Mapping Out a Fulfilling Retirement

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One might say that baby boomers on the cusp of retiring come in two varieties. Some cannot wait to retire and already have a plan. For others, the unknowns fill them with dread.

How will I occupy my days? Should I do something meaningful, or is the goal just to have fun? And how do I figure this out? At 62, this writer really has no idea.

For the other boomers who are feeling this way, take some comfort in knowing you are in good company.

“I can’t say this strongly enough. There are some people who seem to literally not think about what their retirement might look like before they retire,” says Harvard Business School professor Teresa Amabile, whose research team interviewed 83 professionals in their pre- or post-retirement years (or both) to study how they navigate the transition years.

A big part of retiring is letting go of what can be a strong identification with work, and people are reluctant to give that up, she said. This identity might be attached to one’s profession – doctor, professor, carpenter – or to an employer, a specific experiment, or the team on your current project. For others, identity is tied to being the family breadwinner. For many people entering retirement, the basis of that identity is “profoundly shaken,” Amabile said.

Of course, not everyone confronts an identity crisis. Older people who are eager to start a new chapter of their life or are simply burned out by work may find that it’s liberating to shed that old identity and move on.

But, according to Amabile, a more arduous process is common. Many older workers begin to realize, “My identity as a person and my work are really bound up together, so I need to work through that.” A crucial part of planning for retirement is determining “what life is going to be like without work, because work structures your life,” she said.

Amabile described the problems one couple in the study encountered because they didn’t have a solid plan. After retiring, they moved out of the community they’d lived in for 25 years and relocated near some family members. But two years later, they still hadn’t settled comfortably into their new life and “felt at loose ends all the time,” she said.

To prevent this from happening to you, consider that boomers typically must go through four tasks as they transition to a satisfying retirement; Amabile and her team members – Lotte Bailyn, Douglas Hall, Kathy Kram, Marcy Crary, and Jeff Steiner – saw these four tasks in many of their interviews with baby boomers.

The tasks – described below and in a follow-up blog – don’t have to happen in any particular order, though the most common sequence is: Decide to retire. Detach from work. Explore a new life structure. Consolidate a new life structure.

Decide to retire. Beyond the always-crucial financial planning, making this decision should involve contemplating what post-retirement life might look like. Lacking a detailed plan, the process will be smoother if the older worker at least comes up with a list of activities to explore after retiring.

“You’re facing the prospect of being the architect” of a brand new life, Amabile said, “which can be both exhilarating and terrifying.” For some, the decision to retire is simple and straightforward. For others, it’s an agonizing period of weighing multiple considerations.

Besides finances and post-retirement activities, other considerations to keep in mind are whether to remain in your current home, downsize, or relocate to another area. Retirement planning also includes discussing retirement with your partner and negotiating a game plan of time together and time apart that works for both of you.

“It’s not just what are you doing, but who are you doing it with,” Amabile said.

See next Thursday’s blog to learn about the remaining three tasks.

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Ellen Grossman

Ready to semi-retire and in late 60’s. I am self employed and have no social media skills. Finding it impossible to navigate my day to day. Any ideas to transition into my next chapter? I am a Doula, and never needed social media to network. I can e-mail, but the mom millennials can’t find me on my website because I am nowhere to be found. Should I just accept this and retire?

    Steven French

    What’s a Doula?


    Hi Ellen!
    You might be able to find a social media class at a local community center, library, or community college. If not, you could hang a few fliers up at a community college saying that you are looking for someone to introduce you to platforms and figure out a payment that works for your budget. At this point you should focus on Instagram and Facebook. Maybe join a few FB groups to get your name out there. You’re young enough that you can learn and keep evolving! Best of luck!


Your article said it all. Confusion, apprehension, and conflict between partners. What don’t I know. After 30 years of running my own business being in control and now facing the unknown is enough to drive me nuts. I have tried reading everything I can find. I have asked numerous individuals what is or was your biggest surprise once you retired. Interesting answers and no one person is even remotely alike.


Thank you for publishing this.

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