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When Will You Be Ready to Call It Quits?

Weighing the tricky mental decision to retire

By Bart Astor

Mike and Sherry Stahl, of Boise, each came home one day about a year ago with life-changing news from their employers: Both had been offered golden handshakes that would provide them with financial incentives to retire. “It’s not as coincidental as it sounds,” Sherry told me. “We both worked for the same high-tech company. Just in different divisions.”

Mike and Sherry had similar reactions, perhaps as a result of years of discussions they’d had together.

“It was as if a light bulb came on,” Mike said. “As much as I’ve loved my job, even as I turned 70, I’ve been tossing around this question in my head for the last year or two. I really began to see the light, so to speak. I saw a path.”

Ready to Make the Leap and Retire

That pleased Sherry, who’s three years younger, and was ready to retire, too, due to management changes at her procurement position. “I was so thrilled to hear that he was looking forward to leaving,” she said. Sherry had handled the couple’s finances and knew they would be okay financially. A few months later, they made the leap.

The Stahls didn’t have definite plans. But they had previously agreed that whenever they retired they’d initially take an extended vacation. That’s how I met them — over breakfast in a small hotel outside Capital Reef National Park in southern Utah.

But the big decision, which they made a few months prior to our meeting, came after some soul searching.

When Is It the Right Time?

“I just knew that my identity was wrapped up in being an engineer, working on some very cool projects with some wonderful people,” said Mike. So I asked Mike: “How did you know this was the right time?”

It’s a question I think more and more of us in our 50s and 60s will be asking ourselves.

Sometimes, the answer is due to a milestone such as an anniversary of employment or a significant birthday — age 70 in Mike’s case, for example. Other times, changes at work help make the decision for us.

When I interviewed peers for this piece and asked them about their retirement decision, quite a few echoed Sherry’s comments about the direction their organization had taken. They said things like: “I felt left out” or “I felt I no longer had the desire or the energy to adapt to a new culture.”

Others cited health reasons or the feeling that life is short. Said one former colleague: “I only have so much time left. I want to enjoy my later years. I want to spend time with my family.” A friend noted the famous saying, sometimes attributed to the late Sen. Paul Tsongas: “Nobody on their deathbed has ever said ‘I wish I had spent more time at the office.’”


Counting Backwards to Decide

Another pal, Farrel Beddome, offered his personal formula: “I counted backwards. I asked myself, ‘Do I see myself doing this job at 80? No? Then what about at 75 or 72?’”

Those words prompted my wife to cut the ties with a professional life she had enjoyed and been successful at for over 40 years.

Based on my very informal survey of peers and former colleagues, the answer to when to call it quits after your financial concerns are addressed frequently boils down to ego and identity.

Putting Aside Ego and Identity

That is, when you no longer want, or need, to identify yourself as, say, a teacher, manager, director or writer — even if the job title carries some prestige.

The Stahls were ready to put ego aside and shed their former identities. Yes, were given more than a gentle nudge in the form of a golden handshake. But they had had similar opportunities in the past and chose to stay. This time, they felt differently about their work identities.

For Mike and so many others — and me, for that matter — the windmills are no longer worth fighting.

Personally, my ego is now fine just to be Bart Astor, retired person.


Photograph of Bart Astor
Bart Astor, an expert in life transitions and elder care, is the author of the book AARP Roadmap for the Rest of Your Life: Smart Choices About Money, Health, Work, Lifestyle and Pursuing Your Dreams and Baby Boomer’s Guide to Caring for Aging Parents. His website is and he can be reached at [email protected]. Read More
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