The dream of early retirement sounds perfect until you actually live it. Just ask Kevin O'Leary.
The "Shark Tank" investor has become an unlikely critic of the FIRE movement—financial independence, retire early—and his skepticism comes from personal experience, not theory. After selling his first company to Mattel for $4.2 billion in 1999, O'Leary had more money than most people could spend in several lifetimes. So at 36, he did what seemed obvious: he stopped working entirely.
"I achieved great liquidity and I thought to myself, 'Hey, I'm 36, I can retire now,'" O'Leary told CNBC back in 2019. "I retired for three years. I was bored out of my mind."
That experience shaped his view on what's become a popular financial strategy. For those unfamiliar, FIRE devotees save aggressively, invest methodically, and live well below their means—all with the goal of leaving traditional employment decades before the standard retirement age. Some quit work completely, while others shift to passion projects or part-time gigs. The movement has its appeal, but O'Leary's three-year experiment revealed something many people miss.
The Hidden Value of Work
"This whole idea of financial independence, retire early doesn't work," O'Leary said bluntly. "Let me tell you why. It happened to me."
The issue wasn't money. O'Leary had plenty of that. The problem was what disappeared when work did. Structure evaporated. Social interaction dried up. And something less tangible but equally important—his sense of identity—started to fade.
"Working is not just about money. People don't understand this very often, until they stop working," he explained. "Work defines who you are."
It's not that O'Leary opposes financial independence. He's spent years advocating for it. What he's pushing back on is the assumption that freedom from work automatically equals fulfillment. Work provides more than a paycheck—it offers daily interaction, social connection, and a reason to get up in the morning.
"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."
The Science Backs Him Up
O'Leary's observations align with recent research on aging and employment. It turns out staying engaged in work might do more for you than your retirement account.
"It even helps you live longer," O'Leary said. "And is very, very good for brain health."
That's not just motivational speaking. A University of Michigan National Poll on Healthy Aging found that more than two-thirds of adults working past age 50 say their job boosts their physical health, mental health, and overall wellbeing. Nearly half cited a sense of purpose and sharper thinking as primary reasons they keep working. Among those still employed past 65, the reported benefits were even more pronounced—workers in this group were more likely to credit their jobs with positive effects on both health and cognitive function.
The research suggests that work, in the right context, supports mental sharpness, emotional resilience, and longevity. Not every job delivers these benefits equally, of course. But the act of staying engaged, solving problems, and maintaining social connections through work appears to matter more than many early retirement enthusiasts anticipate.
Rethinking FIRE
To be fair, not everyone pursuing FIRE wants to disappear entirely. Many see it as a path to control—choosing how, when, and why they work rather than being locked into a job they hate. That's a different proposition than O'Leary's total exit.
But for those imagining retirement as an endless vacation, his message is worth considering. The freedom you gain might come with costs you didn't expect. The structure, purpose, and social fabric that work provides can be hard to replace, even when your bank account says you don't need to show up anymore.
O'Leary's takeaway after his three-year hiatus? He went back to work. And he's stayed there ever since. For him, the lesson was clear: the paychecks were never the point. Work was doing more for him than he realized—until it was gone.