10 things to do if you're nearing retirement
Retirement isn't one decision — it's a dozen smaller ones, and they're much easier to get right if you start working through them a few years early. Here's what actually matters, roughly in the order people run into it.
01 Ten things to work through before you retire
Most pre-retirement budgets are really just a copy of the current paycheck with "no more commuting" penciled in — which misses how much spending shifts once you actually retire. Housing, health care, travel, and everyday life often move in opposite directions at once. Total that up, then stack it against what Social Security, any pension, and your savings can realistically cover.
Every other item on this list exists to make that comparison come out right. The 401(k) & Savings and Taxes & Paperwork pages cover the mechanics; the Retirement Planner & Modeler is where you can model your own numbers directly.
Filing at 62 instead of waiting until 70 isn't a small difference — it can permanently change your monthly check by around three-quarters. It's also one of the few choices here you mostly can't undo once made, which makes "I'll figure it out when I file" the riskiest plan on this list.
If you're stopping work before 65, Medicare won't be there yet, so you need a bridge: COBRA (typically capped at 18 months and rarely cheap), a Marketplace plan through HealthCare.gov, riding on a spouse's employer coverage, or part-time work that comes with benefits.
Price this out before you pick a retirement date — for an early retiree, it's routinely one of the biggest numbers in the whole budget. See the Medicare page for what happens once you turn 65.
Miss your Initial Enrollment Period and the penalty isn't a one-time fee — it can attach to your premium for as long as you have Medicare. Before that window opens, confirm whether you'll be enrolled automatically, whether your employer plan is large enough to let you delay Part B without a penalty, and whether Original Medicare plus a Medigap policy or a Medicare Advantage plan fits you better.
Full details, including the exact enrollment windows, are on the Medicare page.
A market drop does the most lasting damage in the years right around retirement, because withdrawals from a shrinking account can lock in losses a growing account would have simply recovered from — this is often called sequence-of-returns risk.
The fix isn't dumping everything into cash the week you retire; it's easing toward a mix your plan can survive a rough first few years on, with enough set aside in cash or short-term bonds that you're not forced to sell stocks at a loss early. The Retirement Planner & Modeler's Monte Carlo projection is built to stress-test exactly this kind of early downturn.
Figure out ahead of time which accounts you'll tap first — taxable brokerage, then tax-deferred, then Roth is the common default, though not automatically the best one for you — what withdrawal rate the plan can sustain, and how required minimum distributions down the road will reshuffle that order.
Working this out on paper beats making it up the month your paycheck stops. See the 401(k) & Savings page for RMD and rollover rules.
Once you're not drawing a W-2 paycheck, you often have more say over how much taxable income shows up in a given year — which means more room to plan around it. That can mean Roth conversions timed for lower-income years, setting withholding correctly on pensions and IRA withdrawals, and understanding how each Social Security or IRA dollar you take affects what's taxable.
The Taxes & Paperwork page covers the specific withholding forms (W-4V, W-4P, W-4R).
Beneficiary forms on retirement accounts and life insurance override whatever your will says — so an outdated one from years ago can send money to the wrong person no matter what your estate plan intends.
Check those, along with your power of attorney and health care directive, while it's a routine task rather than an emergency. The Taxes & Paperwork page has more on beneficiary reviews.
Medicare covers only very limited stretches of long-term care, and a serious need can derail a plan that otherwise looked solid. You don't have to buy insurance for it, but you do need to make an active choice — self-fund it, insure against it, or blend the two — while you're still healthy enough to qualify and premiums are still reasonable.
The financial pieces get most of the attention, but plenty of new retirees are caught off guard by how much they miss having somewhere to be. If a hard stop feels premature, easing out through part-time work, consulting, or a lower-stress role can soften both the financial and the personal adjustment — and stretch your savings a little further in the process.