The Social Security Administration issued its 2026 COLA notice last fall, and for millions of Americans approaching retirement age, that letter triggered a fresh round of arithmetic. For Warren Jeffries, 62, of Raleigh, North Carolina, the math has been running on a loop for months.
When I sat down with Warren on a Tuesday afternoon in late March, he had a spiral notebook on the table beside his coffee. He’d been up since 5 a.m. running projections. He is three years from his planned retirement date, and he is not sleeping well.
A Comfortable Number That Doesn’t Feel Comfortable
On paper, Warren Jeffries is ahead of most Americans his age. He and his wife have approximately $680,000 across their combined retirement accounts. Their home in Raleigh is paid off. He still earns a solid salary as an IT project manager. By almost any standard benchmark, he is in good shape.
But Warren doesn’t think in benchmarks. He thinks in 30-year cash flow models, and that changes everything.
“I keep seeing articles about people who retire at 65 and live to 95,” Warren told me. “That’s not a retirement. That’s a 30-year financial product you have to engineer in your 50s and early 60s while you still have income.” He tapped the notebook. “Most people don’t think about sequence-of-returns risk until it’s already happening to them.”
According to SSA’s life expectancy tables, a 62-year-old man today can expect to live, on average, into his mid-80s — and those are averages. Warren’s family history skews long. His mother is 87. His father made it to 91.
The Medicare Gap: Three Years That Cost Real Money
Warren plans to retire at 65, which is also the age of Medicare eligibility. That timing is deliberate. But three years of private health insurance between retirement and Medicare coverage is one of the largest hidden costs in early retirement planning — and it is the variable that worries Warren most after market volatility.
Warren’s employer currently covers a significant portion of his family’s health insurance. The moment he retires, that subsidy disappears. If he and his wife both need private marketplace coverage for even two years before Medicare, the cumulative out-of-pocket cost could easily exceed $40,000 — money that comes directly off the top of his $680,000.
“That’s the number that never gets talked about in the retirement calculator tools,” he said. “They ask you what percentage you want to withdraw annually. They don’t ask you what you’ll pay for a PPO plan in year one when you have no employer contribution.”
Warren told me he has been modeling three different retirement scenarios — at 63, 65, and 67 — largely around this healthcare cost variable. Each additional year he works is one fewer year of private insurance costs, plus additional Social Security benefit accrual. It is not a simple equation.
Social Security Timing: The Decision He Hasn’t Made Yet
At 62, Warren is already eligible to claim Social Security retirement benefits — but doing so would permanently reduce his monthly payment. According to SSA’s early claiming reduction schedule, claiming at 62 instead of full retirement age (currently 67 for Warren’s birth year) reduces benefits by as much as 30 percent.
Warren has not claimed yet, and does not plan to claim early. His concern runs the other direction: he is considering whether to delay past 67, toward 70, to lock in the maximum monthly benefit for what could be a very long retirement. Every year of delay past full retirement age adds approximately 8 percent to the monthly benefit, according to SSA guidelines.
“My break-even math puts claiming at 70 versus 67 at around age 82 or 83,” he explained. “Given my family history, delaying to 70 probably wins. But that means I have to fund five years of retirement — from 65 to 70 — entirely out of savings before a single Social Security dollar comes in.”
The Phone Call That Comes Every Month
There is another variable in Warren’s retirement model that does not appear in any SSA table or insurance rate sheet. His 32-year-old son, Marcus, calls roughly once a month. The calls are not casual. Marcus’s small business failed in 2024, and he has been rebuilding since — slowly, unevenly, and sometimes with financial help from his parents.
Warren did not offer this information quickly. It came out gradually, the way uncomfortable financial realities tend to in interviews. When it did, his voice shifted — quieter, more careful.
“We’ve helped him. We’ll probably help him again,” Warren said. “He’s our son. But I sat down with my wife last December and we tried to figure out exactly how much we’ve transferred to him over the past 18 months. It was more than we realized. Every dollar we give Marcus is a dollar that isn’t compounding for the next three years.”
Warren would not give me a precise figure. He said it was “in the low five figures” since Marcus’s business closed. At a conservative 6 percent annualized growth rate, $20,000 transferred out of retirement accounts today would be worth roughly $33,800 over a decade. Over 20 years, closer to $64,000. Warren has done that math too.
The question Warren keeps returning to is whether the compassion he feels toward Marcus should be separated — formally, structurally — from the retirement plan he and his wife have built over 35 working years. He has not resolved it. He said he and his wife argue about it occasionally, not viciously, but with real stakes.
“She’s more willing to help him than I am. Or maybe she’s better at compartmentalizing it,” he told me. “I see it as the same money. Every time we write a check, I see the spreadsheet change.”
What He Wishes He’d Known Earlier
When I asked Warren what he would tell someone in their early 50s — before the retirement math gets urgent — he answered without hesitating. This was clearly a question he had already asked himself, many times.
He also said he wishes he had set clearer boundaries with Marcus earlier — not because he regrets helping his son, but because the ambiguity of open-ended financial support has added a layer of unpredictability to plans that were otherwise disciplined. He is now considering a fixed, annual amount he and his wife will offer Marcus — a number they can budget for, rather than a reactive response to monthly calls.
Whether that structure holds is another variable Warren cannot fully control. And the inability to control variables is, by his own account, the core of his sleeplessness.
As I packed up my recorder and he closed his spiral notebook, Warren made one last comment. He said he feels lucky — genuinely lucky — compared to people who reach their 60s with nothing saved. He knows the $680,000 is more than most. But luck and anxiety are not mutually exclusive, and the retirement he has been building toward for three decades still looks, from where he stands at 62, like a structure that could be shaken by the right combination of bad timing.
He plans to keep running the numbers. The notebook will not go back on the shelf anytime soon.
Related: At 62 With $680K Saved, Warren Jeffries Still Can’t Sleep — His Son and a 30-Year Retirement Are Why
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