The Outsider Advantage

“There’s no freedom quite like the freedom of being constantly underestimated.”

— Scott Lynch

At the turn of the 19th century, human flight continued to elude civilization. There were experiments, blueprints, and myths surrounding flight from Icarus to Leonardo da Vinci. But no one had figured out how to master human flight. During the late 1800s, this challenge consumed many of the era’s best scientists and engineers—Sir Hiram Maxim, Alexander Graham Bell, Thomas Edison, Samuel Langley, and the Smithsonian Institution, to name a few. 

Meanwhile, Wilbur and Orville Wright ran a bicycle shop in Dayton, Ohio, designing, repairing, and selling bicycles. But they, too, had grown fascinated with the challenge of flight. 

In 1899, Wilbur wrote to the Smithsonian Institution in Washington requesting documents on the subject of human flight. The Smithsonian passed along a stack of pamphlets on aviation, and the brothers started studying. Later that summer, above their bicycle shop on West Third Street, they began building their first aircraft—a glider with double wings spanning five feet made of split bamboo and paper.

Unlimited resources don’t equal better results

No one took the Wright brothers seriously, at least not yet. They were just two entrepreneurs building bicycles and living in the backwaters of Ohio. All the innovation was happening on the East Coast and in major European cities like Paris and London, led by well-funded scientists and engineers. But despite the resource advantage and the money being thrown at the problem, success remained elusive for those pursuing flight.

Sir Hiram Maxim, the inventor of the machine gun, spent $100,000 on a giant, steam-powered flying machine, which turned out to be a spectacular failure, crashing immediately upon take off.

But Samuel Langley was the most notable frontrunner in the race to human flight. Langley was the head of the Smithsonian, an eminent astronomer, and one of the most well-respected scientists in the United States. He was years ahead of the Wright brothers, and his experiments were backed by government funding. Langley held a tremendous advantage in his access to resources—both in terms of capital and information.

But with nearly unlimited resources, the stakes were higher and the pressure greater for Langley. After years of secretive work, he revealed what he called an “aerodome”—a steam-powered flying machine with V-shaped wings that gave it the appearance of a “monstrous dragonfly.” 

The aerodrome cost $50,000 in public money—grants from the Smithsonian and the U.S. War Department. Langley, Graham Bell, and others contributed another $20,000 of their own money. But the device could only “fly” in calm weather where the wind wasn’t a factor, which was as practical as building a boat unable to navigate waves. 

When it came time for a public demonstration, the aerodome was loaded onto the roof of a houseboat in the Potomac River near Quantico, Virginia, before being launched into the sky by catapult. Almost immediately, the wings crumbled, and the airship spun backward and plunged into the Potomac just 20 feet from where it had been launched. Langley’s efforts had taken more than eight years and failed to produce any meaningful progress. 

Resourcefulness wins out

During this same time, the Wright brothers were relentless in their efforts. Wilbur and Orville ran the bicycle shop by day and worked each night on their investigations into flight. After identifying the ideal place to test their first glider in Kitty Hawk on the desolate Outer Banks of North Carolina with windy conditions and sand hills for safe landings, they began their experiments. The first full-sized glider they brought to Kitty Hawk had a wingspan of 18 feet and cost just $15. 

Wilbur and Orville would return to Kitty Hawk every fall for the next four years to run experiments and test new iterations. As competition took notice and patrons reached out to help back the Wright brothers financially, Wilbur and Orville politely refused. They kept the bicycle shop open to help pay for their experiments and bootstrap their exploration into flight. And during frigid midwest winters in Dayton when it was too cold for cycling, they sharpened ice skates at the shop for 15 cents each to generate additional income. 

In their early, self-funded experiments, Wilbur and Orville learned that many of the widely accepted calculations and tables relating to foundational concepts in aviation, like lift and drag, prepared by authorities were fundamentally wrong and couldn’t be trusted. To improve the accuracy of their calculations, the Wright brothers built a small wind tunnel upstairs in their bicycle shop—a wooden box roughly six feet long with a fan mounted at one end. Over the next few months, they tested 38 different wing surfaces at different angles and wind speeds. 

After dialing in their own calculations, by the fall of 1902, they had completed a third iteration of their glider. And in just two months in Kitty Hawk, the Wright brothers had completed a thousand glides and solved the last remaining control problems. With relentless focus, data-driven experimentation, and thoughtful iterations, they had built a machine that could fly, and in the process, honed the skills to pilot it. The next step would be to add a motor. And by the following winter, Wilbur would complete the first powered flight in human history, covering a quarter mile in 59 seconds. 

In contrast to Langley’s $70,000 failed effort, the Wright brother’s expenses over four years, including materials and travel, totaled less than $1,000—all paid for by the proceeds from their bicycle shop in Dayton. Their competitors, with seventy times the amount of resources, couldn’t keep pace.

Despite Wilbur and Orville both lacking formal education or influential connections and living outside of the intellectual centers of the world, they were the first to solve the challenge of controlled human flight. They were both driven by and dedicated to solving the problem. Not because they were supposed to. And not because of the prestige it would garner. But because it was an inspiring challenge that they both felt a connection to. 

Less to lose

The Wright brothers were outsiders. And as outsiders, they could think for themselves while competitors imitated each other’s devices and worked from flawed formulas. The Wright brothers faced less external pressure, which crippled even the best scientists, like Langley. And this freed them to experiment and find their own way. No one was expecting anything from them, and that was just fine by them. They had less to lose. Their competitors had reputations to protect. 

It’s true that in specific industries like politics, you must be an insider to enact real change. But for the rest of us building, leading, and creating something of our own, it’s not always the advantage we believe it to be. 

As an insider in your industry, your worldview begins to narrow. And most of your energy becomes directed toward preserving your ability to think for yourself and avoid getting sucked into what everyone else is thinking. And when you have access to unlimited resources, it restricts your creativity. You’re no longer forced to effectively prioritize or consider different vantage points that allow you to do more with less. You become entrenched in what everyone else is doing, and it’s difficult to see beyond that. 

Many times, the inside track with well-funded, resource-rich, established companies, teams, and figureheads, is where the least amount of work gets done. They grow too comfortable, lack focus, or take on initiatives for the wrong reasons, like ego or fear, resulting in a fragile, reactive approach. They’re playing not to lose, which is very different from the flexibility and boldness that you play with to win. That’s why new startups come along and disrupt big companies each day. They have less to lose.

