False Flats

What Cycling Teaches Us About Resilience, Perseverance, and the Climb.
False Flats
In: Newsletter

Hello everyone!

Many of you may know that as an entrepreneur I’ve had a diverse career. as an entrepreneur and startup builder. But few know the ups, downs, and “false flats” that come with entrepreneurship. My biggest learning: success isn’t always what it seems.

My first false flat was the loneliest moment of my entire adult life.

It's hard enough to realize you've failed to achieve your goals. But it's far worse to feel like you've succeeded before you're ready. Early success can lead to the sad realization that the goals you strive to attain only provide minimal fulfillment—a dopamine rush for hustle addicts.

For me, the question of "how can I become successful?" outweighed the more critical "why do I want to do this?" or "is this worth doing?" questions. It's easy to solve the wrong puzzles in life.

In this week's article, I wanted to share my story along with a few things I’ve learned to help others who go through the “false flats” of life. I believe that these moments make us more resilient, honest, and empathetic.

False Flats — What Cycling Teaches Us About Resilience, Perseverance, and the Climb.

“The human capacity for burden is like bamboo- far more flexible than you’d ever believe at first glance.”


Like it or not, careers are a race. Sometimes you sprint, sometimes you coast, and sometimes you climb. But the key to success is to remain flexible and steadfast in the face of uncertainty.

I started my professional career with unbridled enthusiasm—ready to race. After completing college, students are eager to apply their hard-earned (read: expensive) skills in exchange for a commercial payout. For some reason, I found myself fixated on working harder, faster, and longer to make a name for myself. I was ready to put my name at the top of the leaderboard. Evidently, I am a naturally competitive person, and the business world was my competitive arena.

Straight out of college, I started working for a digital agency in Seattle. From day one, I put my head down and went to work. I worked for long hours every week. I sacrificed holidays, time with friends and family, and even personal health. I did all this to accelerate my career and, as the saying goes, "make hay while the sun shines." And guess what? It worked.

(And I'll let you in on Tech's dirty little secret: companies promote those who work longer hours.)

By the time I was in my mid-twenties, I was ahead of schedule. I played a pivotal part in growing a few well-respected companies, held roles above my tenure, and exponentially increased my income. Now, to be clear, I wasn't Mark Zuckerberg. But, I had by most measures—compensation, title, network—reached a peak.

Or so I thought.

This was the start of my first “false flat.”

What Is a False Flat?

If you're not a cyclist, you're probably not familiar with false flats. Let’s get up to speed:

A false flat is the stretch of road between two steeper sections of the same hill. Though it may look flat, the path is actually a low-gradient towards a steeper climb.

These sections are especially tricky for many riders, as they lure you into a false sense of security. Imagine pushing your body to the max as you race to the summit ahead. "Only a little bit further before I've reached the top," you think as you shift to a higher gear. Just as you approach the top, you realize it is, in fact, a false flat with another steep section that follows.

Your eyes believe it's the top. Your heart assumes you've made it. Your legs scream their own judgment, and your lungs confirm the sentence.

Flats: Personal and Professional

Our careers often imitate this tricky, mind-bending stretch of road.

As students, we gain confidence and prestige through our academic institutions. High-status colleges, grades, awards; our first castles rely on external validation. As professionals, we lean on corporate institutions to further expand our set of external validations. Our parents brag that we work at Google, Amazon, Deloitte, or another prestigious organization their friends recognize. These little boosts work until we're pushed into a false flat. Then our fanciful masks start to crack.

False flats are a reminder and a test of our resilience. At times, we're motivated by our proximity to the summit. It's the same motivation that exists when we stand at the base of a mountain and imagine our conquest. To be candid, this is the purest form of motivation. The harder kind arrives when we're faced with adversity, and our character is called into question. At this moment, our mask is removed, and we're forced to address the test in front of us. The next phase of the journey takes on a different form.

Reaching A False Flat

My first false flat was the loneliest moment of my entire adult life.

It's hard enough to realize you've failed to achieve your goals. But it's far worse to feel like you've succeeded before you're ready. Early success can lead to the sad realization that the goals you strive to attain only provide minimal fulfillment—a dopamine rush for hustle addicts.

