NewsMacroArianna Huffington: Even Highly Successful CEOs Feel Trapped in Their Multimillion-Dollar Roles

Arianna Huffington: Even Highly Successful CEOs Feel Trapped in Their Multimillion-Dollar Roles

Author: Fortune Crypto·

Key Takeaways

  • Arianna Huffington left the Huffington Post in 2016 after building it into a Pulitzer Prize-winning outlet with over 850 journalists to launch Thrive Global, a wellness-focused company.
  • Harvard lecturer Tal Ben-Shahar coined the term "arrival fallacy" to describe the disappointment that can follow achieving a long-sought professional goal.
  • Airbnb cofounder and CEO Brian Chesky described the period around the company's 2020 IPO, which made him a billionaire, as one of the saddest times in his life.
  • Loom cofounder Vinay Hiremath wrote about experiencing an identity collapse after selling his company to Atlassian for $975 million.
  • TIAA CEO Thasunda Duckett emphasized that a job title is temporary and should not be confused with one's true identity.
Arianna Huffington: Even Highly Successful CEOs Feel Trapped in Their Multimillion-Dollar Roles

For many professionals, the ultimate goal is clear: work hard, climb the corporate ladder, and eventually reap the rewards of an executive title and a lucrative salary. But according to Huffington Post founder Arianna Huffington, the reality at the top is far less glamorous than it appears—and many CEOs are eager to walk away, despite seeming to have it all.

"Success can be a trap," Huffington told Fortune. Once someone has invested years into mastering their craft and earning recognition, walking away to start over can feel impossible—even when they are deeply unhappy.

"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."

The forces keeping them in place go beyond the obvious financial obligations—hefty mortgages, private school tuition, and the luxury lifestyles sustained by multimillion-dollar compensation packages.

"The financial trap is much easier to see, while the identity trap is less tangible but no less real," Huffington said. "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."

This sense of feeling stuck at the summit is a phenomenon psychologists have studied for years. Harvard lecturer Tal Ben-Shahar coined the term "arrival fallacy" to describe the disappointment that can follow achieving a long-sought goal—the realization that reaching the destination doesn't resolve the internal questions that drove the pursuit.

Walking Away from the Top

Huffington herself faced this exact crossroads. Over 11 demanding years, she built Huffington Post into one of the largest names in digital media, expanding its newsroom to more than 850 journalists and making history as the first digital-native outlet to win a Pulitzer Prize. She appeared on magazine covers, earned a spot on Time's list of most influential people, and became a fixture at gatherings like Davos.

By every conventional measure, she had reached the pinnacle. Yet in 2016, she left it all behind to launch Thrive Global, a wellness-focused venture aimed at addressing the very burnout and stress she observed among high achievers—a market that has only grown as corporate America increasingly grapples with employee wellbeing.

"There are no guarantees anytime you start a new company," said Huffington, now 76 and a multimillionaire. "But I was ready to throw myself into health, and if I hadn't done it, I would have kind of betrayed myself."

When she was weighing whether to hold on to what she had built or start over, Huffington recalled her mother's influence.

"She brought me up not to be afraid of failing," Huffington said. She noted that women in particular tend to be hit harder by perfectionism, making them more likely to stay stuck rather than take a leap of faith. "My mother used to say failure is not the opposite of success, it's a stepping stone to success."

For Huffington, how a role makes a person feel ultimately matters more than how it looks from the outside.

"I've always believed that there is no job that defines us, no success that defines us," she said. "If we are able to follow our heart, it means we can keep growing and evolving."

Other Leaders Who Found Success Hollow

Huffington is far from alone in describing the emptiness that can accompany reaching the summit—a pattern that aligns with what researchers describe as the arrival fallacy. After cofounding Wingstop UK and selling a majority stake for £400 million (approximately $540 million), Tom Grogan expected to feel triumphant. 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."

Brian Chesky, cofounder and CEO of Airbnb, described a similar experience. Growing up with social worker parents who were not wealthy, he said he "desperately wanted to be successful," believing it would bring him admiration and that money could "solve every problem." Yet he called the period surrounding Airbnb's blockbuster 2020 IPO—despite making him a billionaire—"one of the saddest periods" of his life.

Loom cofounder Vinay Hiremath encountered a comparable reckoning after selling his company to Atlassian for $975 million. In a candid blog post titled "I am rich and have no idea what to do with my life," he wrote about the identity collapse that followed the company's rapid rise and eventual sale.

"I lost myself," Hirehouse wrote. The windfall, he said, left him with "infinite freedom" but no sense of direction.

TIAA CEO Thasunda Duckett, who has no current plans to step down, is already thinking about who she is beyond her job title.

"I rent my title. I own my character," Duckett recently told Fortune, emphasizing that a job title is never permanent and should not be mistaken for one's true identity. "I own my intellectual curiosity. I own my grit. I own my perseverance. I own my compass."

This story was originally featured on Fortune.com.