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.

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.

How I Used Improv as a Growth Hack to Become a Better Public Speaker

A few months ago I shadowed an acting class focused on scene work. And you might be wondering what the hell I was doing. I thought the same thing. I’m not an actor. I have zero natural talent. And the last acting experience I had was in the prestigious role of a truffula tree in a first-grade rendition of The Lorax. 

My intent, besides self-induced humiliation, was to discover a nontraditional approach to help improve my public speaking skills. I considered standard business speaking courses and groups like Toastmasters, but I felt like those were too formulaic and lacked room for individuality. What I needed practice with was being horribly uncomfortable in front of people and expressing myself. 

The scene-study acting class didn’t stick for me. It was more focused on developing the craft, getting comfortable in front of the camera, and immersion into different characters. I wanted to be more comfortable letting loose and being myself. But it led me to test another angle, improvisation. So I found a local comedy club and signed up for an eight-week beginner’s class.

When I walked into the class, I had no idea what I was getting into. I struggle with forced interaction and workshop-type events. I was expecting the three-hour class to drag by. But time flew by and it turned out to be one of the most important experiences I’ve had this year. 

The first class started with “dancing to yes.” It’s a warm-up exercise where one person starts dancing in the middle of a circle (don’t worry, there’s music) and the rest of the group mirrors their dance moves. Once the person in the middle is ready to move out, they make eye contact with someone else, dance over to them, and jump up at the same time to yell “YES!” before that person takes over. It’s just as traumatizing as it sounds. 

The rest of the class followed a series of exercises around active listening, mirroring body language, committing to your first idea, building on other people’s ideas, and getting comfortable on stage. Each offered important lessons in their own way. And as the weeks progressed we dug into more specifics of the craft. But the bulk of the benefit, for me, was during warmups – a point of emphasis in earlier classes. 

While I’m still improving two months later, I can say I’m a more confident, comfortable public speaker for having taken an introductory improv course. This experience provided an opportunity for accelerated growth that I would have been hard-pressed to find anywhere else. Here are the key lessons I uncovered along the way.

Lesson 1) Embrace your inner dumbass

The thing about improv is that it’s so uncomfortable it’s almost unbearable. But at that point you have to make a decision to either walk out or embrace the fact that you’re going to look like a dumbass and there’s no way around it. 

If you’re too worried about how you look on stage, you’ll freeze up and it’s impossible to cope. You might as well accept it and do your best. Besides, if you can get on stage and play make-believe with other adults, you can do anything on stage – whether a presentation at work or a TED Talk. The only thing more challenging is likely standup. 

Consider how much easier presentations or speeches become when you’re talking about something you actually know, as opposed to making up material on the spot.

But even if you’re a subject matter expert, improv will teach you to let go of your quest for perfection. It’s about trusting yourself and doing your best given the circumstances and the person you are at this moment in time. Besides, imperfection is the very thing that defines live performances.

Most of the time, attempts at perfection just end up fueling your nerves. And it’s impossible to perform your best or encourage yourself to take new risks if you’re a nervous wreck. A more effective, albeit counterintuitive, approach is to tell yourself “who cares” before taking the leap. Improv is a useful practice ground to immerse yourself in this mindset.

The “who-cares” mindset isn’t about apathy, it’s about a relaxed state of concentration. It’s a strangely empowering self-talk that helps navigate fears of judgment, failure, or general anxiety about drawing attention to yourself. It helps lower the stakes before taking a new risk.

Improv will teach you to let go and trust yourself. Once you’re on stage, there’s no other option. The same goes for presentations. Quiet your nerves by accepting the inevitable imperfections.

Lesson 2) Get out of your own head

If you want to be successful in improv, you have to focus the entirety of your attention outside of yourself. One of the best things about improv is that it forces you out of your own head. This is another powerful tool for navigating stage fright.

In everyday encounters, you can predict with relative accuracy which direction most conversations are heading. But this doesn’t work in improv. You can’t rely on cognitive patterns and only listen with part of your attention because you can’t possibly predict the crazy shit that someone is going to say next. 

