Roughly 16 million self-employed Americans have no employer-sponsored retirement plan, leaving Social Security as their primary — sometimes their only — financial safety net in retirement. For Robert Kowalski, that statistic stopped being abstract the day he looked at a number on an old desktop screen and went very quiet.
When I pulled up to Kowalski Auto & Repair on a gray Tuesday in February, the bay doors were open and Robert was under a lifted 2019 Ford F-150 he’d been working on for two days. The diagnostic software that truck required, he told me, costs more than three months of his old profit margin. He wiped his hands on a rag and led me to a small office in the back — a room that smelled of motor oil and old invoices.
Robert Kowalski is 52 years old. He has run this shop on Milwaukee’s south side for 18 years. Until recently, he had never seriously looked at what retirement might actually look like.
A Business Built on Reputation, Quietly Coming Apart
Robert opened Kowalski Auto in 2008 — the same year the financial crisis gutted Milwaukee’s manufacturing sector. He survived that. He survived the pandemic shutdowns of 2020. What he didn’t anticipate was the software-locked, dealer-dependent vehicle that would gradually make a large portion of his expertise obsolete.
“Used to be I could fix anything that came through that bay,” Robert told me, leaning back in a chair that had probably been there since the shop opened. “Now these newer cars have systems locked to the dealer. I can’t run a full diagnostic without a $15,000 software subscription I can’t afford.”
Revenue at the shop dropped roughly 30 percent over three years — from approximately $210,000 in annual gross receipts in 2021 to around $147,000 in 2024. Robert’s wife, Dana, works as a school aide. Her income covers groceries and utility bills. The shop, once the family’s financial engine, is now barely covering its own overhead.
Robert has two employees he’s kept on — men who’ve been with him for years. Letting them go, he said flatly, is not something he’s willing to consider. “That’s not who I am,” he told me. He said it the way someone says something they’ve already decided, permanently, and don’t need to revisit.
“I Never Really Thought About Social Security”
When I asked Robert what he expected from Social Security in retirement, he paused for a long moment. “I mean, I know it exists,” he said. “I figured I’d get something. I never really thought about what that something would be.”
Self-employed workers like Robert pay both the employer and employee portions of Social Security tax — a combined 15.3% on net self-employment income. That includes 12.4% directed toward Social Security, applied to earnings up to the $176,100 wage base in 2025, according to the Social Security Administration. Robert has been paying into the system for nearly two decades. But the monthly benefit he’ll eventually receive is tied directly to his earnings record — and that record has taken a measurable hit.
According to the Social Security Administration, retirement benefits are calculated using your 35 highest-earning years. Fewer than 35 years of covered earnings means zeros get averaged in. Lower-income years replace higher-earning ones at the bottom of the calculation as the record grows — pulling the average down over time.
What Three Bad Earning Years Actually Cost
Robert hadn’t looked at his Social Security statement in years — possibly ever. When he pulled it up on the SSA’s my Social Security portal during our conversation, I watched him squint at the screen on the aging desktop in the corner of his office. His estimated monthly benefit at full retirement age — 67, for someone born in his birth year — was listed at roughly $1,640.
Three years earlier, a neighbor who does accounting work had glanced at his numbers and mentioned the figure was closer to $1,900. Robert had forgotten about that conversation until I asked him. He stared at the current number for a moment. “Huh,” he said. That was it. One syllable.
That $260 monthly difference adds up fast. Over a 20-year retirement, the gap in lifetime benefits exceeds $62,000 — before accounting for annual cost-of-living adjustments. The Social Security Administration provides tools on its website that allow workers to model future earning scenarios and see how they might affect projected benefits. Robert had not used them.
He didn’t seem angry about the number. He seemed, more than anything, like a man who had just discovered that a machine he’d been maintaining for years had a part he hadn’t checked. “I guess I should have paid more attention,” he said, and turned away from the screen.
The Son, the $45,000 Question, and Retirement on the Back Burner
The financial picture at the Kowalski household gets more complicated when you add a second layer. Robert’s son, Derek, was accepted to an out-of-state university. Tuition, room, and board runs approximately $45,000 per year. Robert is proud of his son — visibly, genuinely proud, in a way that shifts his whole posture when he talks about it. He’s also caught in a bind he didn’t fully anticipate.
“My son worked hard his whole life,” Robert said. “I’m not going to be the reason he doesn’t go.”
Robert and Dana are exploring federal student aid options for Derek. Robert’s lack of a formal retirement savings structure — no SEP-IRA, no Solo 401(k), no defined contribution plan — means the family’s financial picture on paper looks different depending on which form is being filled out. That absence of documented retirement assets has consequences in both directions.
What that financial picture does not look like, from where I sat across from Robert Kowalski in that oil-scented office, is a plan. It looks like a man who has solved every problem directly in front of him, for 18 years, and is now facing several problems arriving at the same time from different directions.
No Easy Resolution — Just a Man Still Showing Up
I asked Robert whether he’d spoken with anyone — an accountant, a financial planner, a benefits counselor through his county — about his options as a self-employed worker approaching his mid-50s. He shrugged the way people shrug when a question is slightly offensive. “Those people are for rich guys,” he said. “I’m not a rich guy. I’m a guy who fixes cars.”
That stubbornness is almost certainly what kept the shop alive through two economic crises. It’s also probably the thing that allowed three years of declining earnings to pass without anyone looking closely at what was happening to the Social Security statement sitting unchecked on the SSA website.
Robert is still in the shop six days a week. He’s still keeping both employees on payroll. His son starts college in the fall. The Social Security statement on that desktop was probably still open in a browser tab when I left.
The self-employment taxes Robert has paid for 18 years will eventually translate into a monthly benefit — available as early as age 62 at a permanently reduced amount, or at the full $1,640 estimate if he waits until 67. Whether that figure, combined with whatever Dana receives from her own work record, is enough to retire on is a separate question — one that Robert, for now, is pushing to the back of a very full workbench.
I left Kowalski Auto & Repair the same way I arrived: through the open bay doors, past the truck that still needed two more days of work. Robert was already back under it. He didn’t look up.
Related: Up to 85% of Your Social Security Can Be Taxed and Most Retirees Don’t Find Out Until It’s Too Late
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