Breaking Up With The Dream Job

Like buying a tiny Khaite clutch and ghosting a finance bro, crying on the street is a rite of passage for every ambitious city girl.

So when Jazzi McGilbert found herself choking on her tears just outside the Miu Miu boutique in SoHo, she wasn’t too worried — at least at first.

“It’s the beauty of New York,” says McGilbert, then a fashion editor and stylist. “No one really acknowledges you crying on the street. Chances are, they have also cried, especially if they work in fashion or media. Really, any of the ‘dream jobs’ from movies that eventually turn into something much more complicated.”

McGilbert represents one of the 35% of women in their 30s who have reckoned with their “dream jobs” and realized they wanted to wake up. (That number comes from a McKinsey study — but group chats and vent sessions at wine bars worldwide suggest the number is way higher.) How are these women making life work without working in the jobs they always wanted? And can you ever really give up the girl you wanted to be?

Social media is jammed with women trying to figure out these answers in real time.

Look at the designer Batsheva Hay, who worked for a decade as a high-powered corporate lawyer before finally realizing her dress designs were worth creating. Today, she counts Christina Ricci, Celine Dion, and Sarah Jessica Parker as clients. Then there’s Jenny Jackson, whose years as a book agent made her reckon with the fact that she’d always truly wanted to be an author. Using the knowledge she’d learned coaching first-time authors, she created her debut book, The House on Pineapple Street, in 2024; it became a steady best-seller. Ava DuVernay famously taught herself how to direct in her 30s while doing PR for the Spy Kids franchise.

As for McGilbert, she answered that question in her own way — but it took a minute for her reframe to come into focus with the same sharp beauty as the girls in her fashion shoots.

A talented image-maker with an endearing smile and a knack for making everyone feel welcome on-set, McGilbert steadily climbed the media ranks from eager intern to capable assistant, in-the-know stylist, and finally, to editor at a few of her dream publications. She sat front row at shows next to idols whose pictures hung on her teenage bedroom walls, picked out denim for pop stars, and glided through the iron gates of celebrity clubhouses like The Box and Boom Boom Room because she was dating the DJ.

But access to this “dream life” wasn’t free — even if the endless PR freebies spilling out of her gifted Marc Jacobs bag were. She left her long-term boyfriend and a tight-knit crew of best friends back in LA, quietly dealt with a medical scare on nights and weekends, and eventually felt like despite her many wins, there was an unspoken misalignment in her current life and her destiny.

“The fashion industry wasn’t ever going to love me back, for a variety of reasons,” says McGilbert. “So I got to the point where I could keep forcing my way in and feeling out of place, or I could go back home and be with friends and family who loved me…not some version of success sold to me… I really felt that cost adding up.”

Then McGilbert’s mother was diagnosed with breast cancer. She packed up the Chloé boots and Marni dresses in her Brooklyn apartment, flew home, and slept on her mom’s couch. “It’s insane feeling like a success and failure at the same time,” she sighs. “For a little while, I did not know who I was outside of fashion.”

The Reckoning

Jazzi’s experience was singular. But it was also an example of “broken ladder syndrome,” a phenomenon coined by Harvard Business School researchers that highlights the extraordinary number of women in their 30s and 40s who devote decades to reaching the top of their industry — then begin to worry their “success” is leading to a shaky, scary future instead of a great new height.

Sarah Lewitinn remembers a similar reckoning, but hers happened at the historic Wiltern theater in Los Angeles.

“I was seeing a band I really loved,” says the former rock journalist turned record label executive, who was given her own imprint by Universal Music at just 25 years old. “And I looked up at them and realized, I couldn’t even hear the music. I was so checked out.” The next day, Lewitinn stopped accepting the free backstage passes and VIP wristbands that arrived on her desk with the speed and frequency of a daily lunch order at Sweetgreen.

“I actually heard myself saying, ‘I hate going to live music,’” says Lewitinn, who was once so devoted to hyping new bands that she turned her small apartment into a secret concert venue that was shut down by neighborhood police. “That’s when I realized something was very wrong.”

For the first time in her life, Lewitinn preferred driving in silence down the Los Angeles freeway instead of cranking music from her thousands of Spotify playlists. She began to think of discovering new bands as “exhausting and boring” even though it had once electrified her soul with the force of a Hendrix riff. “I thought, ‘Is this depression?’” Lewitinn says. “I mean, I was just so bummed out. It was like a part of my being [was] turned off.”

Like McGilbert, Lewitinn was reckoning with the death of a parent — in this case, her father Marc, an Egyptian immigrant who settled in New Jersey before succumbing to COVID in 2022. But she also cites the changing nature of the music business itself as part of her malaise.