The unpredictability inherent to improv demands that you listen with every ounce of energy you have. Otherwise you’ll fall on your face and make life miserable for the person next to you. If nothing else, improv will train you to be a better active listener. 

While it might sound counterintuitive, by projecting more attention outside of yourself, you’re able to avoid overthinking and settle in. If I fixate on my internal state (nerves), I only make matters worse. And this is one of the most important concepts that translates from improv to public speaking. 

When leading discussions, I channel more energy outside of myself to concentrate on really understanding what other people are saying. When giving presentations I focus on the expressions and non-verbals of individuals in the audience. These are the tactics I use to the avoid internal spirals that come from projecting too far ahead and becoming tangled in my own thoughts. 

Lesson 3) Create a bias towards action

In my day-to-day, whether writing a new article or building products, the behaviors that create the greatest ROI are reflection and calculated action. Due to the nature of the work I gravitate towards, I rarely get an opportunity to cut loose and do more impulsive activities that improv encourages. 

The discomfort you face in improv forces you to use new paths and explore new connections that have grown rusty or never been used. It rattles your routine and forces you into unfamiliar situations. It’s a far cry from the structured routine of everyday life. And that’s what makes it so beneficial for public speaking – both are unfamiliar environments that you don’t face on a regular basis. 

Improv won’t guarantee you’ll stop being nervous on stage. I doubt this ever goes away. But it does help build a greater familiarity with that feeling. It creates a bias towards immediate action so you’re able to overcome nerves and jump in anyway.

This also translates to the content of your presentation. Rather than sitting back and providing a backstory, improv teaches you to dive straight into the action. That means not just talking about the fire that started at the barn across town, but instead detailing what it was like to be in that barn or holding the firehose trying to put out the flames.

Start in the middle. People crave compelling stories. Don’t bore them with the trivial details that aren’t relevant to your core message. Improv helps train this muscle. But it also translates to how your approach speaking engagements – action first.

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There’s a certain beauty in making yourself that vulnerable in extreme moments of discomfort. This mindset creates a shift in how you view presentations or public speaking. It’s about being authentic and embracing the imperfections in your delivery. It’s far more effective to give a presentation with a few stumbles that’s honest and real, rather than give something polished that never gets below surface level.

I recently fueled all these lessons into a presentation I gave at Georgia Tech to students in the College of Computing. And it was the best presentation I’ve ever given. It wasn’t perfect and I still have quite a few things to practice. But it was real. I let go, focused on the students, and jumped into stories to illustrate ideas that would resonate with that audience.

During improv a few weeks earlier, I was acting like a grizzly bear trying to track down a toucan than escaped from the zoo. I reminded myself of this experience before getting in front of the room. I knew if I could do that, I could talk about the products I’m building at work and the key lessons I’ve learned in my own career. These were things I actually knew and believed in. 

If you want to get better at crafting logical arguments, try Toastmasters or a public speaking course. But if you want practice facing uncomfortable situations on stage and channeling your individuality, improv is the way to go. It will help accelerate your own skills and provide an unconventional angle that few consider. 

15 Lessons I Learned Before Turning 31

31 feels slightly less monumental than 30. Last year, I reflected on the most important lessons learned over the course of my 20s. But there are no off-years in life. If you’re doing it right, each one offers new experiences and opportunities to grow.

Every year I create checkpoints to consider lessons learned, challenges I’ve faced, and progress I’ve made. Birthdays are one of those triggers to step back and administer a healthy dose of perspective. 

I’ve found that the true test of how much I’ve learned in the previous year is considering myself at that same point in time 365 days ago. If I laugh at how stupid I was, that’s a good sign. Investor, Ray Dalio, shares a similar sentiment, “It seems to me that if you look back on yourself a year ago and aren't shocked by how stupid you were, you haven't learned much.”

The years I’ve been able to look back and contemplate how much I’ve learned, despite laughing at the expense of my younger self, have been the most rewarding.

