Great Jobs for Retirees

·16 min read

Chanda Torrey found retirement wonderful for the first two weeks. Then, not so much.

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Torrey, 50, of West Palm Beach, Fla., retired in mid 2019 as a Red Cross regional chief development officer. At first, she thought retirement was "paradise," she says. "But after a few months, I didn't know who I was. Not having a goal or something to do every day had an effect on my mental health."

Torrey's experience is not unusual. Retirement may sound wonderful in the abstract, and for some, it's a perfect opportunity to leave the working world behind and travel, volunteer or spend time with grandchildren. But for others, a job is a necessity, either for their finances or for their psyche.

And now the fall-out from the COVID-19 pandemic has left some older people facing particular problems. Some have been forced into retirement before they were ready, and many new and existing retirees have seen their savings plummet along with the stock market.

How do you assess your next step? First, ask yourself some questions. Do you want to work full-time? If your finances don't require full-time work, is part-time a better fit? Are you eager to tackle a whole new career, or do you want to continue primarily in the field you just left? Do you want something that can be all-consuming, such as starting your own business, or a more low-key job with fewer responsibilities? (For more self-assessment advice, see below.)

The outlook may seem grim for finding a job now, particular for those over 50. But there are new possibilities for older job seekers, says Marci Alboher, vice president of, a nonprofit that encourages seniors to use their skills and experiences to help communities. "I think we're going to be seeing needs and oppor­tunities where they weren't before," she says.

For example, with many jobs moving online in March, remote work is likely to become more acceptable to employers than in the past--and many older Americans might be willing to venture into that arena after experimenting with Zoom, Skype or other video chat services and becoming more comfortable with the technology. Plus, remote work is a trend that will likely gain momentum. A recent report from the Brookings Institution predicted that telecommuting would continue long after the pandemic ceases.

New opportunities

Torrey knew what she wanted to do for an encore career. For years, she had thought about starting a website that sells unique gifts from other companies. But she didn't have the time and energy to launch it until she retired. "I did not go back to work for money," she says. "I needed to learn something new, to challenge myself."

For $2,000, she hired an expert to show her how to develop a website and to troubleshoot problems for her. Torrey's background in nonprofit organizations was helpful because she was able to figure out how to make things work with limited resources.

Last November, her site,, went live. She does not sell directly to customers; rather, the companies she links to give her a percentage of the sale. Torrey also offers a free concierge service that will scour the internet for just the right gift.

She currently makes about $600 a month from her site; in a year, she anticipates her income will be $1,500 a month. In five years, "it will be easy money," she anticipates.

The work is wonderful and ter­rifying, Torrey says. "The scariest moment was when I clicked publish and the website went live. I thought I would swallow my stomach," she says. "I was worried about people judging me and finding something wrong. I ended up selling three items that first day."

E-commerce will continue to be a field with plenty of opportunities. Another growing field is health care, with needs ranging from care workers to medical technicians to people who can handle the administrative work related to the medical industry. That includes the relatively new area of patient advocacy.

AnnMarie McIlwain, 59, was in a good position to become a patient advocate. McIlwain is a former business consultant to the pharmaceutical industry, but she always wanted to be an entrepreneur. She tried to start an online job search site, but it was never profitable.

But after taking care of her father-in-law, who had advanced cancer for many years, McIlwain learned that she was very good at supporting and negotiating his medical needs. "I did a business plan and concluded that I could be both competitive and successful" as a patient advocate, she says.

McIlwain, who lives in Summit, N.J., worked on targeting all the areas where her customers might come from, which meant networking, building a strong website and improving search engine optimization -- crafting her online listing so that people looking for a patient advocate could easily find her.

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"Google is my best friend," she says, because it's how most of her customers find her. As her business has grown, however, she is getting more referrals from former clients and health care professionals. McIlwain's company, Patient Advocators, was successful from the get-go, she says. She estimates that most patient advocates charge between $150 and $400; McIlwain charged $95 at first and has increased her fee to $225. At any one time, she works with 10 to 20 people.

Trisha Torrey (no relation to Chanda), who founded the Alliance of Professional Health Advocates and is now its executive director, says most people come to the profession because, like McIlwain, they have had to navigate the health care system for a family member or for themselves during a medical crisis.

Torrey, 68, of Leesburg, Fla., also reinvented her career. She previously ran a marketing consultancy that helped small businesses move online. Then, in 2004, she was diagnosed with a rare and terminal lymphoma. She sought a second opinion, and it turned out the doctors and labs were wrong -- she did not have cancer. "Afterward, I was relieved but also so angry," Torrey says. "I started learning about health care and speaking to patients in an effort to help them make smarter decisions."