The initial taste of "success" turned me into a person I pretended to like, but it wasn't who I was underneath. Under the outward persona, I was fragile, defenseless, evasive, and detached. I took people and relationships for granted. I allowed external motivations of money and prestige to drive my decisions. It felt good to tell people what I was doing with my life and how I was "changing the world." But it was just a narrative. It wasn't who I was, or worse, who I wanted to be.

For me, the question of "how can I become successful?" outweighed the more critical "why do I want to do this?" or "is this worth doing?" questions. It's easy to solve the wrong puzzles in life.

I count myself incredibly lucky. Most people fight their entire career to be in the position I was in. This was my false flat.

Riding The False Flat

You're reaching the top. Or so you think.

To your dismay, you realize not only is it not the top but there's another hill. You feel weak and ill-prepared for another round of suffering. Your legs are gassed. You're not sure you can make it any further.

But let's play this out. Let's think about what would happen if you did actually reach the peak early in life. What now? Do all of your dreams come true? Are you fulfilled and satisfied? No. You search for the next hill to climb.

You become alienated and insufficient. You under-anticipate challenges and overcommit to projects, as confidence and ego rule your decisions.

It’s our social media values played out in life: designed, filtered, perfected.

Instead, life is full of misery. It's part of our existence. If it were easy, what would be the point? Life is the challenges we encounter along the journey.

Olympic athletes experience this deep emotional slump—or under-recovery—after their competition. Think about the journey each athlete has leading up to the Olympics. They push, they fight, they struggle for years. They sacrifice so much for a few seconds (maybe minutes) of glory. And then, just like that, it all comes to a screeching halt once they're done. Everything they've worked for is over, and they're left to feel depleted, both mentally and physically.

Suffering is a feature of our journey, not a bug. It's what keeps these athletes going. They adjust to the normative nature of the ongoing challenge and seek more of it. There are few experiences as sacred as a renewed existence outside the ordinary.

During our most profound moments of suffering, we're exposed to the realization that we're not who we think we are. We are precisely who we are—nothing more, nothing less. We're all a bit broken, a bit flawed. Our lives aren't what we want them to be. In the age of the internet, we're all on display, and we feel forced to hide our flaws. But hiding doesn't eliminate the struggle, it just avoids the truth.

Sometimes, the only option you have is to ride through the pain. We don't always feel ready for what's next, but this is why flats exist—they provide the necessary respite on the journey upward.

Exiting The Flat

Life is a series of never-ending tests. The challenges we face provide meaning to the drudgery of work and life. How do we solve climate change? How can we reduce student loan debt? These problems focus our energy on a particular moment in time, not the continuous, fluid motion of life's ongoing challenges.

Humans are complex beings that strive to extract meaning from what is otherwise ordinary. Our relationship to meaning stems from our ability to look beyond our current circumstances and into a possible future—a better, more fulfilling existence. If we focus on one simple moment in life, we miss the entire point of life itself.

Life's greatest challenges present us with some of the most significant questions. Questions such as: How can we be a better partner? What can we do to improve the world around us? How can we help the less fortunate among us?

When we reach a false flat, we're confronting the most human existence; it’s a test. We can either endure and face the flat head-on or collapse. The choice itself relies on awareness and resilience. Like a highly skilled surgeon, it’s up to us to use these tools carefully and strategically.

Preparing For Future Flats

The most essential meta-skill you can develop is flexibility. Flexibility allows you to be both rigid when needed and pliable when it’s not. Flexibility is a precursor to resilience and strength. When facing false flats, our strength and resilience are called into question.

The struggle is an essential part of learning. The benefits are not felt in the moment, but the post-hoc realization of true resilience carries long-term benefits. The knowledge we obtain and preserve helps us devise more informed strategies for the future. We have to find a test—e.g., a false flat—to know how to approach it in the future. In this way, the challenge is a gift for future you.

World-class competitors all know this feeling. In 2019, Tiger Woods exemplified this resilience in his return to the world of golf. In his quest to be the greatest golfer of all time, Tiger experienced a meteoric rise that earned himself a place in the golf hall of fame. But, not long after reaching the top, he faced challenges that ultimately led to a career low point. After resting and recalibrating his personal issues, he returned to the game of golf completely transformed. His return and ultimate victory at the Masters tournament brought him back to the "person he wanted to be."

