Our Toxic Relationship with Failure

The truth is that we’re only willing to talk freely about failure after it happens, at certain intervals, and in certain contexts. Our psychological relationship with the prospect of failure is far more complicated.

David Giardino
Apr 7 · 5 min read

There’s this pithy turn-of-phrase that episodically makes its rounds across the internet, often attributed to Winston Churchill, occasionally to Abraham Lincoln, that goes like this: “Success is jumping from failure to failure without loss of enthusiasm.”

At a fundamental level, we can all draw energy from those words. We’re taught to embrace failure, to learn from it, and above all, to never be afraid of it. Who doesn’t like to hear stories of wildly successful people — from Ray Kroc to Oprah Winfrey, Michael Jordan to Walt Disney — failing repeatedly before achieving their immortal greatness? These stories are intended to give us all hope. If they can fail, anyone can, right?

I’m fascinated by failure. Not so much in the failure itself, but how we talk about it, contextualize, and rationalize it. Because here’s the thing with those “failure stories” — they’re almost universally told in hindsight. From sweeping autobiographies to viral LinkedIn posts, you’re far more likely to read about tales of rejection and defeat after the narrator has achieved the success they so badly desired. In retelling it this way, I find the story’s most illuminating lesson is not pointed towards the reader, but back at the storyteller. While the storyteller’s text might inspire us to “embrace failure,” their subtext seems to add “… but, you know, only if you ultimately succeed, like I did.”

Reflecting on how we think about failure is timely. Unemployment — particularly for those just entering the job market — remains staggeringly high. Startup failure rates hover between 70 and 90 percent, depending on your source. One-third of kids between the ages of 8 and 12 want to be a YouTube star; almost 97 percent of them won’t make enough from the medium to crack the poverty line. All of these numbers mean that many of us are trying and failing repeatedly — whether we’re applying for a job, starting a new business, or launching ourselves into the creator ecosystem.

But where are all of these failure stories? Doesn’t it seem like success comes easier for everyone around us?

The truth is that we’re only willing to talk freely about failure after it happens, at certain intervals, and in certain contexts. Our psychological relationship with the prospect of failure is far more complicated.

In 1978, researchers Steven Berglas and Edward E. Jones published a breakthrough study in the Journal of Personality and Social Psychology, where they coined the term “self-handicapping.” The researchers invited subjects to take difficult tests (some subjects were even given puzzles that were impossible to answer). No matter how the subject actually performed on the test, the researchers told them that they aced it. In other words, the subjects were told they were brilliant even though they probably had no earthly idea how they achieved that perfect score.

The researchers then invited the subjects to take another test, but first asked if they wanted to take either a performance-enhancing or performance-inhibiting drug. An astounding 70 percent of the subjects chose to take the performance-inhibiting drug (in truth, all drugs were placebos).

Why would they ever request such a thing? The researchers theorized that after hearing the “results” of the first test, the subjects’ egos were inflated. Their self-images had been dramatically boosted — which in turn meant that the stakes were raised for the next test. When humans are given higher thresholds to clear, they tend to do everything they possibly can to lower expectations.

This is self-handicapping: it’s a form of impression-management by which we make choices that will prevent us from taking full responsibility for the later outcomes. We lower the bar, and we’re even willing to self-sabotage so that the resulting failure doesn’t hurt our self-esteem as badly. We don’t embrace failure. We find excuses for it, and ultimately, we cower to it.

Self-handicapping has been observed in academia, politics, and sports. (It’s also been shown that men are more likely to self-handicap than women.) It explains why we might procrastinate before tackling difficult assignments or projects. It’s why we find excuses to explain away why we haven’t pursued employment at a company we’ve always aspired to work for, or why we haven’t invested more time or energy into that “side-hustle” we’ve had on the back burner for the past five years. It’s why, when we do share news with our family or friends of a job we’re applying for, we tend to emphasize the host of (typically uncontrollable) reasons why we’re a long-shot for it. After all, when you’ve lowered your expectations, the full weight of failure doesn’t fall on you.

But there’s a cost to this short-term ego protection; studies have shown that people who engage in behavioral self-handicapping are more likely to blame their future failures on external causes, spend less time working at difficult tasks, and have a generally lower impression of their abilities. In other words, you might feel better at first — but you’ll feel worse later.

The numbers tell us, unequivocally: failure is all around us. But the problem is The Great Filter that is social media doesn’t expose us to it. And if it does, it’s long after the failure has taken place, when the narrator can comfortably look down on it. And lost in these carefully (re)constructed failure narratives is any real inspiration we could have gleaned from it. Instead, it’s a humble-brag of sorts for the narrator, a way to cleanse the rejections of yesteryear, or fit them into the illusional arc of their life’s story.

Look, truly embracing failure means being vulnerable; it means exposing yourself to the prospects of rejection, to the possibility that you might not be as talented, or creative, or experienced as your peers. And while this vulnerability stings harder in the short-term, in the long-term its benefits are innumerable. A healthy relationship with the prospect of failure translates to more confidence, a more balanced self-assessment of your strengths and weaknesses, and ultimately, an increase in your willingness to challenge yourself in the future.

And the next time you’re ogling someone’s LinkedIn profile or Instagram account, remember the stark truth that’s filtered out: everyone fails. All the time. Success often comes not from improving your failure rate, but simply by increasing the amount of chances you take. And while you may never be so bold or brash to post about your failures, rejections, or insecurities on social media, you can start by being more transparent with your loved ones, friends, and close colleagues. My guess is your vulnerability will be reciprocated — and you may be surprised at what you learn.

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David Giardino

Written by

Writing at the intersection of culture and psychology.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +785K followers.

David Giardino

Written by

Writing at the intersection of culture and psychology.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +785K followers.

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