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6 Questions to Ask If You Want to Work in Retirement

They'll help you figure out where, and how, to work part-time

By Nancy Collamer

The percentage of people who work in retirement has been steadily rising for years. And by 2026, the Bureau of Labor Statistics estimates, a whopping 30% of people age 65 to 74 will be in the labor force, up markedly from just 18% in 1996.

Woman working from home
Credit: Adobe

Several factors are driving the trend. Longer life spans, insufficient retirement savings and high levels of debt have many Americans worried about running out of money later in life. But even among those who can afford to quit the labor force, there’s growing interest in part-time work in retirement. According to a 2019 Harris poll for TD Ameritrade, almost 40% of Americans ages 40 and older plan to continue working in retirement, even if there’s no financial need.

Some retirees who’ve stopped working are surprised how much they miss the community, routine and sense of purpose they had found in their jobs.

If you’re one of them, it’s wise to do some advance planning before you start looking for part-time work in retirement. Here are six questions, and six related tips, to help clarify your next steps

1. Does your employer offer a phased retirement program? Gradually reducing the number of hours you work at your current job can be a nice way to help you ease into retirement, try out a new role as a mentor and continue earning income. While formal phased retirement programs open to all staffers are still rare, your employer might be open to considering your request.

TIP: If you’d like to pitch a phased retirement option to your boss, download The Phazer, a free proposal-planning tool developed by, an advocacy group for older workers.

2. What are your income goals? If maximizing income is your main reason for working longer, it’s typically best to look for work that is somehow connected to your “old” career — either as a consultant, freelancer, interim executive or coach. It’s the easiest way to leverage your professional network and uncover opportunities to charge a premium for your expertise.

TIP: Earning a certification to prove your abilities can be a relatively inexpensive way to boost your earning power and improve your marketability. Industry groups are a terrific resource for learning about training options, either within your field or in a new one that interests you.

3. Beyond earning an income, why do you want to work in retirement? Some retirees who’ve stopped working are surprised how much they miss the community, routine and sense of purpose they had found in their jobs. So, understanding the “why” behind your desire to keep working will shed light on which post-retirement opportunities to pursue —and which to ignore.

TIP: Make a list of three to five reasons why you want to work part-time in retirement. Then, consider what those motivators suggest about your best options moving forward.

For example, if deepening your community ties is important, a job at a museum or theater might prove satisfying. Or, if you’re looking for intellectual challenge, a consulting, teaching or research role might be a better fit.


4. What's on your “chuck-it” list? You’ve undoubtedly heard of a bucket list, but have you ever written a chuck-it list? That’s one highlighting the parts of work you’ll be happy to leave behind. Some examples: the long commute, office politics and unrealistic goals. By identifying what you don’t want, you’ll get a better feel for what you do want.

TIP: Make a list of your top three-to-five non-negotiable work factors. Tired of sitting in a car for two hours each day? A virtual gig or a part-time job with a local firm might be best. Fed up with sitting in a drab office all day? Perhaps it’s best to find work that lets you be outdoors, such as a tour guide or landscape gardener.

5. What type of job flexibility do you seek in semi-retirement? Flexible work takes many different forms, so it’s helpful to get clear on your lifestyle goals before initiating a search. That way, you’ll know a good fit when you see one.

TIP: Here are three questions to ponder:

  • Are you willing to stick to a preset schedule? Most part-time jobs require you to report to work at specific hours every week. That could prove challenging if you want more time for grandkids, hobbies or travel and don’t want to be locked into a rigid schedule.
  • Do you want summers or holiday weeks off? If so, you might want to consider working for a school or college offering that type of schedule.
  • Do you need to be home to help take care of a loved one? A work-from-home job might be your best option.

6. What is your appetite for risk? Lots of retirees dream of starting their own businesses. But if you plan to open one, you might need to tap into your savings or take out a loan to get started. As an older worker, that can prove problematic, since there’s a limited time to recoup your investment (or make up your losses).

TIP: Take advantage of free and low-cost coaching and webinars offered by organizations like the Small Business Administration and (free mentorship for startups). These can prove invaluable in helping you assess and mitigate the financial risks of entrepreneurship.

Photograph of Nancy Collamer
Nancy Collamer, M.S., is a semi-retirement coach, speaker and author of Second-Act Careers: 50+ Ways to Profit From Your Passions During Semi-Retirement. You can now download her free workbook called 25 Ways to Help You Identify Your Ideal Second Act on her website at (and you'll also receive her free bi-monthly newsletter). Read More
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