Build Your Side Hustle into a Retirement Job

Martha Himes
3 min readApr 4, 2019

Another aspect of retirement planning

What’s that you said, retirement job? Doesn’t that defeat the purpose of retirement?

If you’re not one of those people who could truly retire and sit around the house, you’re far from alone.

According to David Guydan of Boston non-profit Empower Success Corps, people are retiring younger. Some don’t need to make money, some do. Mostly they need to keep active. Everyone is happier with a purpose.

Empower Success Corps is developing Discovery Centers where trained facilitators (retirees) will assist other retirees in finding their “second act.”

“Forty-eight percent of adults over 50 want to be engaged in purposeful work. Purposeful engagement adds 7 plus years to life,” Guydan said in a lecture.

Photo by Lost Co on Unsplash

There is also a website, www.retirementjobs.com, where they post listings from “Certified Age Friendly Employers.” The certification is one created by RetirementJobs.com and is based on interviews with employer representatives. Companies must show a dedication to employing those over 50, have an age-friendly workplace, and must take seriously any claims of age discrimination.

We’ve all heard about retirees whose IRAs were wiped out, forcing them to go back to work. What I’m talking about is more of a supplemental income than a full-time job, and income for those who are too young to tap into their retirement funds or Social Security, which you can’t or shouldn’t access until you’re at least 60.

Working retirees are found in every economic demographic. I know two people who made enough money in their finance jobs to quit in their early 50s, their childrens’ college funds complete. One is now selling real estate, the other is still searching for her second act.

Many people need to supplement their Social Security checks, which is permissible up to a certain dollar amount. I’ve worked with realtors, golf course and retail store employees who have been working part-time because their Social Security didn’t cover all the bills.

Laborers who need a gentler job as they age are good candidates for second acts, too. A landscaper friend recently got his Construction Supervisor License with the plan to flip houses when he could no longer do the heavy lifting of landscaping.

But why wait until you retire to get started? If you build up your fledgling business as a side hustle while you’re still employed, you have the benefit of the income from your primary job while you’re still developing clients and experience for your retirement job.

Then, a few years later, you can transition that side hustle into your primary income (or supplemental to Social Security/IRA).

Photo by Debby Hudson on Unsplash

Obviously jobs that require extensive post-grad education, like architecture, law, or medicine, probably won’t be feasible for this scenario. But a lot of creative work fits right in. Any job that you can do part-time, such as real estate, bookkeeping, or consulting, can be a side hustle that grows.

Hobbies work for side hustles, too, if you’re willing to make them into a job. I know retirees who teach art, tennis and sailing lessons. The decades spent enjoying those hobbies have made you an expert ready to pass on your skills to a beginner.

It might take some creative thought, and trial and error, to find the right retirement job. Just because you like doing something doesn’t mean someone is going to pay you to do it. You might have a couple of false starts before you land on a profitable endeavor. Better to start the discovery process while you’re still employed than to wait until you need the money.

As another Empower Success Corps counselor, Willia Cooper, put it, you’ll “discover something new about your skills and how to use them in your encore life.”

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Martha Himes

Researched thinkpieces on trends and current events. If there’s a bandwagon, I’m probably on it.