Create a Plan for a Meaningful Retirement

A retirement plan is not just about money. It is also about figuring out how you want to spend all your newfound free time.

When it comes to your nest egg, you made all the right decisions, saving enough to turn your retirement dreams into reality. But as the big day approaches, you realize you've forgotten to answer a couple of crucial questions: What exactly are my dreams? How can I make the next 20 or 30 years purposeful?

Some people enter retirement with a full-blown plan. Other new retirees struggle to fill a blank canvas. And as the soul-searching baby boomers march into this stage of life, a cottage industry of retirement and life-transition coaches are helping them explore the nonfinancial, emotional side of retirement.

The key to a meaningful retirement is not just filling your time but crafting a portfolio of pursuits that are based on what's important to you, experts say. "Many times, work is what you do and not so much who you are," says Catherine Frank, executive director of the Osher Lifelong Learning Institute, which is affiliated with the University of North Carolina at Asheville. "Retirement is an opportunity to create a life that reflects more closely who you are."

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With so many choices and so much freedom, figuring out what you value most can be tough—even for people like Ronald Manheimer, who helped others plan for retirement for 21 years as Frank's predecessor when the organization was called the Center for Creative Retirement. When Manheimer retired in July 2009, he says he "had this idea that I would do things I had never done before." As he always instructed others, he would allow for a "chrysalis period, when these newly creative endeavors would come to me."

Aside from embarking on a fitness regimen and becoming a hospice volunteer, Manheimer says, little else came to him. "I was sort of at loose ends," he says. "I realized that this was much harder than I ever thought."

Eventually, Manheimer began to employ his skills and knowledge in new ways. A former philosophy professor and an expert on Danish existentialist Søren Kierkegaard, Manheimer returned to working on a book he started years ago focusing on philosophers' autobiographies. He used his book research to develop a course he teaches at the Osher center. And he's using his expertise on aging as a consultant to an Atlanta developer who is building senior housing that will incorporate an education component.

Among the lessons that Manheimer learned: "Keep open time to explore, to perhaps research what you may want to do next," he says. "But you should be able to look forward to a calendar of activities." And, he says, while you can explore new areas, "see how you can renew yourself within what you already know."

Retirees who are enjoying this stage in life offer similar advice to those about to join them. "Try things out. If something is not right for you, you have plenty of time to change," says Tom Lashnits, 66, a former magazine and book editor and writer, who was laid off in a downsizing at age 53.

The first couple of years after he lost his job, Lashnits says, he was "feeling that I was not getting anywhere." Over time, he put together a number of activities that he finds enjoyable and productive.

Lashnits, who lives in Granite Springs, N.Y., joined a competitive table tennis clinic, which was fun but too physically taxing. So he dropped it and spent more time playing golf. He began writing a retirement blog under the name of Tom Sightings called "Sightings Over Sixty" ( That's led to freelance writing gigs and consulting work.

With a "vague notion" that he wanted to volunteer, Lashnits got in touch with VolunteerMatch (, which found him a position as a writing tutor at the local community college. "I find it enormously rewarding, and it gives me a place to go and people to meet," he says.

With a Little Help From Friends

Maintaining social connections is an essential ingredient to a successful retirement. If you're feeling isolated, take a step toward meeting new people: volunteer, take an exercise class, or join a hiking group. You also can find a continuing education class at your local community college or at one of 119 college-affiliated Osher lifelong learning centers (

The longing for social interaction is a recurrent theme among retirees who write to Sydney Lagier, 50, a retired finance executive who writes a blog called "Retirement: A Full-Time Job" ( "It's easy to get lonely in retirement, especially if your friends are not retired too," says Lagier, who lives with her retired husband in Redwood City, Cal.

Lagier makes a point of meeting with former work friends during their lunch breaks. She also has met people through volunteering on the finance committee of an education nonprofit. "It turns out these casual relationships are pretty important," she says. "We have common things we are working for."

Men tend to have a more difficult time than working women making the transition to retirement, according to experts. "Women already have outside friendships and outside activities," says Michelle Maton, a certified financial planner with Aequus Wealth Management Resources, in Chicago. "For men, most of their satisfaction comes from working."

Chuck Fink, 64, says he suffered from depression soon after retiring in 2008 to Asheville. He loved the corporate training company that he owned in Cincinnati, Ohio, but his wife, Cindy, a university professor, wanted to retire to a new community. "Moving was a huge shock," Fink says. "I was a P.I.P.—a previously important person."

Fink recalls attending a lecture at the Osher center, where a speaker mentioned that women tend to handle transitions better than men because they're more likely to have social networks. Something clicked for him.

After several months of research, Fink "cajoled" a group of nine other retired men to join the first Men's Wisdom Works group. That was in October 2009. Today, 11 groups totaling 127 retired men—ages 55 to older than 90—meet for two hours twice a month.

Among discussion topics: the loss of identity, changing relationships with family members, life's regrets, and aging and mortality. The groups also go to ballgames, hike, and meet regularly for meals where they discuss everyday topics such as sports and the news. The support groups help the men "find avenues to establish meaning" in their lives, Fink says.

Fink says these relationships gave him the confidence and sense of well-being to pursue new interests. He took a stand-up comedy class and is participating in a personal storytelling group. "I never would have had the chutzpah" if not for the men's groups, he says.

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In their quest for a meaningful retirement, many new retirees look for activities that provide for the greater good or connect to a long-held passion. Sally Conkright had held top management jobs at large companies for decades. In 2009, after a corporate restructuring, she decided to retire.

