Life Lessons

15 Lessons I Learned Before Turning 31

31 feels slightly less monumental than 30. Last year, I reflected on the most important lessons learned over the course of my 20s. But there are no off-years in life. If you’re doing it right, each one offers new experiences and opportunities to grow.

Every year I create checkpoints to consider lessons learned, challenges I’ve faced, and progress I’ve made. Birthdays are one of those triggers to step back and administer a healthy dose of perspective. 

I’ve found that the true test of how much I’ve learned in the previous year is considering myself at that same point in time 365 days ago. If I laugh at how stupid I was, that’s a good sign. Investor, Ray Dalio, shares a similar sentiment, “It seems to me that if you look back on yourself a year ago and aren't shocked by how stupid you were, you haven't learned much.”

The years I’ve been able to look back and contemplate how much I’ve learned, despite laughing at the expense of my younger self, have been the most rewarding.

This year was an important one for me. Although it’s not as big of a milestone as 30, this year was full of little victories, failures, and lessons. I’ve learned as much as I ever have in a single year. Here are some of the most important lessons that have stuck with me.

1) What matters most is the ability to bounce back

There will be times you fail to rise to the occasion. What matters most is the ability to bounce back. It’s one of the most critical skills you can build in life.

I’ve learned this time and time again in my career. You can’t expect perfect conditions each step of the way. Things are going to break, you’re going to run into ignorant people, and there will be times that you face an onslaught of obstacles with no end in sight. What matters is that you find a way to come back with a fresh perspective each day, ready to try again. 

The best teams I know embrace imperfections beyond their control and contribute something meaningful anyway. The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

2) Experiences can still surprise you

I’ve been fortunate enough to have traveled to dozens of beautiful places across the world. I believe the more you travel, the more perspective you build – an invaluable gift in life. But the catch is that the more you travel, the more you seem to lose the novelty of first-time experiences. 

I will never have the same feeling that I did the first time I went dogsledding in the arctic circle, kayaking in the Milford Sound, or camping in the Vietnamese jungle inside Hang En cave.

But this year, I went to South Africa and was surprised to discover that elusive feeling in the raw experience of a safari and in the bliss of the beautiful countryside of Babylonstoren, one of the oldest Cape Dutch farms. If you keep an open mind and maintain an appreciation for life in all its forms, experiences will never cease to amaze you.

3) Convenience is worth paying for

Five years ago, “frugal” would have been one of the best adjectives to describe me. Over the past few years I’ve let that go in favor of convenience. And this comes from learning to value my time properly. 

My routine for years has been to write at a coffee shop on Saturday afternoons. But I would always cut that short to head across town to pick up groceries, an absolute nightmare on weekends. This year, instead of interrupting myself during this time, I’ve started using a grocery delivery service. 

On average, I save two hours of uninterrupted focus time. And it only costs me five extra dollars. At a certain point, you have to learn that time is the most valuable thing you have. 

4) Reversibility matters more than certainty in your decisions 

Time is far more valuable than a marginally better solution. To help make faster decisions, I’ve started asking myself, “How reversible is this decision?” If it’s easily reversible, I make it right there. Assessing decisions based on reversibility, rather than certainty of the potential outcome, has improved my decision making significantly. 

Slow, deliberate decision-making can be a significant advantage in avoiding massive mistakes. But the reality is that most decisions you make on a daily basis aren’t permanent in nature. There’s a time and place to use this level of deep thought and consideration. Not when it comes to picking a restaurant for dinner or testing a new layout for the landing page of your website. 

5) Success doesn’t come from preventing things from falling through the cracks

This is about building a systems mentality. In other words, developing the ability to step back and consider the interconnected whole – the structures, patterns, and cycles – instead of being blinded by a single event or moment in time. This frees you to focus your limited time and energy on what matters most. Success doesn’t come from being better at preventing things from falling through the cracks. It comes from knowing what to let fall through. 

You can identify those who have failed to build a systems mentality by how overwhelmed they get by minutiae – especially when the stakes are at their highest. They become fixated on insignificant things, gripping for control in their foolish quest for perfection. They’re unable to let the little things go.

6) Four things separate you from the top of your field

When I started my career in product, those above me seemed almost lightyears ahead in terms of their intelligence and abilities. I wouldn’t put myself anywhere close to the same category. But the more interactions I have with executives and senior leaders, the more I’m convinced that they aren’t infinitely smarter. The real difference is in their risk-taking, network, growth mindset, and a healthy dose of luck. It’s a good reminder that you’re not that far off. 

7) Don’t get pulled into races that you’re not willing to run

If I don’t create room for reflection, I often find myself getting pulled into other people’s aspirations and playing stupid games for stupid prizes – struggling to position myself on the corporate ladder, equating meetings with productivity, or seeking validation through arbitrary certifications and recognition. 

This is one of the most difficult skills to develop, sorting through the noise and determining what’s your own. As a human being, you are highly impressionable. This is great when it comes to social cohesion, but terrible when it comes to realizing your own aspirations. It’s okay if you don’t want the same things as everyone else. Just make sure you aren’t getting pulled into races that you’re not willing to run.

8) People are amazingly consistent in their behaviors

Another way of saying this is that everyone gets what’s coming to them – for better or worse. It’s just a matter of time. Habits and behaviors projected over the course of years dictate future conditions and outcomes. The trouble is that when you’re young and could use this advice the most, your perspective of time is too shallow to really grasp the lesson.

I see examples of talented, hardworking people catching breaks every month. I also see examples of grown adults clinging to the same identity they had in college who are paying dearly for short-sighted decisions in their careers, health, and relationships.

Use this as motivation to focus on getting the conditions right, developing better habits, and playing the long game. With this mindset, it’s just a matter of time before you start catching breaks. 

9) Compound interest from reading is no joke

After five years of reading 50+ nonfiction books each year, it’s only within the past few months that I’ve felt like I’ve been able to make seamless connections and pull relevant stories on demand. Once you form these connections, you propel yourself forward with a wealth of vicarious experience. 

This is critical to so many areas of life – mastering a multidisciplinary approach, identifying your guiding principles, outthinking misguided people. Without reading, you have to learn this all from direct experience. But books provide you with lifetimes of experience and perspective that you can call upon at will. 

10) Stories > instructions

Stop telling people what to do. Unless you’re running a laboratory, people don’t give a shit about instructions. Stories are the best way to communicate. If you let people interpret things for themselves, you get better results. Especially in fields that demand creative thinking. 

Of course, there are obvious exceptions and integrity matters. But you see the power of this in presentations. Speakers who use stories are able to capture the imagination of their audience. That’s what resonates with people. The same thing goes for brainstorming, design sprints, whiteboarding, and every meeting you have.

Everyone craves stories because that’s how we make sense of the world and piece together our own ideas.

11) Improv makes you a better human

I signed up for improv classes to help improve my public speaking skills. I wasn’t sure what to expect but I wanted to take a non-traditional approach. Fortunately, this has been one of the most profound experiences of my entire year. There are so many positive takeaways and important lessons that I’m planning to write a full article on the experience. 

