Laughter, Tears and Tilting at Windmills
Below are my notes for the talk given to the leaders of student organisations at my alma mater, Tartu University in February 2017. I was asked to talk to the general theme of overcoming difficulties — a topic I admittedly found difficult to get excited about. Having failed to overcome my own motivational difficulties, I decided to take on something much more fun: epic failures in life.
1. Failure is the Juice of Life
“Success is stumbling from failure to failure with no loss of enthusiasm.” — Winston Churchill
I graduated from Tartu University almost 20 years ago. I was in a hurry, determined to do a 4-year law degree in 2.5 years. My top difficulties at the time were all about figuring out how to sweet talk professors into letting me take 3rd and 4th year exams as a 2nd year student, whose lecture notes to photocopy, how to secure enough PC time at the computer lab and how to stay awake through weeks of cramming for exams on coffee & whisky. Admittedly, this is all very #lastcentury and not particularly useful to anyone attending Tartu University in 2017.
This century however I have learned something that could be of some use. In a nutshell, it’s this: Failure is the juice of life. It is the second most powerful accelerator of personal growth (the first one being suffering; it did the trick for the hosts in Westworld and it tends to work for humans, too — but it’s a whole other kettle of fish and not something I can enthusiastically recommend to proactively seek out, so I won’t touch upon it here).
So want to live a meaningful life and become an interesting human being? Learn to fail big. Not unlike Cervantes’ character Don Quixote who decides to fight giants, undo wrongs and bring justice to the world…and who perseveres despite repeated failures and public ridicule. My goal today is to share with you a few observations I have picked up along the way about giants that are worth fighting, failures that are worth having and strategies for stumbling from failure to failure with “no loss of enthusiasm.”
Before we proceed however I should probably disclose my own failure credentials. My five greatest hits so far:
(1) Ideology: “Losing My Religion” — In 1993, a couple of years after Estonia’s independence, I read Friedrich Hayek’s The Road to Serfdom that made the case against central planning and extolled the virtues of capitalism. I was sold, really sold. I read every classical liberal book I could get my hands on — from John Stuart Mill and Adam Smith to Milton Friedman, Robert Nozick, Ayn Rand, Ludwig von Mises and the Chicago boys. I joined Res Publica, then an Estonian political youth association (before it became a political party) where we met every week to explore the libertarian perspective on policy challenges of the day. I wrote my Bachelor’s thesis on the feasibility of law and order without a centralised government. I became a Charles C. Koch Fellow and interned at the CATO Institute, a libertarian think tank in Washington, DC, where I wrote op-eds on NATO and privatisation of social security. I was a Libertarian. I had a noble cause worth fighting for: individual liberty. I was all in…until in 2003 I moved to Singapore, a country widely dissed by my fellow libertarians as an aberration: a curious case of “authoritarian capitalism.” It bothered my purist ideological mind, so I decided to read the autobiography of the mastermind behind the small city-state’s regime. My goal was simple: figure out how Prime Minister Lee Kuan Yew veered off the beaten track. As I progressed through the first volume that chronicled the complex geopolitical and cultural waters Singapore’s PM had to navigate to survive, it slowly dawned on me that I spent ten years of my life blinded by my ideology, passionately firing canned libertarian answers while failing to understand the questions. By the end of the second volume I lost my religion and was left with a burning question: how do I construct my point of view without the crutches of ideology? I was forced to became a pragmatist, something my younger self used to view with suspicion if not contempt.
(2) Career: “No More Ladders” — I spent 6 years working at the top tier management consulting firm (aka the Firm), believing that focusing on lasting client impact and quickly advancing to the top of the neatly laid out career ladder would make a good, meaningful life. I was right — it was a good life and I learned a great deal but it meant very little. The Kool-Aid was addictive, so it took several years but eventually it became painfully clear that climbing a career ladder in the Firm, or any other firm for that matter, was a dead-end for me. Quitting was scary. In the brave new world without the Firm’s brand, resources and relationships, I was left with a new question: if career is a dead-end, how the hell do I build a meaningful life?
(3) Spirituality: “No More Sitting” — my quest for a meaningful life led me to Ken Wilber’s integral philosophy and Genpo Roshi’s Zen Buddhism. The appeal was irresistibly Popperian: you don’t have to take anything on faith, just follow injunctions (i.e., spiritual practices), conduct the experiment (e.g., sit on the cushion, solve koans), see what happens and feel free to question your experience. I loved the promise of a path to understanding the nature of my own mind and the nature of reality. So I sat on the cushion, slayed all of my remaining heroes, struggled through koans, read and explored the maze of my own mind. It proved to be a fascinating trip to… Nowhere. Lots of good things happened along the way — my mind became more transparent, my ego became less interesting, I have experienced fleeting moments where the world really did make sense. But I also lost my motivation to do anything other than more of the same: sit, read, contemplate…so that one day you could teach others to do the same. It was deeply meaningful, and I felt like a frog trapped in a deep, deep well. I had to jump. Jumping was a feat: how do you cajole yourself into doing anything at all when you see through your own bullshit and the sublime futility of it all? Fortunately, I met a fellow kindred spirit and together we staged our escape.
