One Year Before Retirement: The Checklist, in Deadline Order

Updated August 6, 2026. Quick answer: at twelve months the job changes character. Up to now it was deciding; from here it is arranging, and arranging has deadlines. This list is ordered by what closes first rather than by what feels most important — because the items that feel most important (the portfolio, the budget) are the ones that stay open, and the ones that quietly close are the ones nobody thinks about until they have.

Do these first: they become permanent

1. The survivor election on any pension. The form usually arrives near the end, which is the worst time to meet the question for the first time. Decide it now: the arithmetic with a younger spouse, and for federal households the FERS election.
2. Any annuitisation decision. If part of a balance is going to become a guaranteed stream, that is a one-way door — the federal version is the clearest: the TSP annuity, which cannot be changed or terminated once purchased, and where the spouse’s waiver is itself irrevocable. The general arithmetic is here.
3. A lump-sum offer, if one is on the table. It has a deadline set by someone else, and its value moves with rates: why the number changes, and the withholding trap.

Then the windows, because they expire

1. Medicare. Check your specific window against your last day rather than against your birthday: the enrollment window. A late enrollment is priced for life, not for a year.
2. The coverage bridge, if you finish before Medicare starts: COBRA versus the marketplace, and if a spouse is on your plan, their bridge is a separate problem.
3. The income year. If your Medicare start is two years out from a tax year you can still influence, that year is live now — the two-year lookback, and why a dollar matters at the threshold.

The claiming decision, deliberately not last

Social Security is on this list at twelve months specifically so that it does not get decided by the last day arriving. Stopping work and starting benefits are separate decisions that only feel like one: the claiming arithmetic, and the couple’s version, which has a different answer.

The money work that stays open

• Practise the budget for a full year — the last year you have income to correct with. Build it, then check it against where the gap usually opens.
• Final catch-up contributions, including the age band that appears and disappears: 60 to 63.
• The withdrawal order, which is a plan rather than an event: what to draw first and how it interacts with the brackets above.
• The mortgage, if it is still open: the pay-off question.

Set the actual date with the calendar in front of you

Which side of the new year your last day lands on can move a year of income between tax years, and with it the Medicare mark above: December or January. Run your own dates through the milestones and deadlines calculator rather than working from the general shape of a year.

Then

Ninety days out the list becomes logistics: the final-quarter checklist. The whole countdown, printable in one page, is here. And the seven decisions that cannot be undone — worth reading once now rather than discovering individually — are here.

If you want the sequence checked

The items in the first two sections are where advice is worth most, because they are dated and permanent rather than open-ended. Bring your date, your elections, and the two-year mark. What advice should cost is worth reading before you agree to anything ongoing.

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Honest gap. This is a sequencing checklist, not the analysis — every linked page carries its own figures, sources and limitations, and the annual numbers live there so this page cannot go quietly stale. Which items are truly permanent depends on your plan and system; public-sector and federal retirements run their own windows and are not replaced by this list. See methodology and corrections. General information, not financial advice.