The short version is that improv will get you out of your own head, train you to be a better listener, and wreck your comfort zone. 

If you aren’t listening with every ounce of your being, you will fail. You can’t fall back on normal cognitive patterns and predictions that you use in everyday conversations. And the constant discomfort during class forces you to embrace and accept the fact that you’re going to look like a dumbass on stage. There’s no way around it. It’s an empowering realization. I’ve since given up my attempts at perfection during presentations, which has helped me relax and improve my delivery.

12) Routine is essential to creativity

The more automatic my habits and routine become, the more energy I can pour into being creative. Ever since I carved out dedicated time and space for writing, my craft has improved significantly. Most mornings I start writing at 6:30 AM. Since I’ve built this habit over years, when I sit down at my desk in the morning I’m able to shift into a creative mindset without a colossal effort.

I often think of this quote from Gustav Flaubert, “Be regular and orderly in your life, so that you may be violent and original in your work.” With that being said, there is a golden mean. I have to challenge this routine on occasion to make sure it’s still working for me and I’m not becoming too rigid in my approach.

13) Drawdown periods matter

I’m excited to release my first e-book next month. But it was no small undertaking. It required five months of sustained effort. Before jumping off I had to make room for a drawdown period where I was able to prepare, rest, and reflect before starting. I knew I would need every ounce of energy I had if I wanted to get my thinking clean and bring the best version of the idea to life. 

This drawdown period was essential in helping me create a buffer where I was able to piece together and discover my own thoughts on the subject. It was an escape from being bombarded by influences and outside noise. The bigger the project, the more important it has been for me to settle my mind leading up to it. 

14) Time your vacations to avoid burnout

Over the past few years, I’ve kept track of when I start to feel like I'm burning out in a given year. And I've noticed it always occurs around the same time. So this year, I planned vacations and weekend getaways to avoid falling into the same pattern – February, May, July, August, and November.

As ridiculous as it sounds, one of my New Year’s resolutions was to take five vacations. It was a way to self enforce breaks when I would otherwise attempt to be a hero and power through things. This has made a huge difference in my wellbeing, the quality of my work, and overcoming the burnout I’ve faced in recent years. 

15) Purpose starts with meaning

Over the past year, I’ve had conversations with many people struggling with purpose. I love being able to share these deep conversations and I sympathize. That was the first ten years of my adult life – forever tiptoeing on the edge of an existential crisis. Some days I still wonder what the hell I’m doing. Purpose is such an overwhelming thing. 

But what I’ve learned, and what I try to share in these conversations, is that purpose is just the series of pieces you find meaning in. Look for where you find meaning in your day to day. By doing more of those things, you move purpose within reach. And if the quest for purpose ever becomes too much, settle for doing meaningful things instead. 

What’s Really Behind Our Obsession with Failure

In recent years, there’s been a growing obsession with failure. The “fail fast, fail often” mentality is polarizing. Many take it at face value and use it to romanticize their own failures. Others reject this as bad advice that’s intended only to soothe us in our shortcomings.

But regardless of where you stand, there remains an important lesson at the core of this mindset. And it’s not about failure, it’s about reach. If you’re willing to risk failure, you’re able to take more chances and reach further beyond your current ability level.

The goal is never failure itself. And that’s what most people get wrong. The goal is extending your reach and accelerating growth. This requires pursuing opportunities where failure is a potential outcome. Progress is difficult to come by when you limit yourself to situations where success and participation trophies are guaranteed outcomes.

There are two kinds of failure. The first comes from never trying out your ideas because you are afraid, or because you are waiting for the perfect time. This kind of failure you can never learn from, and such timidity will destroy you. The second kind comes from a bold and venturesome spirit. If you fail in this way, the hit that you take to your reputation is greatly outweighed by what you learn.
— Robert Greene

Avoiding contests that you’re not capable of winning makes sense in high-stakes situations. You want to eliminate risk and play the odds. But in modern life, success is rarely a matter of life and death. Most decisions aren’t catastrophic or irreversible.

It’s still important to choose the right opportunities where you have a competitive advantage in terms of your natural abilities or interests. But if you want to accelerate growth in these areas, you have to seek out challenges that test your limits and push you to the brink of your ability level. 

Aiming 4% beyond your current abilities

Habit expert and best-selling author, James Clear, suggests a good rule of thumb is to aim 4% beyond your current ability level. This is where deliberate practice takes place and you’re able to achieve a state of flow. 

Don’t get too hung up on the exact percentage, this is just a system to calculate risk and accelerate growth. If you’re aiming 4% beyond your current ability level, failure is a potential outcome. But it’s not the only available outcome – success is still within reach. This allows you to take advantage of inflection points and make bigger leaps – in your career, your art, or personal qualities you’re focused on improving. 

Ramit Sethi, best-selling finance author, has a similar approach where he keeps a tag in Gmail for “failures” and aims to reach four failures each month. But that doesn’t mean he’s taking stupid risks. He’s making calculated moves to extend his reach and give himself a chance. Sethi knows failure is a natural part of growing and trying new things. This mindset is key to the sustained growth of his business, helping him reach 400,000 newsletter subscribers and launch dozens of successful (and failed) products. 

Discovering the terrain

Both success and failure offer an equal sense of the terrain. Each reveals what to do more of, less of, and which direction might be worth exploring. When you’re just starting out, the map is obscured with certain parts missing. With each success and each failure, you learn a little more and reveal another piece of the map.

The only way to win is to learn faster than everyone else.
— Wade Shearer

Knowing what not to do can be just as powerful as knowing what to do. If you can avoid repeating small mistakes more than once, and avoid the colossal ones altogether, you can bring the full picture into focus, faster. Reflection on your own experiences, paired with vicarious learning (e.g., books or podcasts), helps commit experience into knowledge, shedding light on new corners of the map.

Learning fast, learning often

The driving force behind this fascination with failure is learning, which leads to growth. “Learn fast, learn often” is a more accurate but less buzzworthy rallying cry. Failure is just a mask that learning wears on occasion. 

Learning is what you’re really after. Figuring out what works, what doesn’t, and piecing together your understanding of life. With this you can build momentum in the areas you’ve prioritized. 

The “fail fast” mentality is about making calculated efforts to push your limits. But failure itself is not the goal. The goal is to push your limits, extend your reach, and develop yourself. Growth requires putting yourself in challenging situations that test your abilities. 

If nothing else, the romanticized advice surrounding failure should serve as a reminder that you’re the one who has to go out and live. Books, podcasts, and articles can provide you with strategies, systems, and kindred souls. But at the end of the day, if you want to grow, you have to test these ideas for yourself, risk failure, and fine-tune your own strategy along the way.

The Reality of Failing to Rise to the Occasion

What you don’t see when you look at the synopsis of great people’s lives are the times they fell short. From the outside, it looks like they operated with invincibility, rising up at each pivotal moment. When the stakes were at their highest, there was no stumble.

But when you dig into the details, there’s no one who has actually achieved this. Top performers assume more risk than others. They’re on the frontier, operating at the edge of their current abilities. If anything, this means failure is even more prevalent.

