Everything You Need To Know About Failure

What does failure really mean?

It almost seems like a dumb thing to ask, the kind of embarrassing question that slips out of your mouth and wish you could take back instantly.

Of course we all know what it means to fail, right?

Failure is defined as “a lack of success.” We can also think of it as “coming up short.” But both definitions still doesn’t explain what it actually means to fail.

They’re both incomplete, about as useful as pointing to the word “success” while shaking your head and saying “not that.”

We spend more time running away from failure than actually defining what it is.

As much talk as there is about failure—fail often, fail forward, etc—there’s not nearly as much conversation about what failure actually means.

If we say “he failed,” all we’re really saying is “he didn’t succeed.” There’s no information conveyed other than the fact that something did not happen, that some standards or expectations for success were not met, that something or someone came up short.

But the fact that something didn’t happen still doesn’t explain what did.

Failure, therefore, is an incomplete and subjective term. To define failure in any context, you must first ask: what are you falling short of? What standards aren’t you reaching? By which metrics are you failing?

You can’t truly know what it means to fail if you don’t know what it means to succeed.

SCHOOL SETS YOU UP FOR FAILURE

School sabotages our relationship with failure from the beginning.

In school, failure is objective: when the tests are handed back, you know whether you passed or failed. If you fail there are consequences—your teachers and parents might be disappointed with you, you probably won’t get in to a good college (if any), and you might have to repeat sophomore year or get kicked off the varsity team.

No wonder we have such a screwed up relationship with failure—our school system literally teaches us to associate failing with people being angry with us, opportunity slipping away, and having to spend our entire summers at school while our friends are all having fun outside.

The message we learn from this: if you fail, you’ll be punished. Supposedly, as long as you manage to not fail, you’re pretty much okay. The problem is that this belief is horribly misguided, and it sets us up for a lifetime of failure outside of the classroom.

The important part to understand is that outside of school, failure and success are no longer objective terms. In the real world, failure and success and are entirely subjective concepts, and you have to consciously define what they mean for you.

FAILURE IS THE CURRENCY FOR SUCCESS

In school, failure means lost opportunity. But in the real world, failure is the currency for success.

Some people think it’s actually possible to become insanely successful without ever failing. If success were a house, many believe if they’re just careful or clever enough, they can walk right by failure’s room and still get to where they want to go.

But no matter how brilliant you think you are, you can’t tiptoe past failure on the way to success—failure is the front door.

This is not a question of innate talent. You’re not better or smarter than failure, you’re not above it and you can’t escape it. You’re going to fail many times, probably more than you succeed. If that idea made you queasy, well… get used to it. But there is good news.

What we often consider to be failure isn’t failure at all—it’s data.

In most cases when you fail you’ll know either one or some combination of the following: why you failed, what you did that led to failing, or what you can do better next time.

This data and information you obtain from failure is like a currency you earn through the courage of taking action. The more times you fail, the more data you earn, and the richer and more knowledgeable you become—assuming you’re actually experimenting instead of just making the same mistakes over and over again and expecting something to change.

From this perspective, failure and mistakes shouldn’t be avoided—they should be welcomed, embraced, cherished.

If you want to achieve anything worthwhile, you have to let go of the idea that failure is something to avoid. Nobody wants to fail, but you have to be willing to fail if you ever want the chance to succeed. Counterintuitively, this acceptance and anticipation of failure weakens its sting and helps you regain perspective to get back on track (although you could even argue that failure is the track).

Think of it this way: you win or you learn, and you win by learning. When you’ve finally accumulated enough failures, you might have the chance to exchange your fortune of failures for a tiny bit of success. Of course, simply failing doesn’t mean you’ll succeed, the same way that investing in the stock market doesn’t mean you’ll get rich… but if you invest your failures wisely, you’ll have much a better shot.

YOU CAN’T CHOOSE BETWEEN FAILURE AND SUCCESS

If you could choose between failure and success, you’d probably pick success. But here’s the truth: you don’t have a choice. That’s not the way it works.

Life isn’t a restaurant where you can choose to have whatever seems most pleasant. If it was, we would all pick 100% success and no failure.

In reality, you literally can’t have success without failure—they’re two sides of the same coin, part of the same meal.

To stick with the restaurant analogy, if life were a price-fixed menu, the appetizer would be a small heap of failure. It would smell funny, look awful, and probably be the most bitter thing you’ve ever tasted. Just when the waiter finally takes the rancid plate away, you’ll breathe a sigh of relief knowing that disgrace is no longer in sight, until he comes back moments later with an even bigger mound of failure as the main course — at which point you’ll turn to your friend, bang your first on the table and say “This isn’t what I was expecting!”