Embracing the role of an outsider can work to your advantage. You face less pressure and fewer distractions. And this helps preserve both your ability to think for yourself and the energy you can dedicate to building. If you become too enmeshed in what everyone else is doing, it can be difficult to step back and return to first principles. 

The Wright brothers leveraged available knowledge, but they questioned and validated every assumption they came across. They focused on the problem. They focused on building. They focused on their own experiments. And as outsiders, they were provided an advantage in that they didn’t have to deal with the same level of obligations or distractions someone like Samuel Langley faced. They could operate with greater flexibility and were free to do the work. 

As an outsider, you face greater odds. But those odds act as a natural filter for work you don’t find all that meaningful. If you aren’t motivated by what you’re doing and lack a deeper connection to your work, you will get absolutely crushed. There’s no faking it. Whereas on the inside, you can float by without making hard decisions or determining if you’re doing it for the right reasons. 

Bootstrap your idea into reality

This was the difference between the Wright brothers and Langley. Flight was a quest the Wright brothers found personal meaning in. They weren’t motivated by fame, reputation, or external validation. The reward was the challenge and committing themselves to a cause they cared about. And just as importantly, they embraced their role as outsiders, bootstrapping the whole thing and avoiding the obligations associated with taking on outside capital. 

You don’t need to secure a record deal, an agent, or get into Y-Combinator to create a successful album, book, or company. Andy Weir self-published The Martian, which sold 35,000 copies in its first three months and later grossed over $630 million worldwide in its film adaptation. After getting rejected by every major label in town, Jay-Z started his own label—Roc-A-Fella Records—to release his first record, Reasonable Doubt, selling more than 420,000 units. Yvon Chouinard started what would grow into Patagonia after buying a used coal-fired forge from a local junkyard, teaching himself blacksmithing, and forging climbing gear for his friends. Patagonia didn’t take a dime of outside capital for its first 20 years and has sustained success over five decades, now generating well over $1 billion in annual revenue.

We live in an era where it’s easier than ever to bootstrap our own ideas and embrace the outside track. You can launch your own startup as a side hustle and access thousands of low-cost tools to run your business without diluting your ownership. You can record your own album and distribute it independently without handing over the rights to labels and publishers. And all of this can work to your advantage. 

When you avoid taking on external resources and unnecessary obligations, you simplify decision-making and preserve the integrity of what you’re trying to build. There’s less noise influencing your work. And it helps you to avoid getting caught up in false goals and virtue signaling.

Seek accomplishment in the work, not external validation

Far too many people conflate external validation with accomplishment. But raising a Series-A, signing a book deal, or getting accepted into an Ivy League school is not the accomplishment. The accomplishment is on the other side of the blood, sweat, and tears you must pour into your work. The accomplishment is bringing something of your own to life.

The Wright brothers were just a couple of midwesterners running a bicycle shop. What did they know about aviation? Not much at first, but they were driven to learn and build. One of the few locals in Kitty Hawk, John T. Daniels, remarked, “It wasn’t luck that made them fly; it was hard work and common sense; they put their whole heart and soul and all their energy into an idea and they had the faith.”

Embrace the outside track. And once you’ve gained traction, keep a healthy distance. It’s a gift when people are unsuspecting. You free yourself to focus on creating and gain an element of surprise that keeps the competition off guard. Besides, there’s nothing more motivating than when someone has counted you out. That’s right where you want them.

---

Sources:

1. The Wright Brothers by David McCullough

2. Founders Podcast, #28: The Wright Brothers

3. Founders Podcast, #239: The Wright Brothers

4. Empire State of Mind by Zach O’Malley Greenburg

5. Let My People Go Surfing by Yvon Chouinard

When to Quit and When to Stick It Out

One of the most challenging aspects of your career is knowing when it’s time to move on to your next opportunity.

As you reflect on where you are and what’s next, dozens of questions race through your mind. Is there more to learn here? Should I double down on my current role? Do I still have room to grow and level up my skills? Is this a passing moment of doubt where I feel like quitting because this is hard? Or is it because this experience has run its course and it’s time to move on?

Throughout my career, I’ve pushed the limits of staying too long at certain companies. But I’ve also had moments of doubt where I felt like leaving early because things were hard. Together, these experiences have allowed me to consider the decision point between sticking it out in a current position versus transitioning to something new.

Leaving to pursue a new opportunity at the right time can be one of the best ways to accelerate growth and properly time the Sigmoid Curve—an S-shaped curve that tracks learning, growth, and decline. The goal is to make calculated leaps when you’re at the pinnacle of growth before you reach the decline phase. Otherwise, you risk stagnating and handing back gains you’ve made. But the trick is knowing how to self-assess and recognize once you’ve reached this point.

In October of 2019, I felt like I was reaching the end of the line with my then-current company. But I couldn’t quite articulate why. One afternoon, I took a coffee break with a close friend and colleague. We talked about the challenges we were facing and the patterns we noticed. We also reflected on the problems we were trying to solve as a team and as an organization. 

I voiced my struggles contemplating whether or not it was time for me to move on and try something new. I mentioned how I wasn’t sure if I cared about solving the problem we were focused on anymore. Not just on our individual team, but the underlying problem the company set out to solve. And with this passing thought, I started to identify my true litmus test for knowing when it’s time to look for a new job or double down on the current one. 

I asked myself two questions to better understand my level of engagement:
1) Do I still care about solving this problem? 
2) Would I take this job if I were offered it today?

If the answer to the first question is no, that’s when you know it’s time to move on. It’s also an indicator you’ve reached the decline on the Sigmoid Curve and it’s time for your next leap. 

If the answer to the first question is yes, but the answer to the second is no, maneuvering within your current company to a new role remains a viable option to jumpstart a new phase of growth. 

But if you continue to idle in your current role without being invested in the problem you’re attempting to solve, you’re allowing both comfort and fear to dictate your career. To be fair, it’s easier to sit by and complain than it is to put yourself out there and try something new. It’s also the hallmark of a fixed mindset and the fastest path to unrealized potential—limit all risk and failure. 

