Image: Senior man © Paul Hudson,fStop,Getty Images

If you watch television at all, you've seen him. He's fit, at least 50 and improbably good-looking. He wants to chuck it all and teach inner-city kids the meaning of life, or race his Shelby Cobra at the Sears Point Raceway in California, or . . .

There are variations on the theme, but all lead to the same life destination: early retirement.

The thought of quitting work while still vigorous in mind and body is much more than a carrot dangled enticingly by Madison Avenue. For many Americans, it's the modern equivalent of the Holy Grail; when time becomes precious, it seems, how it is spent becomes urgent.

The fellow in the TV commercial succeeds, we are told, because he picked his investment adviser wisely. That's certainly part of the equation, but it's not the whole story.

Rat-race escapees need to plan

Anyone contemplating an early exit from the rat race faces as many risks as he does rewards. The most obvious challenge: A longer retirement means more nonworking time to pay for. It also means more time to fill in some meaningful way. It seems fair to say that the younger the retiree, the greater the amount of forethought and planning required.

Despite the challenges and risks, early retirement -- or at least earlier retirement -- has been the choice of an increasing percentage of Americans since World War II.

Social Security Administration research shows the median age of retirement falling from age 68 or 69 to 62 between 1950 and 1985. Though the trend has flattened in subsequent years -- gaining or losing steam according to economic variables such as the tech bubble and its bust, the housing bubble and the Great Recession -- the baby boom's aging has reinvested the issue with importance.

Though the boomers are hardly a monolithic lot, they are united in some common beliefs that are particularly relevant to any discussion of early retirement. A survey of the group's retirement attitudes by the AARP found that, compared with their parents, boomers believe:

  • They will need more money to live comfortably in retirement.
  • They are more self-indulgent.
  • They are healthier.
  • They will live longer.

The graying of the largest, longest-lived, most self-indulgent and most prolifically spending generation in U.S. history promises to make retirement -- especially the early variety -- an increasingly complex exercise. Still, by avoiding three central pitfalls, retirement wannabes from whatever generation can at least begin the process with some prospect of success.

They must begin by answering three short but encompassing questions:

  • Why?
  • How long?
  • How much?

The answers will go a long way toward telling them whether they can retire early -- or even should retire.

What do you plan to do over the next 25 years?

The motive for retiring is all-important. Simply ceasing to work -- while undeniably appealing on Mondays and other bad days -- does not in itself constitute a fulfilling retirement lifestyle.

"Be sure you have something to do that occupies your time and interests and takes advantage of your talents," says Tom Gnuse, a principal in HTG Investment Advisors in New Canaan, Conn.