The deadline that Robert Kowalski keeps circling back to is August — when his oldest son, Marcus, is scheduled to start at a university in Indiana that costs roughly $45,000 per year. Robert told me this in March 2026, seated at the small desk wedged into the back corner of his auto shop on Milwaukee’s south side, engine noise filtering in from the bay. He had not yet figured out how to pay for it. He had not yet figured out much of anything.
I first connected with Robert after a reader tip about self-employed tradespeople getting blindsided by the shift toward software-dependent vehicles. Robert, 52, agreed to talk — reluctantly. He made clear from the start that he didn’t put much stock in financial coverage. “That stuff’s for people who already have money,” he said, before waving me toward the only chair in the room that wasn’t stacked with catalogs.
Eighteen Years of Work, and the Ground Shifted
Robert opened Kowalski Auto in 2008, the same year the financial crisis hit. He survived that. What he didn’t fully anticipate was what happened between 2022 and 2025, when his annual shop revenue dropped from approximately $310,000 to roughly $217,000 — a decline of about 30% in three years.
The cause wasn’t a recession. It was the cars themselves. As Robert explained, newer vehicles increasingly lock diagnostic and calibration functions behind proprietary dealer software. Independent shops like his can’t access those systems without expensive licensing agreements that major manufacturers often restrict. He’s watched job after job walk out the door.
“I had a customer bring in a 2023 pickup with a transmission warning light,” Robert told me. “I’ve been doing transmissions for twenty-five years. I couldn’t even read the codes without the dealer’s proprietary tool. Had to send him away.” He paused. “That happened a lot.”
The Right to Repair movement has tried to address this at the federal level, but progress has been slow. According to the FTC’s Nixing the Fix report, manufacturers’ repair restrictions cost consumers and independent shops billions annually — but enforceable national standards for automotive repair access remain unsettled as of early 2026.
No Retirement Plan — and a Self-Employment Tax Bill Every Year
At 52, Robert has no IRA, no SEP-IRA, no Solo 401(k). When I asked him why, he was blunt: in the years when money was good, he reinvested everything back into the shop. In the years when it wasn’t, there was nothing left to save.
What he does pay — consistently — is self-employment tax. As a sole proprietor, Robert is responsible for both the employee and employer portions of Social Security and Medicare taxes, which combined equal 15.3% on net self-employment income, according to the IRS. On net earnings of around $80,000 last year after expenses, that amounted to roughly $12,240 in self-employment taxes alone — before federal income tax.
Robert does deduct half of his self-employment tax on his federal return — a provision the IRS allows to partially offset the double burden — but he told me he hadn’t been aware of several other deductions available to self-employed individuals until a tax preparer flagged them two years ago. Before that, he filed his own returns. “I figured it was just a form,” he said. “I didn’t realize how much I was leaving on the table.”
His Social Security picture is also complicated. Because his reported income has fluctuated significantly over 18 years — and because high self-employment tax years were offset by low-income years — his projected Social Security benefit at 67 is estimated at around $1,420 per month, based on his most recent Social Security statement. According to the Social Security Administration, benefits are calculated on your 35 highest-earning years, meaning gaps or low-income years drag the average down permanently.
The $45,000 Question He Doesn’t Have an Answer For
Marcus Kowalski, 18, was accepted to a business program at a private university in Indiana. Robert is proud of his son in a way that’s plainly visible — he lit up when he said the name of the school. Then the number came back: $45,000 a year, for four years.
Robert’s wife, Dana, works as a medical billing specialist. Her income covers their mortgage, groceries, and utilities — there isn’t much margin. Robert told me the family has looked at federal student loans, and Marcus filed a FAFSA. But with Robert’s shop income and Dana’s salary both counted in the household calculation, the Expected Family Contribution came back higher than Robert felt was realistic given how uneven his actual cash flow has become.
He’s considered taking out a home equity line of credit — they’ve owned their house for 14 years and have meaningful equity — but Dana is worried about tying the house to college costs. Robert said the conversation has been tense. “She’s more careful than I am,” he said. “Which is probably good.”
The Moment Something Actually Changed
When I asked Robert what, if anything, had shifted for him in the past year, he mentioned a conversation he’d had with his accountant in November 2025 — the first time he’d had what he called a “real” conversation about his financial position instead of just filing taxes.
His accountant walked him through what a SEP-IRA could do: self-employed individuals can contribute up to 25% of net self-employment income, with a 2025 contribution limit of $69,000, according to IRS guidelines. On Robert’s current earnings, that would allow him to shelter a meaningful portion of income while reducing his taxable base. He had never set one up. He set one up in January 2026 — though with limited cash available, his first contribution was $2,200.
He also enrolled in a part-time EV diagnostics certification course at Milwaukee Area Technical College in February. The cost was $1,400. He sees it as the most concrete response he has to the revenue problem — if dealers have a lock on software diagnostics for newer combustion vehicles, he wants to position the shop for electric vehicle service, where some of those barriers don’t yet exist in the same form.
“I’m not going to sit here and pretend I figured everything out,” Robert told me. “But I needed to do something other than watch the numbers keep going the wrong direction.”
Where He Stands Now — and What He Can’t Yet See
When I left Kowalski Auto on a gray March afternoon, Robert walked me out to the lot and pointed at a late-model SUV he was waiting on a part for. The repair was something he could still do — brakes, suspension, nothing proprietary. He gets those jobs regularly. It’s the jobs he doesn’t get anymore that are the problem.
His retirement situation remains genuinely precarious. At 52 with a $2,200 SEP-IRA balance and an uncertain business trajectory, the math is hard. He knows it. He is not someone who sugarcoats things, even about himself.
The college question is still open. Marcus may take out federal student loans, which have a 2025–26 undergraduate limit of $5,500 for dependent first-year students in subsidized and unsubsidized combined — far short of $45,000 annually. The family has not ruled out Marcus attending a less expensive school closer to home, though Robert said his son has his heart set on the Indiana program. That conversation, he acknowledged, hasn’t happened yet.
What struck me about Robert Kowalski wasn’t his stubbornness, which is real, or even the scale of the problem he’s facing, which is also real. It was the way he described noticing, for the first time, the gap between the story he had been telling himself — that hard work and a good shop would be enough — and what the numbers actually said. That gap is where a lot of people live, and most of them don’t talk about it to journalists.
“I’m not looking for sympathy,” he said, before I left. “I just figured maybe someone else in the same spot would want to know they’re not the only one.”
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