Roughly one in three self-employed Americans reaches age 55 with less than $10,000 saved for retirement, according to estimates from multiple labor and retirement policy researchers. When I drove out to Milwaukee on a gray Tuesday morning in March to meet Robert Kowalski, I was about to meet someone living that statistic in real time — and not entirely willing to admit it.
Robert runs a small auto repair shop on the city’s south side. He has for 18 years. The bays were busy when I arrived, two cars up on lifts, a third waiting outside in the cold. But busy-looking and financially healthy are two different things, and Robert knew that better than anyone.
A Business Built on Skill — and Slowly Left Behind by Technology
Robert Kowalski is 52 years old, broad-shouldered, with oil permanently worked into the creases of his hands. He poured a cup of coffee in his cramped office before I could even take my coat off, and he made clear from the start that he didn’t usually talk to journalists about money. “I’m not really a complainer,” he told me. “I fix things. That’s what I do.”
What he couldn’t fix, at least not easily, was the shift happening across the auto repair industry. Newer vehicles — particularly models from the last five to eight years — increasingly require proprietary diagnostic software that only franchised dealerships can access. An independent shop like Robert’s gets locked out of the repair chain before a customer even calls.
Over the past three years, Robert’s shop revenue has fallen by roughly 30 percent. He told me the drop happened gradually at first, then all at once. He kept telling himself it was seasonal. Then he stopped telling himself that.
The Retirement Savings Gap That He Stopped Counting
When I asked Robert directly how much he had set aside for retirement, he took a long pause. “Not enough,” he said. Then, after a moment: “Almost nothing, if I’m being honest.” He has no IRA, no SEP-IRA, no 401(k). For most of his adult life, every dollar the business generated went back into the business.
As a self-employed business owner, Robert pays the full 15.3 percent self-employment tax on his net income — both the employee and employer portions of Social Security and Medicare. He’s been doing that for years, which means he has been building Social Security credits, even if he never thought of it in those terms. According to the Social Security Administration, workers need 40 credits — roughly 10 years of work — to qualify for retirement benefits, according to ssa.gov. Robert has well over that.
But qualifying for Social Security and relying on Social Security are two very different propositions. The average monthly retirement benefit in early 2026 sits around $1,976, according to SSA data. For someone who spent years reporting variable self-employment income — some years up, some years down — the actual benefit calculation may come in lower than average.
Robert had never looked up his Social Security earnings record. When I mentioned that the SSA’s online portal lets anyone check their projected benefit estimate, he shrugged. “I figured I’d deal with that when I’m old,” he said. He’s 52. In some retirement scenarios, that’s not far off.
A New Pressure: His Son’s College Costs
Layered on top of the business trouble is a development Robert is genuinely proud of, even as it adds financial strain: his oldest son was accepted to an out-of-state university with a price tag of $45,000 per year. Robert’s wife works, and her income currently covers groceries and utilities. There is no college savings account.
The son’s tuition creates a pull in exactly the wrong direction from a retirement savings standpoint. Every dollar that goes toward tuition is a dollar not going toward closing the savings gap Robert already faces. He acknowledged this plainly, without self-pity. “I know what I’m doing,” he said. “I’m just not sure how it ends.”
Robert told me he has started looking at what age he can realistically claim Social Security. He assumed — as many people do — that 65 was the answer. It isn’t. Under a change that took effect in 2026, the full retirement age for workers born in 1960 or later has moved to 67, according to cbs8.com. Robert was born in 1973, which means his full retirement age is 67 — and claiming at 62, the earliest possible date, would permanently reduce his monthly benefit by as much as 30 percent.
The Bigger Cloud: What Happens to Social Security Itself
Robert had heard the news about Social Security’s long-term finances — he’d seen headlines — but he hadn’t looked closely at the details. When I mentioned that projections suggest the Social Security trust fund could face depletion by around 2033, his jaw tightened. “That’s seven years,” he said. “I’ll be 59.”
He’s right to pay attention. Depletion of the trust fund wouldn’t mean Social Security disappears — ongoing payroll tax revenue would still cover an estimated 75 to 80 percent of scheduled benefits — but it would mean cuts unless Congress acts. Research from the Urban Institute has shown that benefit reductions ripple outward, hitting not just retirees but the small local businesses and communities that depend on that spending, according to urban.org.
For someone whose entire retirement strategy may hinge on Social Security, the program’s financial uncertainty is more than a policy abstraction. Robert put it bluntly: “If they cut it, I’m working until I drop. That’s not a plan. That’s just what happens.”
What Robert Is — and Isn’t — Doing About It
Robert is stubborn about accepting help, which he acknowledged with something close to a laugh. He hasn’t spoken to a financial planner — “that’s for people with money to manage” — and he hasn’t called the SSA to request an earnings statement review, though I mentioned it was free and took about ten minutes online.
What he has done is start looking at whether he can retool part of the shop for older vehicles — pre-2010 models that don’t require proprietary software — and whether there’s a market for that in Milwaukee. He’s also talked, reluctantly, to his son about loan options and work-study programs. Neither conversation was easy.
When I left Robert’s shop that afternoon, the light was fading and he was already back under a car. He hadn’t asked me for answers, and I hadn’t offered any. What he’d given me instead was an unusually clear-eyed portrait of a man watching the ground shift beneath something he spent two decades building — and trying to figure out, in real time, whether there’s anything left to land on.
At 52, with 15 years until his full Social Security retirement age, Robert technically has time to change the trajectory. Whether he uses it is a different question entirely. “I’ve been taking care of myself my whole life,” he told me as I headed for the door. “I’m not stopping now. I just wish I knew what that looks like in ten years.”
That’s not a question I could answer. But after spending a few hours in his shop, it’s one I haven’t been able to stop thinking about.
Sloane Avery Wren is a Senior Benefits Writer at Benefit Beat covering Social Security, Medicare, and government benefits. This article is reported narrative journalism and does not constitute financial or legal advice.
Related: The Medicare Deduction That Quietly Shrinks Your Social Security Check Every Single Month, according to thedailycheck.org
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