There are certainly circumstances and economic conditions when you have to suck it up and deal with it. But you should always be working to anticipate this decline—where learning and growth begin to slow—so you’re able to stay in front of it. 

One alternative to overstaying is flaking from one job to the next. As soon as things get hard, you bail. But the truth is that if you want to make a meaningful difference in your work and the problem you’re facing, you have to be willing to suffer. The same is true for growth. If you’re unable to stick it out when things get tough, a lack of resilience will come to define you. Both your work and experiences will forever lack depth.

On a surface level, those who float from one job to the next might seem like the polar opposite of those who stay too long in a single position. But both are attempts to do what’s easy. When things get hard, the easy thing to do is retreat and cover your ass so you’re not the one who’s accountable. Just as when you’ve started to stagnate and growth has tapered off, the easy thing to do is stick with the familiar and your routine—no matter how unfulfilling it is—rather than putting yourself back out there. 

Instead, do the hard thing. Fight for what you find meaning in. Aligning yourself to this requires reconciling when an experience has run its course versus when quitting is the easy way out. From here you can find the courage to take new risks or push through challenging moments. 

“What man actually needs is not a tensionless state but rather the striving and struggling for a worthwhile goal, a freely chosen task.”

— Viktor Frankl

You’re a better version of yourself when you’re working on problems that you find meaning in. Meaning is a force multiplier for your own engagement and growth.

When you pick a problem you find meaning in, things won’t always be perfect and there will still be noise to sort through. Engagement is cyclical. There will be times you feel close to burning out or struggle to sustain engagement. You will hit low points that you have to push through. But observe your reactions in those moments. Is it because you genuinely don’t care about solving the problem anymore? Or is it because you’re tired, it’s been a hard week, or someone pissed you off? The latter is an indicator that you need to step away and recharge before digging back in. 

When you’ve reflected on these questions, if it’s time to move on to something new your response won’t be riddled with emotion. It’s an observation and acceptance of a fact. Not an impulsive reaction. It’s just time to move on. 

This is the realization that I came to in my last position. I cared about the company and the people I worked with. I just didn’t care about the problem anymore. I felt like I had given all that I was capable of. That was my reality. And accepting it helped me identify the best path forward. 

From here you’re able to make the necessary moves to position yourself for your next leap and optimize for learning and growth. Whether you’re able to make your next move in days, weeks, or months, it’s important to find an outlet to immediately immerse yourself back in a learning phase. Even if you have to pursue this outside of work by writing, reading, or learning a new skill while you search for your next opportunity. 

As your progress through your career, what matters is that you pick a problem you care about. One that’s worth suffering for and resonates with you at that moment in time.

But you must also be able to recognize once an opportunity has run its course. Not because it’s hard. But because the problem you’re solving doesn’t generate the same level of sustained engagement as it once did. That’s one of the best signs that it’s time for your next leap. And timing your leaps is one of the best skills you can develop in your career.

And if you find that deep down you still care about the problem, there’s no better indicator that you’re in alignment and focused on the right thing. 

Using a Growth Mindset to Overcome Your Obsession with Perfection

“We’re ditching you.” I stopped in my tracks, engulfed by a sea of classmates rushing towards the buses lined up alongside Cherry Tree Elementary. This was the drama of fourth-grade in my class of abnormally social ten-year-olds. After I “broke up” with my girlfriend at the time, I was deemed not cool enough to continue hanging out with my current circle of friends. 

We were a strange group of kids, as our parents will likely attest. We did our best impression of teenage life—watching Total Request Live on MTV after school with Dunkaroos and Mountain Dew. We were all new to the dating scene, which at that age consisted of writing on a paper note your “Top Five,” ranked in order of who you wanted to date. If you matched with another person, that made if official. The carousel of dating remained in constant motion, as one’s “Top Five” was subject to change on an almost hourly basis.

While the entire situation seems decidedly stupid now, my friends ditching me was traumatic at the time. Kids are ruthless. And at that age, it felt like the end of the world. It was an early lesson that taught me to keep my ass down. 

I learned to quit drawing attention to myself and found ways to block myself off from criticism and rejection by limiting my exposure to situations where I might fail. This was a defense mechanism driven by my need for acceptance and belonging. It helped me create a sense of safety—however false—as I navigated adolescence.

This became most obvious at school where I was afraid to speak up because I didn’t want to be wrong. Despite being a strong student, this trapped me in a low-learning state for years. The only way I was able to combat this was by reaching for depth outside of the classroom.

In my late teens and early twenties, I largely escaped this by channeling my contrarian nature. Fortunately, I’ve never struggled with peer pressure or listening to myself. But old thought patterns—especially those from childhood—require a deep awareness and years of work to overcome. It’s not an overnight thing. And without having done the self-work, I fell back into this mindset at the beginning of my career.

During big meetings I would feel myself sinking into a corner. I worried the room would judge my every word. Who was I to volunteer my opinion and ideas when everyone else in the room held years of industry experience? 

As author, Carol Dweck points out, this is the hallmark of a fixed mindset which traps you into a low-learning state. The way this reveals itself is through a judge-and-be-judged framework. Your mind projects judgments of others and fuels your own fear of being judged. And this becomes your baseline.

But the antithesis is a growth mindset which shifts the emphasis to learning. Instead of a judge-and-be-judged framework, everything becomes based on a learn-and-help-learn framework. And this is how you better orient yourself towards a high-learning state.

Once you establish self-awareness, it will continue to take years of hard work, patience, and commitment. I still keep this written down in my journal as one of my top areas to focus on for the year. This reminds me to read and reflect on it on a weekly basis so it’s always near the top of my mind. 

But the real benefits of a growth mindset are the threats it allows you to overcome and the bias towards action that it helps you create. 

A bias towards action

One of the biggest advantages of making a conscious shift towards a learn-and-help-learn framework is that it lowers the stakes. It allows you to step back, put things in perspective, and see that not every word has irreversible consequences to you reputation. This frees you to focus on advancing the conversation and exploring different directions, rather than holding yourself hostage to the perfect answer. 

I’ve found in my own career that there’s a tendency to lean on and look towards those with seniority. But everyone’s voice matters. You have a unique perspective that’s all your own. Your own experiences are just as valid. Besides, those who share your commitment to a growth mindset will appreciate where you’re coming from.

