10 Lessons on the Road to 33

Birthdays and New Years serve as two natural checkpoints for me. Birthdays act as a time to reflect on what I’ve learned and consider lessons that have resonated strongest over that year of my life. Whereas New Years signal it’s time to set five primary goals and assess how well I did against the previous year’s goals. Most years I publish these reflections, the following are 10 lessons that stood out most over the past year. 

1) Show up, even when it’s inconvenient 

Fighting through canceled flights, delays, and traffic jams to show up for someone when they need it most, even if you’re only there for an hour, matters. Regardless of what plans you might have made for your evening or weekend. The timing of events beyond your control might be inconvenient. But the universe isn’t on your agenda. And there isn’t some perfect version of the future where your life is free of challenges. The challenges and obstacles are what give life meaning. You can point to those as your excuse, or you can show up anyway when it matters most. 

2) Commitment adds meaning

Just as obstacles add meaning, so too does commitment—whether your relationships, career, hobbies, you name it. Directions in life are mutually exclusive. In my early 20s, I optimized for optionality and never committed to anything. Many of these things were unfulfilling and left me restless. But once I started to cross options off my list and double down on the people and things I cared about most, life became far more rewarding.

Getting married to my favorite person in the world this summer after six years together has continued to deepen our relationship. The same goes for my career and the way it has been accelerated by committing to problems I care about solving and the vision we’ve crafted around solving those. 

3) You don’t have to agree with the entirety of someone’s opinions

Almost everyone has good ideas and bad ideas. And you don’t have to agree with the entirety of them. One good idea doesn’t mean every idea that a person has is worthwhile. Just as one bad idea doesn’t mean the entirety of that person’s ideas are garbage. This lesson shows up frequently for me in books. When I was younger, I would take the entirety of an author’s ideas in a book as truth. Now I find myself more often disagreeing with certain aspects, and that’s fine. This ability to balance multiple opposing views and perspectives is what leads to improved critical thinking. This also speaks to the danger of ideologies and blindly accepting a docket of opinions without thinking for yourself. Guard yourself against this at all costs. 

4) More music, less everything else

During the pandemic, this got away from me. I didn’t have my regular outlets at coffee shops or commutes to let go and listen to music. It was all work, all the time. And in the brief moments when I wasn’t working, we were watching Netflix. But music is the thing that allows me to reach a state of relaxed concentration where I do my best work. Making more time for this, creating focus blocks throughout my day to tune everything else out, and starting my day with music while reading or writing in the morning makes me happier. And the same goes for evenings at home. Just turning on music instead of the TV feels more rewarding than whatever show we might be watching. 

5) Focus on what’s within your control

As long as I’m around, I don’t think I’ll ever shut up about this. Focus more on yourself. Every second you spend projecting or losing yourself in imaginary conversations consumed by others’ opinions is truly wasted. Focus back on yourself. Most people waste away consumed by distractions without ever searching within. If there’s any sort of secret in this life, it’s figuring out what you want out of life, reframing that as an internal goal you can actually influence, and pursuing it with everything you’ve got. 

6) Happiness is knowing less about what’s going on in most people’s lives, not more

Comparison is the death of joy. Most people are far too connected and could use more distance. I can only speak to my life, but I am far happier when I know less about people outside of my closest group of friends and family. And that’s a group of about 10 people. Beyond that, it’s just noise. 

Certainly, you must care for your community. But your capacity to give a shit is limited. You have to pick your battles. Anyone who claims they can keep up with everyone and every cause is virtue signaling. Instead, focus on yourself and your family, fight for your cause, and ignore the bullshit. There’s only one way out of the noise most people find themselves consumed by—distance yourself.

7) In-person interactions hold company’s together

I’ve worked fully remote at different points in my career. I’ve never actively sought it out, it’s just worked out that way and I was rather indifferent to it. But over the course of the pandemic, I’ve changed my stance entirely. If your intention is to create an enduring company of top performers who band together to overcome challenging moments, co-located teams will crush remote teams. Fully remote teams sacrifice camaraderie, morale, and meaning in the name of short-term productivity. My expectation is that most fully remote teams will self-destruct over the next few years because they won’t be able to absorb the higher turnover caused by a lack of human connection. 

