Gerald Levin, the former chief executive of Time Warner who orchestrated the media company’s disastrous $106 billion merger with AOL in 2000, experienced many executives’ worst fear: After more than three decades of climbing the corporate ladder and 10 years as a well-regarded C.E.O., he lost his job and the better part of his professional reputation.

Few now recall that Levin foresaw the profitability of cable and invested heavily in it or that he successfully married Time Inc. with Warner Communications. In fact, about all anyone can remember is that he retired in May 2002 with millions after his company’s stock had plummeted by 70 percent following the AOL merger. As he left, he was dissected in the press and denounced on Wall Street, and he found himself alienated from his former colleagues. It wasn’t so much a fall from grace as it was a jet-propelled nosedive.

Sure, you may tell yourself, “That can’t happen to me.” But deep down, you know that cocksure attitude is just a front. Even the most successful executives worry about losing face, being replaced, or being exposed as having no idea what the hell they are doing—even if they do.

Five years after Levin’s departure, I wondered whether the man once called “the most powerful person in media and communications” had ever anticipated his own career’s demise and what it felt like to lose something even money can’t buy: one’s legacy as a leader.

At 68, Levin now leads a low-profile existence as a director at Moonview Sanctuary, a secluded California facility that treats everything from drug abuse to depression with “neuroscientific technology” and “ancient wisdom,” for prices starting at a mere $175,000 a year. It was founded by Laurie Perlman, a psychologist who would eventually become Levin’s second wife. At Moonview’s offices in Santa Monica, Levin is so unencumbered with the trappings of corporate life that he picks up his own phone and agrees to talk to me when I call.

Pensive and characteristically Zen in his musings, Levin tells me that he never feared failure going into the AOL merger. “I truly believed I was serving my company,” he says. That conviction helped him cope as he became a poster child for fallen executives. “If your view of yourself is based on whether the world is smiling or frowning on you—or the press, the stock price, or whatever your markers are—then you are not going to have a true sense of yourself and everything that is said or written about you cuts to the core.”

Though angst in the senior ranks is to be expected, given that their decisions can affect thousands of employees and investors, expressing insecurity is taboo. No one wants to hear that the boss has the jitters. Concedes Levin, “The C.E.O. is supposed to be Superman.” Translation: Everyone assumes the guy in the skybox is perfect, and that’s a lot to live up to.

From a therapeutic standpoint, Levin is dead on according to Dr. Robert Mintz, a organizational psychologist in Short Hills, New Jersey, who spent 25 years as a top human-resources executive at Revlon, PepsiCo, E.D.S., and Time Warner (under Levin). Mintz not only counsels senior executives who are dealing with insecurities and lofty expectations, but his doctoral dissertation was about why powerful businesspeople unravel. Mintz says men in particular struggle to fit the infallible-hero stereotype, which can lead to substance abuse, overwork, and full-fledged breakdowns. “The average 40- to 55-year-old C-suite candidate knows he has a couple of shots and that the world is so unpredictable that things over which he has no control can blow up,” Mintz adds.

Of course, this kind of anxiety can have its perks. Real estate developer John Hitchcox is only half joking when he says that fear is a “fantastic motivator.” Hitchcox, 46, is chairman of Yoo, a London-based firm he co-founded with renowned French interior designer Philippe Starck. Yoo has upscale residential projects under development in New York, Dubai, Hong Kong, and more than a dozen other cities around the world—about $10 billion worth of moving pieces.

“Fear is basically anticipation of the future,” Hitchcox says. He explains that his anxiety is worst at night, when he feels most out of control. How does he deal? His occasional yoga and meditation sessions with Deepak Chopra help. So does cycling to his meetings; he makes sure a bike is always at his disposal when he’s in New York and London. But ultimately, he says, one has to recognize that fear can be an ally: “It reminds me to always cross my t’s and dot my i’s.”

The notion that fear can be a hedge against risk stands in contrast to Levin’s apparent lack of fear. “I had kind of a perverse personality,” Levin says. “If someone said, ‘You can’t do it,’ or ‘That will not work,’ or ‘No one is onboard,’ I probably was motivated to go even harder.” Levin also told the New Yorker in 2001 that his son’s murder, in 1997, made him “more fearless” when it came to work. But a fearless C.E.O. should scare every shareholder: Fear keeps us alert to things that can go awry.

According to Moonview’s director of marketing, Levin meets with some executive patients to discuss “building their skills as an executive and helping them figure out how to make decisions, even navigate the media.” No doubt Levin can also assure them that it’s possible to survive whatever they most fear. It’s telling that Moonview will open a facility in New York in 2008. Apparently there is no shortage of power players on the verge of a nervous breakdown.

That got me thinking: Moonview—or at the very least, therapy—should be regarded as a legitimate corporate expense for chief-level executives. Fear isn’t the enemy in our offices; those who don’t acknowledge it are the real danger. The prospect that executives may finally get the help they need has Dr. Mintz in a tizzy. “These people are running the economic engines that support the rest of us. They are the stewards of our economy, and if they are falling apart, we are all f-----.”