Risking it All

On the importance of knowing what you're betting on and what you're afraid of.

After enough abject failures in my short life thus far, I’ve learned some things about the relative merits of not succeeding at what you set out to do.

There are the conceptual goals, ones which bear no direct survival impact on our lives in modern society – things like running a marathon or visiting a certain place – and there are the tangible attempts, things like home ownership or taking out large loans for higher education – which have a very measurable cost.

For some people, quitting a marathon due to G.I. distress (read: pooping your pants) is unfathomable, while for others it is no big deal at all. For some, taking on seven-figure loans and seed investors to try running high-risk, high-reward startups has no bearing on their ability to sleep at night, while for others, even a relatively small business or home loan is enough to cause so many sleepless nights that one enters a temporary, blinding insanity.

* * *

So much of life is processes – painting for an hour solely for painting’s sake, journaling with a pen on paper nobody will ever read, jogging around the neighborhood with no race on the calendar – that arguably provide life with all of its richness. Yet, so often these little acts get dismissed as trivial in a results-oriented world. In my own life, I’ve sponged up the messaging that your time should be “used wisely,” and that “wisdom” is profitable. This is the Darwinian strain of Capitalism, that the world is one giant chain of Galapagos Islands, survival of the fittest, based on who accumulates the most resources the fastest.

In this paradigm, most hobbies could be (and are!) dismissed as a waste of time. Tiptoeing around dung beetles on half-forgotten trails is an inconsequential triviality. It is faster and more convenient to not watch your step. Guilt cannot be allowed into a dog eat dog world, because cannibalism is pretty dang guilt-inducing if you stop and think about it.

I’ve been asked how i could possibly be happy in a world where there is inevitable grief, where stepping on bugs is a part of walking and hitting them with your windshield is an innate part of driving. I find myself wondering how you could know the fullness of life if you don’t cry for the many daily twists of fate.

If we believe life can be measured by universal yardsticks, enjoying your life could be dismissed as secondary to achieving a measurable form of “success” as defined by everyone but yourself. Religions and compensation packages alike try to remind us that sacrifice is noble and necessary, but it seems they rarely define the sacrifices or leave room for other value systems.

* * *

I bought a hundred dollar banjo a few weeks ago. I just want to feel my neurons tingle the way they used to, when learning and creativity were facts of life rather than things we must go out of our way to experience. I’m not good at it, but I have figured out a few little riffs just by playing with it when I walk by. The way we learn to play the right notes is by striking the wrong chords, our ears and our guts as good of teachers as any. It has always been that we improve at things by being bad at them first, with some innate desire and passion motivating us to keep trying. If you can’t be bothered to step around the beetles, rolling their Sisyphian balls of dung and dirt along their own tiny paths, how could you ever see the value in your own instinctual urges to put your whole soul into something, regardless of if you may get smooshed along the way?

It is the education system which grades us on our ability to memorize, to perform under pressure, to get a better-than-perfect Grade Point Average which has taught us to fear failure. Getting a poor grade in an elective class haunts our transcripts forever, and so we don’t risk it. At every turn in the society we’ve built, mistakes are labeled as mortifying, costly, and irreversible. What’s more, most of the positive spin on missteps is so focused on value. “You’ve learned a valuable lesson,” and, “Now you know for next time.” As if we are all marching a straight line towards an inevitable ‘success,’ as defined by someone else.

* * *

How do I establish credibility on the subject of failure?

I have seen books on bookshelves by people whose opinions are said to be definitive because of chance happenings – a bestseller by a woman whose parachute didn’t open on a touristy skydiving trip, an investing book by someone who perfectly timed the Dot Com Bubble, a whole memoir by someone who got struck by lightning and survived, as if fluke happenstances alone are what publishers Want to See, as if Greatest Fears are What Sells, as if random events are what grant us publishing deals (well…).

It is decidedly less compelling to have laid in bed staring at photos of tall bridges until two in the morning, wondering if I have the requisite bravery to build up speed and run and leap over the railing. To check the bank accounts, the sales figures, the tax bills, and realize that there’s no way to right this ship. These heartbreaking capitalistic rigors are things “people have to do” and so nobody cares if you don’t like doing it. Having a brain cannibalize itself over grief and regret and slowly meditating my way out of it is not exactly an airport newsstand story, but if I were to hit the water 955 feet below the bridge deck and somehow survive, I would now be an expert on living life without regret. If I don’t survive, well, I become a mildly profitable clickbait story for People Magazine to run, focusing on the height of the bridge and the lack of safety netting beneath it, quoting old high school acquaintances about how “nice” and “quiet” I was and how “they never thought I would “do something like this.” Everyone loves to consume anodyne horrors in their Apple News sidebars.

But perhaps we cannot distill life’s lessons into a regrettable three second plunge into oblivion. If the impact doesn’t kill us, the rapid fire processing of a life poorly-lived as gravity accelerates surely will. But it is so hard to liberate ourselves, to undo the patterns that steer the ship in a convincing and sustainable way. Because we have to live with ourselves after we make changes, and we have to live with ourselves when we don’t make changes. The regrets slowly accumulate and our ability to let go and change course gets harder with every additional sunk cost.

