Subtract To Get To Your Truth

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

— Nassim Taleb

On August 6th, 1986, Bob Dylan walked off the stage at Paso Robles State Fairgrounds alongside Tom Petty and The Heartbreakers and he knew he was done. Dylan had one more stretch of shows lined up with Petty the following year—The Temples in Flames Tour—but after that, it was time to hang it up.

It had been 25 years since an unassuming kid from Hibbing, Minnesota showed up in Greenwich Village to immerse himself alongside his heroes in the folk-music community. And it was a legendary run. But Dylan acknowledged the reality of what his fans, critics, and peers had already voiced, his best days were behind him.

Dylan could no longer fill stadiums on his own and had to rely on big names like Tom Petty and The Heartbreakers or The Grateful Dead to draw crowds. He struggled to write new material—not that he had much desire to do so. And despite the hundreds of songs he had written over the course of his career, there were only a handful he would consider playing. 

During the Summer tour in 1986, Benmont Tench, the keyboardist in Tom Petty and The Heartbreakers, often pleaded with Dylan to include different songs in the set, like “Spanish Harlem Incident” or “Chimes of Freedom.” Dylan would muster up some excuse or play it off until he was able to divert the attention away from himself. 

The reality is that he could no longer remember where most of the songs he wrote came from. He couldn’t relate to or understand how he might even attempt to bring those songs back to life. They were a mystery lost to the past. 

Dylan’s plan was to coast through the final tour with the same 20 songs and try to come out unscathed before he went into hiding. That was the deal he made with himself to get through one more run.

The next year before kicking off his final tour with Petty, Dylan was scheduled to play a few shows with The Grateful Dead. He traveled to San Rafael, California to rehearse with The Dead at their studio. After an hour of rehearsal, it was clear that the strategy he used with Petty wasn’t going to work. The Dead were adamant about playing different songs from the depths of Dylan’s catalog. Material he could barely recall. 

He sat panicked and knew he had to get out. The Dead were asking for someone he felt no longer existed. During a lull in the rehearsal, Dylan falsely claimed he left something at the hotel. He stepped out of the studio and onto Front Street to plan his escape.

After wandering for a few blocks, Dylan heard music coming from the door of a small bar and figured that was as good of a place to hide out as any. Only a few patrons stood inside and the walls were baked in cigarette smoke. Towards the back of the bar, a jazz quartet rattled off old ballads like “Time On My Hands.” Dylan ordered a drink and studied the singer—an older man in a suit and tie. As the singer navigated the songs, it was relaxed, not forceful. He eased into them with natural power and instinct. 

As Dylan listened on, there was something familiar in the way the old jazz singer approached the songs. It wasn’t in his voice, it was in the song itself. Suddenly, it brought Dylan back to himself and something he once knew but had lost over the years—a way back to his songs. 

Earlier in his career, Dylan wasn’t worried about the image that others projected upon him, the expectations, or the fame. All he cared about was connecting with the song and doing it the justice it deserved. He was there to bring the words to life—a conduit of sorts. The old jazz singer had reminded him of this simple truth and where to pull from.

Returning to The Grateful Dead’s rehearsal hall, Dylan picked up where he left off like nothing happened. He was rusty and it would take years for him to truly get back to form, but he settled back into a state of relaxed concentration by returning to his principles that were buried underneath all the success, failure, praise, and criticism.

As he continued the final tour with Tom Petty and The Heartbreakers, over the first four shows Dylan played 80 different songs, never repeating a single one, just to see if he could do it. It wasn’t perfect. It wasn’t always pretty. But he was starting to tap back into himself and knew how to reach the music again. 

Where am I?

In our own lives, we inevitably reach moments where we feel like we’ve lost ourselves along the way. Where am I? How did I get here? What am I even trying to do? We feel like fragments of our former selves. Exhausted rather than energized by the challenges we face. 

