Failure Is the May Forward

I really mean it when I say it: I was fortunate.

I graduated college in 2007, just in time for the financial collapse and Great Recession, and attempted to enter the worst job market in more than eighty years.

Around the same time, I found out that the person who was subletting one of the rooms in my apartment hadn’t paid any rent for three months. When confronted about this, she cried and then disappeared, leaving my other roommate and me to cover everything. Goodbye, savings. I spent the next six months living on a friend’s couch, stringing together odd jobs and trying to stay in as little debt as possible while looking for a “real job.”

I say I was fortunate because I entered the adult world already a failure. I started out at rock bottom. That’s basically everybody’s biggest fear later on in life, when confronted with starting a new business or changing careers or quitting an awful job, and I got to experience it right out of the gates. Things could only get better.

So yeah, lucky. When you’re sleeping on a smelly futon and have to count coins to figure out whether you can afford McDonald’s this week and you’ve sent out twenty résumés without hearing a single word back, then starting a blog and a stupid Internet business doesn’t sound like such a scary idea. If every project I started failed, if every post I wrote went unread, I’d only be back exactly where I started. So why not try?

Failure itself is a relative concept. If my metric had been to become an anarcho-communist revolutionary, then my complete failure to make any money between 2007 and 2008 would have been a raving success. But if, like most people, my metric had been to simply find a first serious job that could pay some bills right out of school, I was a dismal failure.

I grew up in a wealthy family. Money was never a problem. On the contrary, I grew up in a wealthy family where money was more often used to avoid problems than solve them. I was again fortunate, because this taught me at an early age that making money, by itself, was a lousy metric for myself. You could make plenty of money and be miserable, just as you could be broke and be pretty happy. Therefore, why use money as a means to measure my self-worth?

Instead, my value was something else. It was freedom, autonomy. The idea of being an entrepreneur had always appealed to me because I hated being told what to do and preferred to do things my way. The idea of working on the Internet appealed to me because I could do it from anywhere and work whenever I wanted.

I asked myself a simple question: “Would I rather make decent money and work a job I hated, or play at Internet entrepreneur and be broke for a while?” The answer was immediate and clear for me: the latter. I then asked myself, “If I try this thing and fail in a few years and have to go get a job anyway, will I have really lost anything?” The answer was no. Instead of a broke and unemployed twenty-two-year-old with no experience, I’d be a broke and unemployed twenty-five-year-old with no experience. Who cares?

With this value, to not pursue my own projects became the failure—not a lack of money, not sleeping on friends’ and family’s couches (which I continued to do for most of the next two years), and not an empty résumé.‌

The Failure/Success Paradox‌

When Pablo Picasso was an old man, he was sitting in a café in Spain, doodling on a used napkin. He was nonchalant about the whole thing, drawing whatever amused him in that moment—kind of the same way teenage boys draw penises on bathroom stalls—except this was Picasso, so his bathroom-stall penises were more like cubist/impressionist awesomeness laced on top of faint coffee stains.

Anyway, some woman sitting near him was looking on in awe. After a few moments, Picasso finished his coffee and crumpled up the napkin to throw away as he left.

The woman stopped him. “Wait,” she said. “Can I have that napkin you were just drawing on? I’ll pay you for it.”

“Sure,” Picasso replied. “Twenty thousand dollars.”

The woman’s head jolted back as if he had just flung a brick at her. “What? It took you like two minutes to draw that.”

“No, ma’am,” Picasso said. “It took me over sixty years to draw this.” He stuffed the napkin in his pocket and walked out of the café.

Improvement at anything is based on thousands of tiny failures, and the magnitude of your success is based on how many times you’ve failed at something. If someone is better than you at something, then it’s likely because she has failed at it more than you have. If someone is worse than you, it’s likely because he hasn’t been through all of the painful learning experiences you have.

If you think about a young child trying to learn to walk, that child will fall down and hurt itself hundreds of times. But at no point does that child ever stop and think, “Oh, I guess walking just isn’t for me. I’m not good at it.”

Avoiding failure is something we learn at some later point in life. I’m sure a lot of it comes from our education system, which judges rigorously based on performance and punishes those who don’t do well. Another large share of it comes from overbearing or critical parents who don’t let their kids screw up on their own often enough, and instead punish them for trying anything new or not preordained. And then we have all the mass media that constantly expose us to stellar success after success, while not showing us the thousands of hours of dull practice and tedium that were required to achieve that success.

At some point, most of us reach a place where we’re afraid to fail, where we instinctively avoid failure and stick only to what is placed in front of us or only what we’re already good at.

This confines us and stifles us. We can be truly successful only at something we’re willing to fail at. If we’re unwilling to fail, then we’re unwilling to succeed.