8) Appeal to Your audience’s self-interest

Whether it’s a presentation, email, article, you name it, most people start by focusing on what they want to say. That’s exactly the wrong path if you’re hoping to land your message. Instead, ALWAYS start by putting yourself in your audience’s position and emphasizing the benefit from their perspective. Addressing the ‘What’s in it for me?’ question within the first 30 seconds is the only way to capture attention, disarm, and influence.

9) your first responsibility is to shut up and listen

I’m surprised at how common this problem is. A new hire joins the company, insecure and eager to prove their value, they immediately jump to providing feedback and solutions without having any context of the business, the product, or the team. And in doing so, they immediately erode any semblance of trust and have to work twice as hard to rebuild that over months. Seems like a fun way to start. This seems especially rampant in senior leaders who come into companies and should know this lesson better than anyone else, but they turn out to be the worst offenders. 

During your first 30 days at any company, just shut up and listen. Regardless of what level you’re coming in at. True confidence can look like keeping your mouth shut and simply listening. This will help you build deep relationships that will serve you far better than attempting to offer up empty feedback that lacks context and only draws attention to your attempts to overcompensate.

10) to command respect, be fearless

Timidity kills careers. Jump into the deep end. Raise your hand. Aspire to always have skin in the game and never act like you’re above the work. Regardless if you’re a middle manager, executive, or individual contributor, the work matters. You certainly have to know how to delegate. Otherwise, you’ll drown. But there will be occasional points where you must go deep on the subject and fight alongside your team in the trenches. If you avoid this second piece, you will never command respect from your team. 

Reveal More, Signal Less, and Why Your Stories Matter

When I picked up writing again in 2014, for the first few years I shared exactly zero personal stories. I was shielding myself. But that also meant everything I wrote felt more theoretical than practical. I didn’t think I had the level of experiences required to write from a more personal place. I would doubt myself, asking who am I to share my own stories? It’s no surprise that during this time my audience failed to grow and the ideas I wrote about failed to resonate. 

Without a willingness to reveal something about yourself, your stories will forever feel hollow. 

Good storytelling is about creating a sense of shared humanity. That means revealing more of yourself and the struggles that make you human. It’s one of the most powerful ways to connect with people, but you have to approach it from the right angle. It’s not about attention seeking, virtue signaling, or posturing—whether hero or victim. It’s about connecting with others. 

The goal isn’t to create a moat and portray yourself as some fortress devoid of a single flaw—think early Tiger Woods. Sure, people might admire you, but it’s impossible to feel connected with someone like that. 

This was a tremendous benefit to Tiger early in his career. He scared the shit out of everyone else in the field because nothing about him seemed human. And while this aura might lend itself to a highly specialized, individual sport like golf, it doesn’t translate well across the rest of life. Most jobs and challenges you face require connecting with people.

You can’t lead, communicate, trust, parent, coach, teach, or learn without first connecting with the people around you. Growth is impossible if you refuse to ever let anyone in. 

What I struggled with in my 20s, whether knowingly or not, was posturing. I was pulling a Tiger and masking any flaws—though I made a few dollars less than him in the process. I was adamant about presenting a perfect version of myself, in both my career and writing. And while it felt safe for me, it wasn’t relatable. People crave real stories of personal struggles and triumphs that they can relate to in their own lives. Flaws reveal your humanity.

Ego is what holds you back from sharing your own faults and personal stories. It’s what prevents you from making yourself vulnerable. It’s the thing that says, people are watching, don’t reveal any flaws. But the catch is that by revealing your own shortcomings and demonstrating self-awareness, you’re able to connect on a far deeper level. Honesty about the human condition is what resonates with people. Your stories matter. 

“The call to lead well is a call to be brave and to say true things”

— Jerry Colonna

Abstract models and anecdotes only go so far. Most people couldn’t care less about your theories or concepts. In her book Talk Like TED, Carmine Gallo examines the most popular TED Talks and notes that those speakers spent roughly 80% of their time telling stories. That’s what people really want to hear.

Stories are the wrappers for your ideas, lessons, principles, theories, and concepts. Stories are what draw people in to actually listen to what you have to say. 

