Article content

The last year before retirement is easy to spend refreshing a calculator app instead of making an actual plan. There's a lot to settle, but almost none of it has to happen at once, and most of it has a natural order.

Here's that order: what to confirm about your money first, what to lock in for health coverage next, the paperwork that belongs to your last month of work, and how to give your first weeks of retirement some real shape before you get there.

Choose your next move

What feels least settled right now?

Pick the one that's actually keeping you up at night.

Focus on your benefit estimate, pension choices, and account decisions first.

Whatever you picked, retirement tends to go smoother when your calendar has some real shape before day one, so it's worth starting that plan now rather than waiting to figure it out later.

Interactive toolSketch a rough weekly plan nowUse your Whether my income will be enough as the starting point, then build it out as the other pieces settle.Show the toolHide the tool

Turn a general idea into a short weekly plan that fits your budget, energy, and transportation comfort.

Low-cost activity planner

  • Check your library or senior center for one free class, club, or talk.
  • Pick one low-cost fitness or hobby outing that fits your weekly budget.
  • Choose one low-pressure backup activity in case your first plan falls through.
  • Keep the plan to 2 outings or commitments this week.

Twelve to Nine Months Out: Get Your Real Numbers

Pull your actual Social Security estimate at ssa.gov instead of relying on a rough guess. If a pension is part of your plan, ask your employer or plan administrator about survivor benefit options now. Many pensions make you choose a payout option when you retire, and that choice is often permanent once it's made.

Decide what happens to a 401(k) or similar account too: leave it where it is, roll it into an IRA, or set up a plan for regular withdrawals. Each option has different fees and rules, so this is worth a real conversation with your plan administrator, not a guess.

ChecklistConfirm these before you go furtherThese numbers shape everything that comes after them.Show the checklistHide the checklist

0 of 3 done.

Six to Three Months Out: Lock In Health Coverage

If you're retiring before 65, you need a coverage plan for the gap before Medicare starts. COBRA can extend your employer coverage for up to 18 months, though usually at the full premium. A Marketplace plan is often cheaper, especially if your retirement income qualifies you for a subsidy.

If you're within three months of turning 65, start your Medicare enrollment instead. That window opens three months before your birthday month and closes three months after it, and missing it can mean a permanent premium penalty.

TimelineWork through it in this orderCheck off each step as you settle it.Show the timelineHide the timeline

Do this now if you're retiring before 65, since a Marketplace plan usually needs to be chosen during open enrollment or a qualifying-event window.

Sign up for Part A and Part B on time to avoid a late enrollment penalty.

Prices change year to year, so recheck before Medicare's Open Enrollment closes each December 7.

The Month You Retire: Paperwork and People

Update beneficiary designations on your retirement accounts and life insurance before your last day. These forms override what a will says, so an outdated one can send money to the wrong person even if everything else in your estate plan is current.

Get your final pay stub, benefits summary, and any COBRA election paperwork in writing, and give your employer your last day in writing too, not just in conversation. If COBRA applies to you, the election deadline is usually 60 days from when your coverage ends, so don't let that paperwork sit.

ChecklistClose out the month with theseA little paperwork now prevents a confusing call later.Show the checklistHide the checklist

0 of 3 done.

For the fuller version of this document sweep, What Documents Every Retiree Should Organize Now, Before There Is a Crisis is worth reading alongside this section.

Give Your Time a Shape Before Day One

The retirees who feel steadiest in year one usually aren't the ones with the biggest savings balance. They're the ones who had some shape for their week before they needed it: a standing plan, a place to be, a person to check in with. Use the planner above to sketch that out now, even roughly, so week one doesn't start as a blank page.

If you want more on what that first stretch actually looks like, What Retirees Who Feel Prepared Are Actually Doing Each Week is a good next read.

Save your plan

Save what you've confirmed so far so you can pick up where you left off.