Retire Happy

Moppins's arrangement would fit some people's definition of a dream retirement. But it's only the first of three major phases that her postcareer life is likely to undergo — and as she lives the first, she's planning the next two. This October, when she turns 65, she'll start chapter two, the leisure phase. She'll quit working and move to Dallas with her partner, David, building a home closer to their respective children while she devotes more energy to travel and gardening. And Moppins is also looking further ahead, toward a third chapter, talking with her kids about the logistics of assisted living. That exercise has been emotionally difficult, Moppins admits, but "that's a reality I deal with every day in my job. You can't think you'll be independent forever."

To someone in midcareer, retirement can seem relatively unvaried. But thanks to Americans' increasing longevity, the next wave of retirees can expect longer retirements than any previous generation. Sixty-five-year-olds who retire in 2015 will face 17 to 21 years of postcareer life on average, with more than one in four living 25 more years, according to the Social Security Administration. And 65 isn't everybody's retirement "magic number." A recent Merrill Lynch survey found that about 20% of baby boomers — the 78 million Americans born between 1946 and 1964 — already consider themselves retired, even though the oldest members of that cohort are just now turning 60.

With their postwork years potentially stretching across several presidential terms, retirees will face a more complicated future — one that could look like Rebecca Moppins's. Instead of one transition from work to leisure, they'll undergo several. Every person's journey will differ, of course, but most will include three stages. First, work: a new job or volunteerism. Then play: focusing on family, travel and leisure. And finally, rest: a more sedentary period when convenience and access to health care begin to take precedence.

Transitions, of course, require patience, a period of adjustment and, above all, planning. But many working people are so focused on saving and investing for retirement that nonmonetary issues get pushed aside — if they're ever considered at all. And there's a surprising paucity of help available to guide people through these changes. "There's no section in the Yellow Pages called "personal reinventor for the elderly,'" quips gerontologist Ken Dychtwald, founder of market-research firm Age Wave. Indeed, today's retirees find themselves at sea when it comes to everything from pursuing their ideal second careers to getting the most out of leisure time.

The "soft" issues aren't the only ones being neglected. Only recently has the financial-services industry begun to recognize that a 64-year-old with a consulting gig drains her savings at a different rate than her 72-year-old brother who's traveling six months a year. "A generation ago we'd mostly emphasize accumulating money," says Craig Brimhall, vice president of retirement wealth management at Ameriprise Financial. "Now we're asking how on earth do you spread the wealth over 30 years, in a flexible way?" Meanwhile, illness late in life is one of the biggest threats to that wealth, but planning for it remains dauntingly complicated. (For more on how to extend retirement assets, see the following story, "How to Invest.")

If you want to make sure that retirement's stresses don't outweigh its joys, it pays to sweat the details long before you retire. To find out what it takes to forge your own best path, we've talked to people living through each of retirement's major phases, and we've consulted experts who've helped others make the big transitions. As their stories show, the most reliable recipe for happiness in retirement is preparation: taking time away from your workaday life to fantasize about, explore and, above all, plan the three acts of your retirement drama.