Self Improvement

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 Art of Drawdown Periods

Inspiration is important. Your influences matter. But you also need time to process, reflect, and create your own connections before jumping into your next project. Whether that’s a book, startup, or scientific theory, the lesson holds true for artists, entrepreneurs, and scientists, alike.

Best-selling author, Ryan Holiday, refers to these as “drawdown periods.” In the months leading up to writing a new book, Holiday guards himself against new information with the potential to clutter this mind. Instead, he seeks a period of stillness where he’s able to distill information and settle his mind before jumping off and creating something new.

“For one of my books I gave myself a January 1 start date for the writing. Two months before, in November, I entered my drawdown period. No more reading or rereading. Just thinking. Long walks. Resting. Preparing.”
— Ryan Holiday

The danger of neglecting a drawdown period is failing to create a buffer where you’re able to discover and piece together your own thoughts on the subject. Instead, you’re just regurgitating the latest idea or concept you’ve heard, as if it’s your own. To be fair, this is human nature — we’re highly impressionable, social beings.

But creating a little more distance is a good thing. It provides additional perspective that you’re able to bring back to your work. Without this, you’re just facing an onslaught of information and distraction which can be difficult to make sense of.

Is your idea worth pursuing?

Above everything else, drawdown periods help inform whether or not an idea’s worth pursuing. The original source of “drawdown periods” — where Holiday borrowed the concept from — was military strategist, John Boyd. After he encountered a breakthrough or exciting new idea, he would spend weeks examining it, assessing its originality, and stress-testing it for problems. If it survived this period, he knew it was worth investing in.

The greater the endeavor, the more vital a drawdown period becomes. It’s important to act when inspiration strikes as it relates to the little things — an article, a small experiment, a new tactic. But the mountains — new books, startups, theories — are worth reflecting on before jumping in.

This helps create a natural filter for the things you’re not completely invested in. If the idea still resonates with you tomorrow, next week, next month, you might be on to something.

Tapering before the race

Far from killing inspiration, drawdown periods promote creativity. They allow you to find your voice and the guiding principle behind your next project. Without this, it’s impossible to sort through what’s your own.

Drawdown periods are the calm before the storm. If you set off scrambling without first setting your feet, you’re putting yourself behind from the start. While everyone loses their way at some point, it’s important to have a sense of your guiding principle — this initial footing — that you can return to along the way. And the best way to establish an early version of your guiding principle is by creating room to reflect before taking the leap.

Creative work is difficult enough, as is. Don’t make it more difficult by cluttering your mind at the start. Allow yourself time to breathe before setting off on your next pursuit.

It’s similar to tapering before a race. If you’re rested, you’ll be in better condition to handle the strenuous demands of the real race and guard yourself against burnout. In endurance sports, two days before a race, your metabolic fitness level is what it will be for the upcoming race. No matter how hard you train during those final 48 hours, you won’t see any benefits to your endurance in time for the race. Rest matters.

The value of tuning out

In 1902, Albert Einstein took a job at the Swiss patent office. The years he spent there could be considered the ultimate drawdown period. It was challenging enough to keep his mind engaged, but not enough to distract him from his more important focus on comprehending and redefining physics.

Three years later, Einstein published his paper, “On the Electrodynamics of Moving Bodies,” which outlines the special theory of relativity. Its contributions to the field of physics were profound. But one of the most astonishing things about the paper was that it had exactly zero footnotes or citations. It was like he reached the conclusions through years of pure thought, without listening to outside opinion.

While Einstein is an extreme example and a profound abstract thinker, the underlying lesson holds true. For originality and creativity, sometimes you need to allow yourself to tune out.

“If you’re constantly exposed to other people’s ideas, it can be tough to think up your own.”
— Jake Knapp + John Zeratsky

Deliberate or impulsive?

Drawdown periods aren’t an excuse to avoid getting started. You’re never going to be as prepared as you might like. Drawdown periods are more about giving yourself a moment of calm before the grind of creating something from nothing. New startups, books, and theories can take years, if not decades, to develop.

The difference between great artists, entrepreneurs, and scientists is the difference between drawdown periods and procrastination. Drawdown periods are deliberate. Procrastination is impulsive.

At a certain point, it helps to limit exposure and turn things back to yourself. Allow yourself to mull ideas, forge connections on your own terms, and see what comes out of it. It’s impossible to find your own voice if you’re bombarding yourself with other people’s ideas without giving yourself time to breathe.

Drawdown periods offer a temporary refrain when you’re able to step back and see the terrain. This allows you a chance to appreciate the interconnected whole and create connections or bridge ideas that you might have otherwise missed. The more perspective you can build, the better you’ll be for it. And the same goes for your craft.

As a smart creative, drawdown periods are essential. Give yourself time to prepare, rest, and reflect before your next endeavor. You’ll need every ounce of energy you have if you want to get your thinking clean and bring the best version of an idea to life.

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.