A lot of this fear of failure comes from having chosen shitty values. For instance, if I measure myself by the standard “Make everyone I meet like me,” I will be anxious, because failure is 100 percent defined by the actions

of others, not by my own actions. I am not in control; thus my self-worth is at the mercy of judgments by others.

Whereas if I instead adopt the metric “Improve my social life,” I can live up to my value of “good relations with others” regardless of how other people respond to me. My self-worth is based on my own behaviors and happiness.

Shitty values, as we saw in chapter 4, involve tangible external goals outside of our control. The pursuit of these goals causes great anxiety. And even if we manage to achieve them, they leave us feeling empty and lifeless, because once they’re achieved there are no more problems to solve. Better values, as we saw, are process-oriented. Something like “Express myself honestly to others,” a metric for the value “honesty,” is never completely finished; it’s a problem that must continuously be reengaged. Every new conversation, every new relationship, brings new challenges and opportunities for honest expression. The value is an ongoing, lifelong

process that defies completion.

If your metric for the value “success by worldly standards” is “Buy a house and a nice car,” and you spend twenty years working your ass off to achieve it, once it’s achieved the metric has nothing left to give you. Then say hello to your midlife crisis, because the problem that drove you your entire adult life was just taken away from you. There are no other opportunities to keep growing and improving, and yet it’s growth that generates happiness, not a long list of arbitrary achievements.

In this sense, goals, as they are conventionally defined—graduate from college, buy a lake house, lose fifteen pounds—are limited in the amount of happiness they can produce in our lives. They may be helpful when pursuing quick, short-term benefits, but as guides for the overall trajectory of our life, they suck.

Picasso remained prolific his entire life. He lived into his nineties and continued to produce art up until his final years. Had his metric been “Become famous” or “Make a buttload of money in the art world” or “Paint one thousand pictures,” he would have stagnated at some point along the way. He would have been overcome by anxiety or self-doubt. He likely wouldn’t have improved and innovated his craft in the ways he did decade after decade.

The reason for Picasso’s success is exactly the same reason why, as an old man, he was happy to scribble drawings on a napkin alone in a café. His underlying value was simple and humble. And it was endless. It was the value “honest expression.” And this is what made that napkin so valuable.‌

Pain Is Part of the Process‌

In the 1950s, a Polish psychologist named Kazimierz Dabrowski studied World War II survivors and how they’d coped with traumatic experiences in the war. This was Poland, so things had been pretty gruesome. These people had experienced or witnessed mass starvation, bombings that turned cities to rubble, the Holocaust, the torture of prisoners of war, and the rape and/or murder of family members, if not by the Nazis, then a few years later by the Soviets.

As Dabrowski studied the survivors, he noticed something both surprising and amazing. A sizable percentage of them believed that the wartime experiences they’d suffered, although painful and indeed traumatic, had actually caused them to become better, more responsible, and yes, even happier people. Many described their lives before the war as if they’d been different people then: ungrateful for and unappreciative of their loved ones, lazy and consumed by petty problems, entitled to all they’d been given. After the war they felt more confident, more sure of themselves, more grateful, and unfazed by life’s trivialities and petty annoyances.

Obviously, their experiences had been horrific, and these survivors weren’t happy about having had to experience them. Many of them still suffered from the emotional scars the lashings of war had left on them. But some of them had managed to leverage those scars to transform themselves in positive and powerful ways.

And they aren’t alone in that reversal. For many of us, our proudest achievements come in the face of the greatest adversity. Our pain often makes us stronger, more resilient, more grounded. Many cancer survivors, for example, report feeling stronger and more grateful after winning their battle to survive. Many military personnel report a mental resilience gained from withstanding the dangerous environments of being in a war zone.

Dabrowski argued that fear and anxiety and sadness are not necessarily always undesirable or unhelpful states of mind; rather, they are often

representative of the necessary pain of psychological growth. And to deny that pain is to deny our own potential. Just as one must suffer physical pain to build stronger bone and muscle, one must suffer emotional pain to develop greater emotional resilience, a stronger sense of self, increased compassion, and a generally happier life.

Our most radical changes in perspective often happen at the tail end of our worst moments. It’s only when we feel intense pain that we’re willing to look at our values and question why they seem to be failing us. We need some sort of existential crisis to take an objective look at how we’ve been deriving meaning in our life, and then consider changing course.

You could call it “hitting bottom” or “having an existential crisis.” I prefer to call it “weathering the shitstorm.” Choose what suits you.

And perhaps you’re in that kind of place right now. Perhaps you’re coming out of the most significant challenge of your life and are bewildered because everything you previously thought to be true and normal and good has turned out to be the opposite.

That’s good—that’s the beginning. I can’t stress this enough, but pain is part of the process. It’s important to feel it. Because if you just chase after highs to cover up the pain, if you continue to indulge in entitlement and delusional positive thinking, if you continue to overindulge in various substances or activities, then you’ll never generate the requisite motivation to actually change.