In the past, I used shells of stories to guard myself and protect my ego. I didn’t want to reveal any faults. But as it turns out, the less seriously I take myself, the more helpful I can be. I’m able to illuminate feelings and stories that others can relate to and see themselves in. And that’s the power of good storytelling. You reveal fragments that people are able to identify with and latch onto. You give voice and clarity to things that people couldn’t quite put their finger on. 

“Becoming a writer is about becoming conscious. When you’re conscious and writing from a place of insight and simplicity and real caring about the truth, you have the ability to throw the lights on for your reader”

— Anne Lamott

Your goal in storytelling is to reveal what makes you, you. Not the carefully crafted Instagram version you’ve created. By being real, you set the depth at which your audience is able to go with you.

It’s always better to be authentic and nervous than shallow and overly rehearsed. 

There’s an initial shock that comes from opening yourself up. But when you speak from your own experiences and bring out what’s inside of you, you can sustain that indefinitely. 

“A moment a story works is usually a moment of vulnerability.”

— George Dawes Green

Where you start to run into trouble is when you exploit “vulnerability” as a guise for attention. It’s impossible to maintain a facade of something you’re not. When attention seeking or virtue signaling dictates what you reveal, sooner or later you’ll be crushed underneath the weight of trying to keep that up.

Those who overshare fail to grasp this and end up exhausting their audience in desperate attempts for another hit of short-term gratification. There are boundaries.

At its best, vulnerability helps connect you with others. At its worst, it’s an attention-seeking behavior that those who thrive on a victim mentality lose themselves in.

It takes time to learn. If you run your own experiment—whether leading teams or writing articles—sooner or later, you’ll find that people gravitate towards what’s real. Because that’s what they can relate to. That’s what strikes the deepest chord. 

Over the past couple of years, I’ve started sharing real stories—my own fears, challenges, and struggles. This shift in my approach has improved my own storytelling significantly, as measured by the number of people reached and how strongly those stories have resonated with others.

Stories are how you communicate. Not instructions. Let people interpret things for themselves. Give those around you something real to connect with.

It’s easy to feel alone in this. But remind yourself that very few of the challenges you face are unique to you. There’s someone else out there who can identify with the obstacles you’re facing. Write, speak, teach, and lead from your experiences. They matter.

“To live well is to see wisely and to see wisely is to tell stories.”

— Pádraig Ó Tuama

When Growth Gets Tough: How to Push Yourself Past the Trap of What Comes Easy

On the day after Christmas, I booked a last-second flight to Denver. My girlfriend, Meredith, and I had made the decision to leave our home of the past ten years in Nashville and jump at an opportunity in Denver. I had 48 hours to check out the neighborhoods and find a place to rent. But as I walked through different homes and apartments, the reality of leaving our lives in Nashville began to set in and I started to spiral.

To be honest, it wasn’t a difficult initial decision for us. The new position, the company (Snapdocs), the overall opportunity felt like a chance to push ourselves and level up. And Denver wasn’t a hard sell—it fits our lifestyles even better than Nashville. But the hardest part came after accepting the offer and when we started to go through the motions of actually leaving.

Growth always seems easy from the surface. That is, until you’re the one who has to do it. Then you’re reminded of how daunting growth can be.

The trouble is that, for better or worse, we struggle to remember this. Hedonic adaptation and hindsight bias quickly set in. After intense periods of growth—new jobs, cities, relationships, kids, challenging moments—the ups and downs of the experience are leveled out in time. It’s difficult to recall your precise mental state and the struggles you faced in those moments. 

And everything seems so certain in retrospect, as if all you had to do was show up. When you’re on the other side, all the ways you changed and grew now seem inevitable. But when you’re living it and trying to push yourself in the right direction, things feel far from certain.

It’s hard to leave something that’s easy

Growth is difficult. Because the truth is it’s hard to leave something that’s so easy.

That’s why so many people end up settling. If growth were easy, everyone would be doing it. But this tendency to settle and seek comfort is an unfortunate trap the human mind leads us into. 

Growth demands you venture into the unknown and sacrifice the familiar. And, damn, that is hard. 

