Arianna Huffington says even high-flying CEOs are unhappy and feel stuck in their multimillion-dollar jobs: ‘It’s a trap’

Arianna Huffington, founder of the Huffington Post, warns that even high-ranking CEOs can feel unhappy and trapped in their multimillion-dollar jobs. Huffington explained that success can be a trap for very successful people who find it difficult to leave their current positions despite being miserable. She cited CEO friends who stopped loving their jobs but were afraid to leave, citing the financial and identity traps that keep them stuck.

Huffington herself left her role at Huffington Post after 11 years of building it into one of the largest digital media outlets, with over 850 journalists and a Pulitzer Prize win. She founded Thrive Global, a wellness venture, in 2016, driven by her desire to focus on health. Her decision to leave was influenced by her mother's advice not to be afraid of failure, as failure is a stepping stone to success.

Huffington emphasized that a person's role does not define them, and if one follows their heart, they can continue to grow and evolve. She was not the only one to admit that reaching the top can result in a hollow feeling rather than fulfillment. Other leaders, such as Tom Grogan, Brian Chesky, and Vinay Hiremath, have shared similar experiences.

Grogan felt hollow after selling a majority stake in Wingstop, Chesky felt sad after Airbnb's 2020 IPO, and Hiremath described his identity collapse after selling his company to Atlassian.