In 2009, she launched the Alliance, a professional organization that offers information and a national directory of patient advocates.

You don't need a clinical background to be an advocate; the role is not to offer medical advice or refer doctors. Rather, an advocate guides and supports a client through what is often a confusing and frightening process when a serious illness hits.

But you do need "hustle, assertiveness and a willingness not to accept some answers that are good for the medical system but not necessarily for your client," Torrey says. (For help in deciding if patient advocacy is a good path for you, visit

Being a great advocate, however, isn't enough. You must also be ready to run a small business. "You have to be willing to ask for money," she says. You also need to do your own marketing, finances and administration, or hire someone to help you.

SEE ALSO: 7 Great Part-Time Jobs for Retirees

Torrey estimates that getting a patient advocate business up and running costs about $5,000. That includes getting certified (although that's not a requirement), buying liability in­surance and building a website. One option for getting started is to offer your services as a volunteer through friends or a community group. However, Torrey suggests doing it quietly and only for a short time so that clients don't come to expect free services.

Leveraging your expertise

If making extra money is your primary motivation for going back to work, then your best option is to look for a job in a field similar to your previous career. "It's really important to focus on what you are able to do right now, where you have your biggest and best skills and experiences, versus changing to a brand-new career field or following your passion," says Brie Reynolds, career development manager for FlexJobs, a job board and resource for remote, part-time and flexible work.

Think about what you can do as a contractor or consultant,'s Alboher suggests. "Return to your existing network and see what opportunities exist. Sometimes it's an advantage that you're not looking for a full-time role, that you don't need health insurance, that you don't need an office to sit in. In fact, it could make you a more attractive candidate."

Be creative. For example, can you use your current knowledge to carve out a niche in another career? One way to leverage your expertise is by teaching and training, either remotely or in person. That includes positions both in K-12 and in postsecondary schools, such as adjunct professors, tutors, curriculum designers and paraprofessionals, who assist teachers.

One new company, Getsetup), hires people 55 and older to tutor others on how to use online tools, with sessions ranging from learning to use Uber or Lyft apps to creating a LinkedIn profile to working with Google Classroom. The company offers 40 different courses; customers pay anywhere from $10 to $90 for a one-hour class, depending on content and whether it's a small group or a one-on-one session.

Most (although not all) of the clients are seniors. The idea is that older folks often find it harder to be taught by younger people because their comfort with technology can lead them to make assumptions about what the customer knows and become impatient, says Neil Dsouza, founder and CEO of the company. (Dsouza, 35, says he has been known to lose his patience when helping his mother.) "We don't address the skills gap, but we address the fear gap of learning something new," he says.

The teachers -- or guides, as they are called -- are paid $25 an hour. They receive clients through the company, so they don't have to market themselves. Guides are asked to work at least five hours a week, but there is no contract.

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To start, prospective teachers go through a one-week online training, with a specific curriculum for each topic. Then they spend one week shadowing a veteran guide before developing and presenting a mock lesson. About one-fourth of the prospects either drop out or are told they wouldn't be a good fit, Dsouza says. So far, the company has trained 1,500 guides.

Glenda Springer, 59, retired in 2018 from a part-time job in customer service in the airline industry. She went back to school to get a master's degree in education before she left her job, then started teaching a variety of classes, including professional development for teachers and English for Chinese children and adults.

Springer started working with Getsetup in March. "It's addressing the immediate needs of people, which I find refreshing. It's in real time, and it's practical," she says. She also enjoys learning about new technology -- so, unlike some guides who stick with one program, she teaches a number of topics, including screencasting, how to find exercise programs online, and how to stay connected with family and friends.

"You need to be patient, and you need to be able to come up with a solution quickly because you are on camera," Springer says.

Having a basic understanding of technology used in the workplace is a good idea if you're considering returning to any type of job or career these days, says Reynolds. One way to do that is have a familiarity (not necessarily proficiency) with common technology, such as Google Drive, Slack, video chats and Excel. Reynolds suggests looking at YouTube for helpful tutorials and at sites such as or; you can experiment with how the tools work during their free-trial periods. A profile on LinkedIn is also a job-hunting and career-building staple. Besides tapping potential employers and useful contacts, you can get advice about enhancing your skills.

