Retirement planning tends to get treated as a math problem — how much you've saved, how much you'll withdraw. But the insurance and paperwork side matters just as much, and it's the part people put off longest because it doesn't feel urgent until it suddenly is. Here's what's worth reviewing, roughly in the order it comes up.

1. Time your Social Security claim carefully

You can claim Social Security retirement benefits as early as 62, but claiming before your full retirement age (FRA) — 67 for anyone born in 1960 or later — permanently reduces your monthly benefit by up to 30%.1 Wait past FRA, and your benefit grows by about 8% for every year you delay, up to age 70, for a maximum bump of 24%.1

62 -30% 67 Full benefit 70 +24%
Age 62
~30% permanent reduction
Age 67
Full benefit (born 1960+)
Age 70
Up to +24% benefit

There's no single "right" age — it depends on your health, other income, and whether a spouse depends on your benefit too. But claiming without doing this math first is one of the most common — and hardest to undo — retirement mistakes.

2. Coordinate the handoff from employer coverage to Medicare

If you're retiring at or after 65, your health coverage needs to transition cleanly into Medicare — timing this wrong can mean a coverage gap or a permanent late-enrollment penalty. (See our Medicare enrollment guide for the specific windows and 2026 costs.) If you're retiring before 65, you'll need a bridge plan — COBRA, a marketplace plan, or a spouse's coverage — to cover the gap.

3. Reassess your life insurance — don't just assume it's done

Many people let life insurance lapse in retirement, assuming the kids are grown and the mortgage is paid off. Sometimes that's right. But it's worth checking: does a spouse rely on your pension or Social Security continuing? Would your estate owe taxes or debts that a policy could cover? Is a policy's cash value part of your retirement income plan? A quick review — not a new purchase — is usually all this takes.

4. Plan for long-term care costs before you need them

This is the piece retirement budgets most often miss. According to the most recent Genworth/CareScout Cost of Care data, the national median cost of a home health aide is now $77,792 per year, and assisted living runs a median of $70,800 per year — both figures that have been climbing steadily.2 Medicare generally does not cover long-term custodial care, so this typically falls to savings, long-term care insurance, or family.

Worth asking now, not later: Do you have a long-term care policy, hybrid life/LTC policy, or a dedicated savings earmarked for this? If the answer is no, it's worth a conversation before it becomes urgent.

5. Update the paperwork that actually protects you

None of these require a crisis to be worth doing. The best time to put them in place is exactly now, while there's no pressure and every decision can be made calmly.

This article is educational and general in nature and isn't personalized insurance, legal, or financial advice. Long-term care costs, Social Security benefits, and Medicare rules vary by individual circumstances and location — talk with Sheila, an elder law attorney, or a financial advisor before making decisions.