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Leaving your 9-to-5 behind doesn’t mean you’re done using that entrepreneurial spirit—there are ways to stay active, engaged, and even profitable during retirement.

By Kristine Gill
March 01, 2021
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Retirement planning centers around saving and investing enough money to last you from the day you stop working to the end of your life. But what if your calculations were off? Or what if you have plenty of funds, but you find that you're craving some industriousness in retirement?

Many seniors end up working well into retirement for a variety of reasons. Some want to have more money to spend, some want a bit of a cash cushion, some do it out of necessity, and others find that it keeps them active and entertained. Whatever the reason, there are several ways you can continue to work even after you've hit retirement age.

Consider real estate

When California resident Peggy Underwood retired a few years ago, she and her husband purchased a home east of Los Angeles with the intention of renting it out throughout the year both to afford the home itself, and to generate supplemental income. Six years later, the rental brings in nearly six figures a year.

“Using our home as a vacation rental has been a great way to generate income without owning a second home,” she says. “For us, that means having a locked closet or two for our personal belongings and heading out last-minute sometimes for weekend trips or visiting grandchildren.”

Underwood and her husband list the property on rental sites such as Airbnb and even handle the cleaning between visitors themselves.

Of course, if you own two homes, you might consider renting one of them out in the seasons you’re not there. Many retirees buy winter homes in Florida, for example, but only spend half the year in the Sunshine State. If that’s the case, you can make a good amount of passive income by renting the property out when you aren’t there.

Don’t want the hassle of finding renters or being a landlord? Look into hiring a company that can help you manage the property in your absence.

Personal finance expert Anna Barker of LogicalDollar cautions that relying too heavily on rental properties could have its downside, as well.

“While property can be a good investment, it’s not a very liquid asset,” she says. “This means that if you believe there’s any chance that you will need to use the money tied up in the value of the property, you may wish to consider an alternative investment to get you through your retirement.”

Start a business

In retirement, Underwood also started a business selling pickleball paddles for women that she designed herself. She did so with the intent of generating some passive income, and while she’s had to use some serious elbow grease to get things up and running, she anticipates great returns. The business has kept her busy and engaged, and she believes there’s a similar opportunity for most seniors.

“Whatever it is you do, whatever skillset you’ve got, you have to go out there and find the people who need what you have, wherever they are,” Underwood says. “It’s as true for retirees as it is for 30-year-olds or even teenagers. Maybe it’s teaching or writing, maybe it’s administrative work or consulting.”

You’ll set your own hours and work for yourself when you operate a business. What’s even better is that the money you’ll earn will go directly into your pocket.

Dave Hughes, a retiree and author of three books on how to engineer your ideal retirement, says it typically takes a minimum of one year for a new business to turn a profit. If you decide to start one, be patient or consider starting the business before you retire to give yourself a head start.

“For the past several years, the highest rate of entrepreneurial activity has occurred in the 55 to 64 age group,” Hughes says.

The good news is that in a post-COVID world, many of these enterprises can be undertaken remotely, from the comfort of your home.

“The one challenge here will be ensuring that seniors are sufficiently comfortable with using the internet, as well as any applications that may need to be used to get the job done,” Barker says. “Fortunately, there are a number of training options available for this exact point, and so anyone who is interested should ask any local training centers or even their local government for these opportunities.”

Find a side hustle

Millennials aren’t the only generation benefitting from the gig economy. Retirees have also found lucrative side jobs in everything from pet sitting to copywriting.

“Dog walking has seen a surge in popularity. It gets you out and can make you some extra spending money,” says Jody D’Agostini, CFP, an Equitable advisor. “If you love animals and the outdoors, then this is a great option for you. Also, house sitting. If you don’t mind sleeping in someone else’s bed, you can mind the property while others travel or go on vacation.”

If you’re looking for a way to maintain your skills and bring in the occasional paycheck, look into sites such as Rover.com for pet sitting services or Upwork for one-off writing, design and computer programming jobs. You’ll be able to choose when you work and for whom, without the pressure and commitment of a 9-to-5 job.

D’Agostini also suggests driving for Uber, babysitting, tutoring, and working the polls a few times a year for your local elections.

Use the skills you have

Many retirees turn to consulting after a long career with the same company.

“While the gig economy’s pickup work can provide some short-term income, most experienced professionals will find more lucrative and satisfying opportunities by building on aspects of their career accomplishments,” says career researcher and consultant Joanne Cleaver. “Often this involves consulting, training, mentoring younger professionals in one’s industry, and being available for short-term assignments.”

Susan Gilbert, a brand, book, and marketing strategist, suggests a novel approach to the same concept. Rather than charging companies for your expertise, you can use it yourself by writing a book about your skill set and career history. Similarly, offering an online course is a great way to use what you already have to reach a wider audience.

“Let’s say you had a successful pest control business that has now been sold. But people are always asking you questions about it—how you did xyz, etc.,” Gilbert says. “You can still stay active in your vein of genius and active mentally by stepping onto a global stage that earns income and personal satisfaction.”

Try part-time work

Part-time jobs at grocery stores, clothing retailers, and hardware stores abound. If you’re mainly looking for a way to get out of the house and on your feet for a few hours a week, these positions are typically hiring, and in areas where you might end up living. In the process, you can pick up new customer service skills or learn the ins and outs of retail.

Hughes also suggests some less conventional options, such as working as a tour guide or at flea markets as a vendor. The perks of part-time work, Hughes says, is that the flexible schedules allow for traveling and other activities. Seasonal work is also a nice reprieve.

“Many retailers ramp up at the holidays, and an added perk may be a store discount,” D’Agostini says.

Don’t think you have what it takes to try a new skill? Think again.

“There are job sites that are specifically for seniors seeking employment, such as Seniors4Hire, YourEncore, Retiree Workforce, and Workforce50,” D’Agostini says.

Sell your things

Community marketplaces are everywhere in the digital era, with everything from Craigslist to Facebook offering a way to sell directly to local residents in your area.

“You can offload items that you no longer need and want and make some money in the process,” D’Agostini says.

You can treat these venues as online garage sales, or opt to use them to sell more lucrative possessions.

“Collectors of stamps, antiques, guns, artwork, and albums could look to sell your collections for cash,” D’Agostini says. “Places like eBay and Etsy are good starting points.”

Have used clothing? Instead of Goodwill, try selling gently used items online.

“There are specific sites to sell your clothing online including accessories and jewelry,” D’Agostini says.

Consider the benefits

The benefits of working in retirement are plentiful, and reach beyond generating that extra spending money.

“It’s often said that there can be downsides of retiring, so working during retirement can help to keep you on your toes somewhat, without the issues that come from working full time,” Barker says.