What would you trade for a credential that might — or might not — save your livelihood? Would you borrow $74,500 at age 53, betting that a graduate degree would be the thing that finally put your small business on solid ground? Keith Kessler did exactly that. And when I sat down with him on a gray Tuesday afternoon at a diner two blocks from his daycare center in Louisville, Kentucky, he was still counting the cost.
I was introduced to Keith through Pastor Darnell Okafor at Covenant Bridge Church in the Shawnee neighborhood, where Keith has attended services for nearly fifteen years. Pastor Okafor knew I was reporting on how student debt intersects with small business ownership and suggested Keith’s story was one I needed to hear. “He’s not someone who made careless choices,” the pastor told me beforehand. “He made careful ones that still blew up in his face.”
A Business Decision That Became a Debt Crisis
Keith Kessler, now 64, opened Little Milestones Learning Center in 2008 after spending two decades in corporate logistics. The daycare grew steadily — by 2014, it had 47 enrolled children and a staff of nine. But state licensing requirements in Kentucky were tightening, and Keith felt the pressure. Competitors with formal credentials in early childhood education were winning contracts with local school districts and Head Start programs that he simply couldn’t access.
In 2015, he enrolled in a Master of Science in Early Childhood Education Administration program at a private university in Indiana. He was 53 years old. By the time he graduated in 2017, he had taken out $74,500 in federal graduate PLUS loans at interest rates between 6.31% and 7.0%.
“I ran the numbers forty different ways before I signed those promissory notes,” Keith told me, turning his coffee cup slowly in his hands. “The degree was supposed to open doors to contracts worth more than the loan itself within three years. That was the plan. I’m a data guy. I had spreadsheets.”
The spreadsheets, as he put it, didn’t have a row for a global pandemic.
How COVID and Compounding Interest Dismantled the Plan
From 2017 to 2019, Keith made every loan payment on time. His monthly obligation under the standard 10-year repayment plan was $827. His daycare was bringing in roughly $390,000 in annual revenue, and his personal draw was around $96,000. The math, for those two years, worked.
Then March 2020 arrived. Little Milestones Learning Center closed for eleven weeks. When it reopened, enrollment had dropped from 47 children to 22. Keith burned through a $34,000 operating reserve by August of that year. He applied for a Paycheck Protection Program loan and received $41,000, but by early 2021, he had also fallen behind on two credit cards totaling $18,400 and missed three student loan payments — the federal pause had ended briefly before being reinstated, creating confusion he says his servicer never clearly communicated.
“The servicer sent notices to an email address I hadn’t used in two years,” Keith said, his voice flat. “I’m not blaming them entirely. But I was managing eleven employees, a half-empty building, and a PPP application at the same time. I missed those notices. And those three missed payments have followed me everywhere since.”
By mid-2022, his credit score had fallen from 724 to 591. It has since climbed to 603, but the damage to his financial profile has been lasting. Two refinancing applications for his daycare building — which he leases but hoped to purchase — were denied in 2023 and again in 2025.
The Income-Driven Repayment Maze
In 2023, Keith enrolled in the SAVE plan — the Saving on a Valuable Education repayment program introduced by the Biden administration — which temporarily lowered his monthly payment to $610 based on his discretionary income. For a brief period, he told me, it felt like breathing room.
That relief was short-lived. Federal courts blocked key provisions of the SAVE plan in mid-2024, and by late 2025 the program was effectively dismantled through administrative action. Keith was shifted back to a standard Income-Contingent Repayment plan, where his monthly payment is now $748. His current balance, due to years of interest accrual during the pandemic pause and subsequent forbearances, stands at approximately $91,200 — nearly $17,000 more than he originally borrowed.
As Keith explained the repayment timeline to me, he pulled out his phone and showed me a spreadsheet — color-coded, with conditional formatting. At his current payment of $748 per month and a 6.7% blended interest rate, he projects paying off his loans at age 73, assuming no further disruptions. “I’ll be lucky if I’m still running this place at 73,” he said quietly.
The Credit Score That Closed Every Door
The loan balance is one problem. The damaged credit score is another — and in some ways, Keith told me, it has been the more immediate obstacle.
“I bring in close to a hundred thousand dollars a year personally,” Keith said, spreading his hands on the table. “My business has real revenue. I pay my staff on time, every two weeks, without fail. And I cannot get a bank to talk to me seriously because of what happened during the worst eighteen months of my life.”
He has been working since early 2025 with a HUD-approved nonprofit housing and credit counseling agency in Louisville. They helped him dispute two errors on his credit report — an incorrectly reported charge-off from a credit card that had actually been settled — which contributed to a 12-point score increase. The derogatory marks from 2021 are scheduled to age off his report in late 2027, seven years from the date they were first reported.
What He Wishes He Had Known
When I asked Keith what he would tell a small business owner considering graduate loans in their 50s, he paused longer than I expected before answering. He chose his words carefully — he always did, I noticed.
He doesn’t regret the degree itself. Little Milestones Learning Center did win a contracted partnership with a local Head Start affiliate in 2019, worth roughly $62,000 annually, that he credits directly to his credentials. The business survived COVID, rebuilt enrollment to 39 children, and today operates with eleven full-time and part-time staff members.
But the financial scaffolding underneath that success remains precarious. His retirement accounts, which he paused contributing to in 2020, hold approximately $88,000 — less than his remaining loan balance. He is 64 years old. “I tell people my business is thriving,” he told me near the end of our conversation, “because it is. And then I go home and stare at that loan balance and wonder what thriving is actually supposed to feel like.”
Keith’s credit counselor has outlined a path: continue making on-time payments through 2027, when the derogatory marks age off his report, and revisit commercial financing at that point. His projected credit score at that stage, assuming no new delinquencies, is between 660 and 680 — enough, potentially, to qualify for a small business loan to finally purchase his building before his landlord retires and the property goes to market.
It is a plan built on a lot of “ifs.” Keith knows that. He is, as Pastor Okafor described him, a data guy. He just lives in a world where the data keeps changing the rules.
When I left the diner, Keith was already back on his phone — checking, he said, on the staffing schedule for the next morning’s opening. The spreadsheets, apparently, never stop. I drove past Little Milestones Learning Center on my way to the highway. The sign was bright. The parking lot had four cars in it at 5:15 in the afternoon, parents picking up children. From the outside, it looked exactly like a business that was doing fine. Which, in most of the ways that matter most to the children inside, it is. The parts that are still broken are the parts you cannot see from the street.
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