power to keep us from progressing.
Fortunately, while the change may not be easy, it is possible. Our biases will always exist, but our actions may be able to change our default state. We can override our worst impulses and reduce our prejudices, simply by acting out the behaviors and beliefs that counter these default settings.
There is no simple checklist to follow. There are only intentional, sustained actions. Here are the actions I’m challenging myself to employ.
Thoughtful Internal Examination
The bias blind spot is deeply related to another important bias — the introspective illusion. Many people assume they have a clear insight into their mental states, which leads them to believe they’re in control of their actions and behaviors. In fact, studies have shown that “the more we attempt to know ourselves, the less we actually understand.” Instead of attempting to understand the “why,” I find it more productive to think about the “how.”
When a situation arises that triggers an emotional response, ask yourself how you’d feel if someone you loved said or did the same thing. Would you still respond the same way?
Empathic Reconnaissance
You may not be able to walk in someone else’s shoes, but you can certainly try to understand their journey. Whether it’s working in a soup kitchen or just reading the stories of historically oppressed people, knowledge is the key to empathy. By spending time — either directly or indirectly — with people you’re not familiar with, you’re resetting your brain’s default algorithm and redrawing the boundaries between “us” and “them.”
Respectfully Champion
“Thoughts and prayers” have now been passed off as a useless media trope for tragic events. During these moments, it’s easy to post your outrage in social media, which, to be clear, can be an effective path to support. But if we truly want to change our biases, we must be careful not to appropriate others’ experiences. We should respectfully champion and support, but continue to examine our own behaviors. Change starts with us
Listen and Learn
To my friends and community who speak the words of support, I encourage you to continue your efforts and remain supportive. Voice your confusion and ask your questions. But most of all, listen and learn from what’s already been said. The problem — and solution hypotheses — are well documented. Let’s learn from the past, so we can improve the future.
Our ability to change is gated by our ability to learn from our mistakes. If, like me, you’d like to seek knowledge, understanding, and guidance, please feel free to join me as I explore the knowledge of others.
Finding Flow
How to Overcome Distractions and Feel Better
What is Flow? For athletes, it’s being in the zone. For creatives, it’s the intense fire of inspiration. Flow State is that point in work when it doesn’t feel like work. You’re motivated, energized, and deeply focused. The world around you fades to black. You lose your sense of time and become one with that energy.
Many people associate “flow” state with the digital productivity hacks that knowledge workers seek when building and designing software. But the concept was actually coined in the 1960s by Dr. Mihaly Csikszentmihalyi and has been heavily-referenced for years. In an interview with Wired magazine, Csíkszentmihályi described flow as:
“being completely involved in an activity for its own sake. The ego falls away. Time flies. Every action, movement, and thought follows inevitably from the previous one, like playing jazz. Your whole being is involved, and you're using your skills to the utmost.”
Image courtesy of Visualize Value
Flow is the ideal work situation. Distraction is the enemy of flow. And right now, our world is very distracting.
A lot of people are suddenly forced to re-evaluate the common workday. A seemingly idealistic work situation — the pajamas, the coffee, the tv playing just a little — has delivered a drastic new demand for our attention, our adaptability, and our willingness to push forward. And the entire world, and our individual bosses, are all going to look at our productivity at this time as a metric for this new reality.
Are there days where you feel like you worked really hard and yet nothing got done? This new work-life balance, or complete absorption of one another, is a radical adjustment — for everyone. So, let’s dig into it. What is affecting our productivity and what can we do about it?
Challenges to Finding Flow
Lack of prioritization. When we put the same emphasis on all our tasks, it becomes impossible to choose which we should prioritize and when.
Lack of focus. It’s difficult to get anything done when you’re trying to do everything at once.
Inability to say “no”. If you prioritize everything, you end up prioritizing nothing. Saying no is hard, but so is failure.
Steps to Finding the Flow State
Like any other goal, breaking it into small increments makes it easier to achieve the desired results. The steps below can be used in any order and under changing circumstances. Don’t try just one; experiment, learn, and adapt.
1. Ruthlessly Prioritize
Each day write a to-do list, then narrow it down to the top three. Find the places where you can leverage the Pareto principle and get 80% of the value for 20% of the effort. Instead of trying to do it all at once, simplify these tasks to jobs that could be done in no more than 90 minutes. Once you've found your top three tasks, it's time to get focused.
2. Be Intentional
Create a structured and intentional approach to each day by paying close attention to your thoughts and feelings. Mindfulness does not unlock the door to flow state, instead, it tells us which path we should follow in the maze. Throughout the day, remain mindful of how you feel and when in doubt, return to this list.
3. Cultivate Inspiration
We must remain ever curious. Inspiration is a powerful weapon that can be used to further enhance our productivity. When we feel inspired, motivation is triggered and productivity seems to flow naturally.
4. Build Life Hacks
Create mechanisms to reduce the number of repetitive, step-by-step tasks. Enjoy the benefits of the automated processes as well as the tickle of finding newness in the mundane.
5. Be True To, and About, Yourself
Be honest about your workload to yourself and others - this includes saying “no”. Set realistic deadlines and be uncompromising about the things that distract you from your most productive work. Reduce the busy work, cut the meetings, and prioritize your focus time.
6. Take *Real* Breaks
Breaks allow us to reconnect with ourselves and the world around us. They provide a chance to look inward and reset our batteries. Paradoxically, we’re more engaged when we take time to disengage.
7. Adjust Your Perspective, Literally
There's a good reason that you see writers at Starbucks. Shifting our environment is like rearranging your furniture — it changes your perspective. When you look at the same desk, with the same coffee cup, and the same chair every week, you're likely to lose inspiration. Instead, seek spaces that inspire and adjust your perspective.
8. Drop The Perfectionism and Go
One of the biggest impediments to creative productivity is perfectionism. We sit at the computer, thinking about what we're going to do, instead of just doing it. The more we think, the harder it gets. Don’t get trapped in your head. Just start.
The simple truth is that everyone can find flow. The key is not to overthink it. If it’s not happening, explore alternative approaches that help you. There’s no wrong way to do your best work.
Solitude or Isolation
How Mindset Determines Your Experience
With the right mindset, everything 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.
We can’t control the world around us. We only have control over one seemingly small thing: our mindset - in truth, an immensely powerful tool. Mindset controls how we are affected by, and how we perceive, our ever-changing experiences, both good and bad. If our mindset sees negativity or limitation, our world is then viewed as such. Likewise, if our mindset sees positivity and productivity, our world responds with joy and kindness. In both scenarios, the world is not changing - we are.
