Retiring early sounds great—until you try it.
That's the message from "Shark Tank" star and investor Kevin O'Leary, who says the popular FIRE movement—short for financial independence, retire early—might not deliver the long-term happiness it promises.
"This whole idea of financial independence, retire early doesn't work," O'Leary told CNBC in 2019. "Let me tell you why. It happened to me."
O'Leary isn't theorizing. After selling his first company to Mattel for $4.2 billion in 1999, he says he had the money to walk away for good. And he tried. At 36, he quit working completely.
"I achieved great liquidity and I thought to myself, ‘Hey, I'm 36, I can retire now,'" he said. "I retired for three years. I was bored out of my mind."
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For those unfamiliar with FIRE, the movement centers on aggressively saving, investing, and living well below your means—usually with the goal of ditching full-time work decades ahead of the traditional retirement age. Some participants exit the workforce entirely, while others pivot to passion projects, flexible gigs, or self-directed businesses. But O'Leary's experience points to a blind spot that can emerge when work vanishes.
"Working is not just about money. People don't understand this very often, until they stop working," he said. "Work defines who you are."
It's a message that cuts across age, income, and career paths. O'Leary isn't against financial independence—in fact, he's advocated for it for years. What he's pushing back on is the idea that freedom from work equals happiness.
"It provides a place where you're social with people," he said. "It gives you interaction with people all day long in an interesting way."
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The lesson didn't come to him until he stepped away. Once the thrill wore off, he said the days lost their structure—and so did his sense of identity. For people fantasizing about the end of work, he suggests thinking less about escape and more about purpose.
"It even helps you live longer," O'Leary said. "And is very, very good for brain health."
That last part may sound like a stretch, but research in recent years has pointed to the same thing: work, in the right form, can support mental sharpness, emotional resilience, and overall longevity—not just wealth.
A University of Michigan National Poll on Healthy Aging found more than two‑thirds of adults working past age 50 say work boosts their physical health, mental health and overall wellbeing, with nearly half citing a sense of purpose and sharper thinking as key reasons they continue working. Those still employed past 65 were even more likely to report positive health and brain benefits from staying active in the workforce.
Of course, not all FIRE participants aim to quit everything. Many use the strategy as a way to gain freedom over how, when, and why they work. But for those expecting retirement to be one long vacation, O'Leary's advice is simple: think twice. Work might be doing more for you than you realize.
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