Failing to rise to the occasion

The truth is, there will be moments when you fail to rise to the occasion. You’re not always going to make the right decisions or act exactly how you imagined. And since perfection is impossible, what matters most is the ability to bounce back.

Even Warren Buffett had moments when he failed to follow through early in his life. At the beginning of his career, Buffett was terrified of public speaking. And while you might imagine that someone like Buffett stepped up, put himself through deliberate practice, and overcame the fear in one fell swoop — reality was much different.

In a widely-told story, at the beginning of his career, Buffett enrolled in a Dale Carnegie speaking course to improve his skills. But few sources include the fact that he quit the first time around. He was afraid of being called upon to speak so he dropped out of the class. It was only the second time around that he built the courage to follow through. Now Buffett credits this as the best $100 investment he’s ever made.

The ability to bounce back

Anyone can lecture you about decisions you should make, habits you should build, systems you should create. But the most successful people aren’t flawless in their decision making. They just have a remarkable ability to bounce back.

The greatest artists, entrepreneurs, and scientists take the misfortune in stride, turning obstacles on their end and using them as an opportunity to improve their craft. They embrace mistakes and capitalize on them, ensuring they never happen again. And that’s the real difference in top performers — they stumble, but they rarely repeat mistakes.

Whether you’re struggling against your internal limits — uncertainty, doubt, fear — or you’re facing external challenges, you’re going to have bad days. What matters is the ability to reflect, learn, and find the courage to start fresh the next day.

Awareness can go a long way when it comes to navigating failure and being kinder to yourself. It’s okay to hold yourself to your own high expectations, but expecting perfection will often lead you over the edge. Life is as much about resourcefulness and how you respond to challenging situations as it is carefully plotting a long-term strategy. You need both.

Professionals know this space well and embrace mistakes as learning cues. They learn from them, but they don’t obsess over them. Amateurs expect perfection and crumble when they fail to meet their own lofty expectations.

Failure is about reach

The goal is never failure itself. It’s the expansion of your reach and the rate of personal growth. That means pursuing opportunities where failure is a potential outcome. Not limiting yourself to situations where success and participation trophies are guaranteed outcomes.

If you’re willing to risk failure, you’ll take more chances and reach further beyond your current ability level. And this is the fastest way to learn and create more opportunities for accelerated growth. Take calculated risks.

There will be times that you surprise yourself. But there will also be times you fail to rise to the occasion. In those moments, what matters is your resilience and resourcefulness. The lean product mindset applies as well here as anywhere else. Build, measure, learn. Repeat.

Lessons from an Introvert: How to Push Your Limits and Overcome Uncertainty

If you want to achieve any sort of growth in life, you’re going to have to put yourself in uncomfortable situations. Experimentation is the fastest path towards experiences that allow you to learn, develop, and push your limits. Whether new skills, tactics, or techniques – growth comes from change.

But it’s easier said than done, especially for introverts. My perfect day is designed around routine, which helps build discipline and focus. I reserve high productivity times of the day for reading, writing, and creating. Although it’s challenging work, it’s a familiar challenge. It doesn’t generate the same type of discomfort for me as something like public speaking or learning a new skill.

If I’m not careful, it’s easy for me to settle into my comfort zone and ignore uncomfortable opportunities for growth that fall outside of my norm. I have a tendency to take discipline past the golden mean and become too rigid, losing flexibility in my day-to-day. To combat this, I have to disrupt my routine on occasion to make sure I’m still focused on the right things and challenging myself in new ways.

A few weeks ago, after months of deliberation, I shadowed an acting class. I wasn’t sure what to expect–it took everything in me just to show up. I have no desire to be an actor and there’s no hidden talent buried within me. In fact, the thought of acting makes me want to curl up and die. So what was I doing there?

My primary motivation was using it as an experiment to improve my public speaking skills. I came across the idea over coffee with a friend and fellow writer, Lily Hansen. She told me how her background in acting helped improve her stage presence and presentation skills. It was an interesting angle that I thought worth testing out.

The fact remained, I was nervous and in no way looking forward to the class. But I followed through because it aligned with an area of my life that I wanted to improve. The acting class was a vote for my desired identity – not as an actor, but as a stronger communicator and storyteller. I looked at it as an opportunity to arm myself with techniques to build greater comfort presenting in front of an audience.

Everyone’s different, but as an introvert, the question remains – when the stakes are at their highest, how do you take the leap and overcome uncertainty? This is how I’ve learned to navigate that anxiety.

Escaping the narrative

It’s important to know your tendencies. Understanding introversion and extroversion is an important part of self-discovery and awareness. It can help you discover where you gain energy and where your limits are. If you know which way you lean, you’ll know yourself better – when to push and when to ease off.

But keep in mind, it’s a spectrum. There’s a difference between awareness and over-identifying. Humans are incredibly complex. Neatly defined categories are only enticing because they’re easy and allow you to avoid navigating the gray area that defines most of life.

Don’t lock yourself into some narrative you can’t escape. Otherwise, it becomes an excuse to avoid uncomfortable situations. The same goes for extroversion–discomfort means different things to different people. If you want to avoid it, you can find plenty of familiar excuses within your comfort zone.

The power of ”who cares?”

Once you’ve escaped the narrative, it’s about taking the leap. Whether a presentation, high-stakes situation, or looking ridiculous when you’re learning a new skill, how do you take the first step?

When Shaun White, legendary snowboarder and three-time Olympic gold medalist, is at the top of an important run, the last thing he tells himself before he goes off is “who cares.” He doesn’t psych himself up or blast Eminem. He knows he’s put in the preparation. At that point, what happens, happens.

You don’t take new risks or perform your best by fueling your nerves. The who cares mindset isn’t about apathy, it’s about a state of relaxed concentration. This is where you do your best work. It’s a strangely empowering self-talk that helps navigate fears of judgment, failure, or general anxiety about drawing attention to yourself.

When I’m about to do something new or uncomfortable, this mindset provides a moment of calm before the storm. I know I’ll probably look like an idiot (the acting class), but if there’s anything I’ve learned, it’s that most people are too preoccupied with themselves to remember you tomorrow. You’re the only one still thinking about it.

Swim lessons and my life’s finest moments

At twenty-two, after graduating college, I decided to take swim lessons to learn proper technique. I was just getting into triathlons, which necessitate swimming with efficiency unless you want to smuggle in water wings. So I signed up for a month of private lessons at the Vanderbilt aquatics center.

I was prepared to look like a dumbass, but it surpassed even my expectations. The aquatics staff was so accustomed to elementary children signing up for these lessons that they ignored the form I filled out. To their surprise, a grown man, fifteen years older than every other person in the pool, wandered in for lessons.

With seven-year-olds in the lanes to either side, I started my lessons. The instructor (also younger than me) had to come up with a plan on the fly – diving for pool rings in the deep end wasn’t going to cut it. To make matters worse, I couldn’t make it down and back without flailing for air. Overall, these were some of the finest moments of my life.

But the who cares mindset helped me get over my ego and commit to learning proper technique. I looked like a complete noob for the first week, and I was. But with practice and time, I improved. Eight years later, I’m still swimming every week.