Mindset is crucial in the current situation - the COVID-19 pandemic. As we continue to manage the extreme disruption of our daily lives, stress, anxiety, and pain can be helped or hindered by mindset. Our natural tendency to be social creatures has been severely limited due to COVID-19 social distancing regulations thus challenging the way we work, communicate, and live.
It’s a strange duality, we have all dreamed of working from home in our pajamas while binge-watching “Tiger King”, yet we're quickly learning this reality comes with its own baggage. People need time to adjust to the concept of physical distancing. The loss of human connection is jarring. We need new tools to cope with the changing situation. But above all, we need emotional support to help guide us through uncertain times. The psychological toll of events like this is remarkable.
Where do the feelings of being alone come from? How are isolation, solitude, and loneliness connected — and more to the point, do they really have to be?
Solitude/ Isolation/ Loneliness - What’s The Difference?
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.
Solitude
For centuries, some of the world's greatest minds — Nietzche, Woolf, Socrates — have championed the benefits of solitude. Ultimately, solitude is something we should seek and enjoy. It is the art of being alone without being lonely. When chosen, solitude is engaging, positive, and refreshing. 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.
Isolation
Whereas solitude is sought, isolation happens to us. (Again, entirely dependent on mindset.) Isolation is associated with a type of prison, forced abstinence from the world we enjoy. It can be especially harmful during times of crisis, as the path "back" to social connection feels frayed.
Loneliness
Clearly, isolation and solitude are linked to loneliness. But loneliness is not only about being alone. Loneliness is an internal process, a devilishly dangerous mindset. We actively avoid loneliness, viewing it as a prison because, in many ways, it is. Loneliness creates an internal feedback loop that leaves us depressed, exhausted, and afraid.
Why are we so afraid of isolation?
In today's always-on society, the idea of being alone with our thoughts is more terrifying than ever before. In fact, a recent study found that several participants chose to subject themselves to electric shock rather than be alone with their thoughts. This is a behavior that builds upon our evolutionary need to be connected.
In the past, we had to stay close to our tribe to stay safe. Nature has not deprogrammed this fear, because, to some extent, it's still true.
Whether we're looking at people through the five-inch screen in our hand or sitting across the table, we still need human connection. But being around people does not equal human connection. In fact, some of the loneliest experiences can happen when you're surrounded by tens, hundreds, or even thousands of people. No rule says a large group of individuals will automatically be connected. The operative word here is "connected.”
We're not seeking emotional noise, we're looking for the signal.
Do You Have Control?
So much of our fear comes from feeling out of control. Feeling like the world is happening to us as passive participants. But that's a passive mindset.
"If you change the way you look at things, the things you look at change." – Wayne Dyer
By changing the way you view isolation, you change your relationship with it. The situation itself may not change, but your interpretation can. We assign value to things in our lives. By giving it a name, we give it power. By changing the name, we take away some of the power.
Try to feel it as energy. Placing your attention on it robs it of meaning. It’s just an appearance of consciousness, at that moment. It’s not what you are. You’re simply noticing it.
Challenged to Change
Antisocial behavior carries a significant stigma, and rightfully so — stealing, lying, and cheating are some of the more common and extreme antisocial behaviors that come to mind. On the less aggressive side are symptoms like negative attitude and peer rejection. Both scenarios are characterized by negativity, which works it's way into our lives as we transition through stages of life.
As we age, we often become both isolated and lonely. Research studying the relationship between loneliness and psychiatric disorders has shown that impaired social relationships can lead to various psychiatric disorders like depression, alcohol abuse, child abuse, sleep problems, personality disorders, and Alzheimer’s disease.
But a lot of the negative behaviors derived from antisocial behavior can also be viewed as a desperate attempt to create a connection and find meaning in life. Unfortunately, the manifestation of these efforts comes at a cost.
There is a big difference between being alone and being lonely. Isolation is a prison we create for ourselves. Solitude is a gift we give ourselves as a way to rebalance the scales.
Solitude may be the best gift you didn't ask for. Find a way to make this time better. Find a way to stay connected. Find a way to remove the stigma and be happy.
The SOIL Model
Models aren’t always accurate, but they can be useful. Maybe we just need a better model for understanding solitude. Introducing, the SOIL Model.
SOIL: Solitude over Isolation and Loneliness.
Like any good model, our model simplifies the complex, is based on credible scientific evidence, and is related to a target and designed for that specific purpose. To be specific, the variables of this model are described as follows:
Seek out positivity
Limit or avoid media
Give or give back
Stay active
Eat right
Seek pleasure in the routine/mundane
Create and be creative
Seek graceful resilience
Learn from mistakes and grow
Focus on what we can control
Shifting our mindset can alter our reality. Even in times of uncertainty and discomfort, we can look for opportunities to reshape our path and learn from the changing environment.
We’re in a rare moment in time. Or are we? People have lost their jobs in the past. The stock market has collapsed many times over.
We can choose to see this as a disaster, or we can find the opportunity within the crisis.
We all know we’re living through history. The question is, will history happen to you or will you seize the moment and tackle the divergent path ahead?
The Games We Play
It’s difficult to know what really goes on inside a person’s head. In many respects, most of the people we know seem like your run-of-the-mill modern professional; a designer here, an engineer there. But there's something different about their approach to work. While other people are worried about promotions, climbing the corporate ladder, or proving themselves to others, these people are focused on building something great. They aren't just playing a different game, they're playing their own game—and defining their own rules along the way.
We all have a limited amount of time to make our mark on the world. Far too often, we only see the paths that are laid out before us, ignoring our ability to carve a new path for ourselves. In many cases, the only way to truly make an impact is to diverge. Unfortunately, for many, it’s easier to sit on the sideline and criticize those who fight the traditional path in an effort to achieve something great. But, as Teddy Roosevelt reminds us, the credit belongs to those who are actually ‘in the arena’:
“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly…”
Before becoming an entrepreneur, I felt that I needed to play the game in order to be happy and fulfilled. In time, I’ve come to realize that the game I was playing wasn’t for me, and it kept me from achieving what I really wanted in life. I was playing someone else’s game, and therefore, was always subject to their rules.
Can you imagine a sumo wrestler trying to win the New York Marathon? They can train, eat right, and take all the right steps, but in the end, it may just be the wrong game for them.