Nobody wants failure for their main course. But just like a broke student who eats ramen everyday for years while putting themselves through school, you need to accept that failure’s going to be the only thing on your menu for quite some time if you want anything worth having.

It doesn’t matter how much you achieve, or how good you think you are… you’ll never be immune to failure. Expect it often. Anticipate it. Remember that even though you can have failure without success, you can’t have success without failure.

MOST FAILURE ISN’T REAL, IT’S PERCEIVED

We often have intensely emotional reactions whenever we think we’ve failed, and anything that feels remotely like failure seems like the end of the world.

For some strange reason, our brain seemingly gives any supposed failure the power to forever define us as a person—as if this one moment will be some cosmic and ultimate declaration of our worth.

But most of the time, we unknowingly conflate what feels like an in-the-moment failure with eternal failure.

We’re emotional creatures, and in the moment our emotions have the power to hijack our brain into thinking that this actually is game over, making us blind to the fact that this present-moment failure is simply a tiny blip in our life experience.

This happens usually when we mistake a perceived failure for a real one. Perceived failures are false alarms that feel like failure but have no serious or lasting consequence on our lives. They’re also failures that we’re unable to see as part of the bigger picture, and are sometimes even necessary for our evolution, improving our skills, and reaching our definition of success, whatever that may be.

Perceived failures generally consist of the following:

  1. Innocuous, small-time errors that we mistakenly interpret as much more significant than they actually are
  2. A seemingly world-ending catastrophe that we’re unable to identify as part of the bigger picture
  3. Useful data that is crucial to our development

Failure is only truly failure if you expect that you should always and immediately be succeeding every step along the way. Not only is that wrong, it’s also impossible.

There’s an entitlement to success that looms large at both a societal and personal level. We not only expect to be amazing at whatever we touch, but we expect to amazing right now, regardless of the amount of work or sacrifice we put in.

For example, as a teenager I tried to master the piano. One of the first songs in the book was the nursery rhyme Three Blind Mice, and one day I was really struggling with it, making mistake after mistake.

Every wrong note I struck felt like a knife being stabbed into my chest. There was such a gap between where I was and where I wanted to be: my friends in school were busy playing Bach concertos and playing gigs in the East Village and here I was having trouble learning a nursery rhyme for five year olds.

And I was beating myself up about it so much that I couldn’t understand or process the fact that there was actually nothing different between me and my peers who could play the piano, other than the fact that they had started a few years before me and, more importantly, already made the mistakes I was making.

At the time I genuinely believed that the difference between me and them was the fact that I just wasn’t naturally gifted enough to play the piano, and that was why I was having such a hard time learning.

But contrary to what teenage Jesse thought, it wasn’t a question of natural talent, and it’s not like my friends never struggled—of course they did. They might have been young enough to not feel as ridiculous stumbling through a nursery rhyme, but they had already paid their struggle dues to get past this level I was having such a hard time with, whether it was with Three Blind Mice or some other song that was once frustratingly beyond their ability.

So at the time I thought I wanted to master the piano, but in hindsight I didn’t just want to master the piano—I wanted to master it immediately. Without any failure, wrong notes, sacrifice, or struggle. I felt entitled to success, thinking that if I was just naturally talented enough I wouldn’t be struggling, especially with a damn nursery rhyme.

The truth is that those wrong notes that felt like failure were the same mistakes I needed to make to improve.

In the context of Three Blind Mice, then yes, every wrong note was technically wrong. But in the context of actually getting good at the piano, those technically wrong notes actually meant progress, because every wrong note taught my muscles to reevaluate the distance between the keys, where to position my fingers in relation to each other, or to reach a centimeter further with my index finger to hit that A sharp.

While every wrong note was technically failure to play the song correctly, in reality this was a perceived failure instead of a real one; a sign of my own frustration and impatience moreso than a moment from which any ultimate conclusion could be drawn. What felt like a world-ending quality was really just a symptom of emotional tunnel vision, a circus of naive doubt propelled by my own frustration, immaturity, and entitlement that I should naturally be a virtuoso pianist. In hindsight, not only was this wrong, but also an insult to the hard work and dedication of every skilled pianist who undoubtedly labored for thousands of hours to hone their craft.

Getting it right is simply a byproduct of getting it wrong many times. Success usually gets the credit, but mistakes (and wrong notes) are what make success possible. Finally playing through Three Blind Mice for the first time might feel like a victory, but it’s not—it’s just a byproduct of the victory.

The real victory is showing up every day with enough patience, discipline, and respect for the craft to sit and practice for hours and hours, plunk all the wrong keys, and work through the wrong notes.