I reminded myself of this experience in my anticipation leading up to the acting class. Many of life’s most rewarding experiences happen once you let go of your fear of looking like an idiot. Don’t let your ego hold you back. These people aren’t going to remember you. Show up eager to learn and follow through on what you came to do.

Handling nerves in the moment

Almost always, I find that once I jump off and settle in, my nerves calm. But there are still moments when I get nervous in the middle of a challenging situation or new experience. When that happens, instead of amplifying my focus on myself and fueling my nerves, I shift my attention to externals.

In presentations or high-profile meetings, for example, I focus on non-verbals in the audience or the talking points of other people in the room. This helps keep me from spiraling or thinking ten lines ahead. By focusing outside of myself, I’m able to bring my attention back to the room, settle into the moment, and trust myself.

The All Blacks, New Zealand’s most successful rugby team, have a similar technique they use to bring themselves back to the match and avoid allowing the magnitude of the moment to overcome them. They use breathing techniques to put themselves in a clear, calm state. Then they anchor that state to a specific physical action – scrunching their toes, stamping their feet, or throwing water over their heads. This helps bring them back to the situation at hand and a relaxed state of concentration.

If you get too far ahead in what you’re trying to say or do, you’ll only compound the issue. Instead, come back to now. Project and focus more of your attention outside of yourself. It might be the opposite of your initial instinct to turn within, but it’s far more effective.

Jump when others retreat

If you want to become the best version of yourself, you’re going to have to put yourself out there. Growth comes from pushing your limits, experimenting with different approaches, and learning new skills. The greater tolerance you build for discomfort, the further the reaches of your comfort zone will extend. But this is a lifelong effort.

If you build self-awareness and maintain perspective leading up to, and during, the moment, you’ll be well on your way. Avoid over-identifying, be willing to look like an idiot, and avoid projecting too far into the future. This is how you get out of your own head, take risks, and jump when others retreat to familiar surroundings. It’s here where some of life's most valuable experiences are found.

The Two Sides of Discomfort

Last week, after months of deliberation, I shadowed an acting class. I wasn’t sure what to expect–it took everything in me just to show up. I have no desire to be an actor and there’s no hidden talent buried within me. In fact, the thought of acting makes me want to curl up and die. So what the hell was I doing there?

For those committed to personal growth, discomfort is considered a positive. And it often is. But discomfort can signal different things.

Sometimes discomfort is a sign that you’re growing and pushing the boundaries of your comfort zone or current abilities. Other times it acts an alert, warning you of a misguided decision.

The same concept holds true for exercise. There’s a discomfort that you push through to build strength or endurance. But there’s also a discomfort that signals injury. If you attempt to push through the latter, you compound the mistake and end up worse for it. While exercise is based more on feeling and experience, personal growth shares similar elements.

A certain level of stress is important. As Nassim Taleb, philosopher and writer, explains in his book Antifragile, “Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty.” The key is finding the right threshold.

Wind extinguishes a candle and energizes fire. Likewise with randomness, uncertainty, chaos: you want to use them, not hide from them. You want to be the fire and wish for the wind.
— Nassim Taleb

What’s worth sticking out?

Whenever I’m in an uncomfortable situation, I apply the same rule of thumb that I use to evaluate whether or not something is worth quitting.

I start by asking myself, “Do I feel nervous or uncomfortable because this is difficult? Or do I feel nervous because something’s off and this contradicts my character, values, or principles?”

The former is worth sticking out because that’s where personal growth stems from. The latter means it’s probably time to bow out and reassess.

With the acting class, my primary motivation was using it as an experiment to improve my public speaking skills. I came across the idea over coffee with a friend and fellow writer, Lily Hansen. She told me how her background in acting helped improve her stage presence and presentation skills. It was an interesting angle that I thought worth testing out.

But the fact remained, I was nervous and in no way looking forward to the class. It took a disproportionate amount of energy to even schedule it. But I followed through because it aligned with an area of my life that I wanted to improve.

Another way of looking at this is by using a model James Clear suggests, and asking yourself, “Does this behavior help me become the type of person I wish to be? Does this habit cast a vote for or against my desired identity?”

The acting class was a vote for my desired identity, not as an actor, but as a stronger communicator and storyteller. I looked at it as an opportunity to arm myself with techniques to build greater comfort presenting in front of an audience.

Does this behavior help me become the type of person I wish to be? Does this habit cast a vote for or against my desired identity?
— James Clear

The nuance of discomfort

There’s also a nuance to discomfort that’s worth taking into account. As circumstances change, the type of discomfort can shift beneath you. Earlier this year, a few technology companies reached out about open positions. I went through with the interviews–nerves and all–because I knew they would help me hone my skills, clean up my thinking, and explore my options.

But when it came to an offer, it was a different type of discomfort. I was able to step back and identify that my hesitation was because it didn’t line up with my priorities for the immediate future. I was still more excited about my current team, our upcoming challenges, and what we were building.

In that context, the decision to leave such a positive situation seemed foolish. I didn’t want to jump at the first new opportunity I came across, I wanted the right opportunity. And that meant doubling down on my current position.

The difficult part is that you have to preserve a deep sense of awareness to avoid rationalizing decisions beyond all recognition. There will be moments when you fail to rise to the occasion. Your natural instinct will be to seek out evidence to affirm you made the right decision–confirmation bias.

But life is rarely as neat and orderly as you might hope. You won’t always know, beyond a shadow of a doubt, that you made the right or wrong decision. You just have to assess things to the best of your ability and learn along the way. With greater awareness of your cognitive biases and what discomfort means in different contexts, you’ll be able to make better decisions.

Growth and self-preservation

If you take an impulse at face value, you’ll never be able to differentiate between the shades of discomfort. Consider what side of the spectrum the discomfort you’re facing falls on. One leads towards growth and the other self-preservation.

There will be moments when you’re uncomfortable. That’s not always a bad thing. The vast majority of us would be better off with more adventure, discomfort, and randomness in our lives. But you have to know the difference between stupid risks and opportunities for growth.

If it aligns with your character, it’s worth pushing through those difficult moments when you feel like quitting. No matter how uncomfortable you might be. It’s the discomfort from situations that contradict your character or priorities that deserve a second look.

Forget Your Purpose, Start with Meaning

The stories we hear of the successful often make it seem like they were destined for greatness. They identified their purpose from an early age and forged ahead, cutting down distractions in their path. But if you peel back the facade, few encountered sudden revelations. Purpose is hard won.

Child prodigies like Mozart or Tiger Woods are the exception. Robert Greene, best-selling author, worked dozens of jobs as a construction worker, hotel receptionist, translator, and screenwriter, before pitching his first book, The 48 Laws of Power, at age 36. But each step gave him a greater sense of meaning and direction on his way towards writing full time.

It’s human nature to crave a sense of direction. And direction comes from purpose, identity, and authenticity, each of which are intertwined. But they’re not the same thing. If you want to make progress, you have to be able to separate these and lower the stakes. 

Meaning is what purpose is made of

The trouble with taking on purpose from day one is that it appears insurmountable. When you break it down into its individual components, it’s easier to pursue. Purpose is the series of pieces you find meaning in. 