It’s important to separate difficulty from suitability. Difficult challenges are a critical part of growth and development. Without some struggle, life—and work—has little meaning. When the game is just not a fit, the difficulty is irrelevant. In fact, you can be great at a game that has little value to you. But how do we know if the game is not the right game or if it’s just challenging for us?
Zones of Proximal Development
Playing the right game doesn’t mean that you have to play it alone. This is where the zone of proximal development (aka ZPD) becomes critical. In principle, our growth is siloed to our experience and effort. In practice, we often need help to achieve our goals. ZPD is often presented as “the distance between the actual development level as determined by independent problem-solving and the level of potential development as determined through problem-solving under adult guidance, or in collaboration with more capable peers.” Meaning, the more we collaborate with more knowledgable peers, the greater our learning potential.
But in someone else’s game, we’re restricted to learning the curriculum and rules of that game. Our constraints are set. But once we create our own game, we have more opportunities to invite new players; sometimes these players will come from other games, but our expanded ruleset facilitates the expansion of our ZPD.
What does it mean to play your own game?
Every time you’re asked to change the way your work, think, or act, you’re playing someone else’s game. It’s great to start to recognize those signals so you can mentally note a few starting points for creating and playing your own game. For me, here’s how it’s played out:
First, play the game you want to play, not the one others want you to play. Until you realize you’re playing their game, you can’t change it.
Define a few rules, but be ready to rapidly adjust the rules. Just like any game, the longer it goes on the more you learn about its flaws and edge cases. If the rules don’t evolve, you’re essentially playing a game defined by an older version of you (aka someone else).
Don't automatically assume you’ll win, just because it's your game. That's part of the challenge. If you could always win, why even play?
What happens when you start playing your own game?
Once you’ve released yourself from the shackles of someone else’s game, you’ll find that a few major changes take shape. For starters, you’ll notice an increase in productivity and effective output. This is primarily due to the additional focus and willingness to do what others are not. Furthermore, you’ll have the freedom to explore the depths of skill or idea, even if it doesn't immediately map to another game. Others who see you will be inspired to also set their own path and create their own game.
The small sacrifices “game designers” make showcase the possible futures and paths available for the next generation. Additional divergence doesn’t lead to chaos, it leads to freedom. Surround yourself with people who help you learn by doing and then start playing your own game.
10 Ways to Get Away
A Guide to a Productive Escape from the Mundane
Fall is here, our Seattle Sounders just won MLS Cup, and—in a shocking twist—I’m slightly tanner than usual. Life is good. But before we get into the subject of the week, I wanted to share a few quick updates.
Breaks: As you may have noticed, we took a two-week break from the weekly newsletter. The reason, as noted in my previous newsletter, was due to our annual late-fall/early-winter vacation. And in case you’re curious, it was fantastic.
Press-ish: While I was out, my False Flats article was picked up and republished by Indie Hackers. The feedback from entrepreneurs has been incredible and I'm honored that it’s been helpful for so many people. Check it out here!
20 down: As we’ve also made it through another 10 newsletters, I’d love to get your feedback on how I could improve the content. If you’d like to see something specific, please tell me here.
In addition to spending time working on my tan (aka repeatedly applying sunscreen), I read a few books that are worth recommending:
Thinking in Bets – Annie Duke
Awareness – Anthony De Mello
Consciousness – Annaka Harris
While each of these books was particularly interesting, awareness really stood out as particularly relevant. In short, I realized one key thing:
We don’t spend enough time betting on ourselves.
Across many conversations I’ve had within the tech industry, it’s clear that people are longing for an escape. We love what we do, but the landscape of our work—and life—is changing. Our sense of purpose, values, and energy is slowly shifting, creating new demand for more meaningful experiences outside the 9-to-5.
This got me thinking—besides outright booking a vacation for someone, what could I do to help more people find ways to get away? Whether it’s a stressful relationship, a big project at work, or just the ongoing challenge of living a busy, modern life–we all deserve to get away.
Despite this growing need, so few people actually prioritize making time for themselves. If it’s so important, why don’t we prioritize it? I believe a lot of it comes down to our ability to be selfish. In fact, I think many of us need to be more selfish.
Now to be clear, what I’m referring to is the type of selfishness that gives you freedom; the type of selfishness that allows you to prioritize things that make you happy. Far too often, we fall into the unconscious trap of pleasing others. We put work projects, friendship needs, and social events over our mental wellbeing. Each time we do this, we’re silently signaling to ourselves—and others—that our needs are less important. If we want to be happy, we have to see our own happiness as part of the equation.
To help other people capture this feeling and find time for themselves, I put together a shortlist of ideas to help you get away. Each option below is ranked from the lightweight to some-scheduling-required and has served me well in the past.
10 Ways to Get Away:
1. Journal – Journaling is a lightweight way to connect with your thoughts while creating space to disconnect from current stressors.
2. Explore nature – There are so many studies that have shown the mental and physical benefits of connecting with nature.
3. Social outings – When we’re busy, it’s easy to forget about the people who make us happy. Use an app like UpHabit to ensure you find time for those that matter most to you.
4. Anti-social outings – Go somewhere you enjoy and read, relax, or just allow yourself some time to be alone.
5. Start a hobby – Find and start a new hobby or passion project. Here’s a list to kickstart your search.
6. Visioning – Browse National Geographic’s photography archives and get lost in another part of the world for a few minutes.
7. Take a class — One of the best ways to get unstuck is to expand your horizons. Find a class—online or in-person—that sparks interest (and joy?) and make time for improving your mind. Coursera is a classic. Or if you’re looking for something practical, try Meng To’s Design+Code.
8. Change your routine — It’s easy to get stuck in a rut. Mix it up and you’ll start to see things a bit differently.
9. Staycation – Book an Airbnb in your city for a staycation.
10. Vacation – Take a full vacation or enjoy a weekend excursion to a Getaway House.
As the balance between work and life continues to blur, perhaps the most important skill we can cultivate is our ability to disappear.
Two-Faced
The Hypocrisy of Career Hipsters
Hipsters are everywhere. It used to be that we'd only see them in expensive coffee shops or record stores. But now, thanks in part to the magic of the internet, we see them online as well. They've birthed a new breed of hipster—what I refer to as a "career hipster." These new hipsters are the prominent personalities in our professional circles that exist solely to ride—or create—the latest contrarian trends and say whatever garners the most attention or likes/faves within their bubble. They pride themselves on being both digital contrarians and arbiters of authenticity.
While cultural hipsters still rule the physical environment, career hipsters rule now dominate the professional online environment. Cultural hipsters are relatively harmless—don't let the beards and mountain range tattoos scare you. Career hipsters are far more dangerous.