When you reach your first hill, you're energized. As you start to see the crest, you push hard to get there. There's a rest point if you just give it all you have. But as you start to reach the top, you realize it's just an illusion. There's more left. Instead of allowing yourself to sink into a depression or quit, take this time to fuel up. Rest your legs. Devise a strategy for the next hill.

Test Your Limits Early

Sun Tzu, the Chinese military strategist, wrote,

"He who knows the enemy and himself will never in a hundred battles be at risk."

In our context, this means that before you can develop flexibility and resilience, you need to understand your own limits. When we're untested, we're uncertain of our boundaries. The constraints exist, but they're invisible to our minds because we haven’t pushed up against them yet. Tests increase the visibility of these lines and create opportunities for us to expand our previous limits.

Once you stop hiding from the narrative of yourself, you can honestly understand who you are. Only transparency can build resilience.

We spend too much time focusing our lives on the past and what we're building for our future. But we only have this very moment. Embrace it. Opportunities present themselves when it's least convenient and you're least prepared. If you were prepared, it'd be a plan.

Once we lose contact with the present, we lose our connection to life. If we're always looking forward or backward, we can do our best today. Every moment we miss is another missed deposit in our life experience bank.

Mindfulness and meditation is a great place to get to know yourself and understand the suffering. For me, it allowed me to distance myself from thoughts and feelings, allowing me to be more objective and strategic. It also allowed me to really embrace suffering and know that I could make it through. We’re far more capable than we believe, and mindfulness opens a window to our potential.

Rest And Recalibrate

Too often, we choose to ignore our boundaries, overlooking our immediate mental and physical needs. We disconnect from family and friends and lose sight of the more important questions that build a meaningful career and life.

In the false flat, we're presented with a gift—the gift of rest. An opportunity to rest and embrace a tailwind. Take this window and enjoy a bit of rest; your mind and body need it.

Refocus Your Energy

Crossing a false flat is an opportunity to refocus. What comes out during our flat is a new set of beliefs. Our period of reflection opens up new pathways and provides perspective. When we harness this new perspective, we're able to see what we missed before.

The revelation comes in the form of joy, happiness, and fulfillment. Money and fame are not part of the formula in the second round. Gratitude becomes a staple of daily life. We form a new commitment to the present. Focusing this energy is key to succeeding in the next round.

The next hill is not about gathering external validations. Instead, the commitment is to the people and the process. A steady force, driving you up the second climb.

Start Your Next Ascent

When we're young, we don't know much. Our “life experience bank account” is mostly empty. Our ignorance is actually our best ally.

As we age, it's easy to get set in our ways. Our rigid approach to personal growth and development is what keeps us from embracing the next hill. Instead, we should feel encouraged and grateful for the opportunity to push ourselves.

In our journey through life, we can't avoid false flats. Too often we think we've arrived, only to realize we have a long way to go. Whether it's in our relationships, our careers, or our personal development, there's always more to explore.

If you haven't already, I hope you have the good fortune to experience a false flat. And if you find yourself in a flat, find solace in the climb.

Good luck finding and growing through your next False Flat.

Internet Reading

1. The Genius Neuroscientist Who Might Hold the Key to True AI

“For the past decade or so, Friston has devoted much of his time and effort to developing an idea he calls the free energy principle. With this idea, Friston believes he has identified nothing less than the organizing principle of all life, and all intelligence as well.”

2. The meaning of life in a world without work

In his most true dystopian form, Yuval Noah Harari paints a picture of where we can expect to derive meaning in a world where work is mostly automated, and therefore optional.

3. Why Teslas aren't the future

I’m torn. On one hand, I’m a Tesla shareholder. On the other, I’ve grown to almost despise the cult-like following and bro-culture Tesla’s built over the last few years. It’s reasonable to be excited—and supportive—of the environmental impact of modern, tech-first cars like Tesla. But maybe our future requires a step into the past and a reduction of cars altogether.

Apps & Tools

Krisp AI — Mute Background Noise During Calls

Whether you’re dealing with a screaming child or just working from a noisy coffee shop, sometimes you can’t take a call in a quiet place. In a world of remote workers, this little tool is a godsend. Not only does it help mute your background noise, but also allows you to mute the background noise for meeting participants.

Weekly Challenge #16

Don’t check email (or slack) after 5pm.

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Thanks for reading, and see you next week,

— Kevin K.

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