Imagine a 58-year-old dusting off a skateboard he has not touched since the Reagan years, or getting the old band back together: van, amplifier, and all and calling it a retirement plan. It sounds a little funny. But financial planners say there is a real logic behind it.
They have given this trend a name: retiring backward. Instead of dreaming up brand-new pursuits in retirement, as baby boomers did, a growing wave of Gen Xers is heading back to the hobbies of their youth.
Benjamin Brandt, founder of Capital City Wealth Management in North Dakota and host of the YouTube channel Even Better Retirement, has watched this play out across his client base. His explanation is straightforward.
“Baby boomers look forward and make a guess. Whereas Gen X is going backwards with known information.”
That known information includes the cost, the friends, and the gear; no startup risk, no guesswork. A band is cheaper than a golf membership. A skateboard does not need a cruise itinerary.
A Savings Gap That Has Not Closed
The numbers behind this trend are sobering. Fortune reported in December 2023 that Gen X carries the largest wealth gap of any generation. Dan Doonan, executive director of the National Institute on Retirement Security, warned that the American Dream of retirement could become a nightmare for many in this cohort.
The Schroders U.S. Retirement Survey found that 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. More recent Schroders surveys show that gap has not closed. The shortfall between what Gen X believes it needs and what it expects to have saved still exceeds $460,000.
Northwestern Mutual’s 2025 Planning and Progress Study put the target even higher: Gen X now believes it needs $1.57 million to retire comfortably. Against that number, a separate 2025 analysis from the Alliance for Lifetime Income found median retirement savings for the cohort sitting at just $6,000 for women and $13,000 for men. The Alliance described Gen X as having a fragile retirement foundation that could leave it entering retirement less secure than any generation prior.
The First Generation Without a Pension Floor
Baby boomers had a safety net most Gen Xers never got. Over 50 percent of boomers had traditional pensions guaranteeing a fixed income for life. That freed them to plan retirement around aspiration rather than arithmetic.
Gen X did not inherit that option. Only 14 percent have pension access, making this the first American generation to retire almost entirely on self-directed 401(k) plans, plans that did not even widely exist until Gen Xers 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 numbers. Just one in four Gen Xers say they feel confident in their retirement plans. Only 18 percent describe themselves as very confident they will be able to fully retire with a comfortable lifestyle. Subsequent Nationwide research found 16 percent say they will retire later than planned, while 15 percent say they do not know if they will ever retire at all.
Squeezed From Both Ends
The retirement gap is only part of the pressure. A 2024 Harris Poll for Nationwide found that 56 percent of Gen X investors now provide financial support to both aging parents and adult children at the same time. Nearly a quarter, 23 percent, have reduced or stopped retirement contributions specifically because of those obligations. Another 16 percent have already withdrawn from retirement accounts to cover the costs.
Debt adds to the squeeze. Gen X carries more debt across nearly every credit product than any other generation, including 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 same financial pressure shows up in housing. Gen X buys multigenerational homes at the highest rate of any generation, 19 percent, more than double the 9 percent rate among younger millennials. Jessica Lautz, deputy chief economist at the National Association of Realtors, recently told Fortune:
“The ‘sandwich generation’ of Gen X, caught between aging parents and dependent children, is the largest purchasers of multi-generational homes.”
Rather than buying up or moving somewhere new in retirement, many Gen Xers are bringing everyone under one roof and sharing the costs.
What Retiring Backward Actually Looks Like
Sherry, host of the YouTube channel This Gen X Life, sums up the retirement math bluntly: “The ’90s lifestyle might be the only way you retire at 62.”
Gen X is approaching retirement with roughly one-third of the savings baby boomers had at the same age. The old hobbies like the bands, the skateboards, the record collections have a known cost and a built-in social circle. No startup risk. No big investment required.
Strip away the nostalgia framing and what is left is a generation adapting to real financial constraints and finding a path forward that looks a lot like the past.