A bias towards thoughtful action accelerates the rate at which you learn.

“Becoming is better than being. The fixed mindset does not allow people the luxury of becoming. They have to already be.”

— Carol Dweck

When you find yourself silently judging others, it’s a sign of insecurity and concern over being judged yourself. You become fearful based on the past or anxious about the future. This makes it difficult, if not impossible, to remain present. And growth requires some degree of action in this moment or else you’ll never get started. 

By learning how to recognize and navigate this fear, you create more room for action. To perform at your best, you want to achieve a relaxed state of concentration where you’re focused on the task in front of you and what’s within your control. Not the externals and surrounding noise. 

Top performers who take risks in their work certainly face their share of doubts. And if we’re being honest, a fear of judgment that ebbs and flows. But the difference is that they don’t allow that to dissuade them from creating and putting themselves out into the world. A bias towards action wins out because they better align themselves with a growth mindset that favors the impact of doing and learning over the fear judgment. 

This also manifests itself in how we teach others. One of the easiest ways to identify those who are trapped in a fixed mindset is how they react when someone doesn’t know something they deem to be obvious. It becomes a joke and an opportunity to soothe their own ego at the expense of someone else.

Those who focus on a learn-and-help-learn framework see this as a learning opportunity to step back, provide context, and test their own ability to articulate the idea in a simple way. Rather than teasing that person, they appreciate the fact that they spoke up to ask the obvious and gain clarification. 

Feedback isn’t a threat

For the same reason that a growth mindset encourages healthy risks and a bias towards action, so too does it help you reframe the feedback you receive along the way. 

There’s a difference between feedback and criticism. The more sensitive you are to judgment, the more that line becomes blurred. Feedback is constructive and the more important of the two. Criticism is destructive and often comes from those without skin in the game who don’t have your best interests in mind. 

But a fixed mindset takes everything personally. A person trapped in this state considers mistakes a reflection of their character. Everything is an attack, regardless of its source or validity.

Feedback is only a threat when you’re locked into a judge-and-be-judged mindset. 

With a growth mindset, you disarm this threat. Feedback no longer feels threatening to your character and the stakes don’t feel insurmountable. You don’t have to be perfect or know the right answer every time. You’re able to contribute and push the conversation forward because you’re curious and driven to better yourself, rather than being consumed by the risk of judgment. 

The learn-and-help-learn mindset views these as lessons that are just part of life. They don’t mean you’re any better or any worse of a person. Instead, the missteps, unknowns, and difficult feedback become an opportunity to learn and grow. 

When you come to this realization, you’re able to properly sort between criticism and feedback. The criticism loses its sting. The feedback becomes actionable. 

Reinvent and try new things 

This mindset also manifests itself in how you explore new interests and allow yourself to evolve. With a bias towards action and the ability to reframe feedback, you create an openness to try new things. There’s less anxiety about failing when testing a new approach or exploring new interests.

Every data point, especially failures, are an opportunity to discover more about yourself—what’s worth doubling down on, improving, or moving away from. 

Those who view learning favorably as a chance to grow, rather than obsess over the failure or perception it could create when they stumble, are far more inclined to find their niche during each chapter of life. They’re able to go wide, reassess their interests and reinvent themselves when things get stale. Because they don’t allow a fear of being judged or laughed at dictate every move.

With a growth mindset, your deepest fear becomes reaching a plateau in what you’re learning and your own abilities. Life is motion. Attempting to stand still and preserve an identity, worldview, or set of interests that made sense years or decades earlier but no longer resonates with you will leave you empty. Escaping a fixed mindset also allows you to escape the confines of comfort. 

“The secret to happiness is this: let your interests be as wide as possible, and let your reactions to the thing and persons that interest you be as far as possible friendly rather than hostile.”

— Bertrand Russell

A fixed mindset locks you into a place of hesitation. If you’re only concerned about consequences and people’s interpretations, you’ll learn at a fraction of the speed. You’ll be less inclined to jump into action or try new things that you might suck at.

This is not just relevant to your twenties when you’re trying to find your place in life. It’s relevant in each decade. As your sense of authenticity and identity evolves, you can’t expect to remain still. Finding harmony in that motion requires growth of your own and trying out new things. You’ll never be able to find meaning in new areas of life if you’re unwilling to put yourself out there time and time again, regardless of age. 

An opportunity to grow

A shift into this mindset begins with awareness—being able to step back and recognize when your instincts are pointing you towards a fixed mindset and operating within a judge-and-be-judge framework. Once you train yourself to identify this, you can create a buffer before acting and nudge yourself back towards a growth mindset. 

This allows you a moment of reflection to remember that feedback is a learning mechanism each step of the way—rather than something to be feared. Whether you’re in your twenties or sixties, each moment you face is an opportunity to grow. You don’t need always need to have the perfect answer. 

With a mindset built upon a learn-and-help-learn framework, what might have seemed like a sign of failure before becomes a positive sign that you’re putting yourself out there. And that’s how you grow. By showing up and being the one who steps into the arena.

In contrast, those who find themselves stuck in a judge-and-be-judged framework withdraw from contributing their own ideas and shut down when they receive anything less than praise. They watch from a distance.

Everyone acknowledges this at a surface level—some sort of feedback loop is important to progress. But far fewer people can actually face the feedback that it takes to grow. Whether embracing a difficult conversation or acknowledging an imperfect answer. It’s easier to settle back into the coping mechanism that is passive aggression or judgment without taking risks of your own. 

If you want easy, it comes at a cost. But those committed to growth understand that life is about learning, no matter how painful that might be.

If you want to develop yourself, you’ll need to hone your own bias towards action, a deep appreciation for the present, and an openness to challenging feedback. It’s not about perfection. It’s about building the right mindset to carry with you.

Do the Work

In May of 2011, I graduated from Indiana University and joined a workforce that was still recovering from the 2008 financial crisis. Finding a job wasn’t easy. I was an entitled kid who thought the world owed me something because I graduated with honors. I could not have been more wrong. And with a four-year degree, I went back to waiting tables at Don Pablo’s, a Tex-Mex restaurant in Westfield, Indiana to learn this lesson the hard way. 