Your life doesn’t need a single purpose out of the gate. Just as it doesn’t need a single meaning. Meaning is an ebb and flow that tracks the motion of your life. If you follow this, it leads towards things you are uniquely suited to bring to life. 

Charles Darwin (1809-1882) discovered botany only after dropping out of medical school. And he wouldn’t publish his theory of evolution until twenty-four years after his visit to the Galapagos Islands. During that time, he speculated on diversity in the natural world through experimentation and careful observation–breeding pigeons, studying barnacles, and soaking seeds in salt water to see how long they survived. What tied together these seemingly unrelated experiments–where he found meaning–was working to understand the nature of life.

Purpose becomes attainable once you stop obsessing over it and turn your attention to the little things you find meaning in on a daily basis. Meaning is within reach.

What’s meaningful to you?

As you seek meaning in your day to day, there are different strategies worth considering. Robert Greene suggests a three-part approach in his book, The Laws of Human Nature.

  1. Consider inclinations in your earliest years – moments when you were unusually fascinated by certain subjects, objects, or activities. 

  2. Reflect on moments when certain tasks or activities felt natural to you.

  3. Determine what particular form of intelligence your brain is wired for (mathematics, logic, physical activity, words, images, music).

Do more of these things. The key is determining what’s meaningful to you and not absorbing what’s important to someone else as your own. Otherwise, you’ll miss the mark. If Darwin listened to his father and remained in medical school, he wouldn’t have joined the crew of the HMS Beagle or discovered the theory of evolution.

And this is perhaps the most difficult skill of all–sorting through the noise and determining what’s your own. It requires years of exploration, introspection, and reflection to determine for yourself. But this exercise gives you a solid start. 

The long game and force multipliers

When you focus on meaning first, you create a system that favors an action-oriented approach. You shift your mental framework from external to internal–what’s within your realm of control. And this is the mindset you need to play the long game. 

The purpose of setting goals is to win the game. The purpose of building systems is to continue playing the game.
— James Clear

The promise of recognition or reward can carry you for days, maybe months. But not years. Only meaning provides that. Robert Greene’s latest book, The Laws of Human Nature, was the culmination of his life’s work and took six years from start to finish. You can’t fake 72 months of sustained effort without turning things back to what’s within your control and finding a stronger sense of meaning in your daily work. 

Aspiring to win a Royal Medal or become a bestseller can still be productive, if held in perspective. But if that perspective is lost and your self-worth becomes dependent on external validation, you’ll likely give up at the first sign of criticism or apathy–and there will be plenty. 

I find meaning in reading, writing, articulating complex problems, leveraging technology to simplify (rather than overcomplicate), and using storytelling to reveal something to people about their own lives. I can sustain each of these indefinitely because they’re meaningful to me and how I make sense of the world. If recognition comes along the way, I’ll welcome it (always keep the upside). But I also won’t stake my existence on it. 

The catch is that few reach achievement without first pursuing meaning. You can get lucky and reach the top once, but to sustain at that level, like Darwin or Greene, requires something more. Meaning is a force multiplier. The stronger the connection to your work, the more force you’ll be able to exert. 

It’s almost impossible to beat someone who’s engaged, finds meaning in their work, and is committed to the long game. 

You still have to determine what you want out of life, make sacrifices, and focus on a few important things. But it’s not worth agonizing over the search for a single purpose from day one. 

Instead, look for the pieces you find meaning in. Trust yourself. Discover ways to blend your unique abilities, interests, and experiences. With dedication and reflection, you’ll discover a sense of purpose that ties it together along the way. 

More Action, Less Talk

In May of 2009, I was finishing up my sophomore year at Indiana University. Without an internship lined up, I decided to dedicate most of the summer to writing and recording music. That was my path towards perceived significance and I had an ego to match it. 

When one of my friends signed up to lead music at a summer camp in Northern Minnesota for the entire month of June, it was an easy decision to tag along. I used it as an excuse to get away from home and focus on music. I also knew a handful of other people volunteering. One of the camp leaders, Jon, was a mentor and close friend. 

Before leaving for the trip, Jon and I met for lunch. We talked about how excited we were to spend a month together in Minnesota. He also mentioned how he couldn’t wait to hear the music each night. But he had one recommendation, “Keep it quiet…don’t walk around promoting how you’re a musician to other volunteers or campers. Just let people find out for themselves.”

It’s easy to glance over this at a surface level. But it was a profound lesson for a twenty-year-old, self-assured musician. This was the first lesson I learned in navigating ego. And it’s one I’ve continued to visit on an almost daily basis since.

More action, less talk.

With close to a decade more experience in life, Jon saw straight through my shit. But the way he approached it is what made the difference. He could have shrugged me off as an “idiot teenager” or come down with sharp criticism, causing me to shut down. Instead, he led an open conversation and explained one of life’s most important lessons–especially for those doing creative work. 

When you reveal less up front and people discover something interesting about you later on, it builds intrigue. You demand far greater respect than if you volunteered that same information unsolicited. It also adds a layer of depth and authenticity that draws people in.

I would much rather have men ask why I have no statue, than why I have one.
— Cato the Elder

Action outweighs talk. This approach lends you far more credibility. Those who self-promote and overshare at every chance lose the force behind their voice. It becomes noise, lost to the wind.

People don’t need to know everything about you. In an era that’s obsessed with social media and vulnerability, it might seem counterintuitive. But the less you talk about yourself and the less you reveal up front, the more it draws people in. 

The world gravitates towards depth. Not shallow plays at status and virtue signaling.

Silence is a form of absence and withdrawal that draws attention; it spells self-control and power.
— Robert Greene

This is not to say that you should become a hermit and refuse to reveal anything about yourself in conversation. But it is to say that you should use discretion. If you’re able to refrain from oversharing, you provide yourself an opportunity to get beyond your ego. This allows you to actually listen to the person in front of you or shift your focus towards the work that matters.

Live by your principles, not by status. 

Meaningful progress and satisfaction come from deep work and realizing your own potential. In my case, it came from the music itself. And now it comes from quiet moments of writing. It’s the creative process that keeps me going. And I know I can sustain that indefinitely. It’s independent of the fleeting highs of recognition.

Pursue the things you love, create meaningful work, and let people find out on their own terms. Whatever you have to say will be far more effective when you’re not using brute force to get your message across. 

The further you can distance yourself from your ego or your obsession with personal brand, the greater respect you’ll demand. More action, less talk. Reveal your depth little by little. That’s how you draw people in, build lasting relationships, and create something that strikes a deeper chord in others. 

And for God’s sake, please don’t walk around telling people you’re a singer-songwriter.

Authenticity Is Your Now

Authenticity is not a fixed point on a map. It’s fluid, much like your identity, and shifts over the course of your life.

It’s easier to trick yourself into believing the feel-good advice that your voice comes from a sudden revelation. You just have to wait for that moment. And once you’ve found it, the entire picture comes into focus and remains that way for life.

But authenticity is found through fragments. It evolves over time. It’s a moving target that falls out of focus and can be lost to the chaos of life.

