15 Flexible and Fun Ways You Can Work During Retirement

Will working be part of your retirement?

Perhaps your answer is not just “no!” but a resounding, “HELL no!!!”

It may seem like an oxymoron to see “working” in the same sentence as “retirement.” By definition, isn’t retirement what you do after you stop working?

Not necessarily. Retirement comes in many shapes and sizes, and encompasses a wide range of possibilities. Ultimately, it means whatever you want it to mean.

You may find yourself working in one way or another after you retire. 

As many as 72% of all people (in the U.S.) are expecting that they will work after they retire, in one form or another.

This could be driven by financial necessity, the need to feel productive or relieve boredom, the benefits of socialization, or the desire to do something you’re totally passionate about. Hopefully, your decision to work will be part of the retirement lifestyle you choose as opposed to being forced to work.

If you plan to start your own business, you’re not alone. For the past several years, the highest rate of entrepreneurial activity has occurred in the 55-64 age group. These businesses can be anything: consulting, selling art or crafts, a flea market booth, training, speaking, freelance writing… just about anything you can imagine.

If you’re counting on income from your own business to make ends meet, you should realize that it will probably take at least a year, and often longer, before your business starts earning a profit. For this reason, it’s a good idea to start your business while you’re still working, so you can hit the ground running and be closer to earning a profit when you leave your full-time job.

You may prefer a part-time or seasonal job. These jobs allow you the flexibility to enjoy more free time, do some traveling, and indulge your passions and leisure pursuits while still earning money and enjoying social contact.

Here are some options for retirement work. Some involve temporary employment, while others are more entrepreneurial. There are many other possibilities, of course, but these examples should start the ideas flowing and expand your range of possibilities.

1. Catering bartender or server

If you’ve ever been to a banquet or reception, you’ve probably seen these people in their generic white shirts and black bow ties, staffing portable bars or serving dinner plates. This provides a flexible, part-time work schedule. Given that many of these events take place in the evenings or on weekends, these jobs are well-suited to those who won’t be tired after having just come from a traditional Monday-Friday, 8-to-5 job.

2. Tour guide

Being a tour guide can take many forms, and the demand varies depending upon the location and the season. This may involve being a narrator on a tour bus or a walking tour guide at a historical site or museum.

3. Seasonal park worker

If you live near any local, state, or national parks, ski resorts, golf courses, or amusement parks, most of these places have a high season that lasts only a few months. Both the parks themselves and the companies that operate the food and lodging concessions need to hire seasonally. Retirees who travel in RVs can drive their RVs to wherever the jobs are, and they may be able to park their RV on the property.

4. Seasonal mail order employment

Many mail order companies hire additional staff at their fulfillment centers during peak season, usually the weeks leading up to Christmas. This is another option for people who own RVs and don’t mind living in them for extended periods of time.

5. Seasonal retail employment

Similarly, many local retailers hire short-term workers to augment their staff during the holiday season. While I was in college, I worked for several weeks during my winter break at a Hickory Farms store at the local mall. They did 90% of their annual business between Thanksgiving and New Year. Most of their seasonal workers were either college students or retirees.

6. Pet sitting or dog walking

Many pet owners prefer to leave their pets at home in the care of a trusted person when they travel, rather than boarding them at a kennel. For some types of pets (birds, fish, hamsters, turtles, etc.) a kennel isn’t an option and having someone come to their home to feed their pets is their only choice. Some people might need someone to water plants or maintain pool chemicals while they’re gone.

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7. Repair service

If you enjoy fixing things, you could run a small repair business from your garage, in which you repair bicycles, lawn mowers, small appliances, or musical instruments – whatever skills you have. Another option would be a home handyman service. You could accept jobs or not, depending on your desired workload and travel schedule.

8. Holiday decorating or gift buying

Believe it or not, there are people who will pay others to decorate their homes for the holidays or do their gift buying for them. An acquaintance of mine traveled to Dallas every year around mid-November and spent six weeks decorating wealthy people’s homes (inside and out). A Retire Fabulously! reader has suggested inquiring at local malls about decorating for the holidays and taking the decorations down afterwards.

9. Specialty cake or cookie baker

If you enjoy baking and have good decorating skills, you can create delicious treats for parties, special events, or upcoming holidays. A friend of mine does this and promotes her goods via local contacts and Facebook posts. You can also look for upcoming festivals, events, farmer’s markets, etc. and inquire about selling them there.

