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: ‘You don’t want to die at your desk sending an email.’ Beyond the numbers, are you ready to retire?

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Nancy Schlossberg attended a retirement party for a colleague, and afterward heard people remarking how the guest of honor should have retired years before because she was “so old.”

“People were saying she worked too long. It made me realize I never wanted people to say that about me. It triggered me into thinking about my own retirement,” Schlossberg said. “I started thinking I better go while I’m still at the top of my game.”

Schlossberg, 93, did eventually step down as a professor from the University of Maryland, but instead of retiring she built a second career as an author and public speaker on issues related to retirement, transitions in life and aging. 

“There’s no single answer for anyone on when it’s time. There’s something that triggers the thought—and the triggers will be unique for each person—but once the thought is there, it bubbles,” Schlossberg said.

“To retire, you need a financial portfolio and a psychological portfolio. The psychological is as important as the money,” Schlossberg said.

Read: You’re probably not ready to retire — psychologically

To make a successful transition into retirement, you need to check off the financial, emotional and professional boxes to make sure you’re fully ready. And some people never will be ready, experts said.

“We have to change our mind-set on aging and the ‘it’s time to retire’ ageism,” said Catherine Collinson, president and chief executive officer of nonprofit Transamerica Institute. “Societally, we are locked into these ideas that are no longer relevant.”

“As individuals, we can be our own worst enemies. With healthy eating, exercise, we can age better and have the gift of potential time. There doesn’t have to be an endgame,” Collinson said. 

Workers face these questions at a time when the traditional career arc is becoming extinct. The days of spending a career working for one company and retiring at 65 with a gold watch—and a pension—are long gone. Now, workers may be more likely to switch jobs—and even careers—through their working years, and since we’re living longer, a typical retirement can last decades.

Ashley Agnew, a financial adviser and director of relationship development at Centerpoint Advisors in Needham, Mass., calls retirement an “emotionally driven financial decision.”

“A lot of conversations start off with ‘how much money do I need to retire,’ which is not easy to figure out. But that’s not the only factor. You need to be emotionally ready,” Agnew said. “We dive deeper into what retirement will look like. What’s your perfect retirement day? What’s your average retirement day? Will you be consulting or volunteering? How do you transition from go, go, go all the time? Abrupt stops are typically not healthy.”

Read: ‘I needed something to do’: How working in retirement is being embraced by older adults and companies

Dan Schilling, 71, put off retiring during the pandemic and looked for a way to exit his job but still keep his hand in the advertising agency where he worked for 40 years in Birmingham, Ala.

“I had to make a decision at some point in time. I would have retired earlier, but COVID happened and I wasn’t able to travel and see family, so I kept working,” Schilling said.

“But at one point I realized you don’t want to die at your desk sending an email. You want to die parasailing in Cancún or something.”

Schilling said he was fortunate to negotiate what he called a “soft landing” in his retirement this spring by becoming a consultant to the president of the advertising agency, allowing him to maintain contacts, keep his skills sharp and give him a sense of purpose and identity as he transitions into retirement, he said.

Such transitions can make retirement more successful and enjoyable.

Agnew encourages clients to do “wild dreaming” about what their retirement could look like if money wasn’t a limitation. That frees clients up to talk about what they really love and helps them potentially find inspiration for how to spend what could be decades in retirement.

Do you want to spend time with family and friends—is that one big trip a year or weekly Sunday dinners, Agnew asked? Find the answer and then build more social time into your life and budget for trips and gatherings.

There’s no end to ideas of what to do in retirement from studying new skills at a local college (just over 0.3% of university students are over 65), to sharing your hobbies with a local scouting organization to learning while traveling with an educational tour company. Volunteering is a big draw: while retirees make up less than a one-third of the population, they account of 45% of all volunteer hours, according to Merrill Lynch.

“The common misunderstanding is that retiring is not just quitting your job,” said Agnew. “It’s more of a process and the longer runway you have, the more comfortable you will be with the decision.”

Of course, some people postpone retirement a little too long, even though they have the financial resources to retire, said Joe Casey, managing partner of Retirement Wisdom in Princeton, N.J.

About 26.6% of people 65 and older are working, and that number is projected to rise to 32% by 2030, according to the U.S. Bureau of Labor Statistics. 

“Sometimes people stay a little too long at the fair,” Casey said. “What do you do when you’re the dog who finally caught the car he’s been chasing? Now what are you going to do? You need to think about how you’re going to invest this time that often lasts for decades.”

Learn how to shake up your financial routine at the Best New Ideas in Money Festival on Sept. 21 and Sept. 22 in New York. Join Carrie Schwab, president of the Charles Schwab Foundation.

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