The good news about failing at absolutely everything in your 20s

Everything is fine.
Everything is fine.
Image: AP Photo/Gerald Herbert
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A couple nights ago, I stumbled across a cache of rejection letters – possibly one of the largest deposits of rejection letters recorded in human history. They were all addressed to me.

I made this discovery, not coincidentally, while binge-watching Insecure, an HBO show all about a 20-something woman who’s questioning her life choices. I felt guilty about the binging, so I picked up my laptop and began cleaning out an old inbox that I’d used between roughly the ages 22 and 30. That’s when I hit the motherlode. Mixed in with the bills and emails from my dad were dozens of rejections – from jobs, graduate schools, literary agents, writing contests, and magazine and website editors.

I couldn’t believe I’d forgotten about them. I’d been disappointed, sometimes crushed, the first time I’d read them. Now I was smiling. From the vantage point of my 30s, what I saw was not a bunch of rejections – it was a bunch of dodged bullets.

Take the rejection letters from doctoral programs. When I was 26, I’d already racked up $22,000 in debt getting a master’s degree in creative writing. My plan was to spend even more money I didn’t have on a doctorate—except my inquiries and applications didn’t go anywhere. Now I can see that, if I’d been accepted by one of these programs, I almost surely would have come out of school even more unemployable, not to mention in hock to Sallie Mae.

Then there were the rejections from adjunct-teaching jobs. Because I only had a master’s degree, I couldn’t convince anyone to let me teach English 101 for subsistence wages and no benefits. The one offer I did get – at a liberal-arts college 40 miles away, which paid its adjuncts a few thousand dollars per class while charging students nearly $50,000 in tuition – was rescinded when an existing staffer requested more hours. My applications to jobs in publishing and journalism also led nowhere.

In the end, I was forced to take a job in advertising, which came with plush health insurance (including some handy free therapy) and a decent salary. But it was not what I’d hoped for. My disappointment was extreme. At least initially.

Commencement speakers are keen to tell you that you should “follow your passion” and “embrace failure.” In the interest of expedience, let’s leave aside the grating fact that so many of these commencement speakers are boomers who did not come of age in a dire economic recession; they’re like generals still fighting the last war. The problem is that “embracing failure” presents a false choice. Failure is going to happen whether we embrace it or not. What we need are ways to think about it that aren’t facile.

So here are a few things that failing in my 20s taught me. They just might be useful to you if you’re one of the millions of millennials uncertain about what the hell you’re doing in life. Don’t worry – I promise this won’t devolve into inspirational quotes.

Your 20s are a good time to “fail early, fail often.” In The Defining Decade: Why Your 20s Matter, Meg Jay writes, “The twentysomething years are real time and ought to be treated that way.” So how can you treat them as real? You try stuff. Take advantage of the relatively low stakes. Chances are that mortgages and kids aren’t a part of your problem set just yet (or if they are, you still have a lot of energy). This leaves you free to try on different lives, the way you’d try on outfits. Sure, the uncertainty will drive you half-crazy. But as research and a wealth of anecdotal data suggest, we tend to regret the things we didn’t do more than the things we did. The basic formula is: Trying and failing is > not trying.

Failure is a useful data point. Think of yourself as a probe that’s just landed on an alien planet called Adulthood. The territory is strange, but you must start driving anyway. Put your sensors out. See what you come across. Rejections and failures are sources of information. How else will you know what’s possible and what isn’t? (My version of an inspirational quote: You’ll never know till you fail!)

Sometimes what you’re encountering is not failure but a “gravity problem.” Dave Evans, who teaches “design thinking” at Stanford, suggests we make a distinction between fixable issues and immutable circumstances, which he calls “gravity problems.” One example of a gravity problem is how difficult it is to make a living as an artist. Once you accept the basic truth of the situation, you’re in better position to adjust to the constraints. Maybe your art becomes a side hustle, or maybe you move to a much cheaper place that allows you to live on very little money. What you don’t do is feel like a failure when you have a hard time making money with creative pursuits.

The straight path is often an optical illusion. When you read about any successful startup, what you inevitably discover is how many failures the company experienced along the way. The same holds true for talking to successful artists. From the outside, it can look as though a company or a person has achieved overnight success, and this is especially true when big achievements come at an early age. Still, overnight success is largely a myth. It’s worth remembering that you probably don’t know the gory details of the story. Trust me: that Instagrammer with the seemingly perfect life has also spent her fair share of nights crying and staring at the ceiling, worried out of her mind about money and love. It’s just part of the human condition.

Rationalization can be a beautiful thing. In Stumbling on Happiness – which The New York Times praised as a “paean to delusion” – Daniel Gilbert notes that humans aren’t great at predicting what will actually make them happy. At the same time, we are pretty good at rationalizing what does happen. In other words, rationalization is an important, underrated coping skill.

Some fantastic art has been made about failure, too. Is it any wonder that the best TV made by millennials, including Insecure and Girls, is all about one’s 20s playing out as a confused, chaotic mess? Many artists have made great work out of their misspent youths. Just a few examples include Meghan Daum (see her essay: “My Misspent Youth”) and nearly every poem Philip Larkin ever wrote. Your mistakes can give you something to say to the world. And nothing breaks the ice like admitting your life hasn’t worked out quite according to plan.

I tried putting this last point into action by polling my Facebook friends with the question: “What’s something you’re glad you failed at in your 20s?” If you ever want your notifications and inbox to blow up, you should ask this, too. One friend listed a whole series of fortuitous failures: “Getting fired from my first job, homeownership, and not getting a couple of jobs that I REALLY wanted.”

Another friend shared a story about how she’d failed to get an ROTC scholarship – shortly before September 11, 2001. “I’m not at all looking negatively at those who do serve,” she said. “But I know it wasn’t for me, and it might have been a literal bullet that I dodged. I probably wouldn’t have joined Peace Corps or traveled as much, wouldn’t have my dog (from Peace Corps), or half my friends, or be myself,” she explained.

The most common answer I heard, by far, was “my first marriage.” This may seem like blatant bright-siding. But if we can eventually be happy about a marriage ending, it seems there’s no limit on what kind of failures can make us happy—or at least, happier.