What would it feel like to spend your entire career telling other people how to manage money — and quietly know that your own financial house is in ruins? It’s an uncomfortable question. But it’s the one I kept turning over in my mind after I heard Lester Novak call into an Indianapolis radio program last February.
He didn’t sound panicked on air. He sounded flat. Almost detached. He described being 63, still working full-time as a senior accountant, and carrying a graduate school loan balance he hadn’t managed to touch in years. The host moved on. But I didn’t.
I tracked Lester down through the station’s producer and asked if he’d be willing to talk. He agreed almost immediately, which told me something. When I sat down with him at a coffee shop near his Broad Ripple office on a grey Thursday morning in late February, he folded his hands on the table and said, before I’d asked a single question: “I’m not embarrassed anymore. That part wore off a long time ago.”
The Weight of Knowing Better
Lester Novak has worked in accounting for 38 years. He holds a CPA license, has managed payroll systems for mid-size manufacturing companies, and currently earns approximately $118,000 a year at a firm downtown. By most measures, he is exactly the kind of person who should be approaching retirement in comfort.
He is not. His wife Karen retired from her position as a school librarian in January 2026, drawing a modest pension of around $1,840 a month. They own their home outright — that much went right. But when I asked Lester to walk me through his retirement accounts, he shook his head slowly.
“There’s nothing there,” he told me. “I cashed out a 401k during 2009 when we were trying to stay afloat. Paid the penalty, paid the taxes, and told myself I’d rebuild it. I never did. Life kept happening.”
Lester earned his MBA from Butler University in 2009 — right as the financial crisis was bottoming out — hoping to move into corporate finance leadership. The move never materialized the way he’d planned. The $52,000 he borrowed accumulated interest during a deferment period, and by the time he was paying consistently, the balance had barely moved. He’d been making minimum payments of roughly $380 a month for years without seeing meaningful progress.
Karen’s retirement, while something they’d planned together, removed about $72,000 in annual household income almost overnight. The budget math changed completely in January.
A Graduate Degree That Keeps Costing
When Lester called into that radio show, he hadn’t been looking for answers. He said he was driving home and started talking almost without meaning to. That detail stuck with me — the numbness of someone who has accepted a difficult situation as permanent.
As Lester explained over the course of nearly two hours, his loan was a federal Direct PLUS Loan taken out under the graduate program. What he hadn’t done — despite knowing the options existed — was recertify his income for an income-driven repayment plan in the years since his financial situation shifted. He was still on a standard 10-year repayment structure that had long since expired into an extended plan, carrying a 6.8% interest rate from the original 2009 disbursement.
He also hadn’t looked seriously at what happens to that balance at age 65 or 67. Under certain income-driven repayment tracks, a remaining balance can be forgiven after 20 or 25 years of qualifying payments — a provision outlined by the Federal Student Aid repayment plan guide. That forgiveness, however, is currently treated as taxable income at the federal level, which created its own set of complications he hadn’t fully modeled.
What He Found When He Actually Looked
After the radio segment, Lester told me, he spent a weekend actually logging into his Federal Student Aid account for the first time in over a year. What he found was clarifying — though not entirely comforting.
His loan servicer had switched twice since 2020, a transition period that affected millions of borrowers. According to the Federal Student Aid office, several servicer transitions between 2021 and 2024 resulted in missed payment counts and repayment plan disruptions for a significant number of borrowers. Lester’s payment history had a 14-month gap in qualifying payment tracking that he hadn’t noticed.
Here is what Lester’s situation looked like when he mapped it out that weekend:
Lester filed a request to restore his IDR payment count through the IDR Account Adjustment process, a Department of Education initiative that allows past periods of certain payment statuses to count retroactively toward forgiveness milestones. The adjustment had been extended and modified multiple times since its 2022 announcement, and as of early 2026, the Department of Education confirmed that many borrowers’ counts had been updated through the process.
The Numbers Don’t Lie — But They Don’t Comfort Either
What Lester’s story surfaces is a particular kind of financial fragility that rarely gets discussed: the high-income earner who is, functionally, one salary away from serious trouble. His household income dropped by nearly 38% when Karen retired. He has no investment accounts, no brokerage holdings, and a Social Security projected benefit — he’d checked his SSA account recently — of approximately $2,340 per month at full retirement age 67, based on his current earnings record.
Combined with Karen’s pension, they’d bring in roughly $4,180 a month if Lester stopped working at 67. Against their current monthly expenses of approximately $5,200 — including the loan payment, property taxes, insurance, and utilities — that gap is not theoretical. It’s immediate.
The catch-up contribution piece was something Lester described almost with a wince. Under IRS rules, workers age 50 and older can contribute additional funds to a 401(k) beyond the standard annual limit. For 2025, that total reaches $31,000. Lester had not been contributing anything. His employer offers a 3% match on contributions up to 6% of salary — meaning he had been leaving roughly $3,540 in free employer contributions on the table every year for the last several years.
“I knew that,” he said quietly. “I just — I kept telling myself I’d start next month. And then next month was always something else.”
A Story Without a Clean Ending
I want to be careful about how I characterize where Lester stands today. When I followed up with him by phone in late March, he said his IDR adjustment request was still pending. He had enrolled in his employer’s 401(k) for the first time in over a decade and had started contributing $800 a month, with plans to increase that once summer arrived and a remaining car payment cleared. It was a start.
But the structural reality — no retirement savings at 63, a $46,880 loan balance, and a household income that had just contracted significantly — doesn’t resolve quickly or easily. Lester knows that better than most people in the room.
What Lester’s story underscores — and what I think about whenever I consider the gap between knowing and doing — is that financial stress doesn’t discriminate by credential. The numbness he described isn’t apathy. It’s what happens when the distance between where you are and where you thought you’d be becomes too wide to look at directly.
He’s looking at it now. That, at 63, with four years left until full retirement age, is where his story currently sits. Not resolved. Not broken. Just open.
Related: 2026 Tax Refund Delays Are Hitting Millions — The IRS Processing Backlog Nobody Is Talking About
Leave a Reply