Career Hipsters: Who They Are and How to Spot Them
I’ve come to recognize, identify, and name the people who embody this phenomenon as “career hipsters.” For me, they’re defined as a navel-gazing group that claims to be above traditional management opportunities and public career paths while maintaining a single-minded focus on honing their "craft." These people will often arrogantly tout their role in “doing the work,” as-if those who speak at conferences or manage teams are incapable of getting their hands dirty.
Cultural Hipsters and Career Hipsters share similar qualities. It's not hard to draw parallels between the two groups.
They travel in small but passionate groups. They tend to inhabit similar locations both physically and digitally; physical locations like Seattle, Portland, Brooklyn, and Austin; digital locations like Twitter or an obscure blogging platform that is clearly superior. Once something goes mainstream, they lose interest. They pride themselves on being interested in things before they were popular—the modern cultural and career Lewis and Clark. Like Lewis and Clark, Cultural Hipsters love wool, plaid, beards, and fur. Fashion choices aside, hipsters are best known for a nearly universal navel-gazing penchant. Career hipsters love new frameworks, tools, black shirts, and the latest #FutureOfWork trends.
They define themselves as much by what they don't like as by what they like. The career hipsters say things like "I'm not in it for the fame like they are, I just want to focus on my craft." They see themselves as the purest, most honest form of their profession—defining and refining from their community from the inside out.
Creating A Common Enemy
Antagonists are a galvanizing force. The mere presence of a central enemy motivates us to act, to change, to improve, and to focus. Military units are particularly good at bringing people from different backgrounds together to rise up and defend against the enemy at hand. Sports teams, political tribes, and startups use the same psychological principles to motivate and embolden their teams. No matter the circumstances, common enemies are a powerful unifying force.
In the early days of a career, it's valuable to have a personal and professional north star. And to some extent, it's equally valuable to know the areas to avoid. The presence of a north star keeps us focused on the art and craft that led us to a particular profession. When we lose sight of that, we're destined to lose the emotional connection to our work. The irony is, what makes us great at our “craft,” might just be what drives us away from it.
But if we love our craft so much, how could we possibly let it go? As we grow and develop, new opportunities present themselves. This might come in the form of a promotion to management, an opportunity to start a new venture, or simply to change direction. This is when the qualities that we held so tightly early in our career start to conflict with the new paths and opportunities in front of us. This is where the hipster faces a critical idealogical crossroads.
Whether we're designers, engineers, strategists, or sales teams, we're accustomed to interacting with people that embody qualities that don't match our idealistic views of our profession. Our instincts tell us they're insincere and vapid. In most cases, they're either figureheads within a profession or rapidly ascending the ranks. We know that most of these people start off with pure intentions—do great work, make an impact, or change the world. But as time passes, the idealistic trappings fade. Those who once proudly bore the hipster badge have become everything they once despised.
But what happens when the force for good turns on the negativity switch? More importantly, what happens when we become what we despise?
Mainstream Hypocrisy: Must We Become What We Despise?
We spend so much of our time thinking. To most of us, our thoughts seem harmless. But armed with a target, our feelings become habits, our habits become actions, and our actions influence our perceptions.
For example, many professionals see someone in their field and say “I’d never want to be that person.” You know these people; the career types, the professional blowhards, the talking face without clear substance. To you, they represent everything that's wrong with your profession. This is the antagonist that once compelled you to grow professionally while avoiding the traditional management path.
As a young professional, I knew that feeling all too well. After years of comparing myself to others, I finally realized that, for me, these feelings came directly from my own insecurities. The thoughts were an emotional response to someone receiving fame, attention, or notoriety that felt unwarranted. It was a winner-take-all mentality; their success could only mean my failure, and therefore, I must despise them. But, in time, I came to realize that their success was simply that—their success.
The more time I spent thinking about someone else’s success or my failure, the harder it was to actually move the needle on my own work.
“You Either Die A Hero, Or You Live Long Enough To See Yourself Become The Villain”
Our personalities are influenced by what we spend our time thinking about. If you let it, an enemy can absorb your mind and control your thoughts. The more we despise our enemies, the more likely we are to be affected by them. So if we spend too much time thinking about these people, they’ll become a fixture in how we behave, think, and feel. It’s easy to lose sight of ourselves when we’re lost in the dark.
Guarding Your Craft While Building Your Career
Let's be pragmatic for a minute. Being a career hipster is a fine quality in the early stages of your career. If the leaders at the top of your profession help motivate you, either positively or negatively, then great. But guess what—being a career hipster only works for a short period of time, and if everyone buys into your hipster mindset.
The reality is that the career-types—the ones at the top of the chain—were probably just like you one day. In fact, many of them built their careers without realizing they'd ended up as figureheads. It’s easy to lose ourselves in judging others’ success and building a negative narrative to support our own goals and boost our ego.
But the bottom line is the hipster mentality can eventually lead to hypocrisy. If you want to advance in your profession, you’ll likely become exactly what you once despised. Even worse, you’ll look that much more ridiculous because you spent so much time railing against someone else's career, only to eventually find yourself in the same position. But here’s the good news: you can be both a talented craftsperson and a talking-head-style leader.
Though it might seem cool to tear other people down, it’s only going to hurt down the road. Do you know what's cool? Doing great work with great people. It’s that simple.
“Whoever fights monsters should see to it that in the process he does not become a monster.”
People want to work with people who don’t attack or tear down colleagues So put down your weapons, stop the backhanded tweets, and realize that you can be great at your craft without sacrificing your soul. The people you despise might be fighting the same internal battle, so be kind — and avoid being a hipster.
False Flats
What Cycling Teaches Us About Resilience, Perseverance, and the Climb.
“The human capacity for burden is like bamboo- far more flexible than you’d ever believe at first glance.”
Like it or not, careers are a race. Sometimes you sprint, sometimes you coast, and sometimes you climb. But the key to success is to remain flexible and steadfast in the face of uncertainty.
I started my professional career with unbridled enthusiasm—ready to race. After completing college, students are eager to apply their hard-earned (read: expensive) skills in exchange for a commercial payout. For some reason, I found myself fixated on working harder, faster, and longer to make a name for myself. I was ready to put my name at the top of the leaderboard. Evidently, I am a naturally competitive person, and the business world was my competitive arena.
Straight out of college, I started working for a digital agency in Seattle. From day one, I put my head down and went to work. I worked for long hours every week. I sacrificed holidays, time with friends and family, and even personal health. I did all this to accelerate my career and, as the saying goes, "make hay while the sun shines." And guess what? It worked.
