A couple retiring at 65 today can expect to spend approximately $330,000 on healthcare costs throughout retirement, according to Fidelity’s 2024 retiree healthcare estimate. That number does not include long-term care. It does not include dental. And it does not account for a market downturn that could shrink the portfolio funding all of it.
Warren Jeffries knows this figure by heart. He’s 62, an IT project manager based in Raleigh, North Carolina, and he has spent the last two years building spreadsheets that model his retirement down to the month. When I met with him on a Tuesday afternoon in late March, he had a legal pad covered in handwritten calculations sitting next to his coffee cup.
“I’m not a pessimist,” he told me, almost immediately, as if he’d had to defend this before. “I just need to understand the variables before I can trust the outcome.”
The Numbers Look Good on Paper
Warren and his wife Linda, 60, have built what most financial journalists would describe as a solid foundation. Their Raleigh home is fully paid off — no mortgage, no HELOC. Their combined retirement accounts, split between a 401(k) and a Roth IRA, sit at approximately $680,000 as of early 2026. Warren earns roughly $115,000 a year and has three years left before he plans to stop working at 65.
On paper, the picture looks comfortable. In practice, Warren told me, it feels like standing on ice he hasn’t fully tested yet.
The central problem Warren described is one that retirement researchers have studied extensively: sequence-of-returns risk. If a major market downturn hits in the first five years of retirement, the long-term damage to a portfolio can be far worse than a comparable downturn later. Warren has run scenarios where a 25% market drop in year two of retirement — not hypothetical, given 2008 and 2022 — leaves him with a portfolio that runs dry before he turns 87.
“I’ve got the spreadsheets open on my laptop most nights,” he said, letting out a short laugh that didn’t quite reach his eyes. “Linda keeps telling me to close them and go to bed. But I can’t stop running the what-ifs.”
The Son Who Calls Every Month
Roughly one in five adults over 50 in the United States provides regular financial support to an adult child, according to estimates from the Pew Research Center. Warren is in that group, and it’s the part of his retirement calculation that causes him the most visible discomfort to discuss.
His son Marcus, 32, launched a home renovation business three years ago. The business closed last year after a contract dispute drained its operating account. Marcus is rebuilding, Warren told me, but the process has been slow — and Marcus calls his father almost every month.
The $14,000 Warren referenced isn’t a number he threw out casually. He pulled it from a notes app on his phone — he tracks every transfer to Marcus, dated and itemized. It’s the same methodical instinct that fills the legal pad on his kitchen table.
What makes the situation harder, Warren explained, is that Marcus’s calls don’t always come with a specific ask. Sometimes it’s rent. Sometimes it’s a truck repair. Sometimes it’s just a conversation that ends with Warren offering to help before Marcus even frames it as a request. “I can hear it in his voice,” Warren said. “And I’ve never been able to say no to that.”
Linda, he told me, is more protective of the retirement account than he is. They’ve had conversations — some tense — about where the line is. They haven’t found a firm answer yet.
The Healthcare Gap That Changes Everything
Warren’s plan is to retire at 65, which conveniently aligns with Medicare eligibility. According to Medicare.gov, most Americans become eligible for Medicare at 65 — meaning Warren won’t face the multi-year coverage gap that early retirees in their early 60s often confront.
But “65” is an approximation. Warren’s exact retirement date is flexible, and he knows that even a six-month gap between his last employer health plan and Medicare enrollment could expose him and Linda to significant costs. Linda, at 60, would be four and a half years away from her own Medicare eligibility if Warren retired on schedule.
When I asked Warren to walk me through the healthcare cost estimate he uses, he pulled out a figure of roughly $2,400 per month for a marketplace plan covering both him and Linda for any period before Medicare. That number is based on quotes he pulled in January 2026. It does not include deductibles or copays.
“Healthcare is the variable that scares me more than the market,” he said. “At least the market has a historical average. Healthcare inflation doesn’t behave the same way. It just goes up.”
Running the Math on 30 Years
The average American man who reaches 65 today can expect to live to approximately 83, according to Social Security Administration life expectancy tables. The average woman reaching 65 lives to roughly 86. But those are averages — Warren’s family history includes a grandfather who lived to 94 and a father currently healthy at 88.
“I don’t plan for the average,” Warren told me flatly. “I plan for the outlier. Because if I’m wrong in the other direction, I run out of money at 82 and that’s a catastrophe. If I’m wrong in this direction, I die with money left over and that’s fine.”
The Social Security dimension adds another layer of complexity. Because Warren was born in 1963 or 1964, his full retirement age is 67, per current SSA guidelines. Retiring and claiming benefits at 65 would mean a roughly 13% permanent reduction in his monthly Social Security check compared to waiting until 67. Waiting until 70 would increase it by 24% above the full retirement age amount.
Warren knows this math. He’s modeled it. He’s also modeled what happens if he delays Social Security until 67 or 70 while drawing down the $680,000 — and whether the portfolio survives the bridge period before benefits begin. “Every version of this has a trade-off,” he said. “There’s no clean answer. That’s what I keep bumping into.”
Where Warren Stands Today
By the time I finished my coffee, Warren had walked me through four separate spreadsheet scenarios on his laptop. He’s not paralyzed — he’s still contributing the maximum to his 401(k), still planning to retire in three years, still helping Marcus when Marcus needs it. But he carries the uncertainty with him in a way that, as he describes it, doesn’t go away when the laptop closes.
Warren told me he recently had what he called a “hard conversation” with Linda about setting a firm annual limit on what they’d give Marcus going forward — not to punish their son, but to protect their own plan. They settled on a number. He wouldn’t tell me what it was. “That’s between us and Marcus,” he said. “But we have a number now. That helps.”
He also said he’s begun modeling the scenario where he works until 67 instead of 65 — not because he wants to, but because two extra years of contributions, two more years of Social Security accrual, and two fewer years of portfolio withdrawals change his numbers in ways that are hard to argue with. “I may end up giving myself the answer I don’t want,” he said, almost to himself. “But at least it’ll be the right answer.”
When I left Warren’s house that afternoon, the legal pad was still on the table. He’d added a new column while we were talking — something about a conservative 5% withdrawal rate versus 4%, tested over 32 years. I asked him if he ever lets himself imagine just enjoying retirement without the spreadsheets. He thought about it for a moment.
“I’ll enjoy it more if I know it’s going to work,” he said. “That’s just who I am.”
Related: At 62 With $680K Saved, Warren Jeffries Still Can’t Sleep — His Son and a 30-Year Retirement Are Why
Related: Warren Jeffries Has $680,000 Saved for Retirement and Still Loses Sleep Over One Number
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