Authenticity is less about identifying a singular purpose and voice that should define your entire life. It’s about finding and trusting your voice today. In other words, embracing the impermanence of your identity, knowing that it can and will change.

How you live your life–your interests, principles, and priorities–will evolve over time. As you grow, you’ll add depth to your voice. If you remain the same for too long, that’s when you know you’ve stopped learning or are clinging to an expired version of yourself.

It’s easy to get caught up in the expectations you hold for yourself or that others project upon you– who you should be, where you have been. If you fuel these doubts, you can opt out of the unknown and find comfort in your plateau. But you won’t grow through the familiar, and you won’t find alignment.

Your sense of authenticity–your now–is something that’s all your own. It’s discovered, developed, and deepened, by the obstacles you face, the uncertainties you navigate, and the inspiration you find along the way.

If you want to create something that matters–to both yourself and others–you have to create from where you currently are in your life. That’s how you build momentum and depth. Trust yourself.

It’s the difference between artists and entrepreneurs who get lucky once and those who sustain success over decades. If you cling to what got you there in the first place, you’ll fail to evolve and render yourself irrelevant.

Artists who reinvent themselves fight for projects that allow them to grow, stretch their abilities, and discover new things. In doing so, they create from a place that resonates with them at a single point in time.

Over the course of years, a series of single brush strokes reveals an evolving sense of authenticity.

Bob Dylan, one of history’s great songwriters, has reinvented himself time and time again throughout his career. He’s altered his voice and bridged various genres, beginning in folk, shifting towards rock, and experimenting with country and Christian albums along the way.

Five decades later we can step back and admire his trajectory–how he’s pushed himself to grow, defy expectations, and channel that into his art. Time makes this seem inevitable, as if all he had to do was fall in line with destiny. But that fails to take into account the years of criticism, outrage, and uncertainty Dylan faced.

Authenticity–creating from who you are today, despite expectations tearing you in different directions–is not for the faint of heart.

Dylan threw the folk community into a fit of rage when he “went electric.” He could have stuck with what was working and fallen in line with their expectations, but validation was never his primary motivation. He sought meaning over influence at each step of his career. As a result, he achieved exactly that–lifelong influence.

Dylan resonates with people because his songwriting tracks his own development as a human being. His songs reflect who he was–his observations, experiences, and imagination–and who he refused to be at each point in time. Dylan’s career is a master class in embracing the impermanence of identity and authenticity. The fragments of himself that he brought to life shows he understands this in a deep way.

There were a lot of better singers and better musicians around these places but there wasn’t anybody close in nature to what I was doing. Folk songs were the way I explored the universe...
— Bob Dylan

There’s no single template for finding your voice as it exists today. It’s different for each person. Legendary director, Steven Spielberg, was quite different from Dylan. Dylan had unusual depth which he developed at an early age. Spielberg developed his own sense of depth over decades.

Spielberg’s progression from Jaws (1975) to Schindler’s List (1993) demonstrates this. In those eighteen years, he grew by finding projects that spoke to him at a specific point in time. What felt authentic to him in 1965 was entirely different than 1993. That doesn’t negate his early work, he was just creating from a different place.

Spielberg’s voice evolved through his films, just as Dylan’s did through his albums. That’s why they’ve remained relevant for so many years. They’ve changed, adapted, and grown. But most importantly, both have had the courage to speak from where they were in each present moment.

Both faced criticism along the way for unpopular decisions, but that’s the irony of the whole thing. People are enraged by change, but if you stay the same you guarantee failure. You lose touch with yourself, a sense of fulfillment in your work, and a deeper connection to your audience.

Before you release your work into the wild, fight like hell to make sure it first resonates with you.

No one gets it right each time. There will be times you lose your sense of authenticity. Not even Dylan and Spielberg are immune to the chaos of life. But when the intention and awareness are there, it’s easier to rebuild and rediscover a sense of momentum.

Life is motion. Authenticity is about finding harmony in that motion.

It’s not always easy, but it’s meaningful. Allow yourself to evolve through uncertainty. When you find the courage to speak from this place, you add unusual depth and clarity to your voice. That’s what draws people in.

Start by reflecting on what resonates with you at this point in your life–experiences, interests, observations, values. Authenticity is your now. No matter where you are, trust yourself to create from who you are today.

30 Lessons for Living at Your Best by 30

Behind almost everything I’ve done in my 20s there’s been a single motivating factor–discovering what it means to live well. By living well I don’t mean extravagantly. I mean determining what I want out of life, living in a way that aligns with those values and principles, and learning in everything I do. In other words, striving to be the best version of myself.

While there will be inevitable ups and downs, no matter where you are, you want to be able to step back and see a clear upward trajectory which tracks the course of your life.

The best way to ensure this is by learning from your failures, putting in the work, and aspiring to be at your best. There will be days, weeks, even months, when things might seem to stagnate or head in the opposite direction, but you need the mental toughness to adapt and push yourself towards progress, as defined by you.

With my 30th birthday in sight, I’ve narrowed in on a few hard-fought, as well as mind-numbingly simple lessons, which have helped me establish a sense of this trajectory. I don’t presume to have all the answers. These are just the lessons that have resonated strongest with me over the past decade. Remember, there’s no “right” path, but I hope these prove useful as you find your own way.

1. Get the essentials down first

If you expect to feel good and achieve anything in your life, you need to prioritize sleep, exercise and eating well. These are the non-negotiables. You can’t neglect yourself and expect to function at a high level. This is foundational to everything else on this list.

2. Limit the number of do-overs

Don’t underestimate the power of avoiding dumb decisions. Most of the trouble that people run into is self-inflicted. There are enough obstacles ahead of you as is, don’t create extra work for yourself. This doesn’t mean you have to be brilliant in every decision you make, just avoid the big mistakes. Focus on making well-rounded, rational decisions each day, and allow compound interest to run its course.

3. There is no way things are “supposed to be”

The sooner you give up an imagined reality, the better you’ll be able to negotiate the way forward. Close the gap by differentiating between internal and external expectations and assigning each their proper weight. Prioritizing internal expectations is the path towards gratitude and self-sufficiency. External expectations introduce dependencies. Don’t place a premium on things you can’t affect.

4. Create more, consume less

What you consume doesn’t make you unique. The fact that you’re a fan of the Golden State Warriors, listen to Ed Sheeran, watch Game of Thrones, and only buy Apple products, are not unique identifiers. What you create and what you’re putting out into the world is what defines you.

5. Life is a single player game

You can’t expect to retain your sanity if you insist on comparing yourself to people heading in an entirely different direction. Measure you against you.

6. There is no substitute for true resourcefulness

One of the biggest obstacles I faced when I took my first job out of college was my inability to handle ambiguity and uncertainty. The predictability of the curriculum and instruction in school won’t do you any favors here. As it turns out, life is far more about resourcefulness than a checklist of prescribed actions. You must learn to adapt, teach yourself, and create your own momentum. There is no blueprint to walk you through every step of your life.

7. Put in the self-work

It’s not going to be easy, but it’s going to be worth it. Your 20s should be a decade primarily dedicated to yourself so you can figure your shit out. Before you enter into any relationship or realize any of your aspirations–if you don’t want them to go up in flames–you need to be self-aware and self-sufficient.

