The Year Before You Retire: A Checklist From Twelve Months Out to Your Last Day

The year before you retire is when retirement stops being a number and becomes a list of decisions with deadlines: how you will be covered for health care, when you will claim Social Security, how your savings will turn into a paycheck, and what paperwork you need before you hand in your badge.¹ None of it is hard on its own. The trouble is that it all lands at once if you leave it to the last two months, and a few of the deadlines carry penalties that last for life.

I gave myself a year, mostly by accident, because my school district wanted notice by the spring for a June retirement. In hindsight that year was the best planning decision I made. This is the checklist I wish I had started with, in the order the tasks come due, reviewed by a CERTIFIED FINANCIAL PLANNER.

Twelve months out: the big picture

Twelve months before your planned date, gather the three numbers every other decision depends on: your Social Security estimate at each claiming age, the balance of every retirement account you own, and what you actually spend in a year.² Without those, everything else on this list is guesswork.

• Pull your Social Security statement from your my Social Security account. It shows your estimate at 62, at full retirement age (67 for anyone born in 1960 or later), and at 70, and your earnings record, which is worth checking for missing years while you can still find the W-2s. How to read it is in your Social Security statement.
• List every account. Current 401(k) or 403(b), old plans at former employers, IRAs, a pension if you have one, an HSA, and taxable savings. If you suspect there are accounts you have lost track of, finding lost retirement accounts explains where to look.
• Track a year of spending. Not a budget, the real number. Bank and card statements for the past twelve months are enough.
• Run the basic test. Does Social Security plus any pension plus a sustainable withdrawal from savings (a common starting guide is about 4% of the pot in year one) cover that spending? If the answer is no, you still have a year to change the date, the budget, or the plan, and how much do I need to retire walks through the math.

Nine months out: health coverage and the claiming decision

Nine months out, settle the two decisions with the longest tail: how you will be insured between your last day and Medicare at 65, and the age at which you will claim Social Security.¹ Both are hard to undo.

If you are retiring before 65, health coverage is usually the biggest single cost in the bridge years. The realistic options are COBRA from your employer, which generally runs up to 18 months, an ACA marketplace plan, a spouse’s employer plan, or retiree coverage if your employer still offers it. Price at least two of them now, and remember that marketplace premium help depends on your income, which in retirement is partly something you choose through withdrawals. The full comparison is in health insurance before Medicare.

The claiming decision deserves the same attention. Claiming at 62 permanently reduces your benefit; waiting past full retirement age grows it about 8% a year until 70.¹ Retiring and claiming are two separate decisions, and many people bridge a few years from savings so they can claim later. If you are married, the claiming age of the higher earner also sets the survivor benefit, which is easy to forget. When to claim Social Security lays out the trade-offs.

Six months out: savings and the income plan

Six months out, use your last paychecks to top up savings, and decide exactly how money will move from your accounts into your checking account once the salary stops.³ This is the stretch where a little effort pays the longest.

• Make the most of catch-up contributions. In 2026 the 401(k), 403(b), and 457 employee limit is $24,500, plus an $8,000 catch-up at 50 and over, or $11,250 instead for ages 60 to 63. The IRA limit is $7,500, plus a $1,100 catch-up.³ Check that front-loading contributions will not cost you any employer match in the months after you stop.
• Decide what happens to the workplace plan. Leave it, roll it to an IRA, or keep part of it. If you are leaving the job in or after the year you turn 55, the Rule of 55 lets you take penalty-free withdrawals from that employer’s plan before 59½, and rolling it to an IRA can give that up. The 401(k) rollover guide covers the trade-offs.
• Build the cash cushion. Many retirees start with about one to two years of planned spending in cash, so an early market drop does not force sales at a low.
• Choose a withdrawal method. A fixed monthly transfer from an IRA, a bucket approach, or a percentage you review each year; retirement withdrawal strategies compares them.
• Plan the tax side. Once the paycheck stops, nobody withholds for you by default from Social Security, and IRA withdrawals often have too little withheld. Decide where tax will come from before the first April surprises you; the options are in paying taxes in retirement.

Three months out: Medicare, Social Security, and a trial run

Three months out, file the applications that have fixed windows and start living on your retirement budget, so the first real month is one you have already rehearsed.⁴

If you turn 65 near your retirement date, your Medicare Initial Enrollment Period lasts 7 months: it starts 3 months before the month you turn 65 and ends 3 months after it. Miss it and you may have to wait for a later enrollment period and pay a monthly Part B late enrollment penalty for as long as you have Part B.⁴ If you are leaving employer coverage, signing up before your birthday month avoids a gap. If you have an HSA, enrolling in Medicare stops new contributions, so plan the last contribution around the date; Medicare explained covers the parts and the choices.

If you are claiming Social Security at retirement, apply a few months before you want payments to start, which you can generally do while still working.¹ Expect the first deposit to arrive the month after the month it covers; budget for that gap.

Then the trial run. For two or three months, pay your bills from an account that receives only what your retirement income will be. It is the cheapest test you will ever run, and it shows whether the budget is real.

The last month: paperwork you will not get easily later

In your last month, collect the documents that are easy to get from human resources and tedious to chase once you have left: final pay and leave payout details, benefit end dates, plan contacts, and beneficiary forms.⁵

• Final pay. When the last paycheck arrives, and how unused vacation or sick leave is paid. A large leave payout can be taxed differently and may count toward your final 401(k) contribution.
• Benefits summary. The exact dates health, dental, life, and disability coverage end, and whether any can be converted or continued.
• Retirement plan details. Plan administrator contacts, account numbers, and any pension election forms. Ask whether your pension offers a lump sum or annuity choice and when it must be made.
• Beneficiary designations. Check them on every account. They override a will, and the form on file may be decades old.
• Your own records. Last pay stub, W-2 address on file, and a plain list of every account, login, and phone number for the person who would need it if you could not manage things yourself.

The first three months after

After your last day, the job is to watch the plan work rather than to make new decisions: check that the first deposits arrive as expected, that health coverage started on time, and that tax is being withheld or paid.⁶

The first months are also emotionally odd, in a way no checklist captures. I spent my first September waking at 5:40 for no reason and reorganizing a garage that did not need it. If that sounds familiar, the emotional side of retiring is worth a read, and my own account is in my first year of retirement.

Book one review with yourself, or with a fee-only advisor, around month six: compare actual spending with the plan, check withholding against the tax you will owe, and confirm the cash cushion is where you want it. After that, once a year is plenty.

None of this is personalized financial advice. The limits and ages above are for 2026 and change over time, your own figures are at SSA.gov and Medicare.gov, and a fiduciary advisor can check how the pieces fit your accounts, your health coverage, and your household.