In Nashville, everything was easy for us. We lived at the top of the best park in the city, had a beautiful home, knew our favorite restaurants and coffee shops, had a wonderful group of friends. I also had a great routine and strong relationships with everyone at work. These are the things that make growth so hard—the familiar and comfortable. It’s hard to leave that.

But Meredith and I asked each other, are we at a point in our lives where we want to make decisions based on familiarity, comfort, and routine? The answer was no. We still wanted to take risks and be able to look back at our lives knowing we put ourselves out there. Better to try and fail than live in a world of what-ifs. And that’s the mindset that won out. But it wasn’t easy getting there.

Strategies to push yourself in moments of doubt

When you’re the one giving advice, it’s easy to gloss over how difficult risks and challenges are. You just get out there and do it, right? To an extent, yes. But that doesn’t change the fact that growth is scary.

Denver is a risk. Picking up our lives, moving to a new city, and starting from scratch at a new job is difficult. But we used a couple of strategies for overcoming inertia and taking a leap that we believe will help us grow. If you’re facing a similar challenge, start by reflecting on these two questions.

First, ask yourself, what are examples in your life when you were scared but went through with something anyway?

Then, ask yourself, what are examples in your life when you were scared, listened to that feeling, and ended up calling it quits?

In my life, I realized there were examples of both that turned out for the best. Many defining moments have been when I’ve had the courage to quit something I didn’t believe in—fraternities, youth groups, college majors, relationships—most of these came in my early twenties. 

But there have been also been proud moments when I’ve stuck through initial learning curves of new jobs, improvisation classes, speaking engagements, international travel, and moments of vulnerability in relationships. I came out on the other side better for it. 

As I reflected, the opportunity in Denver felt more like this side of the example. We, and I, believed it was a unique chance to grow and push ourselves. 

It was one of those rare moments where we looked at ourselves and thought, we’re really going to have to step up and push ourselves to pull this one off. That’s the feeling you’re going for. If you can maximize the number of moments in life when you feel like you’re being challenged to level up, the better you will be for it. But the fear and excitement can blend together when facing these types of decisions.

Above all else, you must listen when opportunities present themselves. You can’t turn on blinders and ignore moments that challenge you to rise to the occasion. If you do, you’ll lose out on the best opportunities for growth. 

Once you take the leap, you must then trust yourself and commit. The Greeks had a term for this—euthymia, which Seneca defined as “believing in yourself and trusting you are on the right path, and not being in doubt by following the myriad of footpaths of those wandering in every direction.” 

Trust yourself. But prepare yourself. It won’t be easy. 

Prepare yourself for a battle

While you might look to articles, books, and podcasts for inspiration, just know that you’re in for a battle. Don’t kid yourself and imagine you’ll get by without a fight. You will face moments of doubt. If you accept this and you prepare yourself for these challenges, you’ll be better prepared to come out on the other side. 

It’s hard to leave something that’s easy for something that’s difficult. That’s why most people don’t do it. But as author, Sebastian Junger, points out, “Humans don't mind hardship, in fact they thrive on it; what they mind is not feeling necessary.” Just remember that the path of least resistance is rarely the most fulfilling.

If you’re unable to look beyond first-order consequences, you’ll never be able to see past the comfort, what’s easy, and your existing routine. We knew moving was a risk and an unsettling prospect in the short term. But we also recognized that the long-term room for growth was well worth it. 

There are still some days that I’m scared. Terrified, even. But growth is about putting yourself out there. It’s not enough to just talk about these ideas, you have to test them out for yourself and take your own risks in life. 

It’s going to be tough. If you want to grow, you must seek out opportunities to make your leaps. But equally important is preparing yourself for moments of doubt and hesitation. When you know these will come, you guard yourself from being caught off balance. Instead, you create the momentum to push forward anyway.

How to Time Your Leaps and Set Yourself Apart

Using the Sigmoid Curve to reinvent yourself, take risks, and accelerate growth

In January 1961, a nineteen-year-old, unassuming kid from Minnesota hitched a ride and headed eastbound for New York to pursue a career in music. He wanted to get closer to the heart of the folk music in Greenwich Village and see if he could cross paths with his idol, Woody Guthrie. Over the next three years, he would release four critically acclaimed albums and become widely regarded as “the voice of a generation.”

