With the April 15, 2026 federal tax deadline less than three weeks out, self-employed workers across the country are staring at one of the last legal windows to reduce their 2025 tax burden — by making contributions to a retirement account before filing. For most small business owners, that option feels straightforward. When I drove out to meet Robert Kowalski at his shop on the northwest side of Milwaukee on a cold Tuesday in February, that window felt like a cruel joke.
Robert, 52, has run Kowalski Auto Repair out of the same two-bay building on West Fond du Lac Avenue for 18 years. There is a whiteboard near the service counter where incoming jobs get chalked in. When I arrived just after noon, two of the four bays were empty. Robert wiped his hands on a red shop rag and didn’t offer much of a greeting. He said he’d talk to me, but he made clear he wasn’t looking for advice.
A Business Built by Hand — and Slowly Cornered by Code
Robert started the shop in 2008, a year most business owners would rather forget, with $14,000 he had saved working for a dealership. For about a decade, the gamble paid off. He built a loyal customer base in a working-class neighborhood, offered competitive labor rates, and kept overhead low by doing much of the work himself. At his peak, around 2020 and 2021, he told me his gross revenue ran close to $310,000 annually.
Then the cars changed. Modern vehicles — particularly those manufactured after 2019 — increasingly rely on proprietary software and dealer-only diagnostic systems. Certain repairs that Robert could complete in two hours on a 2015 model now require a dealer scan tool he doesn’t own and, in some cases, a manufacturer authorization code he can’t obtain. He started turning away jobs he used to take without a second thought.
By the end of 2025, his annual gross had fallen to approximately $217,000 — a drop of roughly 30 percent over three years. After parts, rent of $2,800 a month, liability insurance, utilities, and equipment maintenance, Robert estimated his net came in around $49,000 last year. That is down from closer to $76,000 at his peak.
The Retirement Number He Didn’t Want to Say Out Loud
I asked Robert directly: how much does he have saved for retirement? He looked at the whiteboard for a moment before answering. “About nine thousand dollars,” he said. “Maybe a little more. It’s in a savings account.” He is 52 years old. He has been self-employed for nearly two decades. He has no 401(k), no IRA, no pension of any kind.
This is more common than most people assume. According to data from the U.S. Department of Labor, self-employed workers are significantly less likely to have retirement savings than those with employer-sponsored plans. Without automatic payroll deductions and employer matches, many small business owners treat reinvestment in the business as a substitute for saving — until the business stops growing.
I walked Robert through the broad strokes of a SEP-IRA — not as advice, but as context for the story. His reaction was muted. “I’ve heard of those,” he said. “But I’m not going to lock money up when I don’t know what the shop’s going to do next quarter.” That reluctance, I found, runs through nearly everything Robert says about money. He sees financial planning as something designed for people who have already solved the hard problem of making a living.
His wife, Dana, works as a medical billing specialist and brings home roughly $38,000 a year. Between the two of them, their combined household income in 2025 was in the range of $87,000 — before Robert’s self-employment taxes, which he estimated cost him close to $8,500 last year on top of federal and state income tax. The IRS self-employment tax rate is 15.3% on net earnings up to $176,100, covering both the employer and employee portions of Social Security and Medicare. Dana’s income, Robert told me flatly, covers groceries and utilities. Everything else comes from the shop.
His Son’s College Dream and the $45,000 Question
Robert and Dana’s older son, Tyler, is 18 and was accepted this spring to a university in Indiana. The total cost of attendance — tuition, fees, room and board — runs approximately $45,000 a year. It is out of state. Robert told me Tyler has wanted to study engineering since he was in middle school, and Robert did not say it plainly, but it was clear he was proud of that.
What he said plainly was this: “I don’t know how we’re going to do it.”
Robert said they filed a FAFSA, but he was uncertain what would come of it. At a household income of roughly $87,000 with minimal assets on paper, the family would likely qualify for some need-based aid, but the bulk of that $45,000 — at least in year one — would probably fall on loans, a parent PLUS loan, or Tyler’s own borrowing. Robert said he hadn’t sat down with a financial aid counselor yet. “I keep meaning to,” he said.
The four-year cost, at $45,000 a year, would be $180,000. That figure — nearly four times Robert’s current annual net income — sat in the air between us for a moment. He looked at his hands.
Where He Stands, and What He’s Willing to Admit
By the end of our conversation, Robert had shifted slightly. Not dramatically — he still bristled when I mentioned phrases like “financial planning” — but he had started doing some of his own math out loud. He mentioned that he’d looked up Social Security estimates on the SSA’s online portal a few weeks before we met. At his current earnings trajectory, his projected monthly benefit at full retirement age (67) would be somewhere around $1,640. At 62, if he claimed early, it would be closer to $1,150.
“That’s not enough to live on,” he said. It was the most unguarded thing he told me all afternoon.
Robert told me he has thought about selling the shop — but property values in the area are modest, and the equipment alone might bring $40,000 on a good day. He doesn’t think that gets him far. He has also thought about adding a part-time employee who could handle computer diagnostics on newer models, but he’d need to invest in equipment that starts at roughly $12,000 for a professional-grade scan tool suite, and he’s not convinced the return would justify it in his neighborhood’s market.
When I left the shop, one of the empty bays was still empty. Robert had gone back to work on a 2009 Chevy Silverado — the kind of job he’s good at, the kind of car that doesn’t lock him out. He waved without looking up. Outside, the temperature had dropped to about 18 degrees. West Fond du Lac Avenue was quiet.
Robert Kowalski has spent 18 years doing honest work. The math of what comes next — for retirement, for his son, for the business itself — doesn’t add up cleanly, and he knows it. He’s not looking for sympathy, and he made that clear. But the numbers are the numbers, and they don’t bend because a man is stubborn.
Related: A Milwaukee Mechanic’s $45K College Bill and Zero Retirement Savings — What He Discovered Too Late
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