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Following Your Dreams Is Probably What’s Making You Miserable

That record contract is never coming, bro

On a cold December night, after a long day of writing and slow night of bombing as a stand-up comic, I defeatedly scrolled through friends’ Instagram Stories in my studio apartment, eating crackers in bed. Right before dozing off, I saw an image that made it impossible to get to sleep — even more impossible than being surrounded by crumbs. The illustration from the handle @saddrawingsbyjace depicted an aged and scruffy smiley face in a sloppy tuxedo, magician’s wand and top hat with the text: “The pursuit of my dreams has ruined my life!”

In that moment, I felt very seen. 

As it turns out, Jace Avery, the L.A.-based artist behind the work, is a former comedian-turned-illustrator who spent a majority of his 20s pursuing stand-up, but ended up feeling let down and set back by his big ambitions. “Now I’m 31, and yeah I have a following, but I don’t make any money from my art,” Avery tells me. “I have the bandaged semblance of a professional career. I feel like a total loser at 31 compared to all my college friends who are VPs of companies and have nice houses and cars. And so I made that drawing — because my dreams ruined my life.”

As bleak as both of us sounded discussing his illustration, it’s fair to assume we’re not alone. With the decline of marriage, home ownership and parenthood, our generation has been, at least in part, defined by the feeling of being perpetually behind in life. And the only hope we have for catching up hangs on us doing something truly extraordinary, which ideally also needs to be something we also fully believe in and that satisfies us creatively. Sure, creatives tend to experience higher rates of depression, but maybe there’s also something to be said about how our own unrealistic expectations — our big, lofty dreams — can ultimately bring us down.  

Executive coach Sharon Podobnik Peterson certainly thinks so. The Harvard-educated founder of The Center for Conscious Leadership is working on a forthcoming book, It’s Not (All) Your Fault: Self-Help and the Individualization of Oppression, on this very topic. With so many unattainable expectations occurring simultaneously, the practical workaround for most people is to “do it all at once — be creative, be really good at it and make money from it,” Peterson says. But like many end-around routes, this proves to be only a long, hard road, paved with burnout and an oft-inescapable sense of failure. 

“It ties self-worth to net worth, which is super problematic,” Peterson points out, referring to this toxic cycle as a “hedonistic treadmill” that leads to “individuals who don’t know how to relax, and who have a hard time feeling like a good person when they’re not being productive.”

Although this sounds like a uniquely American problem, in his recent book, Four Thousand Weeks: Time Management for Mortals, British journalist Oliver Burkeman argues that such a drive toward exceptionalism is a universal human impulse, likely inspired by an evolutionary need to think we’re important enough to keep reproducing. The thing is, “it tends to give rise to a kind of paralyzing grandiosity. It starts to feel as though it’s your duty to find something truly consequential to do with your time,” writes Burkeman in a chapter aptly entitled, “Cosmic Insignificance Therapy.” 

In many ways, Burkeman’s work captures the nihilism of Avery’s sad illustration, but reframes it as a time-management tool by chronicling what he describes as our “absurdly, insultingly brief” life span — a mere 4,000 weeks if you live to your 80s. According to Burkeman, with the support of modern-day philosophers like Iddo Landau, most of us assume that the aforementioned push for exceptionalism will make our dreams more meaningful, but “what actually happens is that this overvaluing of your existence gives rise to an unrealistic definition of what it would mean to use your finite time well. It sets the bar much too high.” 

The better way is to find relief in your own insignificance. “Once you’re no longer burdened by such an unrealistic definition of a life well-spent, you’re free to consider the possibility that a far wider variety of things might qualify as meaningful ways to use your finite time,” Burkeman writes.

After quitting stand-up, Avery admits he’s much happier putting his time into drawing instead of performing on stage. And since making that change two years ago, he’s gained over 35,000 followers on Instagram and maintains a job in sales, which has reduced some of his financial anxieties. He’d love to pursue his art full-time, but he doesn’t want to get into the same miserable situation he was in with his flailing comedy career. As for his more successful friends climbing the corporate ladder? He suspects they’re not that much happier for leaving their dreams behind either. “I don’t know if anyone’s necessarily happy to be honest with you,” he tells me. “I’m sure some people are, but I’m not friends with them.”

Maybe, though, like most things, it’s really about balance. That is, we don’t have to choose between fully following our dreams and abandoning them entirely. Instead, we can just hang out with them for however long we want, and until we start to feel them pulling us down or adding too much stress. 

Maybe that’s what Avery’s magician should be trying to pull from his hat.