Retirees, Take the Off Ramp to a New Career

Faye Fiore, 65, started working for a small newspaper right out of college, and 35 years later, she was a national correspondent at the Los Angeles Times, one of the largest newspapers in the country.

She loved her profession. But about a decade ago, while raising two boys and feeling torn between work and home, she left the news business to become a marriage and family therapist. "Everyone -- my financial adviser, my brother -- told me not to do this," says Fiore, who lives in Arlington, Va. "We were not that far from the recession, and I had a well-paying, prestigious job."

Still, she felt the time was right, so she embarked on a long journey to a new career. Studying for the GRE, which the graduate school she applied to required, and returning for a three-year master's program were daunting. Looking back, she says, "part of me was confident and part of me was really, really scared."

Subscribe to Kiplinger’s Personal Finance

Be a smarter, better informed investor.

Save up to 74%

Sign up for Kiplinger’s Free E-Newsletters

Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.

Profit and prosper with the best of expert advice - straight to your e-mail.

Sign up

Little data exists on older workers changing careers. A 2015 survey, "New Careers for Older Workers," by the American Institute for Economic Research found that anywhere from 16 million to 29 million people attempted a career change after age 45. Of those late-in-life career changers, the survey found that 82% succeeded in making the shift, which came with a nice payoff. Most of the survey participants reported they were happy (87%) and less stressed (65%) after the change.

For some people, pursuing another profession is a long-held dream; for others, it's an unexpected leap into the unknown when a job disappears. Sometimes, boredom motivates a retiree to explore a new occupation. Whatever the scenario, before changing your life and livelihood around, think about why you want to take this step and what the driving force is behind it, says Toni Frana, career services manager at FlexJobs, a website for flexible and remote jobs. Do you need a new career or just a new job? FlexJobs's website has a four-step assessment to help you decide which one it is. "It's amazing how many people grow disenchanted with their jobs because of their colleagues or managers," says Nancy Collamer, a retirement coach in Langhorne, Pa. If you like what you do but dislike the people you work with, it's probably time to leave your job but not necessarily your field.

If you know a career change is right for you but don't know exactly what you want, you'll need to do more soul-searching. For instance, do you want to work for someone else or run your own business? Remote or in person? Full-time or part-time? Once you know what you want, here's the most important question you'll need to answer: Just how do you plan to launch a new career? One way or another, you're going to need a roadmap to navigate this journey.

Financial Realities

You can blue-sky the next possibilities all you want but your dream job will remain a dream if you can't earn enough to survive. You may not have to earn more or even as much as you did in your past career, but be realistic about the lifestyle you expect to maintain and how much it will cost. According to the survey by the American Institute for Economic Research, half of respondents earned more in their new career, 31% earned less, and the rest made about the same.

There are also the costs, both time and money, associated with transitioning to a new profession, such as enrolling in school, finding investors or building up a clientele. "We say a job search can take three to six months, but a career change can take much longer than that depending on where you're starting from and what is required in the field in terms of certifications," Frana says.

Research has shown that people with extra financial resources during the transition usually felt better about their new career than those who made the switch without those resources. "People do read stories about the person who goes from accountant to owning a vineyard, and it sounds really attractive. But the reality is it's hard to do," Collamer says. For radical shifts, you'll need "financial flexibility, because it's generally going to be some time before you can generate income."

That proved true for Cathy Miller, 57, of Ontario, who worked for 22 years in marketing and public relations for the home décor store Crate and Barrel in Canada and the U.S. She was laid off during a downsizing in 2016, and although she was upset about losing her job, she didn't want to do the same thing. A small family inheritance allowed her to hit the pause button before jumping into another career. After mulling it over, she went back to school for a nursing degree. "I was interested in it, but it was also a practical decision," she says. "There are lots of jobs for nurses and should be for a while. I knew I would be able to find work."

Paying for four years of college, however, was out of the question. Miller found a two-and-a-half-year degree program and is now a nurse. She credits that financial cushion for letting her take so much time off.

Fiore and her husband, who worked full-time as a journalist until retiring this year, took out a home equity loan to pay for her three years of tuition and cut back on everything else. "I started clipping coupons. I canceled the house cleaner, and we didn't take any trips," she says. "We got rid of anything we didn't need. We eked it out."

A Good Match for a Lifetime of Skills

A career shift doesn't have to be radical. When coaching people who are considering a different career, Collamer asks them about their work history and meaningful volunteer experiences. "What are the skills and projects and accomplishments that you are happiest doing, that you find most meaningful, that you really value?" she says. "When people have an opportunity to sort of step away from the anxiety and the frustration that they have with the job and really begin to analyze, they often discover there was a lot about the work that they enjoyed." Build on those parts and pieces you enjoy, she says, to find the path forward.

John Myers, 65, of Albuquerque, N.M., a former vice president at a utility, was already accustomed to thinking this way. "I started off as an engineer, but every time I was promoted, I would think, what skill sets can I bring to this job and what are the skills I need to be successful?" he says. "I would acquire the skills I didn't have, monitor my own progress and make adjustments."

