Picture a 58-year-old getting the band back together, literal instruments, amplifier, van, and all, or dusting off a skateboard he hasn’t touched since the Reagan administration, and calling it a retirement plan. Financial planners have given this a name: “retiring backwards,” a wave of Gen Xers returning to the hobbies of their youth instead of dreaming up new pursuits the way baby boomers did.

Benjamin Brandt, the founder of North Dakota’s Capital City Wealth Management and the host of the YouTube channel “Even Better Retirement,” has watched the pattern develop across his client base and offers a clean explanation for why.

“Baby boomers look forward and make a guess,” he says. “Whereas Gen X is going backwards with known information.”

Sherry, the host of “This Gen X Life,” puts it this way: “The ’90s lifestyle might be the only way you retire at 62.” Down the age scale, the children of Gen X are dominating the zeitgeist as Gen Z’s love of all things analog revives many of the specific hobbies their parents grew up with, from physical media collecting to film photography, thrifting, arcade-style gaming, and even going to the movies. Where Gen Z seems to go along as an antidote to digital overload, the same hobbies are the only retirement lifestyle that many can afford.

These hobbies have a known cost, a known social circle, and no startup risk. It sounds whimsical, but Generation X is approaching retirement with roughly one-third of the savings baby boomers had at the same age, no pension safety net, and financial obligations to both aging parents and adult children at once. The slacker generation of latchkey kids has become the sandwich generation with a full house of both grandparents and children.

Strip away the nostalgia framing and what’s left is a generation adapting to scarcity, and a slow-motion shift into retirement like the fadeout on a cassette tape.

The largest generational wealth gap

In December 2023, Fortune reported Gen X has “the largest wealth gap of any generation.” Dan Doonan, executive director of the National Institute on Retirement Security, warned at the time that “the American Dream of retirement is going to be a nightmare” for many in the cohort.

The Schroders U.S. Retirement Survey for that year found Gen X expected to need $1.1 million to retire comfortably, but projected having only about $660,000 saved—a gap of roughly $450,000. Deb Boyden, head of U.S. defined contribution at Schroders, told Fortune the stakes were higher and the margin for error lower. Schroders’ most recent surveys show the gap hasn’t closed—if anything, it has calcified. The shortfall between what Gen X believes it needs and what it expects to have saved still exceeds $460,000, an almost identical gap, and the generation accordingly has little confidence it can comfortably save for retirement.

Northwestern Mutual’s 2025 Planning & Progress Study found Gen X believes it needs $1.57 million to retire comfortably, a number that sits uncomfortably next to what it actually has saved up. A separate 2025 analysis from the Retirement Income Institute’s Alliance for Lifetime Income found median retirement savings for the cohort sitting at just $6,000 for women and $13,000 for men, describing Gen X as having “a fragile retirement foundation” that could leave it entering retirement “less secure than any generation prior”.

Going backward with known information, in this context, means recalibrating what retirement actually costs. A band is cheaper than a golf membership or a second home, and a skateboard doesn’t need a cruise itinerary.

A generation without a floor

Baby boomers retired into a system built to catch them. Over 50% of the generation had traditional pensions guaranteeing a fixed income for life, freeing them to plan retirement around aspiration rather than arithmetic. That option wasn’t available to Gen X. Only 14% have pension access, making Gen X the first American generation to retire almost entirely on self-directed 401(k)s—plans that didn’t widely exist until they were already years into their careers. Only about half of Gen Xers even participate in a workplace retirement plan.

Confidence has cratered alongside the savings gap. Just one in four Gen Xers say they’re confident in their retirement plans, with worries about Social Security’s future compounding the anxiety. Only 18% describe themselves as “very confident” they’ll be able to fully retire with a comfortable lifestyle, and subsequent Nationwide research found 16% say they’ll retire later than planned, while 15% say they don’t know if they’ll ever retire at all.

Caught from both ends

The slacker generation of latchkey kids has become the sandwich generation with a full house. According to a 2024 Harris Poll for Nationwide, 56% of Gen X investors now provide financial support to both aging parents and adult children simultaneously. Nearly a quarter—23%—have reduced or halted retirement contributions specifically because of it, and 16% have already withdrawn from retirement accounts to cover the cost.

Debt compounds the squeeze. Gen X carries more debt across nearly every credit product than any other generation—mortgages, credit cards, and student loans. A New York Life survey found Gen Xers saved just $7,463 in 2024, compared with more than $12,000 for millennials in the same period, while carrying the highest average credit-card debt of any generation.

That caregiving math shows up in housing, too. Gen X buys multigenerational homes at the highest rate of any generation—19%, more than double the 9% rate among younger millennials—according to Jessica Lautz, deputy chief economist at the National Association of Realtors.

“The ‘sandwich generation’ of Gen X, caught between aging parents and dependent children, is the largest purchasers of multi-generational homes,” Lautz recently told Fortune.

It’s the retiring-backward logic applied to real estate: Rather than buying up or moving somewhere new in retirement, you bring everyone under one roof and split the costs.

For this story, Fortune journalists used generative AI as a research tool. An editor verified the accuracy of the information before publishing.

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