Roughly 40 percent of Americans over 55 have no private retirement savings at all, according to estimates from the Congressional Research Service. Malik Pruitt is not one of them — and that distinction, he told me, is almost part of the problem. He has enough saved to feel responsible, but not enough to feel safe.
I first connected with Malik through a social worker named Denise at the Cook County Assistance Office on West Madison Street. She didn’t give me his name right away. She described him as a client who kept coming in not because he needed a specific benefit, but because he felt like something was quietly going wrong and couldn’t figure out what. When she finally got his permission to make an introduction, I drove to a diner in Bridgeport on a cold Thursday morning in late February 2026. Malik was already there, nursing a coffee, with a manila folder thick enough to double as a doorstop.
A Career Built on Routine, a Retirement Built on Assumptions
Malik Pruitt has driven a UPS package car through Chicago’s South Side neighborhoods for 23 years. Before that, he spent 15 years in logistics for a smaller regional carrier. He is 60 years old, single, and has been quietly supporting his younger sister Janelle through her second year at DePaul University — about $8,400 per year in tuition assistance that doesn’t show up in any budget spreadsheet he showed me.
His base salary runs close to $88,000 annually, putting him in a bracket that feels comfortable until you start pulling on the threads. He owns a two-flat in Englewood, which he bought in 2009 for $112,000. He has a 401(k) through the Teamsters with a current balance of roughly $187,000. On paper, he is doing better than most of his coworkers.
“I’ve always been a numbers guy,” Malik told me, sliding a yellow legal pad across the table. It was covered in columns — projected Social Security benefits at 62, 65, and 67, estimated monthly expenses, a rough drawdown rate on the 401(k). “The problem isn’t that I don’t know the numbers. The problem is I run them every few months and the picture keeps getting worse.”
The Insurance Cancellation That Started the Cascade
In April 2024, a severe hailstorm tore across the South Side and punched holes in the roof of Malik’s Englewood two-flat. He filed a claim — his first in 14 years as a homeowner — and received a $9,200 payout from his insurer, Midwest Regional Casualty, to cover repairs. Four months later, he received a non-renewal notice. The insurer was exiting the Chicago residential market entirely, citing weather-related losses across Illinois.
Finding replacement coverage turned into a months-long ordeal. Two carriers declined him outright. A third quoted a premium of $4,100 per year — nearly double what he had been paying. He was still shopping when I met him, carrying a lapse in coverage that had stretched past 90 days.
The insurance disruption coincided with a property tax bill he had been deferring. Cook County’s second installment for tax year 2023 came due in August 2024 at $6,300 — higher than expected after a reassessment. Malik paid $1,500 toward it and rolled the rest, now totaling $4,800 with penalties, into a repayment plan he told me he wasn’t entirely sure he could sustain.
The Retirement Clock and the Social Security Question
Malik’s original plan was to retire at 62 — close enough to feel real, far enough to still adjust. He showed me a Social Security statement he had printed from SSA.gov earlier this year. At 62, his estimated monthly benefit would be approximately $1,740. At his full retirement age of 67, that number climbs to $2,510. The difference — $770 per month — compounds over decades in ways his legal pad made clear he had already calculated.
But Malik’s worry goes beyond the timing math. He has been reading about the Social Security trust fund’s projected shortfall — and the headlines have shaken him. BlackRock CEO Larry Fink has publicly warned that Social Security’s pay-as-you-go structure prevents most Americans from building wealth that grows with markets, arguing for partial investment in diversified assets, according to Fox Business. Whether or not reform passes, the trust fund’s finite runway is now a mainstream conversation.
“I keep seeing these articles saying the fund runs low around 2033 or 2035,” Malik said, flipping to a page in his folder where he had printed and highlighted several news reports. “I’ll be 67, 69 by then. That’s not some abstract future problem. That’s my retirement.”
The Turning Point: What the Social Worker Actually Said
Denise, the Cook County social worker who introduced us, had seen Malik three times over five months. She told me privately that his case didn’t fit the standard assistance profile — he was earning well above income thresholds for most programs — but that he kept returning because the institutional weight of his problems felt too large to navigate alone.
What she told him in their third meeting, and what Malik repeated to me almost word for word, was simple: the issues weren’t unrelated. The insurance lapse, the property tax arrears, the retirement anxiety — they were the same problem in different clothes. Each one was draining the liquidity buffer that was supposed to protect his retirement savings from early withdrawal.
That reframe, Malik said, was the first thing in months that actually helped.
By the time I spoke with Malik, he had taken two concrete steps. He had contacted a HUD-approved housing counselor through the Chicago Department of Housing about the property tax arrears — a free service he hadn’t known existed. And he had stopped dipping into a small emergency fund he had been quietly eroding over the previous year, instead putting the Janelle tuition payments on a formal repayment schedule with her.
The Outlook: Honest, Not Optimistic
Malik told me he has pushed his target retirement age back to 65, possibly 67, depending on how the next two years go. He is not planning to claim Social Security at 62 anymore — the math on his legal pad convinced him of that much. But he is also honest about what he doesn’t know.
The broader debate Malik is watching — whether Congress will reform Social Security before the trust fund pressure becomes a crisis — is one that analysts and executives at the highest levels are now openly addressing. As noted in reporting from AOL Finance, BlackRock’s Larry Fink has argued that prosperity from market growth has “accrued to a far narrower share of people than any healthy society can ultimately sustain” — a dynamic that directly affects workers like Malik who are close enough to retirement to feel the consequences but far enough away to still be shaped by whatever reforms do or don’t happen.
His 401(k) balance of $187,000 is real and it matters. But stretched across a retirement that could last 25 or 30 years, especially if Social Security pays out at reduced levels, it is also thinner than the headline number suggests. Malik knows this. He ran those numbers too.
When I left the diner, Malik stayed at the table. He had already flipped the legal pad to a fresh page. Whatever he was calculating, he was still working on it. That image stayed with me longer than the numbers did — a man who refuses to stop doing the math, even when the math keeps changing on him.
Sloane Avery Wren is Senior Benefits Writer at First Person Finance. This story does not constitute financial, legal, or tax advice.
Related: He Worked 32 Years at UPS and His Benefits Still Leave Him $620 Short Every Month
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