He just hadn't planned on needing any special skills when at age 53 he retired from the utility company. It was a short retirement. "After three months of playing golf with my buddies, I needed something to challenge my brain."

Myers took a one-year job in Florida for a company that built wind farms, but he didn't love it and returned to New Mexico. By then, the country was in the midst of the Great Recession, and Myers knew what he didn't want -- to work for a corporation. His strategy for finding a new line of work was unusual to say the least: He considered which businesses getting crushed by the recession would probably bounce back.

Even though real estate was tanking, Myers had found his new career: buying and selling properties. "The market was horrible, and everyone thought I was an idiot," he says. "But people always have to have a place to live. I jumped in with both feet."

He earned his real estate license and purchased bank-owned properties and turned them into rental property. He flipped homes. He took a class to learn how to do short sales, and when the real estate market recovered, he started Myers and Myers Real Estate (there is no second Myers; he just thought it sounded classier that way).

His wife worked, but if the housing market had continued its downward spiral, they could have faced serious financial hardship, says Myers, who often put in 80 to 90 hours a week at the time. To learn what he needed to thrive in real estate, he turned to everything he could find -- books, webinars, videos and podcasts. He invited everyone he could think of to lunch or coffee for their advice. "Most people are happy to share information," he says. "Now I share as much as I can."

When figuring out the talents you bring to a new career, think beyond specific, concrete skills to broader abilities, such as relationship-building, leadership and time management. "One thing everyone is looking for is adaptability and flexibility to deal with disruption," says Marc Miller, founder of Career Pivot, in Austin, Texas. "Reflect back on your career and how you've dealt with disruption," he says. Then ask yourself how you might apply that resilience in a new profession.

Test Drives and Footholds

Learning new skills or boosting existing ones is much easier now than in the past when that training often involved returning to school for two or four years to earn a degree. Community colleges, online education providers such as Coursera and industry groups offer in-person or virtual short-term courses that lead to certificates.

It's also simpler to test drive a new line of work. For example, one of Collamer's clients, a retired executive, wanted to bring in some income and loved walking his dogs. He read that dogwalkers can make pretty decent money, so he went on rover.com -- a website that offers all types of pet services -- put up a profile and started getting gigs walking dogs. "It was an easy way to test out doing it," Collamer says. "He did end up starting his own dog walking business." Websites built around the gig economy, such as flexjobs.com, fiverr.com and taskrabbit.com, are great places to try a new occupation without a long-term commitment, and sidehusl.com reviews and rates these gig economy sites. For other jobs for retirees, see our Great Jobs for Retirees.

Of course, not all fields make it easy for newcomers without experience to get a foot in the door. If that's the case for you, consider offering your services free for a short time. You may also need to be creative about getting some experience. For instance, someone who wants to become a professional photographer might ask a friend who is getting married if it's OK to supplement the professional photographer by taking pictures at no charge, suggests Collamer. That can help build a portfolio. But move away from freebies as soon as you can. Too often, career changers "end up working for very little money and feel taken advantage of," says Career Pivot's Marc Miller.

The transition from being an expert in your old field to a novice in a new one can also be rough on the ego. "I was so nervous the first few weeks in school. I wondered if I could do it," says Cathy Miller, who went back to school for a nursing degree. "I had been a great student, but it had been years since I was in a university. You really have to be humble and ask for help, and that's not easy."

At one job, the learning curve was so steep that she wasn't sure she could do it. What she discovered, though, is that while not all nursing positions are to her liking -- she doesn't want to work in a hospital, for example -- there are others she is great at and loves. "I'm so glad I did this," she says. "Stepping out of your comfort zone is so rewarding."

Finding Fulfillment

For some people, a career change is not about seeking a challenge, but a more satisfying life outside of work. Lisa DeMers spent two decades working in the financial service industry for major banks in California. In November 2020, with the pandemic roiling employment everywhere, she was laid off. DeMers, then 57, knew she didn't want a job with as much responsibility and stress. She wanted to leave work behind when she left the office for the day. "I was more interested in time off and schedule flexibility than salary," she says.

Her husband, who is retired, had been wanting to move to Boise, Idaho, for years, so they decided to take the plunge. DeMers started looking on job websites and applied for a number of positions in Boise, but nothing was clicking until she found one that seemed to check all the boxes: client experience coordinator for an accounting firm.

DeMers landed the job. Her colleagues are pleasant, the work environment positive and her schedule as flexible as she had hoped. She did take a large pay cut, making one-third of her former salary, which even with the lower cost of living in Idaho is a lot. "I had to really adjust what I was willing to settle for," DeMers says, but she likes where she ended up.

So does Fiore, the journalist turned therapist. Although she misses aspects of her old job, she now has a successful practice, is her own boss and makes more money while working three-and-a half days a week. "I know I will be able to do this work, barring health problems, until I'm 90," she says. "I really love it, and that makes the risk worth it."