The waiting room at Kowalski’s Auto on West Oklahoma Avenue smells like motor oil and burnt coffee. There are two plastic chairs, a fishing calendar from 2023 still on the wall, and a handwritten sign near the register that reads: Cash preferred. Cards accepted. No crypto. When I arrived on a gray Tuesday morning in late March 2026, Robert Kowalski was already under a lifted Ford F-150, talking to it more than to me.
He came out from under the truck wiping his hands on a shop rag, nodded once, and said he had about twenty minutes. We ended up talking for two hours.
Eighteen Years of Work, and the Floor Is Shifting
Robert Kowalski is 52 years old. He opened his shop in 2008 — the same year the economy cratered — which he still laughs about. He survived that. He survived parts shortages during the pandemic. What he is not sure he can survive, he told me, is the computer chip.
“The new cars, they lock you out,” he said, leaning against the tool chest. “Dealer-only diagnostics, proprietary software. I can’t even read the codes on a 2024 without buying a $4,000 subscription. My customers are driving older stuff. And older stuff eventually gets replaced.”
His shop grossed roughly $310,000 in 2021. By 2024, that number had fallen to around $217,000 — a drop of nearly 30 percent over three years. After overhead, parts, and a part-time employee he kept on out of loyalty, Robert’s personal net income from the business was closer to $58,000 last year.
His wife, Dana, works as a dental office manager. Her salary covers groceries and utilities. Robert covers the shop mortgage and anything left over. There is rarely anything left over.
What Robert does not have, at 52, is a retirement account of any kind. No SEP-IRA. No Solo 401(k). No traditional IRA. “Those are for people who have extra money,” he told me, without a trace of self-pity. “I never had extra money.”
The Social Security Record He Hadn’t Looked at in Years
I asked Robert when he last checked his Social Security earnings record. He stared at me for a moment, then said, “Maybe 2019? My accountant mentioned it once.” He pulled out his phone and, with some help navigating to SSA.gov’s my Social Security portal, we pulled up his statement together.
What the statement showed was a story told entirely in numbers. His highest earning years — 2015 through 2019 — showed reported net self-employment income between $72,000 and $88,000 annually. Then the slope turned downward. 2022: $61,000. 2023: $54,000. 2024: $58,000.
Robert’s projected monthly benefit at full retirement age — currently 67 for those born in 1973 — was listed at approximately $1,640 per month, based on his earnings record at the time of the statement. That figure, he learned, will shift as his more recent lower-income years begin replacing earlier higher-income years in the calculation.
“So every year I make less, I get less later,” he said. It was not quite a question.
The $45,000 Question Nobody Warned Him About
Robert’s older son, Marcus, was accepted to a university in Minnesota in the fall of 2025. Tuition, room, and board: approximately $45,000 per year. Robert and Dana had roughly $11,000 in a savings account. Marcus took out federal student loans for the first year. The family is still figuring out years two through four.
“I’m proud of him,” Robert said. “I’m terrified of the number.” He paused and looked at the ceiling of the shop. “I keep thinking — if I help him, I have even less for later. And if I don’t help him, what kind of father does that make me?”
This is not an unusual position for people in their early fifties. But for the self-employed, the tension is sharper. There is no employer match sitting in a 401(k) quietly compounding. There is no pension. Robert’s retirement income, realistically, will come from three places: whatever he can save in the next 15 years, the eventual sale or wind-down of the shop, and Social Security.
Robert had never opened a SEP-IRA. He knew vaguely that such accounts existed. “I figured you needed accountants and lawyers and minimums,” he said. “I assumed it wasn’t for guys like me.”
What the Numbers Actually Look Like at 67
We spent a few minutes on the SSA’s online estimator together. Based on his current trajectory — assuming his net income stays around $58,000 annually through age 66 — his projected monthly benefit at 67 would land somewhere between $1,580 and $1,700, depending on future earnings. That is before any Medicare Part B premium, which in 2026 is $185.00 per month and is typically deducted directly from Social Security payments.
Robert looked at the early-claim column for a while. “I always figured I’d take it as soon as I could,” he said. “Because what if I die early, right? My dad died at 64.” He didn’t say anything else for a moment. “But $915 a month. That’s not enough to rent an apartment in Milwaukee now.”
The 2025 COLA increase was 2.5 percent, according to the Social Security Administration, bringing the average retired worker benefit to approximately $1,976 per month as of January 2025. Robert’s projected benefit, even at full retirement age, would fall below that average — a reflection of the declining income years now entering his calculation window.
A Stubborn Man Sitting With an Uncomfortable Truth
By the time we wrapped up, a customer had come and gone, and Robert’s part-time employee, a man named Darius, had started on a brake job in the second bay. Robert poured himself a coffee from a machine that looked older than the Ford F-150 he’d been working on when I arrived.
I asked him what he planned to do differently, if anything. He was quiet for longer than I expected.
He also said, with a kind of flat honesty I found more affecting than bitterness, that he felt the system was designed for people with W-2s and employers and HR departments. “Nobody explained to me that running my own business meant I was the employer and the employee for Social Security purposes,” he said. “I just paid the tax every year and assumed it was taken care of.”
What Robert is navigating now — a 30 percent revenue decline, zero retirement savings at 52, a college-bound son, and a Social Security projection that keeps inching downward — is not a story with a clean resolution. He has not opened a retirement account yet. He has not restructured his business to chase EV work, though he’s looked into the training costs. His son is in his second semester in Minnesota.
Before I left, Robert walked me out to the parking lot. A Honda Civic with a cracked bumper was idling in the bay entrance — a regular customer, he said, transmission issue. He had work to do.
“I’m not panicking,” he said, and I believed him. “I just wish I’d looked at that statement ten years ago.”
He turned and walked back inside. The Civic followed him in.
Related: The Social Security Claiming Age That Could Cost You $100,000 Over Your Lifetime
Leave a Reply