This year was an important one for me. Although it’s not as big of a milestone as 30, this year was full of little victories, failures, and lessons. I’ve learned as much as I ever have in a single year. Here are some of the most important lessons that have stuck with me.

1) What matters most is the ability to bounce back

There will be times you fail to rise to the occasion. What matters most is the ability to bounce back. It’s one of the most critical skills you can build in life.

I’ve learned this time and time again in my career. You can’t expect perfect conditions each step of the way. Things are going to break, you’re going to run into ignorant people, and there will be times that you face an onslaught of obstacles with no end in sight. What matters is that you find a way to come back with a fresh perspective each day, ready to try again. 

The best teams I know embrace imperfections beyond their control and contribute something meaningful anyway. The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

2) Experiences can still surprise you

I’ve been fortunate enough to have traveled to dozens of beautiful places across the world. I believe the more you travel, the more perspective you build – an invaluable gift in life. But the catch is that the more you travel, the more you seem to lose the novelty of first-time experiences. 

I will never have the same feeling that I did the first time I went dogsledding in the arctic circle, kayaking in the Milford Sound, or camping in the Vietnamese jungle inside Hang En cave.

But this year, I went to South Africa and was surprised to discover that elusive feeling in the raw experience of a safari and in the bliss of the beautiful countryside of Babylonstoren, one of the oldest Cape Dutch farms. If you keep an open mind and maintain an appreciation for life in all its forms, experiences will never cease to amaze you.

3) Convenience is worth paying for

Five years ago, “frugal” would have been one of the best adjectives to describe me. Over the past few years I’ve let that go in favor of convenience. And this comes from learning to value my time properly. 

My routine for years has been to write at a coffee shop on Saturday afternoons. But I would always cut that short to head across town to pick up groceries, an absolute nightmare on weekends. This year, instead of interrupting myself during this time, I’ve started using a grocery delivery service. 

On average, I save two hours of uninterrupted focus time. And it only costs me five extra dollars. At a certain point, you have to learn that time is the most valuable thing you have. 

4) Reversibility matters more than certainty in your decisions 

Time is far more valuable than a marginally better solution. To help make faster decisions, I’ve started asking myself, “How reversible is this decision?” If it’s easily reversible, I make it right there. Assessing decisions based on reversibility, rather than certainty of the potential outcome, has improved my decision making significantly. 

Slow, deliberate decision-making can be a significant advantage in avoiding massive mistakes. But the reality is that most decisions you make on a daily basis aren’t permanent in nature. There’s a time and place to use this level of deep thought and consideration. Not when it comes to picking a restaurant for dinner or testing a new layout for the landing page of your website. 

5) Success doesn’t come from preventing things from falling through the cracks

This is about building a systems mentality. In other words, developing the ability to step back and consider the interconnected whole – the structures, patterns, and cycles – instead of being blinded by a single event or moment in time. This frees you to focus your limited time and energy on what matters most. Success doesn’t come from being better at preventing things from falling through the cracks. It comes from knowing what to let fall through. 

You can identify those who have failed to build a systems mentality by how overwhelmed they get by minutiae – especially when the stakes are at their highest. They become fixated on insignificant things, gripping for control in their foolish quest for perfection. They’re unable to let the little things go.

6) Four things separate you from the top of your field

When I started my career in product, those above me seemed almost lightyears ahead in terms of their intelligence and abilities. I wouldn’t put myself anywhere close to the same category. But the more interactions I have with executives and senior leaders, the more I’m convinced that they aren’t infinitely smarter. The real difference is in their risk-taking, network, growth mindset, and a healthy dose of luck. It’s a good reminder that you’re not that far off. 

7) Don’t get pulled into races that you’re not willing to run

If I don’t create room for reflection, I often find myself getting pulled into other people’s aspirations and playing stupid games for stupid prizes – struggling to position myself on the corporate ladder, equating meetings with productivity, or seeking validation through arbitrary certifications and recognition. 