Dylan is not alone in his experience. When we lose the connection to ourselves, our work, careers, and lives grow stagnant. We can’t create anything meaningful if we’re absently going through the motions. Gradually, then suddenly we become strangers to ourselves. 

As the emptiness creeps in, there’s a temptation to go into hiding. We fixate on our faults and let that feeling wash over us. We lose ourselves in the darkness. And when we get stuck here, we compromise our own integrity and the integrity of our work.

Life is deceptive in this way. We overcomplicate things. We inflate the importance of things that don’t really matter. We lose track of what brings us to life—the things we find deeper meaning in. We let our guiding principles fall out of focus. 

In the messiness of life, we make small compromises that add up over time. We say yes to the wrong things and no to the right ones. Things start to pile up. And the more we stack on top of ourselves, the deeper we bury our own priorities. Eventually, the weight of it all drags us down and obscures our vision. 

At this point, we can continue adding more, doing more, always saying yes, never saying no, breaking ourselves to meet the expectations cast upon us. We can continue floundering and creating more distance from ourselves. Or we can step back and ask, is this still serving me? What do I need to shed to come back to myself? What’s at my foundation?

Finding our way back

Sometimes the way back to yourself is through subtraction. 

This starts with peeling back the layers that have built up over the years.

What’s hidden underneath it all? 
What was your original motivation in your work? 
What got you here in the first place? 
What did you know then that you’ve since forgotten? 
What about this once brought you joy?

Finding a way to return to the simple truths we once knew can help us realign ourselves. Our foundation reminds us of what we set out for.

Far too often we attribute our identities to things that are beyond our control. We get caught up chasing what’s external to us because we trick ourselves into believing that’s what makes us who we are. But we are not our jobs, companies, titles, or paychecks. We are not the criticism, praise, accolades, or rejection we face. We exist beyond that. 

When we are just starting out, we instinctively understand this. We focus on internals and creating from what we know to be true about ourselves. We build from what inspires us. And that is enough. Because that’s all we really know. 

As Dylan faced this struggle, inspiration from an unlikely source brought him back to a beginner’s mindset and the principles he understood early in his career before everything got so carried away. Performing was about reaching for the truth within the song and putting that front and center. 

This mindset allowed him to tap back into himself. He was able to once again find meaning in his songs and remember why he was doing what he was doing. He embraced his responsibility to perform each song to the best of his ability. 

From this point on, Dylan focused on playing smaller theaters and more intimate shows—drawing songs from every stage of his career, reinterpretations, new songs, and rarities. Returning to the basic truths he lost along the way led to his resurgence as an artist. Rather than signaling the end of his career, The Temples in Flames Tour helped Dylan uncover the start of something new.

Letting go to remember

Connecting back to yourself starts with cutting away the nonessentials and reminding yourself how you found your way here in the first place. Subtract to get to the truth of things. 

In the process of letting go, you start to remember who you are and what you find meaning in. 

This doesn’t mean you should try to recreate the past. You can’t go back in time. Dylan wasn’t trying to bring a younger version of himself back to life. He was just returning to the principles that set everything in motion and rebuilding from there.

A beginner’s mindset can help you distill the real parts of yourself—the anchors that give you substance and depth. By paring down to what’s real and what’s within your control, you tap back into what sustains you. And as you sift through the rock, dirt, and debris, you free yourself to move with conviction towards bringing your best work to life. 

3 Questions to Help You Rise to the Level of Mastery

“To rise to the level of mastery requires intense dedication. You have to really want it. What would make you have such commitment and dedication?”

— Robert Greene

At the start of my career, I wondered what I was doing wrong. I wanted to dedicate myself to my career, but I didn’t trust myself to know which potential directions were worth going all in on. I was terrified of making the wrong decision. And my early 20s, ego gave me a false sense of confidence and deluded me into believing I could be anything I set my mind to. Rather than eliminating options and accepting that directions in life are mutually exclusive, I sat in indecision. 

