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.

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 Interview at Your Best

About this time last year I flew to San Francisco to interview for a new product position. It was my first interview in nearly two and a half years. I was out of practice and nervous beyond measure. Ultimately, it wasn’t a good fit—part of that was likely due to the fact that I never allowed myself to really settle in. And this was all despite my own advantageous position with a great job and leverage.

Interviews are hard—they challenge you to distill your ideas and frameworks in their simplest form, they’re time consuming, and depending on where you interview, it might not always feel natural. Early in your career, it’s also easy to compromise on your own principles and attempt to fit yourself into the mold that you think a potential company is looking for. 

(Note: Are you wondering if it’s time to look for a new job? Start with this article, instead.)

As I continued exploring opportunities and interviewing over the past year, I started to settle in a bit. Some days I lost my focus and ended up incessantly checking email and LinkedIn. I had to constantly remind myself to take a step back and breathe. It’s hard not to get too far ahead and trap yourself into a fixed mindset. 

But one year later, I’m excited to announce that I’ve accepted an offer to move to Denver and join the product team at Snapdocs. While I wasn’t perfect during the interview process, practice over the past year allowed me to remain patient, find the best fit, and be myself throughout the interview process. As a result, I have an incredible opportunity that aligns with the problems I want to solve, the people I want to solve them with, and the ways I want to learn, grow, and help others do the same. 

Here are six of the key lessons that allowed me to relax and find my new home while navigating dozens of interviews over the past few months.

1) Maintain a growth mindset

There’s a fine line between a growth mindset and arrogance. If you’re driven by ego, you’ll carry a sense of entitlement. But if you embody a growth mindset, you’re able to balance personal humility and an understanding that there’s no shortage of great opportunities out there for you. 

There are multiple spots that could be a good fit. There’s no single place that will make or break you. If you’ve worked hard and developed a skill set that fits you, you will have options. There’s no need to act out of desperation. But just keep in mind, it’s up to you to discover strategies and build habits that create room for those opportunities.

A growth mindset is about having the calm awareness that there are opportunities out there. You still have to push yourself to take advantage of them. But they’re there for the taking if you keep your eyes open and prepare yourself to take the leap when an opportunity presents itself. 

2) Never come unprepared

There is one thing, and exactly one thing, that’s entirely within your control during the interview process—preparation. Don’t trick yourself into believing that you can wing it or that you don’t need to prepare. 

This is about identifying what’s within your control (internals) and what’s beyond (externals). Preparation is an internal that you have direct control over. You don’t have control over fit, timing, or who the hiring manager is. Focus on you. Don’t put yourself at a disadvantage because you ignored the one thing within your control.

If you miss out on an opportunity because it wasn’t a good fit, the company put a hiring freeze in place, or you didn’t quite hit it off with the hiring manager, that’s fine. It happens. But you should never sacrifice opportunities because you were unprepared. Research the company, read articles on them, ask the recruiters what the team is looking for, prepare for behavioral questions and case studies that you know are coming, keep a list of detailed questions you have, practice!

3) Be true to yourself

Authenticity matters. And if the place you’re interviewing at doesn’t care about that, I promise you don’t want to work there. There’s no reason not to be yourself. You want to work somewhere where the people respond well and are excited about the person you are. 

Part of a growth mindset is looking for somewhere that fits you equally well. Don’t compromise on what’s important to you and your principles by attempting to fit yourself into the mold that you’ve imagined someone else is looking for you. Be you. It’s much easier that way. 

When you pretend to be something you’re not, it’s impossible to keep up that facade for long. But when you start from who you are, you can sustain that indefinitely and you set yourself up for long-term success. 

4) Know what you’re looking for

A big part of authenticity is knowing what you’re looking for and not compromising when it comes to the most important things. Before I started seriously interviewing during the past few months, I made a list of my ultimate goals, as well as my must-haves, nice-to-haves, and can’t-haves. Then I evaluated opportunities in these terms. 