10. Wedding planner or party planner

While it’s true that people can get married at any time of year, more weddings tend to take place during the summer, or whenever the weather is most pleasant in your area. The wedding industry is definitely cyclical. Similarly with parties, some times of year are more conducive to large, catered celebrations, such as graduation, Halloween, and end-of-year holidays.

11. Wedding officiant

If you have good public speaking skills, are well organized and reliable, and enjoy working with people, you can become a wedding officiant. You can obtain an Ordained Minister certification for free from online sources such as the Universal Life Church. That’s legally recognized in almost every state. Many people prefer to have a non-religious or lightly-religious wedding, or they may wish to get married at a time or place that’s inconvenient for full-time clergy with church responsibilities. A secular officiant can fulfill these needs.

I did this for five years after I retired. I officiated over 350 weddings and usually earned an average of $1,000 a month. It was tremendously fulfilling to be part of one of the most important events in a couple’s life. However, it requires a flexible schedule, an open mind, and a willingness to forgo other activities you might want to enjoy on weekends, such as parties or concerts.

12. Author or freelance writer

This may be the ultimate flexible work option. You can write from anywhere, and in fact, there’s a market for travel writers. As a freelancer, you can solicit assignments when you want to work and pull back when you want a vacation or you’re busier with other things. Of course, it’s a competitive business and you have to put a lot of effort into securing freelance assignments. If you lean more towards writing your own books, that can be very fulfilling, but there’s no guarantee of income. The income you do earn will be realized long after the book is completed. Most serious writers attest that in order to be successful, you need to consistently devote several hours every day to your writing.

13. Photographer

What is a hobby for most of us can become a source of artistic fulfillment as well as income after you retire. Wedding photography is one option, especially for those who desire cyclical engagement. The wife of a former boss runs a “boudoir” photography business and reports that there is quite a demand for this particular genre. Another recently-retired friend takes beautiful photographs of landscapes in the southwest US. He sells photos to calendar producers and displays his works at art shows.

14. Music teacher

If you are a retired music teacher or if you are sufficiently proficient on voice or one or more instruments, you can teach private music lessons. You can offer them from your home or travel to the student’s home, as you choose. You can also inquire at local music stores; they will take a cut of your fee, but they offer a neutral space for you to give your lessons and they can generate clients.

15. Antique or flea market vendor

This option allows for total flexibility in scheduling and provides lots of human contact. It is also appealing to RV owners who enjoy traveling to shows and events in other locales. One consideration to be mindful of is that you will probably end up accumulating more stuff, while most other retirees are focused more on downsizing. One friend’s mother got so caught up in flea marketing that her entire house became a warehouse for everything she acquired over the course of many years. It was a nightmare for her grown children to dispose of all of her possessions after she passed away.


These options just scratch the surface of all the possibilities for earning money during retirement. Many of them also allow you to engage in activities that indulge your passions and take advantages of your abilities.

What do you think you might do after you retire? Share your thoughts in the comments!

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© 2021 Dave Hughes.  All rights reserved.

Photo credits:
Walmart greeter:
terry stoudtSome rights reserved.
Banquet table: photosforyou
Forest service workers: USDA Forest Service Alaska. Some rights reserved.
Dogs: Matt Nelson
Wedding: Dave Hughes. All rights reserved.
Photographer: Devin Justesen

4 Responses

  1. Marilyn says:

    “You’re a better man than I am, Gunga Din!” A lot of my gainful-employment work in the past entailed sitting alone at my desk (copying music and proofreading), and I still enjoy doing some of that for the occasional client. But I have ZERO interest in interacting with the public, especially during these pandemic times. As our pensions are increasingly threatened and the stock market (where our IRAs reside) become more volatile, I DREAD being forced back into the work force by financial necessity! We’ve tightened our belts and downsized our expectations for retirement, in an effort to enjoy NOT needing to “go to work” again! ~♥~

    • Dave Hughes says:

      Hi Marilyn,

      You’re right, some of these options aren’t practical or safe during the pandemic, but hopefully that will be over later this year. And while the stock market was certainly volatile during 2020, it seems to have emerged pretty well. Let’s keep our fingers crossed!


  2. William says:

    I will be working with wood carvings and creations, and I want to work at like a campground or with a ranger, something outdoors. I am looking into forestry.

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