(And I'll let you in on Tech's dirty little secret: companies promote those who work longer hours.)
By the time I was in my mid-twenties, I was ahead of schedule. I played a pivotal part in growing a few well-respected companies, held roles above my tenure, and exponentially increased my income. Now, to be clear, I wasn't Mark Zuckerberg. But, I had by most measures—compensation, title, network—reached a peak.
Or so I thought.
This was the start of my first “false flat.”
What Is a False Flat?
If you're not a cyclist, you're probably not familiar with false flats. Let’s get up to speed:
A false flat is the stretch of road between two steeper sections of the same hill. Though it may look flat, the path is actually a low-gradient towards a steeper climb.
These sections are especially tricky for many riders, as they lure you into a false sense of security. Imagine pushing your body to the max as you race to the summit ahead. "Only a little bit further before I've reached the top," you think as you shift to a higher gear. Just as you approach the top, you realize it is, in fact, a false flat with another steep section that follows.
Your eyes believe it's the top. Your heart assumes you've made it. Your legs scream their own judgment, and your lungs confirm the sentence.
Flats: Personal and Professional
Our careers often imitate this tricky, mind-bending stretch of road.
As students, we gain confidence and prestige through our academic institutions. High-status colleges, grades, awards; our first castles rely on external validation. As professionals, we lean on corporate institutions to further expand our set of external validations. Our parents brag that we work at Google, Amazon, Deloitte, or another prestigious organization their friends recognize. These little boosts work until we're pushed into a false flat. Then our fanciful masks start to crack.
False flats are a reminder and a test of our resilience. At times, we're motivated by our proximity to the summit. It's the same motivation that exists when we stand at the base of a mountain and imagine our conquest. To be candid, this is the purest form of motivation. The harder kind arrives when we're faced with adversity, and our character is called into question. At this moment, our mask is removed, and we're forced to address the test in front of us. The next phase of the journey takes on a different form.
Reaching A False Flat
My first false flat was the loneliest moment of my entire adult life.
It's hard enough to realize you've failed to achieve your goals. But it's far worse to feel like you've succeeded before you're ready. Early success can lead to the sad realization that the goals you strive to attain only provide minimal fulfillment—a dopamine rush for hustle addicts.
The initial taste of "success" turned me into a person I pretended to like, but it wasn't who I was underneath. Under the outward persona, I was fragile, defenseless, evasive, and detached. I took people and relationships for granted. I allowed external motivations of money and prestige to drive my decisions. It felt good to tell people what I was doing with my life and how I was "changing the world." But it was just a narrative. It wasn't who I was, or worse, who I wanted to be.
For me, the question of "how can I become successful?" outweighed the more critical "why do I want to do this?" or "is this worth doing?" questions. It's easy to solve the wrong puzzles in life.
I count myself incredibly lucky. Most people fight their entire career to be in the position I was in. This was my false flat.
Riding The False Flat
You're reaching the top. Or so you think.
To your dismay, you realize not only is it not the top but there's another hill. You feel weak and ill-prepared for another round of suffering. Your legs are gassed. You're not sure you can make it any further.
But let's play this out. Let's think about what would happen if you did actually reach the peak early in life. What now? Do all of your dreams come true? Are you fulfilled and satisfied? No. You search for the next hill to climb.
You become alienated and insufficient. You under-anticipate challenges and overcommit to projects, as confidence and ego rule your decisions.
It’s our social media values played out in life: designed, filtered, perfected.
Instead, life is full of misery. It's part of our existence. If it were easy, what would be the point? Life is the challenges we encounter along the journey.
Olympic athletes experience this deep emotional slump—or under-recovery—after their competition. Think about the journey each athlete has leading up to the Olympics. They push, they fight, they struggle for years. They sacrifice so much for a few seconds (maybe minutes) of glory. And then, just like that, it all comes to a screeching halt once they're done. Everything they've worked for is over, and they're left to feel depleted, both mentally and physically.
Suffering is a feature of our journey, not a bug. It's what keeps these athletes going. They adjust to the normative nature of the ongoing challenge and seek more of it. There are few experiences as sacred as a renewed existence outside the ordinary.
During our most profound moments of suffering, we're exposed to the realization that we're not who we think we are. We are precisely who we are—nothing more, nothing less. We're all a bit broken, a bit flawed. Our lives aren't what we want them to be. In the age of the internet, we're all on display, and we feel forced to hide our flaws. But hiding doesn't eliminate the struggle, it just avoids the truth.
Sometimes, the only option you have is to ride through the pain. We don't always feel ready for what's next, but this is why flats exist—they provide the necessary respite on the journey upward.
Exiting The Flat
Life is a series of never-ending tests. The challenges we face provide meaning to the drudgery of work and life. How do we solve climate change? How can we reduce student loan debt? These problems focus our energy on a particular moment in time, not the continuous, fluid motion of life's ongoing challenges.
Humans are complex beings that strive to extract meaning from what is otherwise ordinary. Our relationship to meaning stems from our ability to look beyond our current circumstances and into a possible future—a better, more fulfilling existence. If we focus on one simple moment in life, we miss the entire point of life itself.
Life's greatest challenges present us with some of the most significant questions. Questions such as: How can we be a better partner? What can we do to improve the world around us? How can we help the less fortunate among us?
When we reach a false flat, we're confronting the most human existence; it’s a test. We can either endure and face the flat head-on or collapse. The choice itself relies on awareness and resilience. Like a highly skilled surgeon, it’s up to us to use these tools carefully and strategically.
Preparing For Future Flats
The most essential meta-skill you can develop is flexibility. Flexibility allows you to be both rigid when needed and pliable when it’s not. Flexibility is a precursor to resilience and strength. When facing false flats, our strength and resilience are called into question.
The struggle is an essential part of learning. The benefits are not felt in the moment, but the post-hoc realization of true resilience carries long-term benefits. The knowledge we obtain and preserve helps us devise more informed strategies for the future. We have to find a test—e.g., a false flat—to know how to approach it in the future. In this way, the challenge is a gift for future you.
World-class competitors all know this feeling. In 2019, Tiger Woods exemplified this resilience in his return to the world of golf. In his quest to be the greatest golfer of all time, Tiger experienced a meteoric rise that earned himself a place in the golf hall of fame. But, not long after reaching the top, he faced challenges that ultimately led to a career low point. After resting and recalibrating his personal issues, he returned to the game of golf completely transformed. His return and ultimate victory at the Masters tournament brought him back to the "person he wanted to be."
