Everyone asks the same question about retirement: when should I retire?
It’s a reasonable question.
But I’ve come to think it’s the second question.
The first one is harder, and most plans never ask it: what happens if I don’t get to choose?
Every year, the Employee Benefit Research Institute asks workers when they expect to retire, and asks retirees when they actually did.
The median worker expects 65.
The median retiree stopped at 62. And 46% of retirees say they left work earlier than they planned.
So if your plan only works at 65, you’re betting on the half that gets to choose.
Here are five signs your plan is making that bet, and one test to find out for sure.
If some of these sound like you, that’s not a failure of planning.
Nobody sits you down and asks what happens if the date moves.
It’s a question a lot of people never get around to asking.
Why I ask it
After navigating my wife through terminal cancer, I learned something most financial advisors never experience firsthand.
Healthcare planning isn’t theoretical.
When you’re facing years of unpredictable costs, and you don’t know how long the money needs to last, the numbers on a statement stop meaning much.
What matters is whether reliable income shows up every single month, no matter what’s happening.
You don’t get to pick the timing of the hard parts.
Sign one: your plan has one retirement date on it
One date means one set of projections: one savings target, one Social Security claiming age, one number of years the money has to last.
It feels precise.
But of retirees who left earlier than planned, EBRI found 41% cited a health problem or disability and 35% cited changes at their company.
Some did leave because they could afford to, but for many, the date wasn’t theirs to pick.
Picture a couple, both 61. They’ve circled 64 for his last day. It’s on the calendar, and they’ve told the kids.
Then his company reorganizes, and there’s a package on the table with a two-week deadline.
It’s a fair offer. The problem isn’t the money in the package.
It’s that 3 years of their plan were written around a paycheck that just ended, and the health insurance that came with it.
Sign two: your plan for health insurance before 65 is “we’ll figure it out”
If you stop working before Medicare, there’s a stretch where coverage is your problem.
You’re buying it yourself, usually through the marketplace, and that just got more expensive.
Peterson-KFF reviewed filings from 276 insurers for 2027. The median proposed premium increase is 15%, on top of a 2026 increase finalized around 20%.
If those proposals hold, that’s two years of double-digit increases in the sticker price, before any subsidy.
Sign three: you’ve never priced that coverage at your age
Most people have a vague sense it’s expensive. Very few have looked up a real number, and the market is shifting underneath them.
Healthinsurance.org reports that insurers are leaving the marketplace in 24 states for 2027, and the out-of-pocket maximum for an individual rises to $12,000. A guess made two years ago is outdated.
Here’s what those first three have in common. Each one quietly assumes the date is yours.
Take away that single assumption and all three become urgent at once.
You did everything you were told, and the thing that knocks it over is a decision someone else makes.
Sign four: your plan for the early years draws from whatever account is biggest
This one is a conversation for your tax professional, so I’ll keep it light. Help with marketplace premiums depends on your income.
As healthinsurance.org explains it, once household income goes above 400% of the federal poverty line, that help stops entirely.
So which account pays for a given year can change what you pay for coverage that year.
Sign five: you assume that if your job ends early, you’ll have time to plan
In practice, packages often come with deadlines.
Challenger, Gray & Christmas counted 529,914 announced job cuts from January through August of this year, and artificial intelligence was the leading stated reason, at about 22%.
When an offer arrives, the decision window can be measured in weeks.
The planning has to happen before the call, not after it.
The Gap-Season Budget
If you counted two or more of those signs, here’s a simple exercise.
- First: pick a date 3 years before the one you want. Count the months from there to 65. That’s your gap season.
- Second: put a price on it. Starting November 1 in most states, when marketplace open enrollment opens for 2027, you can window-shop plans in your state, at your age, without enrolling. Multiply that premium by your months. It’s a number now, not a feeling.
- Third: assign the money. Write down which account would carry each year of the gap season, and flag anything that raises your income on paper for a professional to look at.
When you’re done, you’ll know whether an early exit is a setback or an emergency. That’s worth knowing while you still have a paycheck.
Why the gap is its own season
The gap season is the reason Life Season Mapping is Step Four in Phase Two of the Life-Tested Retirement System.
Most plans have two seasons: working and retired. Real retirements have several, and the years between leaving work and Medicare are the first and often the most expensive.
Mapping that season means giving it its own budget, its own income sources, and an honest price on coverage, then checking how those choices ripple into your taxes and your Social Security.
In plain terms, if the date moves, nothing else has to scramble. Think back to that couple with the two-week deadline.
With the season mapped, the deadline is still there, but they’d already know what the gap costs and which money covers it.
The only question left is whether the offer is a good one.
People who’ve priced the gap season can hear about a buyout and do the math in an afternoon. People who haven’t do it against a deadline, with a major insurance decision attached.
Plan for the date you want. Be ready for the date you get.
If you counted a few of those signs and want help mapping your gap season for your situation, you can book a conversation at jonathanpeters.net/consultation.
You’ve worked a long time to choose your date.
Make sure your plan doesn’t depend on it.
Best regards,
Jon
Sources
- Employee Benefit Research Institute, 2026 Retirement Confidence Survey, April 21, 2026.
- Employee Benefit Research Institute, 2026 Retirement Confidence Survey Fact Sheet #2: Expectations About Retirement, 2026 (65 vs. 62; 46% retired earlier than planned; reasons: 41% health problems or disability, 35% changes at their company, 36% could afford to; respondents could give more than one reason).
- Peterson-KFF Health System Tracker, How much and why ACA Marketplace premiums are going up in 2027, July 8, 2026 (updated August 3, 2026). Proposed gross premiums, before subsidies; 87% of enrollees receive premium assistance.
- healthinsurance.org via GlobeNewswire, ACA open enrollment 2027, September 29, 2026.
- Milliman, 2027 ACA out-of-pocket maximum limits released ($12,000 individual, up from $10,600; released by CMS January 29, 2026).
- healthinsurance.org, Marketplace enrollees face return of the subsidy cliff, February 11, 2026.
- Challenger, Gray & Christmas, August 2026 Job Cuts Report, September 2, 2026.
- HealthCare.gov, Dates and deadlines.
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