The Retirement Countdown Checklist (Printable)

Updated August 6, 2026. Quick answer: the whole countdown on one page, meant to be printed and marked up. Items marked ⚫ cannot be undone once done — they are the reason a countdown is worth keeping at all. Everything else can be revisited.

Five to three years out

• Decide whether the date is a plan or a hope; if it is a hope, do the estate documents anyway ⚫-adjacent, since they never have a deadline — estate checklist
• Take catch-up contributions, including the 60–63 band that appears and disappears — the band
• Practise living on the retirement budget while income can still correct it — build the number
• Decide the mortgage — pay off or carry
• Confirm the balance supports the date — can I retire

Two years before Medicare starts

• Mark this year on the calendar. Its income sets your Medicare premiums — the two-year lookback
• Move or postpone anything that spikes income in it: conversions, a business sale, a large option exercise — it is a cliff, not a slope

Twelve months out

• ⚫ Decide the pension survivor election before the form arrives — the arithmetic
• ⚫ Decide any annuitisation — the TSP version cannot be changed or terminated once purchased
• ⚫ Decide a lump-sum offer if one exists — the break-even
• Check the Medicare window against your last day — the window
• Choose the coverage bridge — COBRA or marketplace
• Decide Social Security on arithmetic, not on the last day — claiming age
• Set the withdrawal order — what to draw first
• Full list — the twelve-month checklist

Final ninety days

• Confirm coverage start dates with no gap — a gap here cannot be repaired later
• Measure the gap between the last paycheque and the first retirement payment, and hold that cash outside the portfolio
• ⚫ Sign the survivor election — permanent once payments begin
• Set withholding — what to withhold
• Check every beneficiary designation; they override a will
• Fix the last day with the tax year in mind — December or January
• Full list — the 90-day checklist

The first months

• Verify the first payments arrived in the amounts expected, and query anything that did not
• Re-run the budget against reality rather than against the plan — where the gap opens
• Read the seven irreversible decisions once more if any remain open — the mistakes

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Notes

The full sequence and the reasoning behind the order is on the spine page. Honest gap. This is a sequencing aid, not advice, and the marks are a general guide — whether a given election is truly irreversible depends on your specific plan and system, and public-sector and federal retirements run their own windows and forms. Annual figures deliberately do not appear here; they live on the linked pages so this sheet does not go stale in your drawer without showing it. See methodology and corrections.