Your pre-retirement checklist: What to do 10 years, five years, and one year out

Here is what to focus on at 10 years out, five years out, and one year out.

 

10 years out: Structural decisions

At roughly a decade from your target date, the work is architectural. You are deciding what your retirement income will be built on, not fine-tuning the details.

• Find out what your actual Social Security benefit could be. Set up a free account at ssa.gov and pull your personalized estimate. It uses your real earnings history rather than an average, and it also lets you check that history for errors and gaps.³
• Separate your income sources into two groups. Group one is income that arrives regardless of what markets do: Social Security, a pension if you have one, and annuities. Group two is income you create by drawing from accounts whose value moves with the market. Most people know their total. Far fewer know the split, and the split is what determines how steady the paycheck feels.
• Name your gap. Add up the essential monthly costs you expect: housing, food, insurance, transportation and utilities. Then compare that number against group one. Whatever is left over is the gap your group two income sources need to cover, and a decade gives you time to make adjustments.
• Use the catch-up room deliberately. Adding $8,000 a year for 10 years is not a rounding error, and the higher amount at 60 through 63 lands in the window when many people have the most capacity to use it.

Ask yourself: If you had to stop working three years earlier than planned, which of these four items would you wish you had already done

 

Five years out: Cost, coverage, and the bridge

Five years out, the planning shifts from structure to arithmetic. You are pressure-testing the number.

• Price health care honestly. A 65-year-old retiring in 2026 can expect to spend an average of $185,500 on health care and medical expenses across retirement, and that figure excludes long-term care.⁴
• Solve the coverage bridge before you need it. Medicare starts at 65. If you retire at 62, you may need to cover roughly three years of health insurance on your own, through a spouse's plan, a marketplace policy or continuation coverage.
• Look at where you live as a financial decision. Housing and transportation together account for more than half of average U.S. household spending.⁵
• Review your estate planning documents and beneficiary designations. Only 24% of Americans report having a will, down from 33% in 2022.⁶ Beneficiary designations on retirement accounts and insurance policies generally control who receives those assets, which means an outdated form can override an up-to-date will.

Ask yourself: When did you last open the beneficiary form on your largest retirement account?  

 

One year out: Logistics and the shape of the day

At 12 months, the focus may begin to shift from broader financial planning to timing, logistics and the part of retirement that has nothing to do with money.

• Put the decisions in order. Your last day of work, Social Security claiming date and Medicare enrollment window are separate dates to plan for and coordinate.
• Confirm how you will draw income, and in what order. Which account you touch first affects both your tax picture and how long the rest lasts.
• Plan the week, not just the budget. Retiring from a routine is the part people describe as harder than expected, and a year allows time to build something to plan toward: part-time or consulting work, a class, or a volunteer role.

Ask yourself: What does a good Tuesday in retirement look like?