How to Prepare for Retirement in Your 60s: A Year-by-Year Plan

Start with your date, then work backward

The single most useful thing you can do in your 60s is pick a target retirement date — even a rough one — and plan backward from it. Almost every decision that follows has its own deadline: Medicare has a fixed sign-up window around your 65th birthday, Social Security rewards you for waiting, and your employer's benefits end on a specific day. Line them up against your date and the overwhelm turns into a short, ordered list.

The years below are a guide, not a rule. If you're retiring at 62, you'll compress several of these steps into one year; if you're working to 67, you'll have more room. Either way, the order is what keeps things from slipping.

Age 60–62: Build the money runway

Your early 60s are your last, best chance to add to your savings while the tax rules are unusually generous — and to find out, before you rely on it, what your money will actually cover.

• Use the bigger catch-up window. Once you're 50 you can add extra "catch-up" money to a 401(k) or IRA. A newer rule goes further: in the years you're 60, 61, 62, or 63, your workplace-plan catch-up is larger still — for 2026 that's $11,250 on top of the regular limit. Confirm the current-year figure with your plan and put in what you can.
• Build a real spending plan — then test it. Track what you actually spend for a few months and sort it into essentials, flexible, and one-time. This is the number your whole retirement rests on, so it's worth getting honest about now rather than guessing.
• Knock down high-interest debt. Every dollar of credit-card or car debt you retire before you retire is one your fixed income doesn't have to carry.
• Set aside a cash cushion. A year or two of easy-to-reach spending money means you're never forced to sell investments in a down market in your first years out.

Age 63–64: Bridge your health coverage to 65

Medicare doesn't start until 65 for most people, so if you retire before then, the question isn't whether you'll cover the gap — it's how. Do not go uninsured, even for a few months; one accident can undo years of saving.

• Know your two main bridge options. You can usually keep your employer plan for a while through COBRA, or buy your own plan on the ACA Marketplace. Costs and any subsidies change from year to year, so price both for the actual year you'll retire.
• Run the numbers before you commit. Our free Health Insurance & ACA Subsidy Calculator estimates COBRA-vs-Marketplace costs so you can see the gap you're bridging in real dollars.
• Mark your Medicare date now. Your sign-up window opens three months before the month you turn 65 — put it on the calendar today so it can't sneak up on you.

Age 65: Get Medicare right the first time

Medicare is the one deadline in your 60s with a real, lasting penalty for missing it — so it's worth understanding the window before you're in it.

• Your Initial Enrollment Period is 7 months. It starts three months before the month you turn 65, includes your birthday month, and runs three months after. Signing up in the first three months means coverage can start the month you turn 65.
• Late enrollment can cost you for life. If you don't have other qualifying coverage and you miss your window, Part B and Part D can carry a penalty that's added to your premium for as long as you have Medicare.
• Book your free “Welcome to Medicare” visit. In your first year on Part B you get a one-time preventive visit at no cost — a clean starting point for your retirement health.
• Remember the yearly window. Medicare Open Enrollment runs October 15 to December 7 every year, when you can change plans for coverage starting January 1. Our Medicare Enrollment Calendar keeps the dates straight.

Choosing when to claim Social Security

This is the biggest reversible-until-you-file money decision of your 60s, and there's no single right answer — it depends on your health, your savings, and whether you're married. What helps is knowing exactly what each age gives you.

• 62 is the earliest — but it's a permanent cut. Claiming at 62 can reduce your monthly benefit by roughly 30% for life compared with waiting for your full retirement age.
• 67 is your full benefit if you were born in 1960 or later — 100% of what you've earned.
• 70 is the maximum. Every month you wait past full retirement age adds delayed-retirement credits, up to about 124% of your full benefit at 70. Waiting past 70 adds nothing, so there's no reason to delay beyond it.
• You can file up to 4 months ahead. You don't have to wait until the day you retire — apply a few months before you want payments to start.
• Married, widowed, or divorced? Look at spousal and survivor benefits before you lock in a date — the order you claim in can be worth a lot. Our guide on which benefit to claim, and when walks through it.

The last 90 days: your countdown to day one

The final stretch is all logistics — the notice, the payout, the coverage that switches over. This is where a written checklist earns its keep, because a lot happens in a short window and none of it should live only in your head.

1. Give notice in writing, following your employer's exact process, and confirm your last day.
2. Submit your pension election — and check the survivor option before you sign. This choice is usually permanent and directly affects what a spouse receives.
3. Get your PTO or vacation payout amount and date in writing, along with the exact end dates for health, life, and other benefits.
4. Decide what happens to your 401(k): leave it, roll it to an IRA, or move it — and watch for your COBRA notice, which gives you 60 days to elect.
5. Save your personal files and contacts off any work devices while you still have access.

Turn your savings into a monthly paycheck

For decades your job handed you a paycheck. In retirement you build your own — and the first few months are about making sure it lands reliably and fits the plan you tested earlier.

• Make your first withdrawal and confirm it fits your budget. Watch actual spending against your plan for the first month or two and adjust.
• Handle taxes on purpose. Retirement income usually isn't taxed automatically — set up withholding or quarterly estimates so you're not surprised in April.
• Calendar your RMDs. Once you reach 73, the IRS requires minimum withdrawals from most tax-deferred accounts each year, with penalties for missing them. Note the age now even if it's years away.

The paperwork most people forget

Retiring is a natural moment to get the rest of your affairs in order — the documents your family would need if something happened, and the accounts that would otherwise be impossible to find.

• Update your beneficiaries on retirement accounts and life insurance — they override your will, and they're easy to leave outdated after a job change or life event.
• Refresh your core estate documents: a will, a financial power of attorney, and a healthcare directive.
• Make one list of what you have and where it lives — accounts, insurance, key contacts — so it isn't a treasure hunt for the people you love.

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