Don’t Quit Your Day Job: How to Fight Job Envy and Win

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Recently, I became afflicted with what I’m going to call chronic job-envy. While I usually pride myself on having a group of cool, hard-working friends, everything changed when I found myself in a career rut. What used to be fun, pat-ourselves-on-the-back-drinks with girlfriends quickly became depressing charades spent sipping my gin and tonic through gritted teeth, listening to their success stories while calculating how fast I could get home to refresh my LinkedIn page and cry. Fun, right?

Until, one dreary Monday morning, the headline of Baily Hancock’s General Assembly lecture caught my eye. “Don’t Quit Your Day Job: Finding Purpose in Your Career,” it read, popping up on my Facebook right next to my high school boyfriend’s wedding photos. Through rapid clicking I learned that Baily is a manager at OMD, a leading media agency, and that she teaches workshops on finding happiness in your day job — they’re so popular that she’s even writing a book on it. I reached out immediately and she agreed to meet with me.

The first thing Baily did was assure me that I was not alone in my unhappiness. Millennials, she explained, have been kind of conditioned to be dissatisfied, since we’re the first generation to put such a heavy emphasis on finding our one perfect job. “That’s all we’ve been told our entire lives: ‘follow your passion and you’ll never have to work a day in your life.’ And it’s like yeah, because you’re not going to have a job! It’s totally fine to not follow your passion to a career. There’s no such thing as the perfect job.”

Baily acknowledges that the current landscape of the media doesn’t help with career envy. If it wasn’t enough to be jealous of your stupid successful friends all the time, you can’t open up a magazine or an internet browser without being slapped in the face with some star from Forbes “30 Under 30.” Be it Mark Zuckerberg, Evan Spiegel, Elizabeth Holmes or Tavi Gevinson, we are constantly being confronted with images of very young people who seem to have followed their passions and found massive success. (Just a few hours before this story went live, Man Repeller published a Round Table that was spurred by this same trend.)

“The entrepreneur is definitely glamorized as a rock star these days,” says Baily. “But the media doesn’t talk about all of the start ups that fail. There are so many sources out there telling people to start their own business, but there aren’t enough people saying ‘Hey, it’s totally fine to not be your own boss.’”

Because, really, not everyone can. No matter how many brilliant novels or apps we think we’ve got rattling around inside of us, financially, we can’t all quit our day jobs to pursue our dreams the moment we feel unhappy at work. And Baily argues that we don’t need to. Instead, she feels that the best thing you can do when you’re unsatisfied at work is lean into that dissatisfaction and try to figure out specifically what’s causing it.

“Ask yourself: What would make me happy that I haven’t tried yet? What about my job can I turn into something that’s maybe different, based on knowing what makes me tick?”

For example, if you think you want to be your own boss, what you might really be asking for is flexibility in your work schedule — not the entire burden of a burgeoning company, or the financial stress of a freelance lifestyle. Talk to your boss about working remotely a few days a week. If that fails? “Change your set up. Move your desk around, make it more private, redecorate it, get a standing desk,” says Baily.

The road to career satisfaction isn’t always about the big changes, but about “pivoting a little bit to find the pieces that you don’t have,” and asking yourself some big questions. “Find the things about your job that you’re into, that give you that spark. Focus on those, and see how you can increase your participation in those tasks. But also figure out what you’re not super into, what makes you feel stagnant or unmotivated,” Baily said. If in the end, you’re not able to change your work environment to suit your needs, you’ll have zeroed in more closely on exactly what you want to do next.

The most important key to fighting career envy? “Relax,” says Baily. “Remember that you are seeing the highlight reel of other’s lives. You are seeing the best chapter of their whole story. Try to find comfort in learning from your experience, and remember: nothing is forever, good or bad.”

Photographed by Krista Anna Lewis; featuring a Protagonist shirt dress, Arme De L’Amour bracelet, Maryam Nassir Zadeh shoes.


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