Ultimate goal:
Spend the next ten years pursuing big opportunities for accelerated learning where I’m able to work with talented people on challenging problems that have a real impact on people’s lives. My hope is to be able to write about and teach from these experiences later in life—either by growing into a leadership position within a forward-thinking company or writing/speaking full time. 

Must-haves:

• Skin in the game (out there taking risks and bigger swings)

• Creative freedom

• Authenticity and resourcefulness rewarded

• Opportunity to teach and grow alongside others

• Ability to shape both product and company

Nice-to-haves:

• Advancing the discipline of product

• Helping others grow in their careers and lives

• Product leader in the top 10%

• Compensation/bonus/equity

• Edtech or fintech

• B2C

Can’t-haves:

• Enterprise (>1000 employees)

• Low risk, low reward

• Big company bureaucracy

• Healthcare, insurance, or consulting

• Elementary product culture

4) Aim for 90% and be happy with that

You won’t get through an entire interview process without saying at least one or two stupid things. Accept that. You’re human. As you’re reflecting on an interview, you might cringe at a couple of statements you’ve made. Give yourself permission to move on. I’ve said some really stupid things, the only way forward is to laugh it off and use it as a learning experience. 

5) Beware of projecting

It’s going to happen. It’s impossible not to imagine what your life would look like in a new role or start looking at apartments/houses in a new city. When I felt things were going well during initial interviews with Snapdocs, I’d be lying if I said I didn’t search for Denver’s best neighborhoods to live in. But in those moments when I felt myself getting too far ahead, I had to gently bring myself back. 

If you’re anything like me, you’ll have to do this hundreds of times each day. But what’s important is that you’re able to recognize when you start projecting and bring yourself back to where you currently are.

6) Don’t make irreversible decisions before you have to

New jobs are significant life events. Job interviews are stressful. But one of the cardinal rules of rational decision-making is never making irreversible decisions before you have to (small, reversible decisions, on the other hand, should be made quickly).

It’s okay to have a feeling. But you can’t make the decision to accept an offer, join a new company, or move across the country before you actually have the offer in front of you. 

Allow yourself to be excited. But guard your peace of mind. You shouldn’t make massive life decisions before you’re actually faced with them and have the information that you need to effectively make that decision.

The 6 Most Important Books I Read in 2019

1. The Laws of Human Nature by Robert Greene

Robert Greene is a master strategist—perhaps the best of our generation. This book is the culmination of his lifetime of work on power, influence, and mastery. It’s an instructive guide to human nature based on historical accounts and evidence, rather than a particular viewpoint or moral judgment. 

As Greene, emphasizes throughout the book, a deep understanding of human nature is advantageous for countless reasons. It helps build you into a strategic observer, become a better judge of character, outthink malicious people, develop greater empathy, and realize your potential.

True to form, Greene pulls stories from both sides throughout history—those who have succeeded and those who have failed in spectacular fashion. It’s an incredible resource if you want to hone your strategic mind and will pay immediate dividends in your own life, no matter your position. 

“And in life as in warfare, strategists will always prevail over tacticians.”

— Robert Greene

2. Creativity, Inc. by Ed Catmull

A modern case study of how to harness creativity and build a culture where the creative process can thrive. Catmull discusses the evolution of Pixar Animation, including the philosophies and strategies that helped establish them as a creative force in animation and storytelling. 

Catmull emphasizes how the teams embrace years of ambiguity that are inherent to the creative process as stories evolve into their own. Instead of becoming attached to a single storyline or character, they seek out a deep truth at the core of the film—a guiding principle—and craft the story around that. Catmull also stresses the role of leadership in cultivating creativity. It starts with loosening your grip, accepting risk, trusting your people, and giving them space to do what they do best. 

“Craft is what we are expected to know; art is the unexpected use of our craft.”

— Ed Catmull

3. Range by David Epstein

In a complicated, competitive world, there’s a push to focus early and narrowly. Navigating life seems to demand specialization. And the stories told the loudest (Tiger Woods) push that narrative. 

