How to Transition into Retirement

Shifting into retirement can be bumpy, but having a plan (or stumbling upon one) can make the switch smoother.

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When Ruth Wooden was president and CEO of Public Agenda, a nonprofit research organization, she found herself dreaming at night that she was sitting in a classroom. At the time, Wooden, who had worked in advertising and public service for decades, was turning down offers to teach college courses about advertising. She wanted to do something else. Wooden decided to try teaching — about conflict resolution, not advertising. Once on campus, she realized that she really wanted to study, not teach.

Having retired from Public Agenda, Wooden began teaching in the fall of 2011. Soon after, she entered a master’s program in theology and religious studies, taking one or two courses per semester for four years. “It just energized me,” says Wooden, now 73.

Prepare for the Ride

Transitioning to retirement can be bumpy, but having a plan (or stumbling upon one) can make the switch smoother, experts say. That’s important because people are living longer and staying in the workforce well into their 60s and beyond. Many of them consider this an opportunity to try a new field.

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Wooden found her path through connections and introspection. Others seek retirement coaches to help them through the transition. To help people ages 55 and older adjust to changes later in their lives, Wooden has been teaching the Encore Transition Program (opens in new tab), a four-month class at the Union Theological Seminary.

Most of the participants “are in unfamiliar territory, particularly if they’ve had a long career,” Wooden says. “They’re kind of like lost sheep.” Many “have a sneaking suspicion that there’s something good waiting.” They just have to figure out what it is.

Start a New Chapter

People don’t always realize just how much of their identity, status, daily social connections, structure and purpose are tied to their work. “It sounds great to have all that freedom,” says Joe Casey, an executive coach in Princeton, N.J., who also became a retirement coach five years ago. Yet, with increased longevity, people who quit their long-time occupation at 55 or 65 often find that unstructured retirement “can be a long stretch,” he says. “It can veer into drifting if you don’t have a plan.”

Planning for the nonfinancial side of retirement is crucial to success. “It’s a shocker to see how hard it is to replace what you had at work,” says Robert Laura, author of Naked Retirement: Living a Happy, Healthy, & Connected Retirement (Retirement Project, $15) and founder of the Retirement Coaches Association (opens in new tab). Finding a path takes some effort. “We have to be realistic,” he says. “It’s not an easy transition if we’re not prepared for it. It doesn’t come automatically.”

Laura recommends having a written plan for your everyday life in retirement. How are you going to replace status, social network, structure, purpose and challenge? “How am I going to stay relevant and connected? Money doesn’t buy anything unless you figure out how you’re going to use it or spend your time.”

For Cynthia Heath, who worked as a corporate lawyer for 30 years in St. Louis, retirement was daunting. Her husband had passed away 12 years earlier. “My whole identity was two things: my children and my career,” she says. “Your own mortality is clearer the moment you retire.” She found herself thinking, “How many more years do I think I have?” She first retired at 67 in December 2016, then worked on retainer as a consultant and was called back to her law firm to work again as a consultant until December 2018. Considering the longevity in her family, she’s “counting on” 20 more years of life.

The second time she wanted to retire, she knew she wanted to, but “I did not know who I was. I knew what I did,” says Heath, now 71. So, she contacted a retirement coach, Joanne Waldman, for help. Though Heath already served on a number of boards, including Washburn University’s, she says she was confused about her identity. “I was living the status (I had) with the company,” she says. “I knew I had things I could do. I wanted to get to my heart.”

Build Your Network

Heath has numerous personal and business connections yet still found developing a new social network a challenge. “The social network is the hardest part,” she says. “We lose those connections when we leave that job,” says Waldman, who is director of training for Retirement Options and owner of New Perspective Coaching in Chesterfield, Mo. Once retired, though, you can create a new social network; reconnect with childhood friends, college friends and relatives; or get involved in new activities and classes.

Waldman suggests that you ask yourself, “Who do I want to be with in retirement?” Heath enjoys the company of her daughters and grandchildren, sister, old friends and other sports fans who join her at St. Louis Cardinals games.

Intergenerational connections can be a way to stimulate new ideas and friendships. “People wanted more of those opportunities,” says Charlotte Japp, founder of Cirkel (opens in new tab), a New York-based intergenerational network and mentoring organization. “When not making these meaningful connections face to face, the less connected we actually feel to people.”

Plan for Purpose

Planning for the nonfinancial aspects of retirement is best done three to five years before you retire, Laura says, yet many people wait until much later. Retirement work can range from being a porter at a rental car company to running the pro shop at a golf course. For others, retirement is the time to take a painting class or learn how to cook. Some people start a business on their own or with their adult children.

Having a variety of interests, activities and contacts typically makes for the most successful retirement. Yet, meaning can be elusive. Grief or sadness can be part of aging. “Look inward to find what’s important to you,” says Jacob Brown, a psychotherapist in Corte Madera, Calif., who counsels adults about aging and grief. “Look outward to how you can express that in the world, rather than trying to fill it with cruising, golf or fishing.”

Contributing Writer, Kiplinger's Retirement Report

Harriet Edleson is an expert on baby boomer retirement strategies. She has written the Retiring feature for The New York Times and the Where We Live feature for The Washington Post. A former writer/editor/producer for AARP where she specialized in Social Security, she now writes for Kiplinger's Retirement Report. A graduate of Mount Holyoke College with a B.A. in sociology, she began her writing career at the Gannett Westchester (N.Y.) Newspapers and the Houston Chronicle. Her forthcoming book, 12 Ways to Retire on Less: Planning an Affordable Future, is to be published by Rowman & Littlefield in May 2021. Other areas of interest are real estate, health, and travel.