8. Directions in life are mutually exclusive

For the first half of my 20s I wanted to be everything, so I was unable to commit to anything. But the earlier you cross the irrelevant off your list, the faster you’ll be able to make meaningful progress and give your complete attention to the things you can’t live without. If you’re unsure where to start, try this exercise from Warren Buffett and double down on those things.

9. JOMO (joy of missing out) > FOMO (fear of missing out)

“FOMO” is another way of saying you’re incapable of prioritizing–you want to be everything and everywhere, which is an impossibility. Once you’ve figured out what’s important to you, passing on unnecessary obligations or engagements which you’re not invested in will be a source of great satisfaction.

10. What you walk away from defines you as much as the things you stick out

Whenever you encounter a moment of self-doubt or the urge to quit, ask yourself, do you feel like quitting because it’s difficult? Or do you feel like quitting because it contradicts your character, values, or priorities? The former means you should stick it out, the latter means it’s time to call it quits.

11. Growth is nonlinear

As Nassim Taleb explains in Fooled by Randomness, nonlinear relationships are the rule, not the exception. We mistakingly believe that if two variables are causally linked, a steady input in one should result in a positive linear progression in the other. Life doesn’t work that way. You can’t always expect visible progress when comparing one day to the next. You might have to dedicate years to your craft before something clicks. Remember, it’s your overall trajectory that matters, not the noise you encounter on a daily basis. The shorter the time frame, the more variance there will be–focus on the big picture.

12. Figure out what you can sustain indefinitely

That’s what it’s going take to set yourself apart. Most people drop off at the first sign of adversity or boredom, outlast them.

13. Leverage compound interest

The power of compound interest applies to almost everything in life, not just financial investments. For most hard-working, talented people it’s just a matter of time. Years of consistently showing up, learning, and dedicating time to your craft will pay dividends. The power of small, calculated decisions, habits, and behaviors grows exponentially over time.

14. Physical endurance builds mental endurance

Most people live in fear of the slightest discomfort or inconvenience. If you’re able to practice consistently pushing yourself to the point of discomfort and sustaining at that level, you begin to build resilience. In this regard, physical endurance translates into mental toughness.

15. Lasting comfort is found by embracing discomfort

Intermittent periods of discomfort prepare you to handle a wider range of potential scenarios. This helps you expand the confines of your current comfort zone and, ultimately, experience less discomfort than those who cling to convenience and familiarity. The latter find themselves in positions of considerable vulnerability–rigid and unable to adapt. This is the paradox of comfort.

16. Stillness is the best lesson traveling will teach you

I was an insatiable traveler for most of my 20s, visiting 25 countries and four continents. The only thing I’ve found more fulfilling than travel is learning to be still and content at home. Travel, go see the world, live somewhere new–otherwise, you’ll regret it later on. But this should lay the foundation for you to find peace in your future immediate surroundings. And this is the real value of experiences gained from travel–they help you build a broader perspective and a stronger sense of identity and appreciation at home. There’s nothing more fulfilling than the sense of gratitude that comes from moments when you’re content right with being right where you are.

17. Get a dog

Very few things have had a more profound, positive impact on my life. Presence, patience, empathy, joy–a dog will remind you of these values every single day.

18. Read like your life depends on it

To quote Naval Ravikant, once, “The genuine love for reading itself, when cultivated, is a superpower. The means of learning are abundant–it’s the desire to learn that is scarce. Cultivate that desire by reading what you want.” And twice, “Reading science, math, and philosophy one hour per day will likely put you at the upper echelon of human success within seven years.” The power of compound interest applies as much to reading and building better mental models as anything else.

19. No one alive has all the right answers

Avoid the urge to overidentify and reach for absolutes. Learn to live in the gray area. That’s what separates lifelong learners from pretenders.

20. General advice > specific advice

You will encounter mentors who want to prescribe specific advice. For the most part, it’s ineffective, because there is no single path to success. You will never be able to replicate the lives of those you admire. But you can examine the systems and mental models that give them their edge. This is where you’ll find the truly valuable lessons that you can apply to your own life, direction, and decision making.

21. Avoid ideologies at all costs

As Charlie Munger suggests, “Heavy ideology is one of the most extreme distorters of human cognition.” There’s no better way to impair your own rationality and decision making. Ideologies will drive you towards confirmation bias and close-mindedness.

22. Legacy is a mirage

If you have any sense of historical perspective, you’ll realize that you won’t be remembered. The desire for legacy is narcissism in disguise. This realization should be empowering, not disheartening. It will allow you to go out and make a difference now, instead of attempting to preserve some future image of yourself when you won’t be around to reap any of its benefits.

23. “In victory, learn when to stop.”

Drifting expectations are dangerous. This is one of Robert Greene’s 48 Laws of Power. You have to allow yourself time to reflect on what you have and how far you’ve come. Those who refuse to come to terms with this lesson find themselves as textbook examples of hubris, brought down by the same insatiability and arrogance that led them on an accelerated, unsustainable path towards the top. This is the reason people lose fortunes, families crumble, companies self-destruct, empires fall. More is not always the answer. Know when you’ve won.

24. Money matters

In The Geometry of Wealth, Brian Portnoy explains that wealth and investing are about funding contentment and underwriting a meaningful life, as defined by you. Not about getting rich, having “more,” and losing yourself on the hedonic treadmill. There is a point of diminishing returns when it comes to the impact of income on experiential happiness (around $75,000), but there is no cap on reflective happiness. Wealth is a tool to achieve freedom, self-sufficiency, and spend your time exactly how you want to.

25. You can’t have it all, but you can have what you prioritize

Don’t try to keep up with those living an extravagant lifestyle. If your goal is to fund your own contentment and underwrite a meaningful life, you need to figure out what’s most important to you. Spend money on those things, without hesitation, and invest in yourself. Live frugally and cut costs everywhere else.

26. Moderation is king

This is the single most important value no one has told you about. Avoid excess. As a society, we pride ourselves on extremes. But even our virtues, when taken too far, collapse into their opposite–crippling flaws in character. Find the golden mean.

27. Everyone is facing their own adversity

I’m reminded of this on an almost weekly basis. The carefully curated versions people project of themselves on social media don’t reflect what’s actually going on in their lives. You never know what someone’s going through or what they’ve been through. Be kind.

28. Commit to the people who share your most important values

I can’t say it better than Ray Dalio, “When you have alignment, cherish it. While there is nobody in the world who will share your point of view on everything, there are people who will share your most important values and the ways in which you choose to live them out. Make sure you end up with those people.”

29. Build a philosophy of life that works for you

Philosophy is about the art of living. It will make these lessons easier if you have a reference point that reflects your most important values and principles. For me, this is a version of Stoicism. Go out there and find one that works for you, or create your own. Whatever you do, establish one, because this adds purpose, direction, and serves as a constant reminder of what’s worth attaining in life.