In reality, far more eventual top performers devote less time to deliberate practice early on and instead undergo a sampling period. This offers them an opportunity to learn about and discover their own abilities and inclinations. Only later do they focus on one specific area and ramp up technical practice (Roger Federer). 

This book is a tremendous resource for generalists and those pursuing a multidisciplinary approach in life. It’s something that needed to be written and Epstein does a great job emphasizing breadth over depth, the dangers of specialization, and the importance of match quality along the way.

“We learn who we are only by living, and not before.”

— David Epstein

4. Extreme Ownership by Jocko Willink & Leif Babin

One of the best books on leadership that I’ve ever come across. And this is one of those books that I happened to read at the perfect time when I needed these lessons the most. Willink and Babin, two Navy SEALs officers, recall their time leading the most highly decorated special operation unit of the Iraq War. Each chapter highlights one of their leadership principles in action before relating it back to the business world. 

I found the most relevant section to be on the laws of combat: cover and move, simple, prioritize and execute, and decentralized command. If you want to win, teams must not only know what to do, but they must also know why. As a leader, your job is to ask questions until you understand why. 

There are also great lessons in empowering yourself by accepting total responsibility—no matter your position—and the importance of being aggressive (not overbearing).

“There are no bad teams, only bad leaders.”

— Leif Babin

5. Skin in the Game by Nassim Taleb

One of the best things about Taleb is his eagerness to challenge standard conventions and long-held beliefs about a range of topics. Nothing is off limits. As a result, you’re guaranteed to walk away with a new perspective after reading any of his books. In Skin in the Game he picks apart the way we think about uncertainty, symmetry, risk-sharing, and rationality in complex systems.

Taleb emphasizes the importance of thinking in high dimensions and evolving beyond the shallow. He also digs into how acting by removing is more powerful and less error-prone than acting by addition. This has implications in terms of unnecessary complexity in both our lives and how we think about strategy.

But the core of the book focuses on ethics and morality. Skin in the Game is about putting yourself out there and taking risks of your own. It’s immoral to keep the upside and transfer the downside to others. Besides, it’s impossible to understand the world and develop your own abilities without putting yourself out there and taking risks of your own. 

“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

6. Endurance by Alfred Lansing

A brilliant tale of survival that documents Sir Ernest Shackleton’s failed voyage to cross the Antarctic. Shackleton was a compelling, larger-than-life figure who offered lessons in leadership and strategy at each turn.

The book also contains one of my favorite passages. And it speaks directly to strategy and thoughtful action: “Whatever his mood – whether it was gay and breezy, or dark with rage – he had one pervading characteristic: he was purposeful.” If you want to sharpen your strategic mind, that’s what you’re after. Every action should have intention.

Shackleton’s most profound lessons are revealed in his ability to transcend the fundamentals and shift strategies as the situation required. There are few men who faced more dire circumstances than Shackleton and his crew, and who survived without any casualties. While you can’t separate luck, there was a strong level of strategy and leadership required to come out alive on the other side. 

“Whatever his mood – whether it was gay and breezy, or dark with rage – he had one pervading characteristic: he was purposeful.”

— Alfred Lansing

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. 

Self-Sufficiency: The Ultimate Stoic Virtue

Above all else, the Stoics were masters at assigning things their proper value. The great Stoic philosophers knew the importance of identifying what was within their control, what was beyond, and what fell in-between. And they maintained an unwavering sense of focus on the things within their realm of control.

Nowhere is this more evident than the core Stoic virtues of wisdom, justice, courage, and moderation. But at the foundation of this Stoic range of virtue and your sphere of influence sits one underlying principle that ties it altogether – self-sufficiency. From self-sufficiency stems all other virtues.

It’s a dangerous game to tie your sense of meaning and wellbeing to someone or something else. When you fixate on things beyond your control, you become restricted, dependent, and weak. And you introduce dependencies that can drop you into a state of anxiety, envy, or despair without warning.

