It’s every worker’s dream: You work hard and climb the ladder until eventually you’re rewarded with an executive title and cushy salary to go with it. But according to Huffington Post founder Arianna Huffington, the reality isn’t quite as glamorous as it looks—and plenty of CEOs, she says, are desperate to quit, despite seemingly having it all.
“Success can be a trap,” Huffington told Fortune, adding that once you’ve dedicated years of your life to honing your craft and gaining recognition, it can feel impossible to leave it all behind and start something new. Even if you’re miserable where you’re at.
“It’s a trap because a lot of very successful people have a hard time leaving,” she explained. “I have CEO friends who’ve stopped loving their jobs, but they’re afraid to leave.”
And it’s not just the huge mortgages, private school fees and luxury first-class vacations they’ve become accustomed to bankrolling with their multi-million dollar pay packages keeping them stuck.
“The financial trap is much easier to see, while the identity trap is less tangible but no less real,” Huffington added. “They’re so identified with the CEO role, or the anchor of an evening show, or whatever big job comes with a lot of recognition—it’s become their identity.”
Huffington could have stayed at the top of Huffington Post. She walked away instead.
Huffington spent a grueling 11 years building Huffington Post into one of the biggest names in digital media, growing its newsroom to more than 850 journalists and becoming the first digital-native outlet to win a Pulitzer Prize. She graced the covers of magazines, made Time’s list of most influential people and was a regular at the likes of Davos.
By any measure, she’d made it. Walking away from that to start over would have made no sense to many people—and yet that’s exactly what she did in 2016 to found her new wellness venture, Thrive Global.
“There are no guarantees anytime you start a new company,” the 76-year-old multimillionaire said. “But I was ready to throw myself into health, and if I hadn’t done it, I would have kind of betrayed myself.”
At the time, when she was weighing up whether to hold onto what she had built or walk away, Huffington said that her mother’s voice was in her head.
“She brought me up not to be afraid of failing,” she said, adding that women in particular are hit harder by perfectionism and therefore more likely to remain stuck and not take that leap of faith in case it doesn’t work out. “My mother used to say failure is not the opposite of success, it’s a stepping stone to success.”
It’s why, for Huffington, how a role makes you feel matters more than what it looks like from the outside.
“I’ve always believed that there is no job that defines us, no success that defines us,” she added. “If we are able to follow our heart, it means we can keep growing and evolving.”
From Airbnb’s CEO to Wingstop’s cofounder: These leaders say success felt hollow
Huffington’s far from the first person to admit that reaching the top can leave you feeling empty rather than fulfilled. After cofounding Wingstop UK and selling a majority stake for £400 million (around $540 million), Tom Grogan should have been ecstatic. Instead, he felt hollow.
“For seven years, your whole mind is occupied on making a success of this business,” Grogan told Fortune. “It’s all you think about. And then when you get there, it’s just a bit surreal. It’s like, Okay, it’s done now. Now what? And money doesn’t necessarily fill that void either.”
Growing up, Brian Chesky, the cofounder and CEO of Airbnb, said he “desperately wanted to be successful” because he thought it would bring him adoration. Plus, having social worker parents who were by no standards rich, he also thought a large sum of money could “solve every problem.” But actually, he said the company’s blockbuster 2020 IPO—despite making him a billionaire—was “one of the saddest periods” of his life.
Loom cofounder Vinay Hiremath hit a similar wall after selling his company to Atlassian for $975 million. In a blog post candidly titled “I am rich and have no idea what to do with my life,” he described the identity collapse that followed the company’s rapid rise and eventual sale. “I lost myself,” he wrote, adding that the windfall left him with “infinite freedom” but no idea what to do with it.
It’s why, despite having no current plans to step down, TIAA’s CEO Thasunda Duckett is already thinking about who she is outside of her job.
“I rent my title. I own my character,” Duckett recently told Fortune, noting that a job title is never permanent—and therefore shouldn’t be mistaken for who you actually are. “I own my intellectual curiosity. I own my grit. I own my perseverance. I own my compass.”
