Your Reward for Overcoming Your Challenges: More Challenges!

Small, growing, fast-moving companies are some of the best labs for philosophy the world has ever seen. They’re particularly good for philosophical questions about meaning, effort, and what makes a good life.

Time and change move much faster in startups than in established businesses, making it possible to condense and view more varieties of challenges, transitions, and transformations in less time.

“Economically, you can think of a startup as a way to compress your whole working life into a few years. Instead of working at a low intensity for forty years, you work as hard as you possibly can for four.”

– Paul Graham, “How to Make Wealth

My experience in the past couple of years at BitPay has borne this out, and it’s started up my own thought about what I want to get out of my life’s work.

We All Want to Peak Early

Many of us think about life as a journey. Whether we have a specific end in mind or not, the beginning and the destination are both orienting points in how we think about what we’re doing here on earth. If we get really poetic, we may picture ourselves as brave adventurers scaling a great slope – our challenges. But the simple, if unflattering, truth is that most of us go through life looking for plateaus.

Our vision for the end of our climb through life’s challenges involves us settling in to our achieved greatness and being content with it. After a while, we just want to spend the rest of our days in unchallenged dominance. When we finally get the managerial position, we’ll be happy. When we finally get a raise, we’ll be set for life. When we finally save enough money to retire, our troubles will be out of sight. When we’re finally loved by someone else, we will be content. I won’t go on. We all know these are half-truths at best. Still, we convince ourselves to climb by telling ourselves that it’s a flat, easygoing plateau at the top. The faster we can get there, the better.

Life, however, has other plans.

You Don’t Get to Stop Climbing

My own past year has given me more work than I’ve done in the entirety of the rest of my life – with the promise that the workload will only get more bigger, more challenging, and more demanding on my time and resources. I’m starting to think there’s a pattern to this…

This is true in a company as anywhere else in life. Have you figured out your first job? Now it’s time to figure out relationships. Figured out your marriage? GOOD LUCK, BUCKO. Kids are coming. You’re going to put in 18+ years of work with the slim possibility that your children will ever realize how hard you’ll have worked for them.

In other words, when you achieve the summit of your expectations, often you’ll find a new summit waiting for you to scale. The reward for overcoming your challenges is…. more challenges! Enjoy the view, Sisyphus.

There’s an economic reason for this. The harder you work, the more capable you seem to those around you. Becoming more efficient means you can now do more with less, and your reality will adjust itself accordingly. Whether you’re working for yourself or others (and whether it’s career work or personal life effort), the available work will grow to match your available energies. The better you get, the more you’ll be asked to achieve.

Efficiency and productivity are some of the best things in life. But if your goal is a pat on the back and an easygoing plateau stroll, they can be real pains.

The Road Goes Ever On

In The Horse and His Boy, the protagonist Shasta achieves one of his first heroic feats when he rides for miles to warn the kingdom of Archenland about a coming invasion. He finally reaches the border to warn the inhabitants, only to realize that he is the only one who can warn the King – and now he must run to do it.

“Shasta’s heart fainted at these words for he felt he had no strength left. And he writhed inside at what seemed the cruelty and unfairness of the demand. He had not yet learned that if you do one good deed your reward usually is to be set to do another and harder and better one.”

C.S. Lewis, The Horse and His Boy

I’ve been there. We’ve all been there. When we overcome ourselves and our limitations – when we finish our “quest” – we expect a celebration and a feast. But usually we just find ourselves on a new quest, with little or no thanks from those who we think owe us.

Beyond the simple economics of personal growth, there seems to be something biologically and/or spiritually hardwired into humans to keep us going for more. And there seems to be something hardwired into the nature of reality that “level ups” difficulty of existence as we “level up” our skills and power. Our fears and weaknesses and aching desires rarely go away, but they do change form.

We all get tired of this sometimes. We want to be present in enjoying what we have. Our seemingly restless ambition makes some people despair of ever “finding happiness” or achieving “satisfaction.”

It’s true that if you want to journey on through life, you don’t get to stop climbing. But if you’re willing to stagnate and decay and roll your boulder back down the mountain you’ve climbed, life will give you that opportunity. So what’s a human being to do in the face of this reality?

The Climb Is the Point

“He not busy being born is busy dying.”

– Bob Dylan

So far, so depressed. But I’m by no means trying to either discourage you or convince you of the meaninglessness of the climb. I want to make the case that we’re looking for the wrong thing. The plateau is not the end and the climb a means. The climb is a means that provides its own end.

Overcoming obstacles to goals – making the climb up today’s slope – requires some of the best virtues humans can call on. You have to have the courage to do what you fear. You have to have the honesty and clarity to recognize your own limitations. You have to have the self-responsibility to to gain what you lack without harming yourself or others. We come even closer to the best within us when we continue in these virtues as the obstacles just become bigger and newer and more threatening.

Virtues like these aren’t badges to be worn to impress others – they’re actual modes of human existence. They define our relationship to Reality (or God – the idea here is the same), which goes beyond any momentary goal or need or want.

When your relationship with reality has the same courage and integrity of your relationship to your daily obstacles, interesting things start to happen.

You find yourself living in the moment more – not just the moment of your successes, but the many moments of personal growth.

You stop fearing reality as an adversary. You’ve recognized what your goals require, and you’ve started to “pay” reality for your mistakes and successes in the world. Reality responds in kind. 

Your social anxiety fades away – when you’re secure in your relationship with reality, you don’t give as many damns about what insecure people think of you.

You stop chasing the unsatisfying summits that you were going after because of peer pressure.

You become less self-conscious and more actually conscious of how cool and beautiful the universe is. 

You realize that you’re capable of anything if you’re willing to accept the responsibility to earn it.

You start climbing the summits that you’re uniquely able and ready to enjoy.

Ultimately, you become a more “real” person. You become more of a human being because you continue climbing – in spite of the fact that you could find a plateau.

More Solid As You Go

“Reality is harsh to the feet of shadows. But will you come?”

– C.S. Lewis, The Great Divorce

In The Great Divorce, C.S. Lewis reimagines Heaven as a place not of wispy ghosts but of true, realer reality. In fact, it seems quite hostile to wispy ghosts. You must become more real and more “solid” to even tolerate it. What’s more, it’s not so much a place as a direction. The further up and further in you go into Heaven, the closer you get to the truest things – the things that make life beautiful and good. You get the idea from Lewis that he doesn’t envision that journey as ever ending.

If that’s the nature of the climb that human life requires – and I think it is – it’s not bad at all. When I remind myself that I can choose to chase after this mode of being, I can deal with late nights and early mornings, thankless tasks, weekend work, chaos, backlogs, bullshit, buzzwords, bugs, and everything else that comes with my own startup life. I hope I hold on to it when I start the next leg of my quest, whatever it is. For all of my drama about the challenges of startup life, let’s be honest – I’ll find something harder.

What about you? How far will you go? Life will get harder as your reward for each step, but you can become more solid and more beautiful along the way.

James Walpole

James Walpole is a writer, startup marketer, and perpetual apprentice. You're reading his blog right now, and he really appreciates it. Don't let it go to his head, though.

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