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Try, Try Again

We don’t like to talk about failure much. It’s understandable really. Failure is kind of a downer as topics go, and at least in America we’re fundamentally obsessed with success and improvement as the underlying themes of life and society. We’re a pretty unbalanced culture if you look at it from say a more Taoist slant where you need to embrace an understanding of darkness (and know its value) to stand in the light and appreciate what it has to offer. In America we love to celebrate success, but we don’t even like to acknowledge failure. Even the Silicon Valley mantra of “fail fast” isn’t so much an embrace of real failure as a way to reassure the investor class that the gambles they make will pay off eventually in the next start-up.

The truth is failure is not only a persistent and inescapable life event, but one that can be a ruinous force. This is doubly true because we reject the meaning of real failure as a culture. Failing fast and failing up are great euphemisms that dress failure up as a form of success, but the truth is that if you’re actually failing fast you’re not really failing but experimenting in a context where you have the capacity to do so, and that failing up or failing better aren’t actually about failure but resilience in the face of it. None of these ideas actually acknowledges what real failure is, what it feels like, and that major failures have consequences that can’t necessarily be brushed off with a little bit of gumption.

When you truly, deeply care about something in your life and it fails, or falls apart, or explodes on you, it isn’t so easy to pick yourself up and move forward. In fact, this is one of the key things about real meaningful failure: it robs you of momentum. If you were truly committed to the thing in your life that failed, then it means that you put real effort, care, and maybe even love into it. All of that real work, all of that emotional energy, all of that time and good will that you had been spending is for nought, and while some of those resources can be renewable, none of them are inexhaustible. Committing them towards a project, or a job, or a relationship means tieing some part of the momentum you have in your life to that thing. If it fails, you’ve lost that momentum and the more of your time, attention, and care you were putting into it, the more devastating that loss can be.

One of the worst aspects of these kinds of failure is the mark that it can leave on your spirit. It’s bad enough to know that this thing you wanted to succeed or sustain has failed, but it’s even worse when that event leaves you feeling like you yourself are a failure. For most of us, that’s a natural consequence of failing in things that matter to us and I believe that it generally goes unacknowledged. That feeling, the application of that label to yourself is the part that can make a failure much bigger than the thing itself. It’s one of those things where if you say it out loud to someone who cares about you, that person will be quick to reassure you that you’re wrong. “The thing failed, or you failed at the thing, but of course you’re not a failure.” The reassurances are hollow if you don’t have the capacity to feel it yourself. Once you’ve branded yourself a failure or even worse, a loser, it’s extremely hard to shake it off. If the loss you’ve experienced is extreme enough to bring you to this place, it also means that your momentum in life is likely reduced to the bare minimum of what it takes to keep putting one foot in front of the other. Sometimes that’s the only way to persist, but I can tell you from first hand experience that it’s no kind of way to live.

There’s one additional layer to all of this that’s particularly endemic in American life. We have a strong proclivity in our culture to look at all aspects of life as a zero-sum game. For one party to succeed, another must fail. For one to win, another must lose. Our brand of unfettered capitalism coupled with the deeply litigious nature of our society means that much of the time failure feels, or even is, synonymous with someone making you a loser. Someone else gained something, often directly, from your loss. That means that compounded with the broad array of rather nasty emotions we might point at ourselves after a failure, there’s often potential for a toxic mix of bitterness, anger, and resentment pointed at someone else. These emotions may even be warranted as much of the time the person whose win was your loss conducted themselves with intent and awareness of what they were doing to you. Still, those emotions are destructive and carrying them around eats away at the soul.

Depending on the messed up mix that gets into our heads after a serious failure, there can be the potential for failure to beget further failures. You don’t have to get too far into a cycle of failure for your life to functionally reach a fail state. This is the part where our understanding of failure as Americans and the disproportionate value we put into short term success at any cost is fundamentally problematic. In order to overcome a cycle of failure, we need real opportunities to succeed. Unfortunately, the deeper we get into failure, the fewer opportunities for success we’re granted. If you’re trying, looking, for those opportunities, each additional rejection is another failure heaped on the pile. No matter how you started out, it becomes harder and harder to not simply see yourself as a failure.

If we want to get right with ourselves as a culture, we need to break this way of thinking. I’m not optimistic for that potential, but I’m personally living through the need for it. We can’t rely on each individual’s resilience in the face of failure, and we can’t hinge our successes on the failures of others. We need to acknowledge that failure is usually damaging, and that it doesn’t always present opportunity. We need to recognize that it’s possible for us to succeed without it costing someone else dearly. Every time we don’t we’re burning up the single most valuable resource that we have. One another.

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