But when you guard your self-sufficiency above all else and focus more attention on what’s within your sphere of control, you gain flexibility, independence, and strength.

“If a person gave away your body to some passerby, you’d be furious. Yet you hand over your mind to anyone who comes along, so they may abuse you, leaving it disturbed and troubled – have you no shame in that?”

— Epictetus

Self-sufficiency is about focusing more of your time and energy on the things you can actually have an impact on. And it demands that you assume responsibility for those things.

There are those who argue against self-sufficiency as if it’s the enemy of progress. And there’s an element of truth to this. Since we don’t all have to worry about harvesting our own food, sewing our own clothes, or building our own tools, we can get further up on the hierarchy needs. We can trade chores and focus on what we find meaning in. This is progress.

But I mean self-sufficiency less in terms of technology, and more in terms of the reliance on others for the internal quality of your life and your wellbeing. Assuming you’re healthy, the less reliant you are on others to provide the things that only you’re able to give yourself – meaning, virtue, character, integrity – the greater your capacity to give something back to the world.

And while it might fly in the face of progress, voluntary hardship is an important tool for self-sufficiency. Sometimes you have to do the work, suffer a little, and take the long way home. This is a training ground for your mind. It builds willpower and resilience.

“As wood is to the carpenter, bronze to the sculptor, so our own lives are the proper material in the art of living.”

— Epictetus

Philosophy is about the art of living. By focusing on developing yourself first, you’re able to improve yourself as a human being. And in doing so, you increase your capacity to give and amplify the impact you’re able to have. But so many people want to give advice without first figuring out their own lives and accepting responsibility for themselves.

It’s easier to focus on other people’s problems – the latest gossip, family drama, or outrage featured in today’s news – rather than facing your own uncomfortable truths. Distractions are the crutch we use to avoid facing ourselves.

Self-sufficiency is about recognizing that life is a single player game. The only person you can change is you. It might seem counterintuitive, but if you start here you’re able to increase your capacity to make a difference in other people’s lives.

By becoming less dependent on others for your every need, you’re able to create more than you take. And you provide yourself with more opportunities to demonstrate virtues like wisdom, compassion, and courage.

There are obvious exceptions when it comes to the sick or elderly. But if you’re a provider for someone else and you fail to establish a degree of self-sufficiency, you’ll always have a self-imposed limit on what you’re able to provide. To make up for the discrepancy, you’re likely taking from other people in your life to help fuel that. And if you’re lucky, the world breaks even in the exchange.

Your capacity to give without expecting something in return is directly tied to your degree of self-sufficiency.

By requiring reciprocity for an act of kindness, you negate its impact. With a stronger sense of self-sufficiency, you eliminate the ego-driven need for anything in return. And this is how you flip the script and create a net positive in the world.

In the pursuit of self-sufficiency you increase your capacity to contribute in every other facet of your life. It’s foundational to giving more than you take. And that’s what the world needs. More people giving back to the world. More people taking risks to live at their best. More people with a deeper well of kindness for the people around them.

But it all starts with self-sufficiency. With this foundation in place, the rest of your virtues can grow without limit.

The question, then, is how to begin honing your own self-sufficiency. Here are five first steps to help push you in the right direction.

1. Assign things their proper value

Self-sufficiency begins with identifying what’s within your control, what’s beyond, and what falls in-between. By going through this exercise, you can map out and assign things their proper value. What’s within your control should take precedence, in terms of both time and energy. After all, this is where you can have the largest measurable impact.

2. Create room for reflection

This also requires creating room for reflection each day. It doesn’t matter if it’s a meditation practice in the morning, taking a walk after lunch, or journaling in the evening. What matters is that you create space to process and think for yourself. This helps guard you from being pulled into races that you’re not willing to run. 

As humans we’re highly impressionable. Opportunities for reflection will help you discover what’s meaningful to you and avoid absorbing someone else’s guiding principle as your own. And this is perhaps the most difficult skill of all – sorting through the noise and determining what’s your own.

