Between the higher cost of living these days and a shifting view of what retirement means as people live longer, healthier lives, side hustles have taken on new importance in the years after leaving full-time work — and a growing appeal.
Some 45% of retirees are currently working in some paid capacity, according to a 2026 survey by Western & Southern Financial Group. And many more would like to join them: A report last year by the financial services firm D.A. Davidson found that six in 10 retirees wish they had a side hustle to help support their ideal retirement lifestyle, and nearly two-thirds of those 50 and older who haven’t stopped working full-time yet are considering taking on a side gig once they do.
Money is only part of the motivation. Nearly two-thirds of the retirees in the Western & Southern study who are either working or considering it said their reasons were personal, most commonly about wanting to stay productive and mentally sharp, compared with one-third who cited financial necessity.
Similarly, among retirees with side hustles in the D.A. Davidson survey, more than half (55%) said they pursued the work in order to participate in an activity they find mentally or socially stimulating.
Experts say that fusing your interests with an opportunity to generate income through side hustles can be a smart and integral part of retirement planning, something that helps with financial, lifestyle and personal goals.
Intrigued? Here are profiles of side hustlers who have mastered this mix, along with the lessons and inspiration in their experiences for others interested in following a similar path.
Turning used items into retirement income
Throughout their careers, Wendy A. and Cevin Williamson have followed traditional advice to build a nest egg, diligently setting aside part of their earnings from work in tax-advantaged savings accounts. But they’re banking on their sideline reselling business — Nina’s Jewels, named for Wendy’s daughter — as a primary source of earned income once Wendy retires from her job in nonprofit consulting and the couple closes or sells their framing store, both because it’s lucrative and because it’s fun.
That wasn’t always the goal. By the time the couple married in 2017, Wendy, now 52, had been casually selling things online for about a decade, turning unwanted household items and gently used clothing into cash. The year after their wedding, the couple decided to get serious about growing the reselling business as a way to supplement their income, both now and after they retire.
They started by selling Cevin’s collection of vintage toys and tens of thousands of trading cards, learning more about the resale business in the process. Eventually, they began purchasing items they could sell from garage sales, thrift stores and other online vendors. They even bought the entire contents of an abandoned storage unit.
While eBay is the behemoth of online selling, the Williamsons have branched out to platforms such as Poshmark, Mercari, Etsy and Depop because each marketplace has a different audience, varying areas of specialty and a distinct vibe. “Not every buyer is on eBay,” Wendy says, despite its dominance in the space. She has had items sit for more than a year on eBay, then sold them right away after cross-listing them on another platform. As the couple learned more about reselling, they created the Nina’s Jewels YouTube channel to share their experiences.
In 2025, Nina’s Jewels had $75,000 in gross revenue from eBay alone, but Wendy says she knows many resellers who make well into six figures annually.
The couple formed a limited liability company in 2021 to keep their personal assets separate from the business. Their revenue from the venture primarily comes from reselling, but Nina’s Jewels also has other, smaller income streams. For example, the couple get paid for allowing Google to place targeted ads on their YouTube channel. The couple also have affiliate partnerships with brands such as Amazon that pay them a commission when customers click through and purchase items they’ve promoted.
The business delivers benefits beyond a healthy revenue stream, too. The couple enjoy going to garage sales and Goodwill stores together on weekends. “It keeps us in shape, keeps us active, keeps us going, and we love it,” she says. Environmentally conscious, Wendy also likes helping to give used items a second life and keep them out of landfills.
The big lesson: Limit your initial investment and protect yourself.
Whether you’re already retired or close to it, carefully consider how much money and time you’re willing to commit to a new sideline venture, says Nick Loper, founder of Side Hustle Nation, an online community and information resource for side-hustlers. “If I’m transitioning to a fixed-income situation, I don’t necessarily want to invest a ton of start-up capital,” he says. For example, when the Williamsons began selling, both initially and when they got serious about the business, they started with items they already owned, then invested that revenue in purchasing more inventory to sell; they did not pull any money from savings or income they needed to live on.