(4) Impact, attempt #1: “Too Big to Bite Off” — I emerged with a new hypothesis: putting myself to the greatest possible use in service of the ongoing human project would finally make my life make sense to me. The first order of business was to figure out what needed doing. Together with my best friend and fellow explorer, we spent 5 years researching and writing a book on the future of human civilisation. Our goal was to formulate an agenda for the human species and start a global conversation about our collective priorities. As we progressed through our research, our main thesis became clear: as a civilisation, we are catastrophically disinterested in our own long-term survival, with the bulk of our collective resources being allocated to trivial pursuits while existential risks go largely underthought, underfunded and unaddressed. We published our ideas but failed to start a conversation, or, to be more precise, we did not even try. After five exhilarating years of thinking as one mind, we ran aground, parted ways and stopped talking to each other. Neither of us felt we could lift it on our own. I was back to the drawing board: I had a point of view on what needed doing but how the hell can one person move a needle on anything?
(5) Impact, attempt #2: “Still Bloody Too Big”— My new hypothesis was focus! Space settlement seemed like one of the best mitigation strategies for many of the existential risks on the civilisational agenda. Rockets were a crowded place, so I joined a team working on the next big challenge: building fuel stations in space and supplying them with fuel derived from a lower gravity well, water ice on the Moon. From the outset, it was obvious that a startup with an $18 billion program had dismal odds of success. Yet against the odds, we found a visionary sovereign partner and almost got out of the gate. In the end, the deal fell apart and we were forced to regroup. The key question we had to answer was this: what are the best first steps with a non-zero probability of successfully launching the journey of 385,000 miles (i.e., distance to the Moon)?
We started a new space company with an even narrower focus on industrial robotics with ample terrestrial applications. Things are looking up so far and I am officially in between failures.
2. Three Giants Worth Fighting
“What is the point of being alive if you don’t at least try to do something remarkable?” — John Green
Barring breakthroughs in lifespan extension, the life expectancy for an Estonian man is 73 years, Estonian woman 82 years. On average, that’s all you are going to get. It may seem like a long time when you are 21 but you may come to feel differently about this as your life’s timer keeps counting down. 80-odd years looks laughably insignificant against the 13.8 billion years already lapsed on our universe’s timer and the stupendous temporal expanse of quintillions of years still ahead. Barring breakthroughs in space transport, most of us are doomed to live out our lives on this one planet in a universe packed with trillions of planets (video game No Man’s Sky helps but its not quite the same as being on the starship Enterprise and actually going “where no man has gone before”). Depressing?
Not at all. I believe it’s possible to spend that flash-in-a-pan life of ours with cosmological scope and universal significance. Like Don Quixote, take on a giant! How else are you going to fail big? At the highest level of abstraction, I believe there are three giants worth fighting.
Giant #1: The Unknown
The first giant is hard to see and yet it’s everywhere. It’s made of all the questions we don’t know answers to and all the questions we aren’t smart enough to ask. The sharpest spear we have so far for battling the Unknown is the scientific method. The battle is of universal significance — if the laws governing our universe are truly universal rather than local, your location does not matter! A scientific discovery on Earth adds to the universal pot of knowledge. A scientist from Earth is a universal scientist.
Giant #2: The Unimaginable
The second giant is a white canvas, a blank page with a pulsing cursor, a room filled with static, a landscape without features. The weapon of choice is imagination. The tools are words, sounds, bits, atoms — anything that could be used to create something that did not exist before. An art piece created on Earth, whether it’s a new symphony or a whole new imaginary world, adds to the universal diversity collection. We know that good art can transcend time and space on Earth. Cervantes’ Don Quixote is over 400 years old and we are still talking about it! But it’s quite possible that like knowledge, beauty too might be universal and objective rather then merely local and subjective (unconvinced? see David Deutsch’s talk Why Are Flowers Beautiful).
Giant #3: The Impossible
The third giant manifests as the judgment of the reasonable man and woman. “That’s impossible!” they say. The weapon of choice is a form of madness. You have to be a little mad to take on a mission most reasonable people dismiss as impossible. An entrepreneur from Earth, using universal knowledge and imagination to build something that has never been built before is a universal constructor.
How do you choose your giant? Most people have a natural predisposition. If you don’t, try all of them, mix and match, battle all of them at once. It doesn’t really matter. What matters is that you are going to fail big. And that’s where the fun is.
3. Three Types of Epic Failures
“Failure is only the opportunity more intelligently to begin again.”
― Henry Ford
All failures are delightfully unique. Yet they do lend themselves to classification. Here is one way to classify them, starting with the hardest:
Failure of Purpose
There you are, battling your giant, giving it all you’ve got, dropping exhausted at night yet jumping out of bed in the morning bushy-tailed and impatient to get at it again…until one morning your internal engine just wouldn’t start. You will yourself to keep moving on sheer momentum but deep inside you know you have lost your why. This is not your giant. The fight suddenly feels meaningless, even silly. Cue the dark night of the soul.