School is not a substitute for doing the work. Far too many times over the past decade I’ve heard something along the lines of, “I didn’t go back to get my (insert degree here) to settle for this title or that salary.” But the degree you’re able to afford isn’t a replacement for the work. 

There’s nothing wrong with pursuing degrees if that’s your way of learning or certain qualifications are required for your career. But classrooms and case studies are not the same as creating something of your own in dynamic environments with second-order consequences. There’s far more ambiguity when you’re navigating the world in real time. 

As author, Austin Kleon, observes, “Lots of people want to be the noun without doing the verb.” Your degree is not the verb. Your job title is not the verb. The verb is the work. And this demands resilience—you have to show up and put yourself out there. But if you’re after substance and original experiences, this is the only path forward. 

“Lots of people want to be the noun without doing the verb.”

— Austin Kleon

The fraud, the novice, and the critic

The risk in setting out with a mindset to get by with minimal effort or expecting things to be handed to you is that it bleeds between chapters of your life. And over the long run, it becomes impossible to sustain or cover up indefinitely. 

You see this with managers who want to dictate decisions without ever having built something of their own or having put themselves out there in their own work. When they speak, their words are empty. Everything’s theoretical. They lack a deeper understanding of the concepts they’re talking about and they can’t inspire a group of individual contributors because they’ve never done the actions they’re advocating.

If you want to lead, you need experiences to pull from where you’ve built something of your own. That doesn’t mean floating by on privilege. And that doesn’t mean managing. That means battling alongside your team and knowing how to step in and take action. 

Your words carry far greater weight when you’ve actually done the thing you’re speaking about. Nothing kills morale faster than someone in a leadership position who has never put themselves on the line or taken risks in their own work. 

You also see this with speakers or writers who want to explain to others how to live a meaningful life without having done it themselves. Without your own set of experiences to pull from, your words will forever feel hollow. 

I learned this firsthand when I started writing in my early twenties. Above all, I desperately wanted my words and ideas to matter. And this got me nowhere. 

But the moment I quit worrying about being so damned important, I freed myself up to pursue real experiences, take chances in my work, and connect with others in a way that would lend far more significance to what I had to say down the line. Instead of forcing what I was writing about to matter to everyone else, I just set out to live and speak from that place instead. 

There’s no difference between the critic, the novice of a writer who lacks experiences of their own to speak from, and the fraud of a manager who floats by on the work of others without putting themselves out there. They’re all the same face disguised behind a different mask. 

“The curse of modernity is that we are increasingly populated by a class of people who are better at explaining than understanding, or better at explaining than doing.”

— Nassim Taleb

The key to sustaining near the summit

It’s easier to sit back and allow someone else to take the risk. But it puts you in a fragile place where you become dependent on external factors to go your way. When things get difficult, you don’t have the option to lean on yourself and focus on what’s within your control. Rather than a healthy level of self-sufficiency and resilience, all you have is dependencies. And you can’t expect to sustain something where you don’t have much of a direct impact on the outcome.

Doing the work is difficult. It means putting yourself in a position of vulnerability. It means opening yourself up to struggle and failure. It means reaching not for what’s within your immediate grasp, but what’s just beyond. By doing the work, you add depth to your life that few achieve and set yourself up to sustain at that level indefinitely, no matter the external circumstances. 

Legendary San Francisco 49ers coach, Bill Walsh, knew his team wouldn’t win the Super Bowl every year. There were too many external factors with injuries, weather, scheduling, and luck. But he focused himself and his team on what they could control—putting in the work. Their goal was to “establish a near-permanent base camp near the summit, consistently close to the top, within striking distance.” The only way to sustain at this level was by showing up, each day, and never allowing themselves to believe they were above the grind. The result was three Super Bowl titles in eight years. 

Like Walsh’s teams, those who are able to sustain indefinitely near the summit and rebuild when the circumstances require, know how to put in the work. They have a wealth of experience to pull from and the resilience to match. There’s no room for excuses, entitlement, or major dependencies. 

If you’re the one creating, building, and executing, you’re the one who knows how to make it happen. No matter who takes the credit or adds their name to your work, you will always be able to create your next thing because you’re the one who has trained and performed in the past. You’ve built up both the ability and grit to bring your ideas to life.

The same cannot be said for the critics and coasters who are dependent on the work of others and would otherwise leave the world void of both originality and progress. 

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

— Theodore Roosevelt

The verb matters more than the noun

The world doesn’t owe you anything. If you want people to listen and you want to lead, you can’t be above the work. And if you want the ideas you’re communicating to have an impact, don’t speak from someone else’s life. Speak from your own.

Your voice carries far greater weight when you’re able to speak from the work you’ve done and your own experiences rather than your theories as a bystander. 

It’s far more admirable to try and fail—knowing that you’ve done the best with what you have—than it is to live through someone else’s experiences and explaining things you’ve never attempted and don’t actually understand. This is what separates the great leaders, writers, and artists. They’ve put in the work. They’ve taken the risks. They speak and create from their own experiences. 

When you look back at your life, you want to be able to say that you were a builder, a doer, a creator. You actually did the things you’re telling stories about. You navigated the discomfort and challenges of growth with composure. Rather than cowering and letting someone else do the work so you wouldn’t have to struggle against your own limits and risk coming up short. 

But to live admirably is to risk, to strive towards creating meaningful work, and to grow. To live admirably is to understand that the verb is more meaningful than the noun.

Environment Is Your Force Multiplier

Over the course of his life, Benjamin Franklin’s (1706-1790) contributions to the world were nothing short of astonishing. Franklin taught himself the fundamentals of writing, science, engineering, and diplomacy. He sought practical applications of what he learned each step of the way—emulating his favorite authors and developing his own writing style, running a successful printing business, advancing our understanding of electricity, and positioning himself as an accomplished diplomat with a vital role in the American Revolution.

Franklin’s list of accomplishments is impressive. But equally impressive was his ability to thrive in a range of environments, from printing halls and makeshift laboratories to foreign cities and diplomatic congregations.

Each step of the way, Franklin maintained a deliberate focus on his environment, orchestrating the conditions that were within his control. His environment was fundamental to all of his accomplishments and allowed him to give more back to the world around him.