When I was young, any time my family got a new VCR or stereo, I would press every button, plug and unplug every cord and cable, just to see what everything did. With time, I learned how the whole system worked. And because I knew how it all worked, I was often the only person in the house who used the stuff.

As is the case for many millennial children, my parents looked on as if I were some sort of prodigy. To them, the fact that I could program the VCR without looking at the instruction manual made me the Second Coming of Tesla.

It’s easy to look back at my parents’ generation and chuckle at their technophobia. But the further I get into adulthood, the more I realize that we all have areas of our lives where we’re like my parents with the new VCR: we sit and stare and shake our heads and say, “But how?” When really, it’s as simple as just doing it.

I get emails from people asking questions like this all the time. And for many years, I never knew what to say to them.

There’s the girl whose parents are immigrants and saved for their whole lives to put her through med school. But now she’s in med school and she hates it; she doesn’t want to spend her life as a doctor, so she wants to drop out more than anything. Yet she feels stuck. So stuck, in fact, that she ends up emailing a stranger on the Internet (me) and asking him a silly and obvious question like, “How do I drop out of med school?”

Or the college guy who has a crush on his tutor. So he agonizes over every sign, every laugh, every smile, every diversion into small talk, and emails me a twenty-eight-page novella that concludes with the question, “How do I ask her out?” Or the single mother whose now-adult kids have finished school and are loafing around on her couch, eating her food, spending her money, not respecting her space or her desire for privacy. She wants them to move on with their lives. She wants to move on with her life. Yet she’s scared to death of pushing her children away, scared to the point of asking, “How do I ask them to move out?”

These are VCR questions. From the outside, the answer is simple: just shut up and do it.

But from the inside, from the perspective of each of these people, these questions feel impossibly complex and opaque—existential riddles wrapped in enigmas packed in a KFC bucket full of Rubik’s Cubes.

VCR questions are funny because the answer appears difficult to anyone who has them and appears easy to anyone who does not.

The problem here is pain. Filling out the appropriate paperwork to drop out of med school is a straightforward and obvious action; breaking your parents’ hearts is not. Asking a tutor out on a date is as simple as saying the words; risking intense embarrassment and rejection feels far more complicated. Asking someone to move out of your house is a clear decision; feeling as if you’re abandoning your own children is not.

I struggled with social anxiety throughout much of my adolescence and young adult life. I spent most of my days distracting myself with video games and most of my nights either drinking or smoking away my uneasiness. For many years, the thought of speaking to a stranger— especially if that stranger happened to be particularly

attractive/interesting/popular/smart—felt impossible to me. I walked around in a daze for years, asking myself dumb VCR questions:

“How? How do you just walk up and talk to a person? How can somebody do that?”

I had all sorts of screwed-up beliefs about this, like that you weren’t allowed to speak to someone unless you had some practical reason to, or that women would think I was a creepy rapist if I so much as said, “Hello.”

The problem was that my emotions defined my reality. Because it felt like people didn’t want to talk to me, I came to believe that people didn’t want to talk to me. And thus, my VCR question: “How do you just walk up and talk to a person?”

Because I failed to separate what I felt from what was, I was incapable of stepping outside myself and seeing the world for what it was: a simple place where two people can walk up to each other at any time and speak.

Many people, when they feel some form of pain or anger or sadness, drop everything and attend to numbing out whatever they’re feeling. Their goal is to get back to “feeling good” again as quickly as possible, even if that means substances or deluding themselves or returning to their shitty values.

Learn to sustain the pain you’ve chosen. When you choose a new value, you are choosing to introduce a new form of pain into your life. Relish it. Savor it. Welcome it with open arms. Then act despite it.

I won’t lie: this is going to feel impossibly hard at first. But you can start simple. You’re going to feel as though you don’t know what to do. But we’ve discussed this: you don’t know anything. Even when you think you do, you really don’t know what the fuck you’re doing. So really, what is there to lose?

Life is about not knowing and then doing something anyway. All of life is like this. It never changes. Even when you’re happy. Even when you’re farting fairy dust. Even when you win the lottery and buy a small fleet of Jet Skis, you still won’t know what the hell you’re doing. Don’t ever forget that. And don’t ever be afraid of that.‌

The “Do Something” Principle‌

In 2008, after holding down a day job for all of six weeks, I gave up on the whole job thing to pursue an online business. At the time, I had absolutely no clue what I was doing, but I figured if I was going to be broke and miserable, I might as well be while working on my own terms. And at that time, all I seemed to really care about was chasing girls. So fuck it, I decided to start a blog about my crazy dating life.

