Roughly one in three Americans who reach age 65 today will live past 90, according to actuarial data published by the Social Security Administration. For most people, that sounds like good news. For Warren Jeffries, it sounds like a problem he hasn’t fully solved yet.
I met Warren, 62, on a Tuesday morning at a coffee shop off Glenwood Avenue in Raleigh, North Carolina. He arrived early, laptop bag over one shoulder, a legal pad already open on the table. The handwriting on it was small and precise — columns of numbers, some circled, some crossed out. He pushed the pad aside when I sat down, then pulled it back.
“I know it looks obsessive,” he said, laughing briefly. “But I’ve been an IT project manager for thirty years. I live and die by the numbers.”
The Numbers Look Fine. Warren Doesn’t Believe Them.
On paper, Warren and his wife are in better shape than most. They have approximately $680,000 spread across a 401(k) and a Roth IRA. Their home in Raleigh is paid off. He earns a solid salary and plans to retire in three years, at 65. His wife, 60, works part-time and plans to stop around the same time.
That retirement portrait would satisfy most financial checklists. Warren has studied every item on every checklist. That’s exactly why he doesn’t find it comforting.
“The 4% rule says we should be fine,” Warren told me, referencing the widely cited guideline suggesting retirees can withdraw 4% of their portfolio annually without depleting it over 30 years. “But that rule was built on historical data. I’ve watched markets crater twice in my working life. What if we hit year 12 of retirement and the market drops 40%? We don’t recover from that the same way a 45-year-old does.”
He isn’t wrong to think carefully about sequence-of-returns risk — the danger that a market downturn early in retirement can permanently damage a portfolio’s longevity, even if the market eventually recovers. For a couple planning a 30-year retirement, the margin for error is real and narrow.
The Social Security Timing Dilemma He Can’t Escape
Warren was born in 1964. That matters enormously for one number: his full retirement age for Social Security is 67, not 65. He plans to stop working at 65. That creates a two-year gap during which he would receive no Social Security income at all — or accept a permanently reduced benefit by claiming early.
According to the SSA’s retirement age reduction table, claiming Social Security at 65 instead of waiting until full retirement age at 67 reduces benefits by approximately 13.3%. Claiming at 62 — the earliest possible age — would cut his benefit by roughly 30%.
Warren has modeled it both ways. “If I claim at 65, I get the money sooner, but I take a haircut on every check for the rest of my life,” he explained. “If I wait until 67, I’m drawing down the portfolio for two years with no Social Security income coming in. And if I somehow hold out until 70 for the maximum benefit — that’s five years of drawing down $680K while we’re still paying for everything ourselves.”
He paused and looked at the legal pad. “There is no clean answer. Every option has a cost.”
The Healthcare Gap That Keeps Moving the Goalposts
Because Warren plans to retire at 65 — the same age Medicare eligibility begins — he avoids the most painful version of the pre-Medicare coverage gap. But the costs of healthcare in retirement, even with Medicare, are not small.
Medicare Part B premiums in 2026 are $185.00 per month per person, according to the Centers for Medicare & Medicaid Services. For Warren and his wife together, that’s $370 per month before they’ve paid a single co-pay, deductible, or prescription. Add a Medigap supplemental plan, and the couple could easily spend $800 to $1,200 per month on healthcare premiums alone.
“Healthcare is the number I trust the least,” Warren said. “I can model the market. I can estimate Social Security. But healthcare inflation has been running at multiples of regular inflation for decades. I can’t put a hard number on what we’ll spend at 80 if one of us gets seriously ill.”
His wife has a history of migraines and some early joint issues. Not serious now, but Warren thinks about the tail risk of long-term care — a category that Medicare covers poorly and that can cost $5,000 to $9,000 per month for skilled nursing facility care, according to industry surveys.
The Phone Calls That Are Quietly Changing the Math
Near the end of our conversation, Warren brought up something he hadn’t written on the legal pad. His 32-year-old son, Marcus, launched a meal delivery startup in 2023. It failed in early 2025. Marcus is working part-time now, living with a roommate, and calls Warren roughly once a month — not always directly asking for money, Warren said, but often enough that the request is implicit.
Warren and his wife haven’t set a formal limit on what they’ll give Marcus going forward. That ambiguity is its own kind of cost. “My wife says we have to help him. I agree. But I also think about the fact that we can’t borrow for retirement the way he can still borrow for his life. He has 35 years to rebuild. We don’t.”
The tension in that sentence was not lost on him. He said it quietly, and then looked out the window for a moment.
What Warren Has Decided — And What He Hasn’t
In the three years before retirement, Warren has made a few concrete decisions. He’s committed to maximizing his 401(k) contributions — the 2026 catch-up limit for workers 50 and older is $31,000, including the standard $23,500 deferral plus a $7,500 catch-up contribution, per IRS guidelines. He’s doing the same for his wife’s IRA. Every dollar matters now in a way it didn’t when he was 45.
He’s leaning toward delaying Social Security until 67, accepting the two-year portfolio draw rather than locking in a permanently reduced benefit. But he hasn’t committed to it. “If the market drops hard between now and 65, that calculus changes completely.”
As for Marcus: Warren and his wife are talking about setting a defined, finite amount — perhaps $10,000 total — they’re willing to give over the next two years, framed to their son as a one-time bridge, not an open account. Whether they’ll hold that line is a different question.
“He’s a good kid who made a hard bet and it didn’t work out,” Warren said. “But I also have to take care of myself and my wife. I can’t be his safety net forever, because there won’t be a net left.”
When I left that coffee shop, Warren was still at the table. He’d flipped the legal pad to a fresh page. The columns were already forming.
Three years is not a long time. For a methodical planner trying to account for every variable in a 30-year retirement — the market, the healthcare system, a son who needs help, a Social Security decision with permanent consequences — it might not feel like enough. Warren Jeffries is doing what he’s always done: running the numbers, circling the ones that worry him most, and refusing to look away from what they say.
Related: His Son Calls Every Month Asking for Money. At 62, Warren Jeffries Is Running Out of Time to Say No
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