An Apprentice in the Printing Shop

Franklin’s ability to adapt and maneuver across environments was evident from an early age. Almost as soon as Franklin’s formal education began, it was over. At eight years old his father sent him to Boston Latin School to prepare for a path towards Harvard. Franklin excelled, jumping a grade in his first year, but due to either financial constraints or his father’s recognition that Franklin’s personality was not particularly suited to a life in academia, he was pulled out.

Franklin enrolled for one more year at a writing and arithmetic academy near his family home. After that, with just two years of formal schooling under his belt, he left to work full time at his father’s candle and soap shop. 

But Franklin’s defining characteristic, his insatiable curiosity, endured. What he lacked in academic opportunities, he made up for with his voracious reading habits.

When he turned twelve he became an apprentice under his brother, James, in the printing business. For the next five years, he gained direct access to hundreds of articles, books, and essays being printed. He would strike deals with other apprentices under booksellers so he could borrow early copies, as long as he returned them in good condition. At night he would rewrite his favorite passages, honing his own writing style and testing his ability to form logical arguments. 

While he poured over everything he could get his hands on, practical subjects resonated strongest with Franklin. He demonstrated a particular interest in books on science, history, politics, writing, and business skills. He had little patience for memorizing abstract concepts, isolated facts or learning for learning’s sake.

It was thanks to his brother’s printing shop in Boston that he began honing his own writing skills and digging into practical subjects. This was the environment that set the stage for the rest of Franklin’s remarkable life. The print shop was a catalyst for Franklin—a place where he could channel his wide-ranging curiosity and explore his own multidisciplinary approach to life.

An Escape to Philadelphia

After five years alongside his brother, Franklin’s time in Boston came to an abrupt halt. James discovered that Franklin was behind the popular, anonymous submissions to the paper written under the pen name, “Silence Dogood.” As his brother lashed out in retaliation, Franklin took off for Philadelphia to escape the remaining terms of his apprenticeship. At seventeen, he officially set out to create something of his own. Philadelphia would become his lifelong home. 

Upon arriving in Philadelphia, the skills that Franklin honed in his brother’s printing shop, allowed him to find a job in the same space. As he began establishing himself in this new city, he was approached by the governor of the colony of Pennsylvania, William Keith. Keith urged Franklin to start his own printing shop and assist in his efforts to transform Philadelphia into a cultural center. 

Keith promised to lend Franklin the money for the machines and materials required to get things off the ground, but Franklin would need to head to London to secure them. Franklin saw this as terrific news, so he quit and bought a ticket for his passage to London. Keith assured him that the required letters of credit would be waiting for him upon arrival.

But when Franklin reached the shores of England, there were no letters of credit to be found. He discovered that Keith was full of empty promises. Franklin was now alone, halfway across the world, without enough money for a return ticket. 

Stranded in London

After allowing a brief moment for self-pity, Franklin set back out, determined to make his own way. He went to work at a large-scale printing shop in London. During this time he developed an even more extensive understanding of the printing business—learning new manufacturing methods and the importance of developing relationships with key customers and merchants.

After a year and a half in London, Franklin had finally saved the money for his return journey to Philadelphia. Upon his return, he leveraged the experiences and resourcefulness that he honed in these early environments to finally launch his own printing business. In short time, Franklin would become one of the most successful newspaper publishers and authors in the colonies. And this was all before he turned thirty.

If you study Franklin’s life, you see this time and time again. Franklin was a master at orchestrating the right environment for himself at each point in time—or making the most of it, as was the case when he was stranded in London in 1724. 

Whether his brother’s printing shop, the opportunity of a fresh start in Philadelphia, or setting up America’s first foreign embassy on the outskirts of Paris in 1776 to help negotiate a critical alliance during the American Revolution, Franklin was deliberate about his environment and putting himself in a position to learn and contribute the most he was capable of.

The Constitutional Convention

The importance of environment was something he never lost sight of. Even well into his later years, at eighty-one, Franklin positioned himself to play a significant role in the Constitutional Convention of 1787 where delegates from thirteen states set out to improve the Articles of Confederation. 

In those halls, Franklin established himself as the voice of reason. He was more receptive to the needs of each state and open to the diversity of opinions. His wide-ranging knowledge across subject matter, professions, and geographies helped him find common ground between delegates and resolve key issues facing a young country.

Many of the other delegates felt their integrity was tied to winning arguments and the accuracy of their initial opinions. Franklin stepped in multiple times to urge humility and an open mind, “For, having lived long, I have experienced many instances of being obliged, by better information or fuller consideration, to change opinions, even on important subjects, which I once thought right, but found to be otherwise.”

Despite heated debates and slow progress for the first two months, over time he imbued these qualities in the rest of the delegates. Franklin advocated for compromise and deemed the Convention a success because they were willing to concede they might be wrong and did not expect the new government to be without faults. The end result was the Constitution of the United States. 

Each step of the way, Franklin’s environment was a catalyst for his greatest work. 

And as his life demonstrates so well, the environment that resonates with you and challenges you to grow will evolve over time. Franklin held a strong sense of which environment was right for him at each moment in time. And it all started back in his brother’s printing shop in Boston.

Songwriting, Evolution, and Exploration

Franklin, though, is not alone in how he sought out the environments he found meaning in and the importance they played in his life. 

For Bob Dylan, it was moving to New York City and immersing himself in the folk-music scene of Greenwich Village during his formative years. It was here that he found his community, built confidence, and honed his craft. In the decades since, Dylan allowed his environment and influences to evolve. He’s explored different genres, different sounds, and different sources of inspiration to stay in touch with his own sense of authenticity. Even when it went against what his audiences expected.

For Charles Darwin (1809-1882) it was setting out on the HMS Beagle and sticking it out for five years despite treacherous seas and becoming deeply homesick. During this time, Darwin turned his attention to subtle observations of surrounding natural environments and the tiny details he found meaning in. This was the starting place for what would become the theory of evolution. 

But Darwin 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 saltwater to see how long they survived. What tied together these seemingly unrelated experiments—across natural landscapes and laboratories—was working to understand the nature of life.

For one of Darwin’s greatest influences, Alexander von Humboldt (1769-1859), a Prussian naturalist and explorer, it was his three-year expedition across South America that served as the spark for the rest of his life. While he didn’t set off on his voyage until he turned thirty-years-old, those three years of exploration opened up a whole new world of possibilities. 