The world would soon know that kid as Bob Dylan. And it was precisely that moment in time — after four successful albums — when he decided to completely change his sound from his acoustic roots and “go electric.” As he defied expectations, he threw the folk community into a fit of rage.

The obvious thing would have been to stick with what was working and fallen in line with his audience’s expectations. But validation was never Dylan’s primary motivation. He cared more about his own growth as an artist, seeking 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. Each album reflects who he was — his observations, experiences, and imagination — and who he refused to be at each point in time. Dylan’s life is a master class in embracing the impermanence of identity and authenticity.

In the almost six-decades since, he’s altered his voice and bridged different genres. Beginning in folk, moving towards rock, and experimenting with country and Christian albums along the way. His entire career demonstrates a remarkable ability to shift strategies and reinvent himself.

But Dylan is not alone in this. Most top performers are obsessively focused on reinventing themselves and changing strategies as they near the top. It’s what gives them their edge and helps them lock into a “learn + grow” pattern while circumventing the decline.

Houston Rockets guard James Harden works tirelessly during the NBA off-season to experiment with new shots and develop new moves. But it’s not like his existing repertoire stopped working during the previous season. This is just how he challenges himself to stay engaged and push the limitations of his own game. Harden never confines himself exclusively to the things that have worked in the past. He’s always looking ahead, focused on accelerating his own growth.

As a result, Harden is able to suspend his opponents in a cloud of confusion — they never know what to expect and rarely have time to adapt. Harden’s ability to reinvent himself creates a walking nightmare for other teams on the court. The best they can often hope for is that he’s having an off night.

The same mentality applies to Tiger Woods changing his golf swing at the top of his game. And it’s the reason companies like Apple, Amazon, and Google have been able to sustain success over decades.

This is not to say that you’ll never miss. Bob Dylan’s released albums and experimented with sounds he would likely laugh at today. James Harden’s had his share of flops that didn’t quite work out. And Apple’s launched failed products — some you’ve heard of and others that have died before ever making it to market.

But it’s much easier to recover if you’re out there taking risks, looking forward, and committed to a growth mindset.

The Sigmoid Curve

Growth comes from allowing yourself, your strategy, and your sense of authenticity to evolve. At a certain point in time, the strategy that worked for you up until now will falter. That’s part of life.

One way to adapt is to think of personal growth as a sigmoid curve — an S-shaped curve that follows learning, growth, and decline. The goal is to maintain an upward trajectory. This means hijacking the curve and your experiences, as best you’re able to, when you reach the peak of a growth curve.

In the early days, growth is nonlinear. Outcomes rarely match input. Think about starting a new job — for the first six months you’re just trying to keep your head above the water. Eventually, things start to come together and you reach an accelerated period of growth where you begin to realize some of the rewards and outcomes you set out for.

But you likely won’t get through life on a single strategy without it growing stale or ineffective. 

Remember, life is motion. You will evolve. Obstacles will evolve. Context will evolve. That’s why it’s important to shift strategies when you’re at the top of your game. Otherwise, you often end up giving back the gains you’ve made.

If you want to keep moving forward and reinvent yourself, you have to outwit the inevitability of the sigmoid curve. As James Kerr suggests in his book, Legacy, “The key, of course, is when we’re on top of our game, to change our game; to exit relationships, recruit new talent, alter tactics, reassess strategy.”

Bob Dylan, James Harden, and every top performer who has sustained success over the course of decades demonstrate a fundamental understanding of this principle. They seldom give back the gains they’ve made. Instead, they build upon them. They remain insatiable in their desire to learn and grow. Even when it comes at the expense of personal comfort and opens them up to outside criticism.

Close to six decades later we can step back and admire someone like Bob Dylan’s trajectory — how he 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 he faced.

Staring Down the Criticism

The real challenge is that when you reinvent yourself and shift strategies, you’re sure to be criticized. People hate change. And people are convinced they know what’s best for you. Pair these and you’re guaranteed to face a barrage of commentary from those without skin in the game. Critics will be quick to point out that you should have stuck with what was working instead of taking what appears to be a step back into a learning phase.

