Seven Ways to Approach Retirement Challenges

Shortly after he retired, my friend attended a cocktail party. He had been head of a high profile company in town. A guest who knew he looked familiar but couldn’t place him asked, “Didn’t you used to be somebody?” He laughed when he told me. “Does that mean I’m nobody now that I’ve hit retirement?”

For some, work defines them or how others see them. Interacting regularly in a job can provide friendships, a common goal, and a sense of purpose. When that’s gone, there can be feelings of loss and soul-searching.

Does this sound familiar? You’re not alone. Approaching life as a retiree isn’t always easy so we’ve pulled together strategies to help you cope with common challenges in retirement.

Who am I now and what do I do?

Whether you can’t wait for the day you are gainfully unemployed or you are a surprise retiree, one thing is certain: Retirement is changing. Better medicine and health has led to greater longevity—on average, providing 20-30 extra years—than in the old days.

“Our research repeatedly shows that retirees are shocked at just how long retirement actually is. No longer is it a few short years of golf, beach walks, and bike rides. Today we are talking decades,” says Joseph Coughlin, director of the AgeLab at the Massachusetts Institute of Technology and author of The Longevity Economy. “Retirement is no longer simply about relaxing.” Many people are finding that, after a while, something is missing.

“People of all ages seek lives of meaning and purpose,” says Paul Irving, chairman of the Milken Institute Center for the Future of Aging. That’s never been truer than for older adults today who talk often about “leaving a legacy” and “making a difference.”

Purpose can be anything: getting involved in a cause or campaign, teaching English to immigrants, using your skills from a former job into paid or volunteer work, starting a business, learning to draw or getting better on the piano, or moving so you can be an integral part of your grandchildren’s lives.

“People get stuck because they think there has to be this grand plan. It might be a little thing that gives you pleasure, like taking a course,” says Dorian Mintzer, a Boston-based therapist, career coach, and co-author of The Couple’s Retirement Puzzle. “There are many options. But going from working to not working can be an abrupt change, so it’s good to start thinking about it.”

Some people plan to wing it in retirement. Others haven’t thought about the next phase or don’t know what they want to do. Still others, by contrast, have their later years carefully mapped out. “There’s no right way to approach retirement,” says Mintzer. But there are ways to think about it so that you don’t find yourself adrift—or, as they say, up a creek without a paddle.

Seven ways to approach life in retirement.

1. Conduct a self-evaluation.

Do you need or want to work? Think about what interests you but that you never had time to pursue. If you loved to act back in the day, is there a senior theater group nearby? If you adore kids, why not volunteer to cuddle preemies at a hospital or to tutor? If it’s animals you love, think about being a dog walker (set your own schedule, get good exercise, extra money) or helping out at an animal shelter. Maybe you feel passionate about a social cause. What has made you happy in the past or what have you always wanted to do but never had the time—learn to meditate or tackle Spanish?

Scrutinize your skill set. Are you good at managing people? Are you organized? Are you an idea-generating machine? Can you parlay these strengths into something new?

If you are stumped, ask friends what they think your strengths are and if they have ideas, hire a retirement coach, or read books on the topic of encore careers.

2. Approach retirement holistically.

“Planning for retirement is a lot of work. Your health and financial security are simply the bookends,” says Coughlin. “In between, you must consider where you can live that will help you remain engaged in life and age well. How you will get around if you no longer drive? Will you have access to healthcare, and have friends nearby to have fun with and support you when you need them.”

3. Get involved.

As Irving puts it, “Be a joiner.” Develop relationships with people of all ages. Many towns have intergenerational initiatives or boards and committees with members from different generations. If there’s new development in your neighborhood or an override of your local ballot, what can you do to learn more, meet people, and help make a difference? Staying involved will keep you socially engaged and is a way to reduce isolation in retirement.

4. Keep learning.

Are there any adult education classes offered near you? If not, you could take online courses, many of which are free. You could also join a book group. If you can’t find your own, municipalities and bookstores often sponsor them. (My mother, at age 90, was in three book clubs!)

5. Give yourself permission to not know what’s next.

There’s pressure on us to have that perfect retirement plan. It’s okay to not know what’s going to happen next. It doesn’t mean you have to stay static, but rather that retirement can be a time to experiment.

Having a long period for retirement encourages fluidity. Many people find themselves going in and out of this life phase. They take time off, then reenter the workforce or volunteer, take time off again, and find something else to do. So try out your retirement lifestyle and, if it’s not what you want, it’s okay to change your mind.

6. Don’t feel guilty.

Retirement is not about judging your choices. If you’d rather kick back and play 24/7, it’s your right. But maybe you’ll decide you want to play and do something else, too, that gives your life meaning and pleasure.

Another nice thing about a longer retirement is that you don’t have to choose just one thing. You can do several—or not!

7. Think positively.

As social worker and life coach Mintzer sees it, “Retirement is no longer a destination. It is a transition, a time of new beginnings.” With the right positive attitude, the years—even decades—after your primary working years may become a time filled with entirely new adventures.