3. Practice voluntary hardship

In a world of mental hacks and shortcuts, there’s no substitute for discipline and resilience. To develop this, look for occasional opportunities to remove automation and assistance. These can act as barriers to your own abilities and your natural filter for priorities.

This might mean cooking tonight instead of ordering out or going for a run instead of watching another sporting event. The ability to embrace a little bit of discomfort goes a long way when it comes to self-sufficiency. If you want to create something meaningful and transform yourself, it rarely comes through the path of least resistance. 

4. Master a multidisciplinary approach

As you push yourself, you create more opportunities to pursue a wealth of experience across disciplines and dial in a multidisciplinary strategy. This begins with fueling your natural curiosity, drawing connections between your wide-ranging interests, and exploring new ways to stack the skills that set you apart. 

From here you can assess things from new angles, identify your gaps, and survey the range of available options. It also guards you from false patterns and foolish attempts to apply a single model to every problem you face. If you only have a narrow range of mental models available when you negotiate the challenges inherent to life, self-sufficiency is impossible. You need multiple weapons if you want to outthink and outmaneuver obstacles.

5. Embrace the silence

But self-sufficiency doesn’t mean you need to have an opinion about everything. It’s more about the ability to subsist without validation. If you’re focused on the right things, for the right reasons, you won’t need external recognition each step of the way. Everyday conversations are a good place to begin practicing this. 

Another way to practice this is when you experience something memorable – a landscape that humbles you or a concert that inspires you. Allow that to be enough. Avoid the temptation to reach for Instagram. Not everyone needs to know every minute detail of your life. The meaning you find in that moment is worth far more than the short-term high that comes from someone mindlessly scrolling through their feed and tapping your post.

““These are the characteristics of the rational soul: self-awareness, self-examination, and self-determination. It reaps its own harvest…It succeeds in its own purpose…””

— Marcus Aurelius

Self-sufficiency doesn’t mean you need to live off the grid. You can and should enjoy the conveniences of modern life. But you should also assume responsibility for your personal wellbeing.

Living well is about eliminating internal dependencies. No one can tell you what’s meaningful to you, what your guiding principles should be, or what the right decision is each step of the way. You have to determine this yourself.

If you want to make a measurable difference in the world, it starts with assuming responsibility for yourself. This is perhaps the most important lesson the Stoics had to offer. You can’t create anything meaningful without first taking responsibility and transforming yourself.

If you’re a well-rounded human being, you can give more back to the world and the people around you. It starts and ends with you.

*This article was originally featured on Daily Stoic.

The 5 Best Books to Sharpen Your Strategic Mind

Ever wonder if you’re focused on the right things? This fear defined my first five years out of college. I was mainly reacting to the things happening around me, bouncing from one distraction to the next. I tried to be purposeful but I had no sense of direction and failed to grasp the nuance of the long game. In other words, I failed to recognize the importance of strategy. 

At their core, strategies are the frameworks you stack to help advance your principles, move you closer to your goals, and realize your aspirations. Strategies sit above tactics, but below guiding principles. They pave the way forward and help create momentum.

A strong strategy helps to direct your focus and anticipate the obstacles or adversaries standing in the way. This requires long-term thinking – an ability so see multiple moves ahead and an understanding of the interconnected whole. But it’s also about knowing what you’re working towards and what’s within your control. 

This story will be familiar to those who have read my new ebook, 7 Strategies to Navigate the Noise. It’s all about connecting your guiding principles with your day-to-day. Life gets easier when you develop a stronger sense of strategy and are able to take thoughtful action. 

Over the past ten years, I’ve faced this question day in and day out, pouring over hundreds of books in an attempt to figure it out. In 7 Strategies to Navigate the Noise, I recommend twenty-two different books to improve your strategic mind. I’ve narrowed that list to the five most influential books on strategy to get you started.

Each book offers something of its own and was a major influence in helping me develop a stronger sense of strategy and self-sufficiency. If you’re struggling to determine whether or not you’re focused on the right things or need help sharpening your strategic mind, these books should provide a solid starting place.