That first morning that I woke up self-employed, terror quickly consumed me. I found myself sitting with my laptop and realized, for the first time, that I was entirely responsible for all of my own decisions, as well as the consequences of those decisions. I was responsible for teaching myself web design, Internet marketing, search engine optimization, and other esoteric topics. It was all on my shoulders now. And so I did what any twenty-four-year-old who’d just quit his job and had no idea what he was doing would do: I downloaded some computer games and avoided work like it was the Ebola virus.

As the weeks went on and my bank account turned from black to red, it was clear that I needed to come up with some sort of strategy to get myself to put in the twelve- or fourteen-hour days that were necessary to get a new business off the ground. And that plan came from an unexpected place.

When I was in high school, my math teacher Mr. Packwood used to say, “If you’re stuck on a problem, don’t sit there and think about it; just start working on it. Even if you don’t know what you’re doing, the simple act of working on it will eventually cause the right ideas to show up in your head.”

During that early self-employment period, when I struggled every day, completely clueless about what to do and terrified of the results (or lack thereof), Mr. Packwood’s advice started beckoning me from the recesses of my mind. I heard it like a mantra:

Don’t just sit there. Do something. The answers will follow.

In the course of applying Mr. Packwood’s advice, I learned a powerful lesson about motivation. It took about eight years for this lesson to sink in, but what I discovered, over those long, grueling months of bombed product launches, laughable advice columns, uncomfortable nights on friends’ couches, overdrawn bank accounts, and hundreds of thousands of words

written (most of them unread), was perhaps the most important thing I’ve ever learned in my life:

Action isn’t just the effect of motivation; it’s also the cause of it.

Most of us commit to action only if we feel a certain level of motivation. And we feel motivation only when we feel enough emotional inspiration. We assume that these steps occur in a sort of chain reaction, like this:

Emotional inspiration → Motivation → Desirable action

If you want to accomplish something but don’t feel motivated or inspired, then you assume you’re just screwed. There’s nothing you can do about it. It’s not until a major emotional life event occurs that you can generate enough motivation to actually get off the couch and do something.

The thing about motivation is that it’s not only a three-part chain, but an endless loop:

Inspiration → Motivation → Action → Inspiration → Motivation → Action → Etc.

Your actions create further emotional reactions and inspirations and move on to motivate your future actions. Taking advantage of this knowledge, we can actually reorient our mindset in the following way:

Action → Inspiration → Motivation

If you lack the motivation to make an important change in your life, do something—anything, really—and then harness the reaction to that action as a way to begin motivating yourself.

I call this the “do something” principle. After using it myself to build my business, I began teaching it to readers who came to me perplexed by their own VCR questions: “How do I apply for a job?” or “How do I tell this guy I want to be his girlfriend?” and the like.

During the first couple years I worked for myself, entire weeks would go by without my accomplishing much, for no other reason than that I was anxious and stressed about what I had to do, and it was too easy to put

everything off. I quickly learned, though, that forcing myself to do something, even the most menial of tasks, quickly made the larger tasks seem much easier. If I had to redesign an entire website, I’d force myself to sit down and would say, “Okay, I’ll just design the header right now.” But after the header was done, I’d find myself moving on to other parts of the site. And before I knew it, I’d be energized and engaged in the project.

The author Tim Ferriss relates a story he once heard about a novelist who had written over seventy novels. Someone asked the novelist how he was able to write so consistently and remain inspired and motivated. He replied, “Two hundred crappy words per day, that’s it.” The idea was that if he forced himself to write two hundred crappy words, more often than not the act of writing would inspire him; and before he knew it, he’d have thousands of words down on the page.

If we follow the “do something” principle, failure feels unimportant. When the standard of success becomes merely acting—when any result is regarded as progress and important, when inspiration is seen as a reward rather than a prerequisite—we propel ourselves ahead. We feel free to fail, and that failure moves us forward.

The “do something” principle not only helps us overcome procrastination, but it’s also the process by which we adopt new values. If you’re in the midst of an existential shitstorm and everything feels meaningless—if all the ways you used to measure yourself have come up short and you have no idea what’s next, if you know that you’ve been hurting yourself chasing false dreams, or if you know that there’s some better metric you should be measuring yourself with but you don’t know how—the answer is the same:

Do something.

That “something” can be the smallest viable action toward something else. It can be anything.

Recognize that you’ve been an entitled prick in all of your relationships and want to start developing more compassion for others? Do something. Start simple. Make it a goal to listen to someone’s problem and give some of your time to helping that person. Just do it once. Or promise yourself that you will assume that you are the root of your problems next time you get upset. Just try on the idea and see how it feels.

That’s often all that’s necessary to get the snowball rolling, the action needed to inspire the motivation to keep going. You can become your own source of inspiration. You can become your own source of motivation. Action is always within reach. And with simply doing something as your only metric for success—well, then even failure pushes you forward.