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SuccessRetirement

Gen X retirees have regrets over how much they saved—they’re copying Gen Z and turning to side gigs

Preston Fore
By
Preston Fore
Preston Fore
Success Reporter
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Preston Fore
By
Preston Fore
Preston Fore
Success Reporter
Down Arrow Button Icon
April 28, 2025, 10:19 AM ET
With 41% of retired Americans feeling like their savings fall short, many are turning to part-time work for both income and company.
With 41% of retired Americans feeling like their savings fall short, many are turning to part-time work for both income and company.hobo_018—Getty Images
  • Millions of Gen X and baby-boomer retirees are panicking that their savings are not enough, with troubled Social Security, inflation, and market turbulence fuelling concerns. They’re turning to side gigs like teaching, selling real estate, and Uber driving for extra income and social stimulation.

Gen Xers and baby boomers have long waited for the day when they can ditch the nine-to-five work schedule altogether and enjoy their golden years in peace.

However, many are waking up to a worst-case-scenario financial reality: Their savings are not cutting it.

Over two in five retired Americans worry their nest egg won’t fund their ideal retirement, according to a new survey from investment banking firm D.A. Davidson. That is possibly equivalent to over 20 million Americans. And whether this was caused by not saving enough, inflation, or an unexpected life event, it is a frustrating sign for families who may have spent years living paycheck to paycheck—just to experience déjà vu in retirement. 

The “tides are shifting,” Andrew Crowell, vice chairman of wealth management at D.A. Davidson, told Fortune, with more retirees than ever deciding not to throw in the towel completely on work. Some 60% of retired Americans wish they had a side gig to supplement their savings.

“A side gig doesn’t have to be a last resort in retirement,” Crowell said. “It can actually be an integral part of retirement planning, supplementing savings while also encouraging engagement in the community and keeping the mind sharp.”

Gen X’s shifting perceptions of retirement 

Retirement can be a time of mixed emotions. Some retirees may be eager to relax with their grandchildren or finally find time to travel internationally, whereas others may not know how to function without the rhythm of their nine-to-five. It’s why, as life expectancy increases, people are not only working longer in their primary careers, but also making the pursuit of part-time second careers a norm.

“Unlike past generations, current retirees are staying active longer in retirement and living longer, which increases the amount of money they need throughout retirement,” said Patrick Doherty, senior vice president at Wealth Enhancement. “Generally, we see clients spending similarly in retirement as they did while they were working.”

Doherty told Fortune he has increasingly seen retirees take on side gigs alongside their retirement like being a substitute teacher, selling real estate, or serving on the board of a business.

However, it’s not always for the money. More than half, or 55%, of retirees with a side gig report doing it for mental or social benefits, according to the D.A. Davidson survey. Just 20% cite paying off existing debts as a motivator, and 17% said it’s to financially support their more ideal retirement lifestyle.

The cross-generational levitation toward the side gig

Retirees are not alone in their affinity for a side career. Gen Zers and millennials, too, are embracing the gig lifestyle. 

In fact, one survey found that nearly two-thirds of young people aged 18 to 35 have either started a side gig or plan to use one for supplemental income. Interestingly, their reason for doing so isn’t necessarily just for the money—but because they’d mostly rather be their own boss and follow their passions. 

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  •  

    And it makes sense considering how easy it is to start a side gig with the aid of technology. For example, many young people can earn extra dollars just by streaming video games on YouTube, dancing on TikTok, or selling products on Etsy. 

    For young people who play the side-gig game right—and save more than they spend—it can lead to a situation where retiring earlier, and in financial comfort, is possible. 

    “There is an old saying that says, pay ourselves first,” Doherty said. “If you contribute to your 401(k) and stock money away in brokerage accounts on a systematic basis before discretionary spending starts, you will find it easier to save.”

    Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
    About the Author
    Preston Fore
    By Preston ForeSuccess Reporter
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    Preston Fore is a reporter on Fortune's Success team.

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