Fearing failure at something we deeply desire is a valid feeling, but the problem is how we have been taught to view failure. To find out that our dream of this version of our manuscript getting published is not going to come true is heartbreaking. So we put it off, and never write the novel, because we are guaranteed to not fail if we don’t try. What if we viewed life more symphonically, each wrong note bringing us closer to finding the right one? I miss the days when I played wrong notes for hours in an uncomfortable stool in my childhood bedroom, when my brain hadn’t been altered by the structural changes that Newsfeeds and algorithms and handheld screens.

I am just a human, and I was made for calloused fingers and breathtaking light brushes of skin-on-skin. I was not made to go numb to the subtle joys of playing music by a campfire. My mind is not meant to be bombarded with trivialities, it is meant to delight in the natural unfolding of life on Earth’s Time. I should not lose sight of my own dreams just because I can Google videos of virtuosos or stream music via satellite, for free, to play on a bluetooth speaker by a campfire instead. There was a time when music was hard to come by, and the easiest way to hear it, especially away from the home radio, was to play it yourself.

There is one thing far more painful than failing at something we deeply want to do: failing at things we thought we were supposed to do, while our dreams lay dormant, gathering dust, getting buried beneath society’s expectations of us. While it might hurt to lose my life savings trying to write a book, then another, then another, until one day I learn what the chord is supposed to sound like, that failure would feel altogether worthwhile. It’s what I deeply desire, and that journey is priceless regardless of the outcome. I want to believe that every cup of coffee and hour spent turning gooey brain matter into words is somehow worth it, but when it doesn’t “go anywhere,” it gets awfully hard to justify in a world that has a lot more formulas for ROI than it does for personal satisfaction.

What hurts far worse than writing a dozen Shitty First Drafts is losing one’s life savings following the wisdom and schemes of others, trying to grow your money by letting another person manage it, living your one wild and precious life in accordance with other people’s value systems – watching it all evaporate in a fluke market crash or a shocking automobile accident, neither grown savings for another day nor gratifying time well spent to show for it all.

* * *

I recently listened to a podcast about a small-town preacher who got quite good at investing and then started his own hedge fund, growing his congregants’ dollars in a way that felt ordained by the Lord Himself. Only, like anyone who focuses too much on the bottom line, he found one day that the greater the sums, the faster they fall when the market zigs when you expect a zag. He took to cooking books, riskier investments, and falsifying the statements he sent out to his investors. The story crescendos with the man faking his own death to avoid the wrath of the government and the heartbroken blue collar people whose retirements were obliterated by wrong guesses made with a mouse and a keyboard.

I find this story so insightful – the way that people entrust certain figures with their money, the blind faith that doing things “by the book” will lead to some better life than the one we’re living today. Whether heaven or retirement, we put off all our earthly pleasures for some other day, until it scarcely matters whether that day will come or not because we no longer have any connection to our own yearning at all. What good is retirement, or heaven, if we never develop the transcendent passions that we wish we had a million more days for?

Indeed, the belief that we should not chase our most indulgent dreams because they are somehow “reckless” or “sinful,” and that so-called experts know more about what we want out of our futures than we do. Losing the things you once had because you didn’t feel “free” to use them is one of life’s great tragedies. Chasing more and winding up with less is a lesson I hope not many people have to learn the ways I have. We pejoratively label dreamers as “risking it all” and rarely label straightlaced compromise as the very-real risk that it is. Gambling your one wild and precious life with a series of choices by committee is very high-risk indeed.

* * *

This is the root of failure that becomes impossible to stomach. Earth-shattering grief is not buying a new musical instrument and sucking at it, it is spending real time and money on things that are not aligned with our souls’ songs. Regret is not painting an amateurish watercolor while listening to good music, it is chasing the wrong things for so long that we start to feel the very real pain of lost time we cannot get back.

And indeed, part of a healthy mindset is being grateful for the lessons we learn along the way, in triumph and in setback. But it is hard to be grateful for lessons borne of eviscerating mistakes made while living someone else’s vision for our lives.

This is the important part. Fail at the things you want to succeed at. Try things you want to try, that you daydream about when you take a long blink in the middle of the day, that you secretly wish you could do “if only things were different.” Things won’t get different until you make them so.

*

There is a real difference between the feeling of being “along for the ride” on a train that is bound to a set of tracks and “enjoying the ride” in a raft on a wild and scenic river. Loosening the reins and relaxing into the unknown is liberating and beautiful. Relinquishing volition and accepting a predetermined path is hollow, even if it does tickle our primordial need for predictability. Humans have a proclivity for being told what is right and wrong, and we take this way too far. This is why art serves a spiritual, survival function for our species. There is no right and wrong way to play a song or paint a painting. We find what pleases us through soulful experimentation, not chasing outcomes or prepackaged dreams. May we be liberated enough to experiment joyously.