30. There’s no secret to happiness, other than gratitude

The single trait that the happiest people all have in common is a profound sense of gratitude. They wake up in the morning and feel lucky, with an appreciation for life and their current position. I achieve this by reflecting on all the good things I have, worst-case scenarios, and the finer details in my immediate surroundings.


The only true failures in life are moments of apathy or defiance, when you’re unwilling to learn. Knowledge and experience count for little if you’re unable to commit them as life lessons.

Determine what you want out of life, live in a way that aligns with those values, and never stop learning. That’s what it takes if you want to discover what it means to live well and maintain an upward trajectory over the course of your life. Go out and find the lessons that resonate strongest with you.

Top 6 Books for Better Mental Models (<200 pages)

Many of the smartest minds throughout history–those who have demonstrated mastery in their respective fields and contributed something meaningful to the world–have favored a multidisciplinary approach over specialization. They’ve recognized that the more flexible and wide-ranging your mental models, the stronger your cognitive abilities, and the less rigid your thinking. At an individual level, it’s not only more effective but also more fulfilling.

A multidisciplinary approach leads to resourcefulness, ingenuity, and resilience. It better prepares you to develop each of these skills, navigate inevitable obstacles, and build your own momentum. It’s the antithesis of confining yourself to a single discipline with a shallow skill-set and isolated mental models.

In fact, the defining feature of a multidisciplinary approach is its dynamic latticework of mental models. This is achieved by broad exposure to a range of subjects, which allows you to leverage and connect the most relevant knowledge from each. By positioning yourself at the intersection of multiple disciplines, you cultivate the ability to tie together seemingly unrelated concepts in a way the vast majority are incapable of. It’s here where the most creative, innovative ideas are discovered.

Last year I wrote an article on the beginner’s guide to a multidisciplinary approach and recommended four books for building better mental models. It resonated with quite a few people who were looking for an introduction to this concept. In revisiting this theme, I’ve wanted to provide a new reading list that’s even more accessible–each book is under 200 pages.

While this is in no way comprehensive, it is my hope that this will help you begin building your own framework across multiple disciplines. If you’re up for a short read, dig in.

1) The Obstacle Is the Way — by Ryan Holiday

One of the most accessible modern introductions to Stoic philosophy. Holiday examines the inevitable obstacles we all face in life, how to better frame them as opportunities to practice virtue and harness them to create momentum of our own. He structures the book around the three interconnected disciplines required to overcome any obstacle: perception, action, and will. There’s an incredible amount of knowledge packed into these 200 pages. No matter what challenges you face or where you’re trying to go, it’s a great resource for fine tuning your attitude, strategy, and mental toughness. Inspired by Marcus Aurelius, “The impediment to action advances action. What stands in the way becomes the way.”

Talent is not the most sought-after characteristic. Grace and poise are, because these two attributes precede the opportunity to deploy any other skill.
— Ryan Holiday

2) The Geometry of Wealth—by Brian Portnoy

A look into the relationship between money and meaning. Portnoy suggests that wealth and investing are about funding contentment and underwriting a meaningful life, as defined by you. Not about getting rich, having “more,” and losing yourself on the hedonic treadmill. He explains that simplification is the path towards effectively managing expectations in money and life–and the trajectory of a happy life is shaped by expectations. The Geometry of Wealth is as practical as it is philosophical. À la Charlie Munger, Portnoy emphasizes individual behavior, mainly self-control and self-awareness, as the most important factor in investment success. He suggests we focus on being “less wrong” over being “more right,” in the sense that asset allocation is far more important than security selection and market timing. But on the path towards adaptive simplicity in investing, he also digs deeper into its importance in our broader lives, offering an enlightened discussion of experienced vs. reflective happiness, expectations, and human nature.

The ‘good life’ is not the tweak of ephemeral pleasure, but the engagement with more meaningful, virtuous pursuits. Momentary pleasures are distinct from the enduring gravity of meaningful experience.
— Brian Portnoy

3) The Bed of Procrustes — by Nassim Taleb

Great introduction to Taleb’s ideas on uncertainty, which he discusses in detail in his other books that make up the Incerto series: AntifragileFooled by Randomness, and The Black Swan. This book offers a succinct look into how we deal with what we don’t know. Taleb considers our tendency to package and reduce ideas into neat narratives that fit within the constraints of our limited knowledge. I would argue that he’s one of the most original, brilliant minds of our time.

Knowledge is subtractive, not additive–what we subtract (reduction by what does not work, what not to do), not what we add (what to do).
— Nassim Taleb

4) Real Artists Don’t Starve — by Jeff Goins

Practical and refreshing resource for smart creatives and entrepreneurs. Goins picks apart the myths surrounding the Starving Artist and offers an improved alternative of the Thriving Artist. There are dozens of useful rules of thumb you can apply to your own position, no matter where you are. Thriving Artists build their creative dreams step by step (not overnight). They focus on rearrangement and building upon the work of those who have influenced them (not obsessing over originality). They leverage their existing jobs for resources (not quitting too early and without reason). They recognize the value of a multidisciplinary approach and multiple revenue streams (not mastering a single skill and risking it all on a single bet). Goins follows this same pattern throughout the book, detailing the difference in mindsets, how to position yourself in the market, and how to make a living. It’s a modern-day guide for living a better, more creative life, without struggling for the sake of struggling.

Thriving Artists don’t just live off their art. Like good investors, they keep diverse portfolios, relying on multiple income streams to make a living. Rarely do they go all in on any single area of work. The challenge, then, is knowing what investments to make and when.
— Jeff Goins

5) The Inner Game of Tennis — by W. Timothy Gallwey

I’m usually skeptical of anything that remotely resembles sports as a metaphor for life, but this a tremendous read. It’s less a book about tennis (although there are a few sections) and more about the art of relaxed concentration. It’s a simple but profound concept that suggests the secret to performing your best is in developing a quiet confidence, and most importantly, not trying too hard. Gallwey draws a line between Self 1–the conscious teller, and Self 2–the doer. He advocates developing greater trust in Self 2, which helps to cultivate effortless concentration (flow), instead of a more tense, overly controlled approach which creates an unnecessary obstacle. Gallwey also offers an insightful perspective as he digs deeper into concepts including judgment, awareness, ego, and mindfulness, which adds another dimension to the book.

The player of the inner game comes to value the art of relaxed concentration above all other skills; he discovers a true basis for self-confidence; and he learns that the secret to winning any game lies in not trying too hard.
— W. Timothy Gallwey

6) Tribe — by Sebastian Junger

Clear, concise, and thought-provoking read that examines the struggle to find loyalty, belonging, and meaning in modern society. Junger spotlights military veterans and the growing rates of post-traumatic stress disorder, but he also takes a step back to examine the human condition at large. He discusses hardship, raw experiences, social bonds, community, mental health, and what we can learn from tribal societies. Tribe explains that there are three essential needs that must be met if we wish to feel content–the need to feel competent at what we do, the need to feel authentic in our lives, and the need to feel connected to others. Junger considers the effects of their absence and makes a compelling case that we should strive to rediscover and prioritize their importance.

Human beings need three basic things in order to be content: they need to feel competent at what they do; they need to feel authentic in their lives; and they need to feel connected to others.
— Sebastian Junger