“The reality is that everything is so corporate now, and authentic discovery is harder. Community is harder. And I’d worked so hard, poured everything into this, and then, you know, robots are deciding what people should listen to.” Lewitinn also cites the rising difficulty artists face in getting paid, even when their song clips rack up zillions of TikTok plays. “It’s disheartening,” Lewitinn says, “when you believe in people as artists, and they can’t get basic support to make their work, even though everyone wants their work.”

The loss of faith in the industry that had essentially raised her was a giant psychic blow to Lewitinn, who felt “so, so tired” that she found herself hiding out at home instead of rocking up to dance floors and secret shows. “I could not have run fast enough from my former industry,” she said. “But then it’s like, ‘what now?’”

The Pivot

What now is a question that slams against all ambitious women, whether we’re facing burnout in a once-cool career, navigating a layoff in the middle of today’s economic chaos, or frantically trying to upskill during tech panic.

Sometimes the answer is as simple as finding a better job in the same field. When my friend Melissa (her middle name) left her post at the top of a major lifestyle brand, she did so in part because her boss was actually kind of a monster who enjoyed, among other things, locking her senior staff in their office’s stairwell, then asking why they weren’t “fit” enough to climb the 10 stories up to the building’s next open entrance.

Melissa did the usual stuff — network tapping, job board perusing, jumping on an email chain when someone announced their departure — and landed a new gig at a beauty brand within six months of her last emergency exit exile. “I feel like I got very lucky,” she told me about her swift-ish landing. “But I also took a small salary hit. Although I’m saving a lot of money because I don’t need therapy every five seconds.”

As for Sarah Lewitinn, she realized that her grand plan echoed what the author Jenny Blake said in her 2016 book, Pivot: “What you can plan is too small for you to live.”

Last year, Lewitinn turned down a pair of tickets to a Hollywood Bowl concert and ended up on her couch in West Hollywood. She didn’t know that her husband, the chef Daniel Patterson, had invited friends over to plot a new restaurant concept — one that Lewitinn herself would end up helping to pioneer.

“We were all talking about how fine dining could be a little intimidating, a little more austere,” Lewitinn says. “It’s closer to a museum than a lively, super comfortable time. I cannot handle that. I’m not a fan. I don’t want my food to be a museum.”

Lewitinn suggested making a new restaurant that felt more like the back room of a cool club — the kind of places where she used to DJ in New York’s Lower East Side — where diners would “feel like both VIPs and old friends” and where food inspired chats and connections among diners. “I was like, ‘Why can’t there be a fine dining restaurant where you talk to the people around you? Like, please. Sit back. This is a party.’”

The resulting restaurant, Jacaranda, opened in May of this year and combines Lewitinn’s friend-happy vibes with Patterson’s acclaimed food. This month, the New York Times named it as one of the 50 best restaurants in America, but to Lewitinn, it’s just the new place where she cranks music on Thursday nights. “I’m playing the new Interpol album and stuff from my Gen X youth,” she says. “I finally feel like I love what I do again. I could not be happier to have reset my life.”

McGilbert had a similar awakening.

Chasing a spark of inspiration back in Los Angeles in 2018, she found an empty storefront near West Adams, a historically Black neighborhood in her hometown. Long inspired as a fashion editor by cool concept stores like Opening Ceremony and Colette, she realized it could be a creative space for Black culture and storytelling — one that also welcomed IRL visitors into a curated space.

With a little money from her late mother’s life insurance, she could pay the security deposit on what is now Rep Club, a thriving bookstore and cultural clubhouse with fans like Tessa Thompson, Issa Rae, and Tyler, the Creator — along with neighborhood children and longtime South LA locals… and the occasional movie studio scout.

“It felt good to get back to my childhood love of reading, and to have a mission that reflected my fuller self,” says McGilbert of the store. It also served as a reminder that the LA native was more than just capable of achieving her dreams in a singular industry — she could build a new world in the process.

But trendsetting didn’t quite leave McGilbert: In 2023, she created a branded, fluorescent yellow tote bag for the store that is currently a street style staple frequently spotted in Paris, Tokyo, and New York.

“I’m always shocked when people text me pictures of Rep Club totes in the wild,” McGilbert says. “I can’t believe something so personal has traveled so far.”

And what about the joke-not-joke that, like the mafia, you can’t ever leave fashion?

“I still bring a certain style to the work,” says McGilbert — not to mention those status totes. “So I guess, maybe, it’s true.”