When you reach your first hill, you're energized. As you start to see the crest, you push hard to get there. There's a rest point if you just give it all you have. But as you start to reach the top, you realize it's just an illusion. There's more left. Instead of allowing yourself to sink into a depression or quit, take this time to fuel up. Rest your legs. Devise a strategy for the next hill.
Test Your Limits Early
Sun Tzu, the Chinese military strategist, wrote,
"He who knows the enemy and himself will never in a hundred battles be at risk."
In our context, this means that before you can develop flexibility and resilience, you need to understand your own limits. When we're untested, we're uncertain of our boundaries. The constraints exist, but they're invisible to our minds because we haven’t pushed up against them yet. Tests increase the visibility of these lines and create opportunities for us to expand our previous limits.
Once you stop hiding from the narrative of yourself, you can honestly understand who you are. Only transparency can build resilience.
We spend too much time focusing our lives on the past and what we're building for our future. But we only have this very moment. Embrace it. Opportunities present themselves when it's least convenient and you're least prepared. If you were prepared, it'd be a plan.
Once we lose contact with the present, we lose our connection to life. If we're always looking forward or backward, we can do our best today. Every moment we miss is another missed deposit in our life experience bank.
Mindfulness and meditation is a great place to get to know yourself and understand the suffering. For me, it allowed me to distance myself from thoughts and feelings, allowing me to be more objective and strategic. It also allowed me to really embrace suffering and know that I could make it through. We’re far more capable than we believe, and mindfulness opens a window to our potential.
Rest And Recalibrate
Too often, we choose to ignore our boundaries, overlooking our immediate mental and physical needs. We disconnect from family and friends and lose sight of the more important questions that build a meaningful career and life.
In the false flat, we're presented with a gift—the gift of rest. An opportunity to rest and embrace a tailwind. Take this window and enjoy a bit of rest; your mind and body need it.
Refocus Your Energy
Crossing a false flat is an opportunity to refocus. What comes out during our flat is a new set of beliefs. Our period of reflection opens up new pathways and provides perspective. When we harness this new perspective, we're able to see what we missed before.
The revelation comes in the form of joy, happiness, and fulfillment. Money and fame are not part of the formula in the second round. Gratitude becomes a staple of daily life. We form a new commitment to the present. Focusing this energy is key to succeeding in the next round.
The next hill is not about gathering external validations. Instead, the commitment is to the people and the process. A steady force, driving you up the second climb.
Start Your Next Ascent
When we're young, we don't know much. Our “life experience bank account” is mostly empty. Our ignorance is actually our best ally.
As we age, it's easy to get set in our ways. Our rigid approach to personal growth and development is what keeps us from embracing the next hill. Instead, we should feel encouraged and grateful for the opportunity to push ourselves.
In our journey through life, we can't avoid false flats. Too often we think we've arrived, only to realize we have a long way to go. Whether it's in our relationships, our careers, or our personal development, there's always more to explore.
If you haven't already, I hope you have the good fortune to experience a false flat. And if you find yourself in a flat, find solace in the climb.
Good luck finding and growing through your next False Flat.
Your Most Valuable Asset
Why we place so much value on finding and generating inspiration
The invention of the internet changed how we access artistic inspiration, and we’ve never looked back. Whether we’re consciously aware, we spend countless hours trying to manifest inspiration. Sometimes the time we spend messing around on Reddit or Instagram is adding more garbage to the creative backlog. But now and then, we sift through the trash to find a little creative nugget.
Though the internet is a wonderful tool, many of our most inspiring moments come from experiences that exist outside the reach of the internet; noticing a bit of graffiti on the street or admiring an especially attractive building. Inspiration is a chameleon—always adjusting to blend in or stand out.
Creative origins aside, our never-ending search begs the question: why do we place so much value on finding and generating inspiration?
Let’s start with our work. There’s a new generation of workers. These mostly white-collar workers are what we call “information” or “knowledge workers.” The job of these new workers is different than the jobs of the past—the mission is creativity ingenuity. The work starts and ends in different places. The ideas come from sources of inspiration. The skills are not physical; they’re mental. This work requires that we manipulate pixels, craft content, analyzing data, and presenting ideas. Our lives revolve in a pixelated idea maze.
In the age of the information worker, ideas are the new currency. This currency is exchanged for money, opportunity, and fame. But the thoughts aren’t always equal, and the inspiration is unusually unanimous.
All of our creative influences permeate our work. Inspiration comes from the broadened perspective and newly formed neural connections in our brain. Spending more time grinding away on menial tasks rarely leads to breakthroughs or moments of creative inspiration.
Furthermore, inspiration is the precursor for insight.
Our ability to capture and act on inspiration is what fuels ideas and insight. Insights are a critical creative and market advantage in the modern workforce. The difference between the world-class artists, designers, and builders is not in their ability to generate a single insight. Instead, their brilliance lies in their ability to capture insights and build creative solutions from those insights consistently.
You can't brute force inspiration, but you can shape the circumstances in which it flourishes.
Many of us have great ideas, but they sit in storage, waiting for us to reach the last stage of inspiration: motivation. What if Picasso never actually picked up the paintbrush? What if Frank Lloyd Wright never sketched a single line? What if Ernest Hemingway never wrote such beautiful prose?
Most people get stuck ruminating on ideas. They have the motivation but cannot capture inspiration and maintain the spark across time. They get stuck in the inspiration trough of despair, never moving from realization to motivation.
The only way to improve your creativity and ideas is to take the first step during the critical moments of inspiration.
In that way, inspiration serves a uniquely valuable role in our creative endeavors. Inspiration acts as a catalyst for the active expression of new ideas or qualities.
For example, the observation of positive characteristics in another person or object can act as a trigger, either inspiring us to or leaving us inspired by. In this process, inspiration translates the stimulus-response through our phased conceptual framework, compelling an individual to bring the idea from the abstract and into realization.
In short, we value inspiration for one very simple reason: inspiration generates new, more creative forms of being.
Originality requires the blending of new ideas and concepts in a novel way. Meaning: the larger our body of inspiration, the greater our range of possible idea combinations. The originality does not stem from a single source or linear pathway. Instead, much of our creativity stems from access to a wide body of knowledge. If we wish to retain creativity and increase the value of our ideas, and therefore our market value, inspiration is a renewal resource that we must continuously seek our and harvest. Time to harvest.
Inspired by or inspired to?
The difference is more important than you think.