But the truth is that you can’t be anything in this life. There are things you are uniquely suited to do based on your skill set, interests, and experiences. And the sooner you accept this reality and cross options off the list, the more time you give yourself to dedicate to the things you’re uniquely good at. But this demands reflection—you have to allow yourself to reflect on the skills you’ve excelled at, the subject areas you’re naturally drawn towards, and where you find meaning. 

What are you naturally good at?

At 24, I was living in Nashville with no idea what I wanted to do in my life. One weekend, I forced myself to go to a coffee shop around the corner, put my headphones on, and write. It was the first time since I was eight years old that I was writing for fun.

Over previous months of reflection, I asked myself what I was naturally drawn towards in childhood and what skills I excelled at without trying as hard as other kids. I remembered that writing was one of those things so I pushed myself to reconnect with this. The connection was immediate and the state of flow I was able to achieve in writing was addicting. That’s how I knew I was on the right track. 

As I used writing to reflect on who I was, I also started to recall how industrious I was as a kid, working to generate extra money. From as early as I can remember, I was working my way through the neighborhood mowing yards, shoveling snow, or starting a mobile snow-cone operation on the back of a wagon that I’d roll door to door during the summer. I loved testing new ideas.

And finally, as I searched for how to fit the pieces together and what to focus on, I began reading for enjoyment again—another thing I loved as a kid and lost through school over the years. This allowed me to hone my sense of focus. I also began to develop stronger strategic thinking skills and stack mental models from different disciplines against each other to improve my decision-making.

All of this led me to a career in product management that I’m deeply invested in. Product demands an elite level of resourcefulness, focus, and communication skills. You have to be driven to create, take risks, and articulate stories in a way that resonates with different audiences. And you have to be able to quickly evaluate directions from multiple perspectives. These were all things I showed aptitude in from an early age. I just had to reconnect with those things and forget all the shit that happened between age 8 and 24 to get back there and align myself to that. 

Perhaps the most important aspect of this is that when you leverage skills that come naturally to you, you can outwork everyone else around you because the work itself is deeply rewarding and where you find your flow state. Your validation comes from the craft itself—internal, not external.

If your goal is mastery, the first step is reconnecting with your childhood interests and skills that come naturally to you. These are the places you must invest in.

To achieve alignment and build from a place of authenticity, you must first remember who you are.

What subject matter are you drawn towards?

During the early part of my career, I bounced between different industries—music, film, healthcare, and insurance. And what I learned through exploration was that those weren’t the things I cared deeply about. After a year or two in each, I was bored and struggled to sustain a connection with the problems we were tackling.

When I started my career in film production working on set for major music videos, I was barely able to sustain two summers in that line of work. It seemed glamorous from the outside looking in. But the inefficiency of working 22 hours for a three-minute music video drove me insane. And most importantly, I wasn’t willing to struggle for the end result because I didn’t connect with many aspects of the work that I was exposed to—whether finance, set design, project management, or cinematography.

I also found I didn’t have a natural interest in the entertainment industry or the value we were providing. And if you don’t care about the subject you’re focused on, it’s going to be tough to stick it out.

But early on, finding something that doesn’t resonate with you can be just as valuable as finding something that does. Because it helps you eliminate a direction and move on. The goal is to learn and refine to better align yourself with each move. 

Through trial and error, the subject areas that I’ve found a deeper interest in are philosophy, education, and finance. After close to a decade of exploration, before I applied to my current job, I knew I was going to stick with edtech and fintech as the sectors I wanted to work in. And it worked. Snapdocs is in the broader fintech category and I find the work endlessly fascinating. So I can stick it out despite the challenges and obstacles in the way of achieving our vision.

There are subjects you’re naturally drawn towards. Consider what you enjoy reading and learning about right now. That’s your starting place. The more you invest in these things, the better. Because it’s very difficult to sustain interest in a field or subject that you aren’t pulling from a deeper sense of curiosity about.

