90 Minutes With Megan Hellerer

An advice session with Alexandria Ocasio-Cortez’s career coach.

Megan Hellerer, a post–Lean In career coach for women. Photo: Tracy Dungo
Megan Hellerer, a post–Lean In career coach for women. Photo: Tracy Dungo

There is likely no career coach in the world with a better pitch for disaffected millennials than Megan Hellerer, whose list of past clients includes a 28-year-old bartender who became a United States congresswoman. Before we met for a session on a recent Wednesday morning, I couldn’t help but imagine all the potential Hellerer would unlock in me at 29: Would I also become a politician? Write a book? Finally stop biting my nails? Hellerer, 35, calls herself the Conscious Career Coach. She works only with women, more specifically “underfulfilled overachievers”: high-performing teacher’s-pet types who have followed every mandate for success and remain desperately unhappy. In addition to private coaching and workshops, she has an eight-week online course called “WTF Am I Doing With My Life?” (The price is $900, but women of color can get a 15 percent discount via a coupon code on her website in acknowledgment of statistical income gaps.) “We’re trying to get away from the ten-year plan,” Hellerer says of her strategy of “anti-career career coaching,” a kind of post–Lean In style informed by her own decision to leave Google after eight years in 2014.

Hellerer was raised on the Upper West Side, went to Chapin, then Stanford, and was ostensibly doing exactly what should come next: making a ton of money, with great benefits and stock options, as something called a strategic-partnerships executive. But she was also having anxiety attacks and throwing up in the bathroom at work. “It felt like I was going to die if I left,” she says of her time at Google. She eventually quit, taking six months off in an effort to find her purpose in life. She tried meditation, cooking, and, on a whim, a coaching class. She started her own practice in February 2015, and a Boston University grad and hospitality worker named Alexandria Ocasio-Cortez took one of her workshops through Ladies Get Paid, a professional-development organization for women, the next year.

Sitting across from me in a booth at Le Pain Quotidien on Bleecker Street, Hellerer starts with a “Mind Mood Body” check-in, or the MMB. (She likes acronyms: FOBM, for “fear of being mean”; LMGTFY, for “Let me Google that for you.”) I pick three adjectives to describe how I’m feeling in my mind, mood, and body, then she asks, “If you had a magic wand, and you walked out of here and into a totally different world, how would you know? What would be different?” Hellerer is all about clearing outside voices and listening to your “authentic self,” what she calls your “inner GPS.”

“Most of us have been taught to ignore that,” she says, and to favor our “saboteur” or “fear self.” The fear self manifests in several ways: “There are the toos,” Hellerer tells me. “ ‘I’m too old,’ ‘I’m too young.’ ” There are the enoughs: “ ‘I won’t make enough money.’ ” And the shoulds: “Mine was ‘No one should go to Stanford and become a career coach.’ ” While talking, she sketches out a diagram of my authentic self, my fear self, and my social self in her white Moleskine notebook. I tell her that my mom thinks everyone should to go to business school, and she writes “Mom” under my “fear self” box. We make a “fear flowchart” connecting my self-doubt (“I will never have original ideas”) to its worst-case-scenario outcome (“I will die broke, miserable, unfulfilled, and alone”).

“Do you know about Saturn returns?” she asks me. She explains that it occurs when Saturn, “the planet that governs structure,” returns to the point in the sky at which it was during a person’s birth, typically between the ages of 27 and 30. I’m usually a skeptic of astrology, but I find immediate relief in this concept. “There’s a whole generation of elder millennials hitting this point,” Hellerer says of the quarter-life crisis. And our unique circumstances — graduating into the global recession, with the looming possibility of another — make it worse. “But there’s so much potential in that uncertainty. I call it the gift of desperation.”

Hellerer won’t disclose many specifics about her coaching sessions with Ocasio-Cortez. But she did say that, after her first workshop, she and AOC worked one-on-one, as the Bronx native had her own Saturn-returns freak-out. Hellerer counseled her in the virtues of “directional versus destinational thinking,” which she explains with corny but helpful metaphors: On a road trip, instead of picking a place to end up, pick merely east or west. Instead of hitting goals, think of “warmer or colder” steps. Warmer, for Ocasio-Cortez, was going to community-board meetings. Then it was volunteering for the 2016 Bernie Sanders campaign and taking time off work to go to Flint, Michigan, and then Standing Rock Indian Reservation, and after that getting the call from the PAC Brand New Congress, which would ask her to run for the NY-14 congressional seat. “Even when she decided to run for Congress, she wasn’t like, ‘I’m going to win!’ ” Hellerer says. “And that’s where the courage comes in. If she was like, ‘I’m only taking a next step if I’m positive that this is going to be my career for the rest of my life’ — you don’t run for Congress in those circumstances, against [Joe] Crowley and all that.” On the occasion of Ocasio-Cortez’s April 2019 Time cover, Hellerer asked if the congresswoman would submit a testimonial she could post on Instagram. “Your guidance, help, and support was pivotal, in a time when I felt very lost. You helped me reframe a lot of my thinking and were part of a series of events that culminated in the big adventure of a Congressional run … and win!” it reads. As a result of Hellerer’s coaching, Ocasio-Cortez continues, “I opened a door I didn’t even know existed.”

Hellerer hasn’t rebranded as the “Socialist Career Coach.” Her client roster remains filled with PR executives and founding CEOS as well as journalists and artists. “I’m not anti-capitalism,” she says, “but I do think the system is broken.” Her methods speak to a millennial crisis of confidence not just in themselves but in the institutions that gave their parents security. Millennials’ “human operating system,” as Hellerer puts it, “isn’t built for the 21st century and the life we’re living today. You should be able to say to your bosses, ‘I don’t work best with 900 Slack messages.’ ” She gestures at my phone. (When, earlier, it lit up with notifications, Hellerer had exclaimed, “Oh my God. That’s a huge HAYWALT: a ‘How are you walking around like that?’ ”)

The irony of my needing to be directed by someone to stop following other people’s directions doesn’t escape me. But I’m still learning, like so many women my age, how to think for myself about work and happiness in an era in which the two seem increasingly at odds. After years of Girlboss feminism encouraging young women to “rise and grind” our way to personal fulfillment, Hellerer’s approach feels fresh, at least in its simplicity. I did not delete Slack, but I left my session feeling less resigned to letting it control my life. “Millennials are told we’re entitled for thinking about what would make us feel fulfilled,” Hellerer says. “AOC thought it would be selfish to stop working, to follow her curiosity. In reality, what is selfish is not taking responsibility for your own happiness. And that is a political act.”

*This article appears in the October 28, 2019, issue of New York Magazine. Subscribe Now!

An Advice Session With AOC’s Career Coach