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Caroline Hall turned 65 last fall. She’s watched her recently retired husband enjoy his leisure time, but she’s not convinced she wants to spend the rest of her life entertaining grandchildren.

Will my brain and skills atrophy? the Sausalito, Calif.–based executive coach wonders. Will I still get the same respect out there? Will life have as much meaning?

These kinds of concerns led Hall, a cofounder of Life Reinspired, a program that supports baby boomers entering elderhood, to consider whether “retirement” is even the right way to describe what she wants out of the years ahead. “What if the next chapter were an encore performance?” she asks. “What if it were filled with meaning and contribution, and included all the things we love to do? What if it could be the very best chapter of our lives?”

Such questions can be game-changers for anyone approaching so-called retirement age, especially as we anticipate living longer than our parents and grandparents. (By 2050, an estimated 21 percent of elders will be 85 years old and older.) Reframing what “senior living” means can help us make the most of our time and resources.

“People might live another 30 years or more after retirement. That’s a whole lifetime,” says Jaye Smith, an executive coach and coauthor of The Retirement Boom: An All-Inclusive Guide to Money, Life, and Health in Your Next Chapter. Increasingly, people are moving away from conventional retirement expectations that are dominated by leisure time and toward a new vision.

This perspective may well include a longer work life. In recent decades, about 60 percent of retirement-age workers who left career roles moved into “bridge jobs,” shorter-term positions taken — by choice or out of necessity — prior to retiring fully from the workforce. It’s a healthy option, according to a recent study from Oregon State University. Researchers found that study participants who kept working after 65 had an 11 percent lower risk of death from all causes than those who retired.

To help you envision possibilities for your own encore performance, we asked experts for their insights.

Ask New Questions

“With the rise of the 401(k) 20 to 30 years ago, the conversation around retirement focused on one thing: What number do I need to have so that I can retire and not run out of money?” says Chris Farrell, senior economic correspondent for American Public Media’s Marketplace and the author of Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community, and the Good Life. But now — thanks to our longer life expectancy and the near demise of employer-funded pensions — we’re in a different situation, he says. “So a better question is: What can I do next?”

Sabrina Roblin, one of Hall’s Life Reinspired coaching partners, suggests digging into values-clarifying questions: What lights me up? What am I passionate about? Whom do I care about and why? How do I want to spend my time now? Were there any dreams I had in my younger years that I abandoned?

This last question proved important for Roblin after she retired at 58 from her position as chief learning officer at the Coaches Training Institute in San Rafael, Calif. “When I was working full-time, I didn’t have a lot of time for friends and family, for being outside and active, or for my lifetime passion for music,” she says. So Roblin, who admits to having been terrified about losing the structure, paycheck, and professional identity of her 35-year career, was deliberate about planning for a fun and meaningful retirement.

“Instead of having fun, she experienced the grief that can accompany the loss of identity and purpose after leaving a long career: “Where were the projects? Where were the 100-plus emails every day? Did anyone need me anymore?”

After leaving her job, she moved to the outdoor playground of Sun Valley, Idaho, and gave herself a year to explore, hike, and recover. But instead of having fun, she experienced the grief that can accompany the loss of identity and purpose after leaving a long career: “Where were the projects? Where were the 100-plus emails every day? Did anyone need me anymore?”

It wasn’t until Roblin recalled her dreams, picked up her guitar, and started writing music and singing again that she truly started enjoying herself. “At this stage of life, whether I end up on a world stage like Carole King or not doesn’t matter,” she says. “I have regained what I thought I had lost back in my childhood, I’m having a lot of fun, and my life truly is reinspired.”

Gather Information

Our fears and uncertainties about aging often center on the unknown, which can leave us feeling stuck or anxious. While we can’t anticipate everything — it’s life, after all — we can explore what’s possible and make plans that align with our values.

To envision a satisfying postretirement life, Smith recommends recalling the activities that moved you in the past. “What got you up in the morning?” she asks. “What has always made your heart sing?”

Imagining a life without limits can also help you identify your core values, Smith adds. “If you had all the money in the world, how would you spend your time? If there were no restrictions, what would it be?” Most people find that what matters to them — things like being of service and spending time with friends and loved ones — usually doesn’t require great wealth.

It’s also valuable to look beyond your own perspective. “Dream in conversation with other people,” advises Hall. “Find out what other people have on their bucket lists and where other people are exploring. Keep your eyes and ears open. Notice what’s needed in your world and what would be fun and fulfilling to do.”

That could be as simple as inviting colleagues out for coffee. “Similar to informational interviews after graduating from college, connecting with people in your network can be inspiring,” Farrell says. Ask others: What do you think I’d be good at doing? What do you think I should be doing? Then ask yourself the same questions.

Take some time with this process, says Hall. “Open up and create a compendium of possibilities. Get a hundred ideas and then prioritize them. Then ask: What else? What has the most heart and meaning?”

Make Your Plan

You don’t need all the pieces in place to make an initial plan and move forward. “Your vision can change over time,” says Smith. “So when making a decision, ask: Right now, what does my vision look like and what’s important to me? Where should I not compromise?”

It’s wise to look at your bucket list and think honestly about your health, she adds. “What you can do in your 50s and 60s is not necessarily what you want to do in your 70s, 80s, 90s, or 100s. What are the things you want and are able to do now? What do you need to sort out and spread out?”

This will help you reinvent strategically. “People have been reinventing in such interesting and wonderful ways,” Smith notes. “Nothing is out of the question or silly or odd.”

One man she knows took care of his wife while he was in his 80s. At 90 he became a substitute teacher beloved by students for his wisdom. Another man in his 60s works in financial services Tuesday through Thursday, writes music on Monday and Friday, and plays in a band on the weekend. “He could not be more passionate and joyful about what he’s doing,” Smith says.

After a year off, Roblin — in addition to making music — decided to start a coaching and consulting business. She’s not alone. Twenty-six percent of start-ups are now launched by people between the ages of 55 and 64. These entrepreneurs, with plenty of experience under their belts, tend to be more successful.

Everyone’s plan will look different, but Hall and other experts agree that planning is key. “Are you going to design it on purpose or are you going to let it happen to you?” she asks. “How much more rewarding is it to design it with intention?”

This article originally appeared as “What’s Next?” in the March 2017 issue of Experience Life.

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