This is one of the most difficult skills to develop, sorting through the noise and determining what’s your own. As a human being, you are highly impressionable. This is great when it comes to social cohesion, but terrible when it comes to realizing your own aspirations. It’s okay if you don’t want the same things as everyone else. Just make sure you aren’t getting pulled into races that you’re not willing to run.

8) People are amazingly consistent in their behaviors

Another way of saying this is that everyone gets what’s coming to them – for better or worse. It’s just a matter of time. Habits and behaviors projected over the course of years dictate future conditions and outcomes. The trouble is that when you’re young and could use this advice the most, your perspective of time is too shallow to really grasp the lesson.

I see examples of talented, hardworking people catching breaks every month. I also see examples of grown adults clinging to the same identity they had in college who are paying dearly for short-sighted decisions in their careers, health, and relationships.

Use this as motivation to focus on getting the conditions right, developing better habits, and playing the long game. With this mindset, it’s just a matter of time before you start catching breaks. 

9) Compound interest from reading is no joke

After five years of reading 50+ nonfiction books each year, it’s only within the past few months that I’ve felt like I’ve been able to make seamless connections and pull relevant stories on demand. Once you form these connections, you propel yourself forward with a wealth of vicarious experience. 

This is critical to so many areas of life – mastering a multidisciplinary approach, identifying your guiding principles, outthinking misguided people. Without reading, you have to learn this all from direct experience. But books provide you with lifetimes of experience and perspective that you can call upon at will. 

10) Stories > instructions

Stop telling people what to do. Unless you’re running a laboratory, people don’t give a shit about instructions. Stories are the best way to communicate. If you let people interpret things for themselves, you get better results. Especially in fields that demand creative thinking. 

Of course, there are obvious exceptions and integrity matters. But you see the power of this in presentations. Speakers who use stories are able to capture the imagination of their audience. That’s what resonates with people. The same thing goes for brainstorming, design sprints, whiteboarding, and every meeting you have.

Everyone craves stories because that’s how we make sense of the world and piece together our own ideas.

11) Improv makes you a better human

I signed up for improv classes to help improve my public speaking skills. I wasn’t sure what to expect but I wanted to take a non-traditional approach. Fortunately, this has been one of the most profound experiences of my entire year. There are so many positive takeaways and important lessons that I’m planning to write a full article on the experience. 

The short version is that improv will get you out of your own head, train you to be a better listener, and wreck your comfort zone. 

If you aren’t listening with every ounce of your being, you will fail. You can’t fall back on normal cognitive patterns and predictions that you use in everyday conversations. And the constant discomfort during class forces you to embrace and accept the fact that you’re going to look like a dumbass on stage. There’s no way around it. It’s an empowering realization. I’ve since given up my attempts at perfection during presentations, which has helped me relax and improve my delivery.

12) Routine is essential to creativity

The more automatic my habits and routine become, the more energy I can pour into being creative. Ever since I carved out dedicated time and space for writing, my craft has improved significantly. Most mornings I start writing at 6:30 AM. Since I’ve built this habit over years, when I sit down at my desk in the morning I’m able to shift into a creative mindset without a colossal effort.

I often think of this quote from Gustav Flaubert, “Be regular and orderly in your life, so that you may be violent and original in your work.” With that being said, there is a golden mean. I have to challenge this routine on occasion to make sure it’s still working for me and I’m not becoming too rigid in my approach.

13) Drawdown periods matter

I’m excited to release my first e-book next month. But it was no small undertaking. It required five months of sustained effort. Before jumping off I had to make room for a drawdown period where I was able to prepare, rest, and reflect before starting. I knew I would need every ounce of energy I had if I wanted to get my thinking clean and bring the best version of the idea to life. 

This drawdown period was essential in helping me create a buffer where I was able to piece together and discover my own thoughts on the subject. It was an escape from being bombarded by influences and outside noise. The bigger the project, the more important it has been for me to settle my mind leading up to it. 