First off, congratulations! You’re in the middle of the best and worst kind of failure. A few things to try to speed up the process:
Alternate futures. Pretend your life is a blank canvas and try imagining an alternate future or two for yourself. Try different giants, different geography, different people around you. Don’t skimp out on the details, fill out the canvas with as much detail as you can imagine and see how any of the new details make you feel. If you feel moved by any given aspect, that might be your lead, a little ray of light for you to explore.
Sancho Panza. Who would Don Quixote be without his marvellous conversations with his loyal squire Sancho Panza? These two really listened to each other and changed through the grinding mill of their exchanges. Find your Sancho and spend hours, days, weeks talking about everything under the sun.
Wait & see. If all else fails, just wait it out. This too will pass. Even black holes decay if you throw enough time at them. Dark nights do not last forever and one beautiful morning you will emerge with a refined sense of purpose, a better why that will give you back your mojo.
Failure of Imagination
You are sure you’ve got the right giant but you feel you are failing to make any progress, you are stuck with your wheels spinning, unable to imagine how to get out of your predicament. Here are a few things to try:
(Auto)biographies. You are not the first human being to get stuck. All 100 billion people who came before you got stuck a few times during their lifetimes. Find human beings who fought the same giants and led an interesting enough life to merit an (auto)biography. Those pages are filled with stories of creative ways of overcoming plateaus.
Obituaries. No time to spare on autobiographies? Here is a shortcut: read The Economist’s obituaries. These guys have managed to transform the morbid subject of someone’s passing into an art form, a word painting outlining the arc of someone’s life. It’s just 1–2 pages a week but it gives you lots of great ideas.
Random walks. Still not sure how to get unstuck? Try a mental circuit breaker by simply straying off your beaten track. Read obscure French philosophers. Watch indie movies no one has ever heard of. Lose yourself in Chinese science fiction. Climb a bloody mountain. Strike up conversations with total strangers. Travel as far from your cultural frames of reference as you can (Japan never disappoints). Volunteer for the cause you never cared about. Whatever it is you normally do, now do the opposite. Go off the damn script. Hunt for new dots to connect.
Failure of Nerve
You’ve got the right giant, you know exactly what you need to do…and yet you simply can’t do it. Whether it’s lack of courage or a paralysing fear of failure, you just can’t jump. Here are a few things to try:
Breathe. First, take deep breaths — physiologically and metaphysically speaking. Trying to make yourself jump through the brute force of your will alone might not be the most effective strategy.
Reframe. Fear is a funny thing. If you let it, it can expand and take over your entire mindspace. So let it and see what it is exactly you are afraid of. I have been afraid of many things – losing friends when I left my ideological and spiritual communities, adding up to nothing when I quit my career, becoming a laughing stock when I was considering joining some crazy space startup. These fears were very real but if placed in the bigger frame – living a life that I knew I would come to regret – those fears looked small, almost irrelevant.
Plan B&C. Another practice I find helpful is contingency planning – imagine that your worst fear has materialized. Now what? Invest time into crafting a credible plan B and C, and you’ll find a bit of pressure lifted off plan A. Going ahead would feel less scary if you have an idea what you’ll do in case your fears materialize.
4. The Special Case of Failure: When Giants Turn Out to Be Windmills
“No human ever became interesting by not failing. The more you fail and recover and improve, the better you are as a person. Ever meet someone who’s always had everything work out for them with zero struggle? They usually have the depth of a puddle. Or they don’t exist.” — Chris Hardwick
I did not care much for Don Quixote when I first read it in high school. An old fool reads too many chivalric romances, loses his sanity and lives in a fantasy world where windmills become giants, inns become castles and unsuspecting peasant girls become damsels in need of saving — while in the real world, the protagonist himself becomes the laughing stock. It was just too painfully tragic.
Today I see it so differently. I see Don Quixote — and human life in general — as tragedy and comedy, tears and laughter rolled into every moment. The separation between the “fantasy world” and “the real world” is no longer as clear as it once seemed. Sometimes you have to camp out in the world of your vision to will it into existence. Or in the words of Konstantin Tsiolkovsky:
“First, inevitably, the idea, the fantasy, the fairy tale. Then, scientific calculation. Ultimately, fulfilment crowns the dream.”
Three giants slayed one after the other!
Or not — because sometimes a giant is just a windmill. And that, too, is fine. In the end, I am not sure it matters. We are here for the briefest of moments and it’s all over in a flash. So what’s the point of Don Quixote’s or anybody’s quest? Perhaps, our knight was fighting the final injustice — death. What if he is not a fool or a madman but a pathfinder? Battling giants — that could very well be nothing but windmills — and failing might be a better path than letting life pass you by without putting up a fight. What’s the worst thing that can happen? You’ll have battle scars to show, good stories to tell and you probably won’t have the depth of a puddle.
Here is to laughter, tears and tilting at windmills!
