Growth

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.

What Your Painfully Slow Hiring Process Says About Your Product

A few years back I interviewed for a product role with an event management company. The beginning of the process was typical – I visited their local office for three hours of initial interviews, followed by another three hours of virtual interviews with their San Francisco office.

At that point, the fit was a maybe on both sides. And if it’s a maybe after 10 hours of interviews and preparation, that means it’s a no.

Instead of either of us calling it what it was, the company requested that I complete a four-hour homework assignment to gather just a bit more information. The circus continued with dozens of texts, emails, calls, and another on-site interview. And finally, I was extended an offer.

While I should have drawn the line before the homework assignment, the indecision on their part gave me a more accurate understanding of their product development approach.

How you hire reflects how you build

How you hire your product team reflects how you build product. Slow, timid, and scavenging for just one more piece of information? Or knowing what’s critical, pushing forward, and making the best decision based on the available information?

There’s always going to be uncertainty and risk involved in hiring, just as there is in building product. But it’s the amateur product teams who spend weeks agonizing over decisions, failing to account for the value of time.

During interviews, if you experience tactics intended to stall or an exaggerated struggle to make decisions, there’s no reason you should expect anything different in how the product team operates.

I turned down the offer, despite the sunk cost, because of the worrisome parallels. You can tell a lot about product leadership based on the quality of communication and the speed of decisions.

This was one of the determining factors I used to evaluate my current position. It was a no bullshit interview process – the best I’ve ever been a part of. And the hiring process on our product team has proven to be an accurate reflection of our approach to product development.

What does your hiring process say about you?

Consider what your hiring process says about you and your team. If you’re drawing out your interviews for weeks, you’re likely asking the wrong questions or afraid to call a “maybe” what it is, a no. Instead, determine what you’re looking for, move quickly, and operate with conviction (strong opinions, loosely held).

For a better starting place, seek out high-integrity, curious people who add diversity of thought to your existing team. Questions should be geared around this, as well as some combination of analytical skills, creativity, cross-functional experience, and leadership.

And when you’re on the other side of the interview, consider the product, culture, and growth. But don’t give a free pass on the hiring process. If you look close enough, you’ll catch a glimpse of how the product is actually being built.

The best product teams know what they’re working towards – in both their day-to-day and hiring. They’re able to identify what matters, push things forward, and make quality decisions based on the available information. Seek out, and aspire to build, product teams who demonstrate this in every aspect of their work.


*This article was originally featured on Mind the Product

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.

Indecision in Product: How to Avoid Becoming a Bottleneck

A few years ago, comedian Aziz Ansari released a Netflix special called “Live at Madison Square Garden”. During his set, he joked about the effort required to buy a new toothbrush. Not just any toothbrush would do, he had to have the best. He researched for hours, Googling “best toothbrush” and reading articles on the pros and cons of bristle strength. As he reflected, he questioned his indecisiveness and his desire to have the best when any toothbrush would have done the job.

For most of my twenties, I did the same thing. I researched every purchase – headphones, winter jackets, coffee grinders – in painstaking depth before making a decision. But, as I’ve learned, the quest for a perfect decision often does more harm than good.

Time is far more valuable than a marginally better solution. And if you’re leading product, the sooner you learn this lesson, the better. As a product manager, the worst position you can put yourself in is creating a bottleneck by making slow decisions.

A Case Study in What Not to Do

When I started my career, I joined a team building a web-based patient portal for healthcare providers. At the time, I was unaware “product” even existed. But I was forced to learn the space out of necessity. My first manager, Eric, was a walking case study in how you shouldn’t handle product decisions.

With something as simple as our landing page, Eric went back and forth for months. His opinion fluctuated on a daily basis. Without the autonomy to make decisions, our development team wandered without any real sense of direction or progress.

Each week followed the same pattern. The team would align on the problem, collaborate on ideas, prioritize features to build and test, then have the tables turned on them a few days later. Eric was obsessed with surveying every available option. He operated with the constant fear that we might have missed something better. As a result, we wasted months of time and energy considering alternatives with negligible differences.

And if we were unable to make decisions on something as simple as the landing page, imagine what that did to our product which was heavy on integrations with practice management and electronic health record systems. Not to mention the most important piece–the user experience of patient-facing features.

The lesson: hesitation kills creativity, morale, and momentum.

Be Wrong as Fast as You Can

Leaving your team in limbo without a sense of direction is a far worse position to be in than taking a wrong step. It’s easier to forgive a wrong decision than it is a painstakingly slow decision or the failure to make a decision.

For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus.
— Scott Belsky

If you’re wrong, you want to be wrong as fast as possible. Andrew Stanton, director at Pixar, uses a similar model to evaluate decisions on his films. When faced with two hills and you’re unsure which to attack, the best course of action is to hurry up and choose. If you discover it’s the wrong hill, you can always turn around and attack the other. But you will fail for as long as you continue standing still or running in between the hills.

There will be things you miss and ideas you haven’t thought of. But you’re going to learn more by putting yourself and your product out there than you will trying to make the perfect decision each step of the way.