14) Time your vacations to avoid burnout

Over the past few years, I’ve kept track of when I start to feel like I'm burning out in a given year. And I've noticed it always occurs around the same time. So this year, I planned vacations and weekend getaways to avoid falling into the same pattern – February, May, July, August, and November.

As ridiculous as it sounds, one of my New Year’s resolutions was to take five vacations. It was a way to self enforce breaks when I would otherwise attempt to be a hero and power through things. This has made a huge difference in my wellbeing, the quality of my work, and overcoming the burnout I’ve faced in recent years. 

15) Purpose starts with meaning

Over the past year, I’ve had conversations with many people struggling with purpose. I love being able to share these deep conversations and I sympathize. That was the first ten years of my adult life – forever tiptoeing on the edge of an existential crisis. Some days I still wonder what the hell I’m doing. Purpose is such an overwhelming thing. 

But what I’ve learned, and what I try to share in these conversations, is that purpose is just the series of pieces you find meaning in. Look for where you find meaning in your day to day. By doing more of those things, you move purpose within reach. And if the quest for purpose ever becomes too much, settle for doing meaningful things instead. 

What’s Really Behind Our Obsession with Failure

In recent years, there’s been a growing obsession with failure. The “fail fast, fail often” mentality is polarizing. Many take it at face value and use it to romanticize their own failures. Others reject this as bad advice that’s intended only to soothe us in our shortcomings.

But regardless of where you stand, there remains an important lesson at the core of this mindset. And it’s not about failure, it’s about reach. If you’re willing to risk failure, you’re able to take more chances and reach further beyond your current ability level.

The goal is never failure itself. And that’s what most people get wrong. The goal is extending your reach and accelerating growth. This requires pursuing opportunities where failure is a potential outcome. Progress is difficult to come by when you limit yourself to situations where success and participation trophies are guaranteed outcomes.

“There are two kinds of failure. The first comes from never trying out your ideas because you are afraid, or because you are waiting for the perfect time. This kind of failure you can never learn from, and such timidity will destroy you. The second kind comes from a bold and venturesome spirit. If you fail in this way, the hit that you take to your reputation is greatly outweighed by what you learn.”

— Robert Greene

Avoiding contests that you’re not capable of winning makes sense in high-stakes situations. You want to eliminate risk and play the odds. But in modern life, success is rarely a matter of life and death. Most decisions aren’t catastrophic or irreversible.

It’s still important to choose the right opportunities where you have a competitive advantage in terms of your natural abilities or interests. But if you want to accelerate growth in these areas, you have to seek out challenges that test your limits and push you to the brink of your ability level. 

Aiming 4% beyond your current abilities

Habit expert and best-selling author, James Clear, suggests a good rule of thumb is to aim 4% beyond your current ability level. This is where deliberate practice takes place and you’re able to achieve a state of flow. 

Don’t get too hung up on the exact percentage, this is just a system to calculate risk and accelerate growth. If you’re aiming 4% beyond your current ability level, failure is a potential outcome. But it’s not the only available outcome – success is still within reach. This allows you to take advantage of inflection points and make bigger leaps – in your career, your art, or personal qualities you’re focused on improving. 

Ramit Sethi, best-selling finance author, has a similar approach where he keeps a tag in Gmail for “failures” and aims to reach four failures each month. But that doesn’t mean he’s taking stupid risks. He’s making calculated moves to extend his reach and give himself a chance. Sethi knows failure is a natural part of growing and trying new things. This mindset is key to the sustained growth of his business, helping him reach 400,000 newsletter subscribers and launch dozens of successful (and failed) products. 

Discovering the terrain

Both success and failure offer an equal sense of the terrain. Each reveals what to do more of, less of, and which direction might be worth exploring. When you’re just starting out, the map is obscured with certain parts missing. With each success and each failure, you learn a little more and reveal another piece of the map.

“The only way to win is to learn faster than everyone else.”

— Wade Shearer

Knowing what not to do can be just as powerful as knowing what to do. If you can avoid repeating small mistakes more than once, and avoid the colossal ones altogether, you can bring the full picture into focus, faster. Reflection on your own experiences, paired with vicarious learning (e.g., books or podcasts), helps commit experience into knowledge, shedding light on new corners of the map.