January hits with a wave of inspiration. Our list of resolutions includes: go to the gym every day, take more photos, write in a journal, eat healthy, run a marathon, win the Nobel Prize, build a house, paint a mural, call our friends, etc. It’s so long, it’s laughable. Unsurprisingly, only a few weeks later, most of the items remain incomplete. Our gym shoes sit unused in our closet. Our journal has only a few sad entries. Where’d did we go so wrong?
We’ve all experienced this type of inspiration—the type that helps us build absurdly long lists of to-dos and unattainable goals. In a recent post I examined the three phases of inspiration that drive us from being inspired to turning our inspiration into action.
Motivation plays a clear role in the path to delivery, but it’s only part of the story. In fact, if we notice, it’s the last part of the story. And, just like a story, the conclusion is the result of a long-awaited journey. We should focus on the journey itself, not just the finish line.
Inspiration may arrive in a snap, but it changes over time. It’s a complex network of reactions and stimuli. If we want to maintain it, we must develop and encourage it consistently. To build a lasting inspiration system, we have to expand our three phased definition to also include the types of inspiration.
Let’s start with the two types—or processes—that gently inform our inspiration phases. Each of these types of inspiration plays a specific, often complementary role in our conceptual framework—the process of being inspired by, and the act of being inspired to.
These processes are not mutually exclusive. One can be inspired by the beautiful colors during a sunset and also inspired to run a marathon.
The process of being inspired by allows us to appreciate a particular stimulus. For example, experiencing the beautiful colors of a sunset may stimulate inspiration. The wonderful part of being inspired by is that what we're inspired to do is not necessarily related to what we're inspired by. This form of inspiration is incredibly potent and, to me, feels entirely pure. Albeit a more passive process, it grounds us in our senses and unlocks wonder and creativity. The challenge is that this form of inspiration can often be passive, not actually leading to action. And there goes our six-pack abs.
The second type of inspiration is the process of being inspired to. When you're inspired by that beautiful sunset, you might then be inspired to capture it with your phone or start that new business. Inspiration moves linearly, progressing from being inspired by to being inspired to. The processes align with the conceptual framework we discussed earlier, noting that instigation, realization, and motivation states fall within the stages of inspiration. This is what we often value most, as it actively places us in the creation process.
No matter the inspiration stimulus, our ability to capture inspiration improves as we ready ourselves to recognize an encounter with an idea, object, event (i.e., being inspired "by") and wish to actualize this newfound vision (i.e., being inspired "to").
The main lesson from these two forms of inspiration is that they each play a pivotal role in our inspiration system.
Being inspired by is about appreciation and discovery. It unlocks great potential within us and helps open new conceptual pathways.
Being inspired to is about taking action. Grabbing those little bolts of lightning and turning them into a rocket ship.
Too often we get stuck between these forms of inspiration, letting insights and ideas slip right through our fingers. The key is to grab these ideas quickly so you can translate them into actions. This is where inspiration compounds and grows. This is where you learn and expand your mind. Remember to pay attention to these types of inspiration—if you don’t, they just might pass you by.
The Three Phases of Inspiration
Understanding how we can instigate and motivate.
It should come as no surprise that most scientific studies avoid the topic of inspiration—and for a good reason. Inspiration has a unique quality that makes it difficult to distinguish and even more difficult to quantify. It's like describing air—you know what it feels like, but the language falls short in producing a clear, lasting, and universal description. Furthermore, the word itself carries with it a plethora of implicit personal definitions. Scientists prefer to concisely craft a succinct description that can be tested and validated.
Even as we pen words that help us create a framework, the concept remains too abstract to operationalize. Knowing the definition does little to increase our ability to capture or act on inspiration. In that way, inspiration remains ambiguous. It is used interchangeably about a mythical state of insight and creativity. But it’s easier to understand than it may seem.
To form a more robust and active understanding, we must parse the conceptual characteristics into phases. In doing so, we realize there are three key states of inspiration: instigation, realization, and motivation.
Phase 1. Instigation refers to the involuntarily generated and influenced nature of inspiration. Inspiration is instigated and responsive to an external stimulus before it is internalized. This instigator can arrive in the form of an idea, a work of art, a beauty realized in nature, or even a characteristic discovered within another person. Inspiration appears in a free-flowing fashion, passing seamlessly from phase to phase.
Phase 2. Realization takes place during the transition between our reaction to the stimulus and the impulse to act on the revelation. It produces a small opportunity to apprehend the inspiration from the stimulus. The general characteristics of the realization phase are expressed through what is often recognized through creativity or creative output. This is where many of our inspirations are translated into ideas or insights.
Phase 3. Finally, we arrive at the final stage of inspiration: motivation. The new awareness produced by our reaction to a stimulus, which is then translated into a new response, is then advanced to an intent to actualize and express this new vision.
Since each of these phases feels quite atomic, they often go unrecognized. But, through our mindful recognition of these details, we’re able to harness each in order to accelerate our creativity. Armed with this newfound understanding of the phases of inspiration, go explore and appreciate your inspiration at a deeper level. You might be surprised by what you notice.
What Is Inspiration?
Inspiration affects everyone. It's not reserved for an elite class or a particular form of creative endeavor. It is universally experienced but privately defined.
The difference between persistent hard work and the lighter spark of creative fire that allows an idea to take flight is deeply elusive. These rare moments of internal creative combustion are what we informally refer to as inspiration. But what actually separates inspiration from any regular, mundane moment of our lives? What is actually happening behind the scenes?
As noted in the paragraph above, the scientific and historical definitions of inspiration refer to the process of breathing in or inhaling. But in the more colloquial, albeit amorphous definition, inspiration is defined as "breathing in or infusion of some idea, purpose, etc. into the mind; the suggestion, awakening, or creation of some feeling or impulse, especially of an exalted kind."
Well, that feels a bit overwhelming and, in all honesty, poorly connected to the emotions evoked during moments of inspiration. To really understand inspiration, we have to move beyond such a simple structure. A definition that illuminates the delicate phenomenon of inspiration. One that captures the insurgent descent into madness or brilliance. One that extracts the intense sensations that course through our veins, sending goosebumps down our spine as we're struck by the all-too-elusive spark of inspiration.
Inspiration is not solely determined by serendipity or hard work. Inspiration is the delicate mix of these ingredients, only extracted following creative ventures. It passes through you, surfacing our most exciting and meaningful moments. Inspiration pushes us to make great leaps of faith. To be brave in the face of adversity. To embrace ambiguity and power ahead.