The piano doesn’t owe you anything, but if you honor it enough to repeatedly make yourself vulnerable in front of it and show it how badly you want to improve, eventually it will hear your case, drop its stiff upper lip and grace you with a touch of skill.

And the entire process will be both quicker and more pleasant once you can accept that. Once you’re willing to hit the wrong notes for the sake of improvement, you get better faster, and everything gets lighter, easier, and more fun.

Those who are willing to fail and view mistakes as “boosts” along the timeline of their own development are more likely to succeed than those who consider those same mistakes as indicative of their identity, worth, or natural inability. Because in the end, it’s not about you. It’s about the timeline, your patience, discipline, and willingness to make even the most frustrating mistakes over and over again in the name of progress.

THE OPPOSITE OF SUCCESS IS NOT FAILURE, THE OPPOSITE OF SUCCESS IS NOT TRYING

There are two ways to fail:

  1. Failing with courage
  2. Failing through avoidance

The difference is that the former gives you data, along with the knowledge that you’ve tried. The latter gives you nothing.

You could argue that you’re better off if you never try at all, because you don’t run the risk of failing. But shielding from yourself from failure is still failing. And in fact, it’s worse. If you fail with courage you can least say you’ve tried, and maybe know that you’ve given it your best shot. 

There’s a huge difference between trying and failing versus not trying at all. The biggest price you’ll pay is embarrassment, and once you get used to embarrassing yourself, you’re pretty much invincible.

Not trying is simply an act of cowardice. If you don’t step in the ring, you haven’t just failed — you’ve turned your back and ran the other way. As Hunter S. Thompson puts it, “A man who procrastinates in his choosing will inevitably have his choice made for him by circumstance.”

Failing through avoidance is like failing at failing. Avoidance might save yourself the short-term discomfort of coming up short, but you pay a brutal price of losing the long game, and this’ll be much more painful than any embarrassment that comes from putting yourself out there. “Playing it safe” is a myth— you’re not playing it safe, you’re slowly disqualifying yourself under the guise of safety.

The things that scare you offer you the most opportunities for growth. 

Wear your failure as a badge of pride instead of a source of shame. Leave your identity out of it, failure has less to do with you than you think. Be patient. Adjust your scope of failure to look beyond the sting and consider this moment as part of the bigger picture. Look for the data. Remember that emotions give you tunnel vision, and that this is not all as urgent as it seems.

THERE IS NO PERFECT MOMENT, AND IT’S NEVER THE RIGHT TIME

If you wait for the perfect moment, you’ll be forever waiting. Considering and backing out, pondering and falling back, folding your hand each turn. I’m not the world’s greatest poker player, but I do know that you can’t fold every hand and expect to win.

At a certain point you have to feel the uncertainty—the pulsing unsteadiness beneath your feet—and accept it. The joke is that it will always be there. Most feel they have to wait for it to disappear… but it will always remain. You can never eradicate this inherent uncertainty with achievement, qualifications, experience, money, success, or time.

Because you’re never to going to be certain. Nobody is. The myth is that people do bold things when they’re certain, and then a lot of people never feel that certainty, so they remain paralyzed. The trick is to get used to that uncertainty, to make it a familiar feeling.

Be honest with yourself. Is “it’s not the right time” actually just code for, “I’m uncomfortable with the prospect of doing this right now and will delay it until the moment when I think I won’t be uncomfortable anymore?”

But what if you will always be uncomfortable? What if that’s the joke? What if the difference between the bold and the cowardly isn’t the absence of uncertainty, but the courage to act in spite of it?

Sometimes it just feels too risky. But remember that everything you do is a risk. Waiting is a risk, because you might not be here tomorrow. Waiting assumes that time is guaranteed — but the reality is that the plug might be pulled tomorrow. You could be 21 or 41, in the prime of your life, and meet a tragic, unexpected fate at the drop of a dime. You could be 88 and ready to say your goodbyes and live another twenty years. We don’t know, and it’s not fair. But we weren’t given the choice, and it doesn’t matter how we feel about it. All we can do is make the most of the hand we’ve been dealt.

Tomorrow you might fantasize about starting a business on the bus, excited at the prospect before eventually convincing yourself that you don’t have what it takes or you don’t know enough or you’re not ready, suffocating that dream until it finally stops gasping for air, its corpse forever lodged inside you, slowly rotting a toxic combination of regret, resentment, shame, and guilt.

There will always be a reason to wait. You will always find a way to rationalize. Stop rationalizing the reasons to ignore the burning in your chest and pushing it back down under the surface.

In the end, failure is just a feeling. And the only true failure is the failure to try.


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