(MONEY Magazine) – When it comes to the money part of retirement--the "how you'll pay for it" part--you have a pretty good grasp of the challenges: the cost of health care, the riddles of a portfolio, the shaky math of Social Security. But there's another, deeper retirement issue to reckon with--the part about your life. When you have crossed the career finish line, how do you give your spirit a second wind? When you have no job to go to and no kids left in the house, where do you find purpose and satisfaction? What, in other words, have you retired for?

The five couples you'll meet on the following pages have already successfully tackled the big what-for question. They are indulging passions, forging new careers, giving back to others. Some of them had meticulously planned for this time of life, knowing that interests cultivated early would deepen over time. Others, well, maybe it looks like they just backed into a good thing, but that's not how it happened. They kept themselves open to fresh ideas, and when inspiration arrived, they embraced it. The key message is that a retirement well lived is not just about getting the money right but also about things money can't buy: engagement, activity and meaning. Without them you'll be running blind in the decades after work. Find them, though, and you'll easily understand why one 61-year-old retiree (on page 128) swears, "Life just doesn't get any better than this."

Risk? Bring It On!

HILDA AND EARL JONES Proprietors of Abacela Vineyards & Winery Roseburg, Ore.

"Yes, starting a vineyard with no real experience was a calculated risk. But hey--life is short."  --Hilda

Earl Jones, a physician, had devoted 37 years to medical research, much of it at Emory University in Atlanta. But the profession had changed. For Earl, who's now 65, medicine had become too entangled in paperwork and red tape. So more than a decade ago, he and his wife Hilda, now 52, started dreaming one of those timeless mid-life daydreams: turn an old country house into a B&B; open a bookstore; grow grapes. The Joneses opted for the last of those--and not just any grape, but a gutsy Spanish varietal called Tempranillo. The couple loved its wine so much that they resolved to make a go of growing it. What did it matter that they had no prior experience at all?

They began their quest by poring over books, intent on finding just the right place for their beloved grape. One of Earl's grown sons, a climatologist, helped steer the Joneses to the town of Roseburg, in Oregon's Umpqua Valley. Here conditions mirror those of Ribera del Duero, a renowned wine-growing region in Spain. The Joneses bought 500 acres, investing a big chunk of sweat equity into planting almost 60. Within three years, they had produced their first vintage and found themselves the proud, if bone-tired, proprietors of Abacela Vineyards & Winery.

What, in the end, does it take to realize a retirement reverie like this? Well, a good amount of money and, just as important, a willingness to take on risk. Over the years, Earl guesses, they've sunk $3 million into the vineyard (including reinvested earnings). It now enjoys positive cash flow, and the Joneses plan to keep production at 6,000 cases a year.

As for the risk, the Joneses say they simply never doubted. Asked what he'd have done had the dream failed, Earl says, "I guess I could have bitten my lip and gone back to medicine, but I didn't really think about it." Hilda admits the vineyard was a gamble. So? "Life is short," she says. "Besides, how could I go wrong? I've always loved playing in the dirt."

Make Promises, Then Keep Them

KITTY AND FRED LIPP Guidance counselor, founder of the Cambodian Arts and Scholarship Foundation Whitefield, Maine

"The most important thing in my life right now is to be part of the answer."  --Fred

Before he retired, Unitarian Universalist minister Frederick Lipp believed that he and his wife Kitty had a pretty good fix on their future. Nothing grand, mind you: They'd retire to a small arboretum in Maine established by Fred's father. Shortly before this idyll was to begin, however, Fred, then 58, found time to write a children's book. It changed everything.

Called The Caged Birds of Phnom Penh, the book is based on a Cambodian custom. For a few pennies, a person buys a small caged bird and makes a wish. The bird is then released. If it flies free, the wish is granted. But because the birds are domesticated, they usually return to the seller's cage. Lipp wrote of a Cambodian girl who yearns to escape poverty and eventually discovers how to release a bird that finds freedom and grants her wish.

In 2001, a year after the book was finished, he visited Cambodia for the first time. He was overwhelmed by the plight of countless girls who were unschooled, exploited in the sex trade, living in wretched conditions. With a few thousand dollars drawn from his and Kitty's modest assets, he established the Cambodian Arts and Scholarship Foundation (cambodianscholarship.org). Its mission: to help as many girls as possible, affording them clean water, health care and a basic education.

Today, running the foundation leaves little time for the arboretum or anything else. While Kitty earns a modest salary as a school guidance counselor, Fred raises money. "When I'm in Cambodia," he says, "I promise the girls I'll do all I can to make their dreams happen." Does he ever long for the peaceful golden years he once anticipated? Hardly. "Retirement," he says, "is a lousy word."

Start Early, Stay Late

GAIL AND MICHAEL HOLMES Volunteer and mom, nonprofit business consultant St. Louis

"I felt I wanted more meaning in my life now. There's a big need for people to be helped out there."  --Michael

Michael Holmes was around, oh, say, age 30 when he first realized he needed to plan for a life in retirement, not just for an income. A human-resources pro throughout his career (which culminated in the top HR job at St. Louis brokerage Edward Jones), he says he has seen too many people exit work without a clue as to how they'll fill the next 30 or 40 years. "You have to figure out what will really matter to you," he advises, "then put a toe in the water before you leave." Now 10 months into retirement at the tender age of 47, he is a cheery, Gospel-quoting perpetual-motion advertisement for his own advice.