Upon returning to Europe in 1804, despite his desire, he would never have the opportunity to return to South America. But he found meaning in new environments which made him come alive in different ways. One such example being the auditoriums in Berlin where he fascinated crowds by weaving together art, science, and poetry, bringing distant landscapes to life. We can imagine Humboldt’s series of lectures as a 19th-century precursor to Carl Sagan and Neil deGrasse Tyson’s Cosmos.

Environment was critical to each of these people—Franklin, Dylan, Darwin, Humboldt—at pivotal moments in their lives. And while they didn’t always find themselves in a perfect situation, when they were afforded the opportunity they were deliberate about which environment they chose to immerse themselves in. The end result helped each person find their footing so they were able to contribute the most they were capable of.

The Nashville Years

One of the most important moments in my own life, which set the trajectory for the past seven years, was when I decided to leave my hometown of Indianapolis in December of 2013. I was twenty-five when I packed up a moving truck and set off for Nashville, Tennessee. I found a cramped one-bedroom duplex that had seen better days. But rent was cheap and that was my best option to get down there. 

Although it wasn’t my job that led me back to Nashville. I interned there in college and fell in love with the city. In fact, I negotiated to keep my job in Indianapolis and work remotely from Nashville—that’s how committed I was. 

At the time, I was trying to figure myself out and felt drawn towards the creative community in Nashville. A new city allowed me to escape the narrative I locked myself into in Indianapolis growing up. Nashville presented an opportunity to struggle through what I wanted to do with my life and push the boundaries of my comfort zone.

In the early days, this wasn’t easy. I missed home. I missed routine and familiar surroundings. But as I struggled through this period, eventually I found my way back to writing, launching my own startup, and learning how to stack the skills that set me apart. I started to believe in myself, building confidence in what I wanted to do with my life and how I wanted to spend my time. 

By giving myself space to explore in Nashville, I returned to two of the most important outlets for learning and creativity than I lost years earlier—reading and writing. It’s hard for me to overstate the importance that these have played in my own growth—personally and professionally.

Reading offered me lifetimes of wisdom to find the way forward. Writing provided me room to reflect on these lessons. Together these allowed me to challenge myself, explore questions, channel curiosity, and find kindred spirits. Nashville was the space I needed to step back and reevaluate what mattered to me. 

Ultimately, seeking an environment with room to explore led me back to not only an outlet for creative expression in writing, but also towards a career that fit me. As I honed my own multidisciplinary approach and considered what I was naturally drawn towards, I found my way into product management. 

I’d be lying if I said I wasn’t terrified when I drove away from Indianapolis—my home for the past two decades—towards Nashville on that cold December morning. But the easiest path is rarely the most fulfilling. A deliberate decision to seek out the environment that resonated with me at that point in time had a profound impact on the course of my life.

But just as Benjamin Franklin demonstrated so well, you can’t expect your environment to remain the same throughout your entire life. And after seven amazing years in Nashville, we recently relocated to Denver. This time it was for a job opportunity and a new community, as I’ve found my niche and an opportunity to grow my career. 

Leaving Nashville was just as difficult as it was leaving Indianapolis over seven years ago. But we felt like it was the right thing. This new opportunity presented an amazing chance to grow, face new challenges, and push ourselves. 

For me, Nashville was the single most important environment I found during my twenties. It helped me rediscover a creative outlet and led me to a new career. It introduced me to a community of beautiful, deeply talented people who challenged me to discover myself, push forward, and trust in those things. I’m better for having grown up there. Everything about Nashville—the community of creatives, the distance from home, and opportunities it presented—made me a better person.

Environment Is Your Force Multiplier

Much of our lives hinge on finding the right environment. This might mean surrounding ourselves with the right community, finding somewhere that feels like home, being in the right place at the right time, or seeking out challenges that we find meaning in. And this evolves over time. Whether community, geography, or opportunity, we value different environments at different points in our lives. 

Decisions about your environment should be deliberate. And you can’t cling to the same environment for the rest of your life. Things change. You change. The best you can hope for is to remain in harmony with the motion that defines life. 

By seeking out an environment that resonates with you, you can accelerate the rate at which you grow and create room to have a far greater impact. Environment is a force multiplier. You still have to put in the effort. But paired with the right place, it goes significantly further. 

In the words of Nassim Taleb, “You want to be the fire and wish for the wind.” Think of your environment as the wind. Pair this with the fire within and that’s how you catch hold of life—giving the most to yourself and the people around you.

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.

How to Overcome Your Fear of Falling Behind

The secret of discovery periods, stacking skills, and accelerating your growth curve

Early in my career, I was constantly worried about falling behind. I had this idea of a growth curve in my head, but in comparison to both my peers and my imagined potential, I felt like I was falling behind. There seemed to be a perpetual gap between where I was and where I thought I should be.

I would often tell myself, “I wish I wanted the same things as everyone else.” But what I’ve discovered is that when you provide yourself with a discovery period and allow yourself room to explore early in life, you always come out ahead. You just have to expand your perspective of time. 

The trouble is that at the start of your career, you only have a tiny corner of the map for reference. But the older you get and the more experience you gain, the more obvious this becomes. 

Those who start their careers without any level of introspection or sense of a discovery period might land a safe job, a decent signing bonus, and jump out to an early lead. But that type of growth follows a linear path which is incremental at best. Exponential growth is what you’re really after. 

“Not all who wander are lost”

For me, the first six years out of college were a discovery period. And from the outside looking in, the first twelve months probably seemed like a train wreck. 

I went from working on the set of major music videos, to considering medical school, signing up for pre-med undergraduate courses I missed the first time around, dropping out, waiting tables at a Tex-Mex restaurant, and taking a job in communications at a healthcare startup.

From there I worked my way into product management, as I discovered a gap between our sales team and our engineers. When I first assumed a product role, it was without knowing that product management was even a thing or potential career path. It just aligned with my natural interests – blending business, design, and technology. And the more I learned about product, the more I dug in. 

A few years later, I furthered that skill set by launching my own startup to connect people with local farmers markets and food sources. Alongside a talented engineer from my first job, we built FarmScout from the ground up. A few years later, it was acquired by another entrepreneur based in Portland. 