Learning fast, learning often

The driving force behind this fascination with failure is learning, which leads to growth. “Learn fast, learn often” is a more accurate but less buzzworthy rallying cry. Failure is just a mask that learning wears on occasion. 

Learning is what you’re really after. Figuring out what works, what doesn’t, and piecing together your understanding of life. With this you can build momentum in the areas you’ve prioritized. 

The “fail fast” mentality is about making calculated efforts to push your limits. But failure itself is not the goal. The goal is to push your limits, extend your reach, and develop yourself. Growth requires putting yourself in challenging situations that test your abilities. 

If nothing else, the romanticized advice surrounding failure should serve as a reminder that you’re the one who has to go out and live. Books, podcasts, and articles can provide you with strategies, systems, and kindred souls. But at the end of the day, if you want to grow, you have to test these ideas for yourself, risk failure, and fine-tune your own strategy along the way.

The Reality of Failing to Rise to the Occasion

What you don’t see when you look at the synopsis of great people’s lives are the times they fell short. From the outside, it looks like they operated with invincibility, rising up at each pivotal moment. When the stakes were at their highest, there was no stumble.

But when you dig into the details, there’s no one who has actually achieved this. Top performers assume more risk than others. They’re on the frontier, operating at the edge of their current abilities. If anything, this means failure is even more prevalent.

Failing to rise to the occasion

The truth is, there will be moments when you fail to rise to the occasion. You’re not always going to make the right decisions or act exactly how you imagined. And since perfection is impossible, what matters most is the ability to bounce back.

Even Warren Buffett had moments when he failed to follow through early in his life. At the beginning of his career, Buffett was terrified of public speaking. And while you might imagine that someone like Buffett stepped up, put himself through deliberate practice, and overcame the fear in one fell swoop — reality was much different.

In a widely-told story, at the beginning of his career, Buffett enrolled in a Dale Carnegie speaking course to improve his skills. But few sources include the fact that he quit the first time around. He was afraid of being called upon to speak so he dropped out of the class. It was only the second time around that he built the courage to follow through. Now Buffett credits this as the best $100 investment he’s ever made.

The ability to bounce back

Anyone can lecture you about decisions you should make, habits you should build, systems you should create. But the most successful people aren’t flawless in their decision making. They just have a remarkable ability to bounce back.

The greatest artists, entrepreneurs, and scientists take the misfortune in stride, turning obstacles on their end and using them as an opportunity to improve their craft. They embrace mistakes and capitalize on them, ensuring they never happen again. And that’s the real difference in top performers — they stumble, but they rarely repeat mistakes.

Whether you’re struggling against your internal limits — uncertainty, doubt, fear — or you’re facing external challenges, you’re going to have bad days. What matters is the ability to reflect, learn, and find the courage to start fresh the next day.

Awareness can go a long way when it comes to navigating failure and being kinder to yourself. It’s okay to hold yourself to your own high expectations, but expecting perfection will often lead you over the edge. Life is as much about resourcefulness and how you respond to challenging situations as it is carefully plotting a long-term strategy. You need both.

Professionals know this space well and embrace mistakes as learning cues. They learn from them, but they don’t obsess over them. Amateurs expect perfection and crumble when they fail to meet their own lofty expectations.

Failure is about reach

The goal is never failure itself. It’s the expansion of your reach and the rate of personal growth. That means pursuing opportunities where failure is a potential outcome. Not limiting yourself to situations where success and participation trophies are guaranteed outcomes.

If you’re willing to risk failure, you’ll take more chances and reach further beyond your current ability level. And this is the fastest way to learn and create more opportunities for accelerated growth. Take calculated risks.

There will be times that you surprise yourself. But there will also be times you fail to rise to the occasion. In those moments, what matters is your resilience and resourcefulness. The lean product mindset applies as well here as anywhere else. Build, measure, learn. Repeat.