Dylan was shredded by the folk community when he went electric. Harden gets ridiculed by the press every time he goes a few games and struggles against his own limits with a new shot.

Reinventing yourself is not for the faint of heart. But it’s a risk that pales in comparison to remaining still and failing to evolve.

If you listen to outside advice and never switch things up, you all but guarantee a life void of meaning and a spiral towards irrelevance. By clinging to the same strategy, tactics, or identity for too long, you fall out of harmony with the motion that defines life.

And this is how you wake up to John Daly, Sugar Ray or Blockbuster staring back at you in the mirror. The same people who told you to stay the same have abandoned you because you’ve abandoned yourself.

Timing Your Leaps

Above all else, you have to allow yourself and your own sense of authenticity to evolve. That’s the only path towards peak performance, and it demands occasional discomfort.

To outwit the sigmoid curve, you have to make a series of carefully timed leaps. The trick is knowing when to make those leaps.

When you feel like you’re nearing the top of your growth curve, that’s when it’s time to start thinking about what you can switch up. This might mean testing a new strategy or taking on more responsibility. Or it might mean pursuing a new career path or an outside learning opportunity. Or perhaps it’s just switching to a new team to preserve your sense of engagement and continue challenging yourself.

A shift in strategy doesn’t always need to be drastic. But it does need to be deliberate.

Otherwise, things become too easy and too familiar within the confines of your comfort zone. And when you become trapped in a decline, it’s all too easy to cling to an expired identity and give away the progress you’ve made.

Much of life is knowing when to shift strategies — when to call it quits, when to stick it out, when to evolve your approach. If you can perfect this, you can bypass the decline phase altogether, and jump from one “learn + grow” period to the next. And this is what sets apart the top performers in every discipline.

It’s difficult to realize when you’re nearing the end of a growth phase. It requires first developing a deep sense of self-awareness and prioritizing room for reflection. This should be paired with experience — both personal and vicarious.

The usual signs are when you start to notice a decline in personal engagement and the meaning you find in the work. This signals that it’s time for a new approach.

Remember, you’re a human being. Emotion is an inherent part of your decisions. The best you can do is pause and create space for reflection. The more dispassionate you are in coming to a decision, the more you should trust it.

For example, when you’re pissed off at a manager, that’s not the time to make abrupt decisions. Create space. Allow yourself to be upset for a few hours. After a week, when you’re less entrenched in that moment, you can see things for what they are and make a more rational decision.

When I feel a calm sense of it is what it is, I’m not upset, but I accept it’s time for a change that’s when I know it’s time to switch things up and test a new strategy. When I’m in an emotional state — especially when I’m upset and playing through imaginary conversations in my head — that’s when I know I need to pause before making a decision on a potential leap.

Allow Yourself to Evolve

It’s easy to get locked into a rigid thought process with a single strategy if you stick to the map without ever looking up. But when you stop reaching for absolutes, you’re able to embrace the motion inherent to life. Everything is fluid.

The best thing you can hope to do is remain in harmony with your own sense of authenticity and the motion that defines life. By embracing this, you’re able to better challenge yourself, embrace a growth mindset, and create meaning.

If you want to create your best work and make a meaningful difference in the world, you’re going to have to grow to get there. This comes from timing your leaps and finding the courage to reinvent yourself — especially when it feels uncomfortable, counterintuitive, and the world least expects it.

Bob Dylan’s determination to evolve as an artist and his refusal to accept what people expected of him helped him grow into one of the greatest songwriters of our era.

James Harden’s ability to reinvent himself every NBA off-season is what allowed him to go from the sixth man behind Kevin Durant and Russell Westbrook is his early days with the Oklahoma City Thunder to an MVP and the cornerstone of a franchise.

In visualizing the sigmoid curve, you’re trying to jump at the precipice of growth and catch hold of another learning curve one layer above — just as Dylan and Harden demonstrated. This is how you lock yourself into a “learn + grow” mindset.

Strategies are tools that you can use to take thoughtful action and connect your guiding principles with your day-to-day. Put them to use for you. Blend them. Change them. And always be willing to shift directions when something’s become stale or no longer works for you.

Above all else, allow yourself to evolve. Growth is born from a willingness to leap before you feel ready.

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.