Unsure what to do next, Conkright, now 61, who lives in New York City, sought the guidance of New Directions, a Boston firm that helps executives navigate career transitions. Extensive coaching confirmed what she was already thinking: She wanted to work for a nonprofit. Early in her career, Conkright worked for a health care company and wanted to return to the field. "There is the sense you get that you are making a difference," she says. Through her connections, she found paid part-time work consulting on strategic planning for two medical centers in Brooklyn.

Conkright also is using her executive skills as a volunteer for two nonprofits in Marion, Mass., where she has a cottage. After she retired, she was invited to sit on the boards of directors of the local historical society and the Buzzards Bay Musicfest, an annual four-day concert series. Today, Conkright is president of both. She never played an instrument, but she always loved music. The Musicfest board job "melded with one of my passions," she says.

Outside Help to Find the Inner You

Need guidance with your quest for self discovery? You can hire a coach, enroll in a life-transition program or go to a retirement workshop. Or you can visit a financial life planner who will help you figure out your passions and ways to afford them.

Twice a year, about two dozen retirees and those approaching retirement visit Asheville for a weekend program called Paths to Creative Retirement ( Participants engage in exercises that probe everything from fears of loneliness to fantasies of taking risks.

One exercise is called "Making a Dream List Come True." Over five or so minutes, participants must list all possible things they might like to do, such as traveling, moving, painting or spending more time with family. They circle the dreams they would like to pursue in the next few years, and then choose the three most important dreams and list steps to make them come true.

If one of your top three is spending several months making pasta in Tuscany, Frank says, you need to figure out how to make it happen. How do you find out if there's a course you could take? What kind of arrangements would you need to make? Thinking through the practical steps helps participants realize that a dream "doesn't have to seem insurmountable," Frank says. "People don't see retirement as the same thing as planning other parts of their lives, and they should."

Unlike the Asheville program, New Directions ( provides one-on-one coaching. Preretirees are likely to enter the Life Portfolio program, which helps participants find a mix of activities that provide meaning—perhaps some income-producing work, ongoing learning, more time for recreation and family, and community service. "These executives don't want to work 80 hours a week, but they want to be engaged as fully as possible," says Mark Shepard, a senior consultant, who worked with Conkright.

Clients are given exercises to help them dig deep to determine their values, motivations, aptitudes, interests and skills. They also undergo extensive interviews with the senior consultant and a psychologist. In addition, the organization interviews a group of friends and relatives who know the person well.

Shepard says clients explore what may have been left undone and what engaged them even in their childhood. He also helps them figure out their "drivers." For example, Shepard says, many retirees "want to be involved with boards of directors, but you really shouldn't be on a board if strategic planning doesn't appeal and you'd rather be in the midst of the action." Starting a small business might be a better idea.

Jim Dawson, now 62, entered the program in 2013 after working 38 years in the banking industry, most recently as president and chief operating officer of Boston Private Bank & Trust. "In the back of my mind, I always thought I would ease into retirement by working part time at my family's hardware business," he says. He recalls his dad talking about the business at the dinner table.

Decision-time came sooner than he had planned when his bank underwent a restructuring. While considering a senior executive position at another bank, Dawson went to New Directions to ponder his priorities. "I spent a lot of time soul-searching," he says.

In the end, he decided that he did not want to commit to working 50 to 60 hours a week for the next several years. He preferred to spend more time with his wife and two adult children and pursue some interests he had postponed because of his time-crunching career—stand-up paddling, bike riding, learning a new language and taking up the piano.

Today, Dawson, who lives in Beverly, Mass., is working 25 hours a week with his younger sister at the family's two hardware stores. "My dad built a wonderful business, and I want to carry on his legacy," he says.

Perhaps you need help figuring out what you want to do in retirement—and you need some financial advice as well. You can see one of a growing number of "financial life planners," mostly fee-only certified financial planners. These advisers help you determine what kind of life you want to lead—and then design a financial plan that will enable you to pursue it.

The movement is the creation of George Kinder, president of the Kinder Institute of Life Planning, which has trained financial advisers in 25 countries. "Before you can make any appropriate decision about money, you need to know what you're passionate about," Kinder says.

Financial life planners often start the process by asking three questions: If you had enough money, how would you live your life? If your doctor told you that you have just five to ten years to live (but you would feel healthy), would you change your life and how would you do it? If your doctor told you that you had one day to live, is there anything left unfinished?

Kinder says that these questions—as well as other exercises—encourage people to focus on what's most important. For instance, he says, one person may regret that he didn't spend more time with his family, while another may realize that he'd like to move to the country after living for decades in the city.

The planner offers the client concrete steps to turn a goal into reality, Kinder says. The planner also looks at financial assets. Perhaps the client already has enough money to retire early. Or maybe the retiree can achieve certain goals by cutting expenses.

You can find a registered life planner near you and try some exercises by going to Or you can buy Kinder's book, Life Planning for You (Serenity Point, $17).

Susan B. Garland
Contributing Editor, Kiplinger's Retirement Report
Susan Garland is the former editor of Kiplinger's Retirement Report, a personal finance publication whose subscribers are retirees and those approaching retirement. Before joining Kiplinger in 2006, Garland was a freelance writer whose work appeared in the New York Times, the Washington Post, BusinessWeek, Modern Maturity (now AARP The Magazine), Fortune Small Business and other publications. For 12 years, Garland was a Washington-based correspondent for BusinessWeek, covering the White House, national politics, social policy and legal affairs. Garland is a graduate of Colgate University.