Mastery requires a relentless level of focus and effort.

Where do you find meaning?

And finally, you must also search for meaning. Because no matter how naturally talented you are and how interested you are in a field, you have to find meaning in the work or you’ll forever lack the persistence that mastery requires. 

This can show up in different ways but once unlocked it’s the force multiplier that allows you to endure. Whether it comes from the group of people you’re building alongside or the end result you’re driving towards or the brokenness you’re working to fix. There will be weeks and months that test your limits. If you lack meaning, it will be impossible to continue showing up. Mastery demands endurance. 

“Almost nothing in the world can resist persistent human energy. Things will yield if we strike enough blows with enough force.”

— Robert Greene

I find meaning in accelerating personal growth and pushing the confines of my current limits. I find meaning through the people I’m collaborating with on a daily basis to solve challenging problems. And I also find meaning in solving problems that translate directly to human outcomes. That’s one of the reasons I love my current position, I’m motivated to make the disaster that is the home buying experience less shitty. I want it to be accessible and more transparent for everyone involved. And it’s incredibly challenging. But worth it, because the end result we’re working towards is meaningful to me and I’m able to test myself along the way. 

Another way to think of this is asking yourself, what are you willing to suffer for? You’re going to struggle regardless of the line of work you enter. It’s going to be hard. There will be moments that piss you off or lead you to question what you’re doing. To get through these moments, you have to recognize and reconnect with a deeper reason that keeps you going.

Where do you find meaning? You can endure anything if there’s a deeper connection to your craft and the problem you’re focused on. Keep this front and center and you will be able to persevere when the inevitable obstacles stand in your way. Endurance is foundational in the pursuit of mastery. So what are you willing to show up for every single day?

Rising to the level of mastery

Once you’ve achieved alignment with the answers to these three questions, you’re on your way. But you still have to put in the work. You still have to show up. There is no path towards mastery without having skin in the game. 

As tempting as it might be to distance yourself from the work and make it easier on yourself, this works in opposition to mastering your craft. You can never be above the work. This also helps ensure your incentives are aligned and you have a vested interest in the outcome. Because even when you come up short, you can always take solace in the fact that the credit belongs to the man in the arena. 

When you’ve aligned yourself to skills that differentiate you, subjects you’re naturally drawn towards, and focused on where you find meaning, this all acts as a force multiplier for your work. 

You are uniquely positioned to bring certain things to life. You can’t be everything. And if you want to maximize what you’re giving back to this world, the sooner you focus on mastering what you’re uniquely positioned to contribute, the more fulfillment you will find.

10 Lessons on the Road to 33

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

1) Show up, even when it’s inconvenient 

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

2) Commitment adds meaning

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

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

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

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

4) More music, less everything else

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

5) Focus on what’s within your control

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

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

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

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

7) In-person interactions hold company’s together

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

8) Appeal to Your audience’s self-interest

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

9) your first responsibility is to shut up and listen

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

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

10) to command respect, be fearless

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

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.

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.

Reveal More, Signal Less, and Why Your Stories Matter

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

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

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

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

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

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

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

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

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

— Jerry Colonna

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

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

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

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

— Anne Lamott

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

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

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

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

— George Dawes Green

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

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

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

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

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

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

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

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

— Pádraig Ó Tuama

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

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

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

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

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

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

It’s hard to leave something that’s easy

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

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

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

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

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

Strategies to push yourself in moments of doubt

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

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

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

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

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

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

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

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

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

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

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

Prepare yourself for a battle

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

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

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

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

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

How to 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. 

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

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

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

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

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

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

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

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

Escaping the narrative

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

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

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

The power of ”who cares?”

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

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

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

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

Swim lessons and my life’s finest moments

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

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

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

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

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

Handling nerves in the moment

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

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

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

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

Jump when others retreat

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

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

The Power of Your Early Influences

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

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

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

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

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

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

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

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

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

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

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

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

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