Holmes left Jones to found his own consultancy, which helps nonprofit organizations run smarter. He trained for his second act for a couple of decades, carving out time from work to serve on the boards of such groups as the Sickle Cell Disease Association of America and the United Way. Work, meanwhile, was going fine. On his watch, Holmes notes, Fortune named Edward Jones the best company to work for in America.

Open-heart surgery last year gave him the impetus to leave. "I had time for reflection. I realized I had all the money I needed," he says. "I wanted a more meaningful way to make a contribution." His experience on nonprofit boards gave him instant credibility in his new endeavor, and he's now as busy as ever. (He is working with the National Institute for Youth Entrepreneurship and the local chapter of 100 Black Men of America.) He joined a golf club in March but rarely picks up his sticks. His wife Gail, 46, just smiles. "Michael thought he could go from 110 mph to zero," she says. "But Michael is just not a zero-mph kind of guy."

Focus on the Flowers. Forget the Weeds.

PAM AND JAMES WEIL World travelers and retirement entrepreneurs Westport, Conn.

"Don't focus on the money. Instead, ask yourself what is the experience you want most in your life."  --James

Six years ago, James Weil was a stressed-out senior executive at Metropolitan Life, a self-described slave to the job who knew all about the price of retirement but nothing about its value. At home in Westport, Conn., he and his wife Pam faithfully put aside 15% to 20% of their income, and when they envisioned life beyond work, all they saw were numbers. "I'd spend hours looking at my cash flow, projecting it out to age 90," James says. "Today, however, I don't think it's about the money at all."

Immediately after retirement, James began taking adventure trips organized by groups such as Elderhostel. But the lightbulb didn't really switch on until he took a cross-country bike trip with people who were 10 and 20 years older. The trip cost $2,000 or so, and few of the seniors he went with could be considered wealthy. "But they were the happiest and most vital people," he says. It was through their example that the great freedom of life after work began to dawn on him. Once you had enough money to get by, you could finally forget all the stress of getting and saving and focus exclusively on what you want to get out of life.

The Weils, now both 61, say the key to a dream retirement is to pare life down to what you enjoy and to discard all that is dutiful and dull. The couple marvel, for example, that after decades of marriage they have mastered what they call "parallel play for grown-ups." He likes adventure travel; she likes Paris. So when he heads for the Himalayas, she takes a solo holiday in France. Sometimes they meet up in Europe, sometimes not.

The same philosophy infuses the businesses that the couple have started. Pam, who had been a stay-at-home mom, pursued her love of gardening to the point of founding Connecticut Gardener, a four-times-a-year magazine with a circulation of more than 2,000, for which she acts as editor, publisher and sole employee. The publication makes enough from subscriptions and ads to fund Pam's travel, and it gives her a deep sense of accomplishment. Besides, it takes only about 60% of her time, leaving her free to travel and tend her own garden. "Life just doesn't get any better than this," she says.

James, meanwhile, is starting a company called My Time Centers, which will counsel new retirees struggling with the question of what they are going to do with the next 20 years of their life. One answer they'll all get, he says, is drawn from the Weils' own experience: "Eliminate everything that doesn't matter," he advises. "Then put all your focus on what makes you happiest."

Never Slow Down

IONE AND BOB PERRY Real estate agent, occasional veterinarian Omaha

"The day I turned 65, I played bridge with Bill Gates. You know, you can have fun when you're older."  --Ione

The retirement of Dr. Robert Perry and his wife Ione is proof that if you keep a foot on the pedal, amazing things can happen--even in your seventies and beyond. The couple are stalwart citizens of Omaha, where Bob ran a successful animal hospital for nearly four decades. When he sold the hospital and retired in 1999, he helped wind down his practice and spent a lot of time on the tennis court. ("And getting bored," interjects Ione.) But not for long. "All of a sudden," Bob explains, "there was an emergency." A foot-and-mouth epidemic was decimating the cattle herd in the U.K., and beleaguered British agriculture authorities needed veterinarians from around the world to help. Perry worked seven days a week with fellow vets from dozens of countries, helping to get the problem under control. Not long after, he pitched in again, in California, where a raging case of exotic Newcastle disease had broken out, posing a severe threat to the local poultry supply.

Ione, meanwhile, barely slowed down at all. When she retired from teaching high school home economics 23 years ago, she immediately started a fashion accessories business, making belts and scarves that were sold at Macy's in New York, among other retailers. Eventually she turned that business over to Goodwill Industries and gave traditional retirement a quick test drive. She now describes the experience in a single, six-letter word--boring. At age 70, she began selling real estate. Why real estate? Ione insists that it's not for the money (though she has sold a respectable seven houses this year). "It's about the people," she says. "I like to see them find the right home. The ones I've helped are practically family now."

Selling real estate helps to keep her busy and out in the world, where--bam!--those amazing things can happen. Like the time, seven years ago, when she and her bridge partner entered a local tournament, only to look across the table at the opponent they'd drawn: Bill Gates, who'd come to town to visit his pal Warren Buffett. Ione's side lost, but she still laughs over the photo that ran in all the papers: a beaming Ione in a smart blue suit looking, well, even a little richer than the two wealthiest men in America.

Lee Eisenberg is the author of The Number: A Completely Different Way to Think About the Rest of Your Life, to be published by Free Press in January 2006.

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