Inspiration is persuasive and fleeting. When it leaves us, we desperately try to find it. To receive its energy, we must be present and mindful. To capture it, we must firmly understand the process and phases of inspiration. What we choose to do with it is up to us.
20 Podcast Recommendations for 2020
Hi, my name is Kevin, and I’m a podcast-aholic. I guess the first step to recovery is admitting you have a problem, right? Well, here we go.
Hi, my name is Kevin, and I’m a podcast-aholic.
I guess the first step to recovery is admitting you have a problem, right? Well, here we go.
I love podcasts. In fact, I might even be obsessed with podcasts. Upon last check, I subscribe to 85 podcasts; a list that seems to grow week-over-week. My obsession has become so pervasive that it has sparked a running joke in our household. On any given weekday, it’s not uncommon for me to begin at least one conversation with the phrase “so today, I was listening to this podcast…” I do hope that my family receives a well-deserved award for bearing with my all-too-predictable, poorly timed conversational segue. They’re the real heroes here. But, I digress.
Besides my delightful conversational tactics, there’s another upside to my love affair with podcasts–a collection of audio reference material available for recall at a moment’s notice. I’ve never been a fan of audiobooks, so in the early 2010s, I approached podcasts with a certain reticence. But, after listening to a few moving episodes of The Moth and This American Life (thanks, NPR), I was hooked. But it still felt like podcasting was only designed for media giants. That is until Joe Rogan broke that barrier, bringing casual podcasting into the mainstream.
Like him or hate him, Joe Rogan is largely responsible for transforming the podcast industry into what we see today. That’s right, Joe Rogan. You remember, the guy from Fear Factor. His podcast, the Joe Rogan Experience, started as a fun project with his comedian counterparts. Over time, Joe raised the bar, interviewing some of the most notable public figures, including Neil deGrasse Tyson, Edward Snowden, and Elon Musk. So what makes his podcasts so special?
The beauty of podcasts is in their freeform structure. So much of what makes conversations valuable gets lost or cut in our current media formats. We emphasize easily digestible, to-the-point content, that reduces everything to a binary decision tree. Along the way, we lost the most important part of thinking: nuance. Joe Rogan was one of the first podcasters to bring nuance back to the public discourse.
Personally, I use podcasts as a way to not only fill my long walks to work but as an opportunity to test my own thinking. I, too, know how guilty I am of existing in a filter bubble–but I do continuously attempt to pop it. So this week, I wanted to share a few podcasts that really hit home this year.
20 Podcast Episodes for 2020
The Knowledge Project with Shane Parrish #62 - Dr. Sue Johnson: Cracking the Code of Love. Listen here.
The Joe Rogan Experience #1309 - Naval Ravikant. Listen Here.
Making Sense with Sam Harris #171 - Escaping a Christian Cult. Listen Here.
Broken Record with Malcolm Gladwell(+) - Jack White & Brendan Benson of the Raconteurs. Listen here.
WorkLife with Adam Grant - When Work Takes Over Your Life. Listen here.
The Knowledge Project with Shane Parrish #32 - Earning Your Stripes with Patrick Collison. Listen here.
The Portal 7: Bret Easton Ellis - The Dark Laureate of Generation X. Listen here.
Below the Line with James Beshara - #DeepDive into Remote Work — With Hiten Shah. Listen here.
Broken Record with Malcolm Gladwell (+) - Vampire Weekend Returns: Ezra Koenig with Ariel Rechtshaid. Listen here.
Making Sense with Sam Harris #165 - Journey into Wokeness. Listen here.
Self? Help! - Susan Cain’s Career Transformer. Listen here.
Revisionist History - The Tortoise and the Hare. Listen here.
Longform 348 - David Epstein. Listen here.
Recode Decode - Ronan Farrow: Here’s how predators like Harvey Weinstein covered their tracks. Listen here.
Rationally Speaking #233 - Clive Thompson on “The culture of coding, and how it’s changing the world”. Listen here.
The Tim Ferriss Show #371 - Ramit Sethi Automating Finances, Negotiating Prenups, and more. Listen here.
Intelligence Squared - The Social Media Addiction-Machine, with Richard Seymour and Jamie Bartlett. Listen here.
The Pay Check - What About Dads?. Listen here.
Modern Wisdom #064 - James Clear - How To Build Habits That Last. Listen here.
All Songs Considered - Woodstock At 50: The Unheard Recordings. Listen here.
As we transition to a new decade, it’s important to look back on the defining characteristics of the previous decade. From my perspective, the loss of nuance and the expanded emphasis on tribalism is what set this decade apart. With 2020 only a few weeks away, I hope you’ll join me in this reflection and imagine what we can collectively do to bring back nuance and find more ways to connect with each other along the way.
2019 Summer Reading List
Nothing wraps up a sun-soaked day like a good cocktail and a great book. Here’s my list for the summer, 2019.
It has, undoubtedly, been an interesting year. As the world around me speeds up, I like to slow down and spend time enjoying life outside the office. And nothings wraps up a sun-soaked day like a good cocktail and a great book.
With summer officially underway, I decided to put together a list of the books I’ll be prioritizing for the next few months. While summer is a great time for most people to dive into the latest or greatest works of fiction, I prefer to explore the non-fiction realms. If you’re in the market for a few “beach books,” grab some of this literary goodness and start mixing up that cocktail.
Range - A book I wish I had written. As a long-time advocate of the generalist approach to learning, I have incredibly high hopes for this book (meaning: confirm existing bias).
Insight - We can all stand to learn a bit more, especially if it allows us to be more self-aware. I strive to remain as self-aware and objective as possible but, like many people, I often fall short. I hope this book enables me to know myself better and, in return, be better to those around me.
Reading Like a Writer - If you want to be like the best, you have to study their work. This book stood out as an analysis of the great writers of the past, and what we can learn from them in our thinking, reading, and writing. Excited to see what this book unearths along the way.
Super Thinking - "The essence of the independent mind lies not in what it thinks, but in how it thinks." — Christopher Hitchens.
The best thinkers use models and frameworks to support data-backed decisions. This is, yet again, another book about mental model (they’re all the rage). I like to read in themes, so once I’ve completed the book, I’ll be sure to compare it to The Model Thinker and other books of a similar genre.
The Second Mountain - I love David Brook’s work. The Road to Character—his previous best seller—is one of my most recommended a gifted books. His work speaks to the soul, and is meant to help us all lead more meaningful lives. If The Second Mountain is anything close to The Road to Character, it will be worth the time.