Retirement Planning, Elder Law, and Senior Finance

1/15/2021 | By Annie Tobey

Retirement has changed over the past few decades, leaving many retirees looking for second acts after retirement.

When lifespans were shorter, retiring at the age of 65 gave people just a few years to relax and play with the grandkids; but some who retire today have too much energy to simply put up their feet. When pensions from long-held jobs were commonplace, retirement was typically secure and comfortable; but many retirees today don’t have sufficient savings to kick back and relax.

More Americans are working well into “retirement” years, business and finance publisher Kiplinger reported in May 2020. “Labor force participation rates for men ages 65 to 69 reached 39% this year, up from 28% in 1995. Rates for older women climbed to 30% from 17%, government figures show.”

In considering second acts after retirement options, ask:

  • Do I need money or fulfillment? The answer will influence whether you should pursue a job such as consulting that potentially pays well or one like visual arts that probably won’t, or whether you could simply become a “professional volunteer.”
  • What are my passions? Imagine spending your second act doing something you love!
  • What are my existing skills? Forty-plus years of experience has certainly built a skillset that can be useful in other jobs.
  • What skills could I gain from additional education? Whether you get a degree or simply take useful classes, a new skillset can take your work life in a new direction.
  • How much flexibility do I want or need? After working 9 to 5, Monday through Friday, for 40-plus years, you may want to take more days off. If your nest is empty, you may be willing to put in weekend hours.

Where will your second act after retirement take you?

Some late-life career options may be obvious to you, if they’re already a part of your industry – consultant, career coach, board member, advisor, tax preparer, and so on. Whether your reason is for fulfillment or finances, consider these less-obvious second acts after retirement.

1. Teacher or College Instructor

If you already have an advanced degree, you might be able to share your knowledge and experience with students at a university or community college.

On the other hand, you could meet younger students’ emotional as well as educational needs by devoting yourself to teaching elementary or high school. Check your state’s department of education website for certification requirements and programs or visit

2. Real Estate Agent

Realtor is one of the best second acts after retirement

If you’ve lived in your community for much of your adult life, you have a base of knowledge for helping people find a new home. Real estate agents are self-employed, which means you can set your own hours (though you’ll be subject to the schedule of clients).

The route to becoming a real estate agent begins with coursework on basics such as titles, deeds, contracts, and property ownership. Education is followed by a licensing exam, which you must pass, then file a real estate license application and find a real estate broker to work with (at least initially).

3. Caregiver or Health Care Worker

If you’d like one of your second acts after retirement to be of direct help to individuals, consider work as a caregiver or in the health care industry ­– for adults or for children. Although the salary of these jobs isn’t always commensurate with their importance, they can be very fulfilling.

If you’re a parent or grandparent, you won’t need childcare training to be a babysitter, but a refresher first aid course from the American Red Cross is advisable. Some organizations, such as Naborforce and Care Advantage, provide non-medical assistance to those who are homebound – think meal and snack preparation, errands, transportation, and companionship. You can also seek out specialized training to become a personal care aide, home health aide, etc.

4. Sports Coach

Recent retiree Joseph Tedino became a high school tennis coach. He was invited to coach by all three athletic directors who interviewed him. “Each [was] pleased with my cert­ification, enthusiasm for the game and (most important) my idle afternoons,” he said. Tedino received a stipend of several thousand dollars per season, which was sufficient for him.

Other coaches on the team taught him the ropes: “how to evaluate players, run skill-developing drills, boost the players’ fitness level, and give positive feedback to help them do their best in match play.”

Sports skills can be used to teach lessons, too.

5. Retail Clerk

Pick a field that you love so you can share your passion – and get discounts! Spend your time in a fashion boutique, learning about and promoting the latest fashions; in a running store, mingling with other runners; in a garden center, sharing your love for home gardening; in a craft store, dabbling in artistic pursuits; in a bookstore, drinking in the bestsellers; in a flower shop, designing floral arrangements; and so on.

The easiest path to working in retail is to become a clerk. If you have the entrepreneurial spirit and the means, you could open your own store.

6. Tasting Room Server

Wine is one of the best second acts after retirement

Few of us spend our careers surrounded by people having fun. But if you work in a brewery, winery, distillery, or other maker of craft beverages, that’s exactly where you’ll be! If you already have a basic knowledge of craft beer, wine, spirits, etc., working in a tasting room allows you to share your knowledge – and learn even more.

While most positions don’t require specific certifications for entry-level positions, you can take basic sommelier, Cicerone training, or Hospitality/Beverage Specialist training (for wine, beer, and other beverages, respectively). Those lessons are much more interesting than those freshman classes you took back in the day!

7. Visual Artist or Crafter

Your creative muse may have been hibernating during your decades working for corporate America, fulfilling after-work responsibilities, and living a non-stop lifestyle. Now that you’ve got some time on your hands, it’s time to let the muse out of the box!

Take a class from a professional. Open an Etsy shop or set up booths at local makers’ markets and craft shows. If your creative skills are in web design, graphic design, or other artistic pursuits valued by businesses, consider gig work. Which takes us to …

Gig work

The “gig economy” refers to jobs arranged through temporary contracts or assigned as freelance jobs, often using online platforms to connect with clients or customers. The benefits for workers include flexibility. The disadvantages include lack of health insurance and other benefits (which may not matter if you already have health insurance). Three top websites for connecting workers with clients are Upwork, Freelancer, and Fiverr. Consider some of these positions when thinking about second acts after retirement.

8. Writer

Writing is one of the best second acts after retirement

Perhaps you’ve been unwittingly sharpening your communication skills during your career. Chances are, your knife will need some honing, since your message and audience will change. Learn important communication principles from reading evergreen writing books such as William Zinsser’s On Writing Well: The Classic Guide to Writing Nonfiction, taking local classes (many universities have discounts or free audit options for senior adults), or joining a writing group. Writing groups often provide guidance in marketing members’ works, too.

Gig work outlets offer easy ways for writers to get writing experience (though not necessarily lucrative experience). Use the long-time rule of thumb for writers, “Write what you know,” to find assignments that benefit from your knowledge as a subject matter expert.

9. Virtual Assistant

Office skills that you gained during your career can be applied virtually. These include word processing, data entry, schedule maintenance, email correspondence, transcription, file management, and more. Gig platforms connect you with those who need your experience.

10. Driver

Uber and Lyft have gotten plenty of press lately. Both taxi-like jobs offer flexibility and can offer decent income, especially if you’re willing to drive during peak times. Driving jobs are also available for medical transport, chauffeurs, tour guides and drivers, food delivery, and so forth.

Before you finalize your decision when considering second acts after retirement, thoroughly research skills you’ll need, any necessary training, and probable income. Chat with people who are already in the field, and volunteer or intern to learn about the job firsthand.

Changes in retirement, health, and longevity over the past few decades have modified Americans’ later years. Be proactive to make the best of yours!

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Annie Tobey

Annie Tobey has been a professional writer and editor for more than 30 years. As editor of BOOMER magazine, she explored a diversity of topics of particular interest to adult children of seniors. When she’s not writing, she can be found running the trails or enjoying a beer with friends.

Annie Tobey