1) The Laws of Human Nature by Robert Greene

Robert Greene is a master strategist in his own right and perhaps the best of our generation. This book is the culmination of his lifetime of work on power, influence, and mastery. It’s an instructive guide to human nature based on historical accounts and evidence, rather than a particular viewpoint or moral judgment. 

As Greene, emphasizes throughout the book, a deep understanding of human nature is advantageous for countless reasons. It helps you grow into a strategic observer, become a better judge of character, outthink malicious people, develop greater empathy, and realize your potential.

True to form, Greene pulls stories from both sides throughout history – those who have succeeded and those who have failed in spectacular fashion. It’s an incredible resource if you want to hone your strategic mind and it will pay immediate dividends in your own life, no matter your position. 

2) The Tigress of Forlì by Elizabeth Lev

The biography of Renaissance Italy’s most courageous countess, Caterina Sforza. Her tale is one of clever strategy, boldness, and determination. Sforza’s entire life reads like a storybook, as she fights off her husband’s assassins, the French Army, and Cesare Borgia. 

Sforza is an archetype of a dimensional thinker who was able to consider second and third-order consequences at every pivotal moment. And this was how she fought her way through life, outthinking and outmaneuvering every adversary and obstacle she came across. 

Throughout her life, powerful men viewed her as a pawn on the chessboard of Italian politics. They doubted her ability to rule and refused to take her seriously. She would prove this to be foolish, time and time again. It’s a fascinating and inspiring biography one of history’s most underrated strategic leaders. 

3) Meditations by Marcus Aurelius

A cornerstone of Stoic philosophy. At its core, it’s about the art of living. This is the true value of practical, functional philosophy. And there’s no better starting place than Marcus Aurelius. 

If you want to be more strategic, you need a bedrock of principles that you can call upon at any moment. You must also have a strong understanding of your sphere of influence – what’s within your control, what’s beyond, and what falls in-between. Stoic philosophy and the frameworks emphasized in Meditations are one of the best places you can start. 

4) Endurance: Shackleton’s Incredible Voyage by Alfred Lansing

A brilliant tale of survival that documents Sir Ernest Shackleton’s failed voyage to cross the Antarctic. Shackleton was a compelling, larger-than-life figure who offered lessons in leadership and strategy at each turn.

The book also contains one of my favorite passages. And it speaks directly to strategy and thoughtful action: “Whatever his mood – whether it was gay and breezy, or dark with rage – he had one pervading characteristic: he was purposeful.” If you want to sharpen your strategic mind, that’s what you’re after. Every action should have intention.

Shackleton’s most profound lessons are revealed in his ability to transcend the fundamentals and shift strategies as the situation required. There are few men who faced more dire circumstances than Shackleton and his crew, and who survived without any casualties. While you can’t separate luck, there was a strong level of strategy required to come out on the other side. 

5) Skin in the Game by Nassim Taleb

One of the great things about Taleb is that he challenges standard conventions and long-held beliefs about a range of topics. As a result, you’re guaranteed to walk away with a new perspective. Here he picks apart the way we think about uncertainty, symmetry, risk-sharing, and rationality in complex systems.

In terms of strategy, Taleb emphasizes the importance of thinking in high dimensions and evolving beyond the shallow. He also digs into how acting by removing is more powerful and less error-prone than acting by addition. This has implications in terms of unnecessary complexity in both our lives and how we think about strategy.

But the core of the book focuses on ethics and morality. Skin in the Game is about putting yourself out there and taking risks of your own. It’s immoral to keep the upside and transfer the downside to others. Besides, it’s impossible to understand the world and develop your own strategic abilities without putting yourself out there and taking risks of your own. 

The best strategic thinkers have grown from the chaos they’ve faced and developed resilience. Strategy isn’t about accruing power and sitting back while others take the risk. It’s about using long-term thinking to improve your position and build your capacity to give more back to the world. At its core, strategy is about taking calculated risks for the things you care about most – thoughtful action.