New adventures

Then there are retirees who are looking for a job as far away as possible from a desk or computer. Welcome to the job site, which offers jobs in remote places and has a section specifically for retirees 54 and older called "Older and Bolder."

The site primarily caters to seasonal work at national parks, ski areas, dude ranches and similar locations. Those locales can especially appeal to retirees who are traveling around in RVs, says Matt Moore, vice president of CoolWorks, because many of the places offer free hook-ups for their vehicles.

The jobs, which generally last four to five months, usually don't pay more than $17 an hour; many pay less, Moore says, and are typically full-time. Some offer free room and board or charge a nominal rent. "Most of the places are pretty remote and can't pull on the local community for jobs," he adds.

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Moore suggests that older workers look at the national parks, which hire thousands of people per season, because they are likely to have a wider range of jobs and housing options. Hiring for the summer begins around Christmas and for the winter around mid August, he says--although this year, due to the pandemic, far fewer employers than usual are hiring. If you're hesitant to commit for several months, you can always try the shoulder seasons--late summer, early fall--when employers need additional short-term workers.

And don't let the fear that you're not as fit as younger workers discourage you, Moore says. Jobs working in reservations or in accounting, among others, are available and won't keep you on your feet all day.

Donna Perry, a New York native, was miserable as the manager of a dental practice in Florida, where she had worked for 16 years. A patient had told her about CoolWorks years before; she would occasionally check out jobs but was too afraid to make the leap.

Then in 2015, her parents died in quick succession. "I was 55, and I said, I'm not dying behind a desk." She applied for a job she found on the site, at a bed and breakfast in Montana, that required everything from handling reservations to doing housework and cooking breakfast. Two weeks later, after a Skype interview, she was offered the position. She sold her house, packed up her car and dog, and drove cross country with her daughter, a newly minted college graduate.

Says Perry, "When I was leaving Florida, my friends were incredibly supportive, but my aunts and uncles thought I was out of my mind." But, she says, it was the best decision she ever made. The job was a perfect combination of her management experience and her love of cooking (which she completely took over for the bed and breakfast). And she was 12 miles from Glacier National Park.

She worked there for about five months, then returned for three more summers (she bunked with family in New York or Florida in the off season), until the owners decided to sell the place. She made a little above minimum wage, but wasn't paying rent or board, and she managed to save money. On one of her breaks she went to England on the cheap by finding a pet-sitting job there.

Perry, now 60, was working as a chef at a Cornwall, N.Y., inn until the pandemic hit. She has been offered a place to live at the inn, "but I want to keep moving," she says.

"My daughter asks me, 'Do you think you've gotten this out of your system?' And I tell her I'm going to keep this lifestyle happening as long as I can."

Earn extra money from home

If you would prefer to earn extra money by working for someone else, consider scanning the listings at a job board such as FlexJobs or Both list employers offering remote work right now, including jobs in customer service, health care, and computer and IT services and sales.

Jobs such as customer service have "lower bars to entry," says Brie Reynolds, career development manager for FlexJobs. For example, recent postings on FlexJobs included customer service reps for United Healthcare, Wayfair and Liveops, which operates call centers.

FlexJobs offers some free job-related information, but to access the full listings you have to be a paid member (subscription packages start at $14.95 for one month). is free. AARP also sponsors a free job board with filters for location at

What are your goals?

Alison Bouwmeester, 59, spent 28 years working at the CIA, and then another 10 years in the defense contracting in­dustry. She now runs her own business, Futurity, as a career coach. She has also written a book, Mission: Career Transition, aimed at retiring federal employees. What she found while interviewing former government workers is that people who leave a long-term career tend not to stay put very long -- often just a year or two--in the first job they take as they transition out of that career.

"Sometimes it's not a great fit; sometimes they want to move on to something else," Bouwmeester says. "When I'm coaching people, I need to persuade them that they've had their career. Whatever they do next is not a mistake, because they'll learn a lot and then move on to something else."

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She uses herself as an example: She didn't find the first job she had after leaving the CIA very fulfilling, "but it took going through that step to realize what mattered to me and what didn't." Leaving any long-term career, she says, involves thinking about what you really want. These questions can help clarify your goals:

  • Do you want to work? Why?

  • What are your monthly expenses, and what is your income, including from pensions and Social Security? What are your future financial needs?

  • How ambitious do you want to be in your next step? How important is having a prestigious job and title?

  • What is your vision for your future, and what do you want your legacy to be?


Copyright 2020 The Kiplinger Washington Editors