Also, consider how much time you have to devote to your side hustles, as well as how you want to spend that time in retirement. “The last thing you need is a second job that you come to dread,” Loper says. In the Williamsons’ case, reselling offers the couple an opportunity to spend time together doing something they love.
Also be sure to protect the savings you’ve amassed for your retirement years, advises certified public accountant Catherine Roe, president and CEO of Cowart Roe, an accounting and business advisory firm in New Orleans. Starting any business involves some risk — something could go awry and cause property damage, say, or a dissatisfied customer might threaten to sue. To minimize potential losses depending on the size and scope of your side hustle, you might consider getting liability insurance, which can cover any claims against the business. Or, as the Williamsons have done, you could form a legal business entity such as a limited liability company, which will keep your personal assets separate from those of the business.
Depending on the type of side hustle you take on and how big the business becomes, you might also want to line up an accountant and business adviser or attorney who, as needed, can answer questions and help manage challenges. “You want to have an array of professionals in your court,” Roe says.
Cashing in on what you know through side hustles
“Mostly retired,” with four grown children and 13 grandchildren, Todd Tripp, 62, prioritizes a flexible schedule that allows him both to spend time with family and to shuttle between homes in Utah and Alaska. Tripp, who has been an electrician, plumber and general contractor over the course of his career, has stepped back from his family-owned construction business, but he has found a way to use his lifetime of experience and make extra cash by dispensing advice to homeowners, remodelers and do-it-yourself repair people.
Three years ago, he learned about JustAnswer, a platform that pays knowledgeable professionals to answer questions from users, and reached out to learn more. Soon after the JustAnswer team reviewed his credentials, Tripp was fielding online inquiries ranging from how to fix a garage door opener to what to do about a leaky toilet to how to obtain the proper permits for a home remodeling project.
JustAnswer charges users a monthly membership fee of up to $65 based on the category of questions they need answered. Experts like Tripp get paid per answer. Between January and August this year, he had made $27,000 responding to users. He estimates that he spends a couple of hours on it per day, using his five decades of construction, trades and landscaping experience.
Depending on the category and how many questions they answer, experts can earn $2,000 to $7,000 per month, with top experts in categories such as technology and legal subjects earning as much as $14,000 per month, according to JustAnswer.
Part of Tripp’s success has been developing a rapport with some users, who return to ask him questions repeatedly. Recently, he advised one repeat customer in Massachusetts how to pot her lily bulbs for the winter.
“They get a hold of me, and it’s amazing how quickly you can make that connection,” he says. “And you just feel great when you get done helping them.”
The big lesson: Capitalize on the expertise you built over your career.
You can parlay the knowledge and contacts you have from a career or longtime hobby into side hustles, giving you the chance to be your own boss or explore something you’ve always wanted to do, says financial adviser Cade Bekanich, a certified financial planner and founder of West Pittston, Pennsylvania-based Park Lane Financial Group. He points to his grandfather, who collected coins while he worked full-time as a teacher. When he retired, he opened a shop that sells coins and precious metals.
“It really started with the relationships that he’d developed throughout his career,” Bekanich says — a network that his grandfather tapped to help him turn coin and metal sales into a profitable venture. That type of transition can be enormously rewarding, as Tripp is experiencing.
Besides JustAnswer, there are a number of platforms that can connect you with side hustles that pay for your knowledge and skill. Among them: Respondent, which enlists business professionals to provide their opinions on a wide array of topics, from remodeling to tech; and Wyzant and Varsity Tutors, two of several sites that enlist tutors in subjects from math and science to foreign languages and music.
Gwen Moran is a contributing writer at Kiplinger Personal Finance magazine. For more on this and similar money topics, visit Kiplinger.com.
©2026 The Kiplinger Washington Editors, Inc. Distributed by Tribune Content Agency, LLC.
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