Out of all the early experiences I had, this was the most important in terms of a discovery period. If you want to accelerate your growth, determine what you’re good at and identify your gaps, try creating something from nothing. 

Around this same time, I also found my way back to writing. The formulaic essays from school had turned me away from the craft. But at 25, I decided to spend a random Saturday evening putting some thoughts on paper at The Well, a local Nashville coffee shop. I ended up writing for three hours. Before I knew it, I was there five nights each week, rekindling my love for writing – something I find meaning, clarity, and a deep sense of fulfillment in. Months later, I launched an early iteration of this blog from that exact spot. 

Growth is nonlinear

This period of six years was full of other ups and down – traveling internationally, exploring philosophy, building perspective. But around age 28 things finally came together.

By that point, I found my niche in product management, something I feel uniquely suited to do. I rediscovered writing and moved it back into a focal point of my life. I dedicated more of my time to the things and the people I cared about most. I began to stack the skills that made me, me. 

While I didn’t know it at the time, looking back, this is when my dedication to a discovery period began to pay off. My trajectory completely shifted. 

When setting off on a discovery period, you need to understand that input rarely matches results early on. Growth is nonlinear. You have to stick with something long enough to get through the plateau before you reach a breakthrough moment. It often takes months, if not years, to see the results. That’s why it’s so important to find the things you can sustain indefinitely and stick with those.

While I don’t presume to have it all figured out, I feel like I have a stronger sense of who I am and what’s important to me because of the discovery period I was able to carve out for myself. My hope in explaining the past decade of my life is that I’m able to provide you with a real example that you can pull from and relate to. 

History is also full of similar examples. Every influential historical figure in my latest ebook, 7 Strategies to Navigate the Noise, faced similar challenges early in their life during their attempts to figure things out. From Alexander von Humboldt and Charles Darwin to Queen Elizabeth and Caterina Sforza, each person faced a discovery period where they felt like they were falling behind as they searched for something different than the lives neatly prescribed to them. But as they came to understand, what matters most is the trajectory you’re setting yourself up for. 

Those who follow a neat and orderly path might be a few steps ahead early on. But if you expand your perspective of time, it’s those who have explored and followed their natural inclinations that come out ahead. This is how you find real meaning and engagement. And both act as force multipliers. 

In the early days, you just have to remain patient and allow yourself to sit in the gray area between the two growth curves.

Focus on getting the conditions right, seek opportunities that allow you room to explore, and it’s only a matter of time before you catch your break. 

Stacking the right skills

During this discovery period, what you’re really after is determining what matters to you and how to stack the skills that set you apart. These will help move you closer to your guiding principle – what you find meaning in and your fundamental goals. 

Stacking the right skills is what allows you to hit this exponential growth. If you attempt to specialize in a single skill, it might work out if you’re a prodigy or operating in a rare field that has a neatly defined set of rules. 

But when facing the ambiguity inherent to the majority of life and work, this demands creativity and resourcefulness. If you’re only competing with a single skill at your disposal, it’s difficult to be creative and even more of a challenge to set yourself apart. 

But when you stack skills, layering one on top of the other, you begin carving out your own niche. From here you can create your own playing field and accelerate your own trajectory.

I’m not in the top ten percent when it comes to design or technology. But when I stack those alongside business, communication, storytelling, strategy, and a fierce sense of focus, that’s when I’m able to set myself apart. By wielding each of these skills, I put myself in a position to be more creative and resourceful. And this is the path towards authenticity and creating work that matters.

Tech
Design
Business
Storytelling
Communication
Strategy
Focus

The same lesson holds true for something like machine learning (ML). It’s incredibly difficult to establish yourself at the top of that field in its purest form. But if you stack skills in music composition, programming, analytics, and ML, it’s a rare group of people whose natural interests align and are able to combine those skills. And suddenly instead of competing against 50,000 industry experts, there are only 20 people who even remotely overlap.

Learning which skills to stack is about coming into your own. What makes you unique? What are your natural inclinations? What comes easy to you that other people find difficult or impossible? What can you sustain indefinitely? A discovery period allows you to begin uncovering answers to these questions. 

Law of the hammer

The added benefit of stacking skills is that you’re able to begin mastering a multidisciplinary approach. This is how you outthink and outmaneuver people. And it helps guard you from becoming trapped in a one-track mindset where you attempt to apply a single approach to every problem you face.

When all you have is a hammer, everything looks like a nail. A multidisciplinary approach is the antithesis of the law of the hammer. It helps you avoid the cognitive bias that is the over-reliance on a single model. 

The more mental models you possess, the stronger your cognitive ability, and the greater your capacity to grow. Remember, when you only have a single model to work with, growth is often incremental at best.

If machine learning is the only interest and skill you’ve developed, chances are that every problem you face is going to look like an ML problem. But when you’ve armed yourself with a multidisciplinary approach and you’ve stacked the skills that set you apart, you can see problems and opportunities for what they are. From here, you’re able to determine a more effective course of action.

Be loyal to the best opportunities for growth

Early in your career, the most important thing you can look for is opportunities that allow you room to explore.

If you’re in technology, this could mean working somewhere that provides exposure to different programming languages, frameworks, technologies, and products. Or it might mean seeking out an opportunity on a diverse, cross-functional team that provides you with exposure to a range of disciplines and perspectives. 

Whatever you do and wherever you are, remain loyal to the best opportunities for growth. 

Don’t allow yourself to get locked into an isolated career early on. It might seem like a head start for the first few years, but you’ll pay dearly later on in your own growth and sense of engagement. Prioritizing short-term gratification over learning and growth is how you end up in a dead-end career with regrets.

Give yourself time to figure yourself out. Allow yourself room to explore. Prioritize the places and people who appreciate this need. 

By creating space and pursuing opportunities that reward a discovery period, you can start figuring out how to stack the skills that set you apart. This is how you develop yourself, accelerate your own growth, and avoid the traps that most people find themselves lured into. 

Channel what makes you, you. With this mindset and room to explore, you’ll run laps around your younger self and make it impossible for others to keep pace. By committing to the long game, you unlock the power of compound interest and exponential growth. And this is how you accelerate your trajectory and create real meaning. 

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.