How Reversible Is This Decision?

For many product managers, faster decision making is the most significant improvement you can make. Especially when it comes to the trivial.

While somewhat elementary, the Pareto Principle should be foundational to your decision making. Which solution generates 80% of the value? Forget the other 20%. As Aziz points out in his toothbrush dilemma, perfection requires far more deliberation and research than it’s often worth. If your default position is hesitation – pausing to consider every alternative – you’ll stifle creativity and lose your team along the way.

You can also make immediate improvements by asking yourself a single question, “How reversible is this decision?” Tobi Lütke, Shopify’s founder and CEO, uses a similar strategy by asking himself, “How undoable is this decision?” Decisions that are reversible – most of the ones you make on a daily basis – deserve quick answers.

Better yet, if you have other product managers, developers, or designers coming to you with trivial decisions, empower them to make the call. Performance will improve when there’s a greater degree of autonomy and teams have more creative control over the product.

The decisions that aren’t easily reversible are the rare ones that Lütke spends his time deliberating before coming to a decision. In 2008, he had to decide whether Shopify would remain the lifestyle business he set out to build or shift towards a growth company. With venture capital implications, it warranted thoughtful consideration.[1]

Slow, deliberate decision-making can be a significant advantage in avoiding massive mistakes. But the reality is that most decisions you have to 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 buying a toothbrush or choosing between two styles on a landing page.

Far too many product managers are focused on perfection from day one – an impossible task. Instead, with proper context, you should focus on making faster decisions. You’ll always be able to adapt along the way as you learn.

If you want to avoid becoming a bottleneck, just keep things moving forward. You’ll be better for it, your team will be more engaged, and you’ll be able to build better products. Decisions lead to progress because they improve the rate at which you learn.

Both life and product become much easier when toothbrush decisions aren’t monumental efforts. Learn to value your time over a marginally better solution. People appreciate decisiveness. And above all, that’s the sign of a true leader in product.



[1] Lütke still felt like he was far too slow in coming to this decision (lifestyle vs growth). To help speed up bigger decisions, he now tries to get as far ahead as he can in terms of vision and where the company is heading. In other words, being less reactive to inevitable, significant decisions that need to be made.

*This article was originally featured on Mind the Product

The Power of Your Early Influences

Many of us are embarrassed by our early influences. No one admits to how much they loved listening to Matchbox Twenty, watching Spielberg films, or reading The Hunger Games. Everyone’s too worried about promoting how refined their tastes are.

But underneath all that virtue signaling, the truth is that your early influences were foundational to many of the things you find inspiration in today. They’re the branches who first led you to the mediums and ideas that resonate strongest with you.

One of the most important influences of my early twenties was author Tim Ferriss (and he continues to be to this day). But because of how many people he’s reached–also known as success–he has his haters. While an aversion to the mainstream might be inherent to high-brow culture, it’s ridiculous to think you’re above your early influences. Without Ferriss, I wouldn’t have discovered eighty percent of the most influential books I’ve read in recent years.

The Branches: Tim Ferriss led me to Derek Sivers, who led me to Nassim Taleb and Stoicism, which led me to Ryan Holiday, who led me to Robert Greene. These are the authors, entrepreneurs, and philosophers who have had the most profound influence in my life over the past ten years. 

Foundational influences matter because they connect us with more specific interests and allow us to explore those in greater depth. For me, Ferriss is brilliant in orchestrating these connections.

The same concept holds true for influences in any other area of interest or field of study. Those who first peaked your curiosity–regardless of reason–helped lay the groundwork for where you are today. If you trace the past decade of your deepest interests, you’ll start to see a map similar to the one above. 

If you’re too worried about virtue signaling and showing off your refined tastes, you’re not only missing the point, you’re actively discouraging others. 

It’s important to allow your tastes to evolve, but don’t dismiss someone who’s just starting out. Allow them the an opportunity to explore on their own without telling them what they should care about. 

Investor and entrepreneur, Naval Ravikant, offers advice for early readers that’s applicable across disciplines, “Read what you love, until you love to read.” People who love to read and dig into books on complex ideas started by reading simpler subjects that resonated with them years earlier. 

You begin based on where you are today and what your natural interests are. Otherwise you don’t learn to love reading (or music, film, sports, finance, international business, teaching, technology). And if you don’t develop a love for reading itself, you’re never going to make it from R.L Stine’s Goosebumps to Nassim Taleb’s Incerto

If you’re too busy feigning interest in what you’re supposed to care about, instead of what you actually enjoy, you’ll kill your natural curiosity trying to keep up with the connoisseurs. 

Your early influences, based on your unique interests, are the ones who help build your latticework of mental models and network of influences. From here you can begin branching out to connect different ideas, authors, concepts, and styles.

Embrace your early influences. The only thing that matters is what resonates with you at this point in your life and what you find inspiration in. It’s okay to listen to a catchy pop song or read a pop-fiction title just because you enjoy it. That’s reason enough. Let the foundation lead the way.