Retirement Planning in Your 60s: A 2026 Checklist

Your 60s are the most consequential decade for retirement planning. The decisions you make now — about Medicare, Social Security, income, and insurance — will shape the next 20 to 30 years. Here is a practical checklist to work through.

1. Enroll in Medicare at the Right Time

If you are retiring at 65 or leaving employer health coverage, enroll in Medicare Parts A, B, and D during your Initial Enrollment Period to avoid permanent late penalties. Decide between Original Medicare with a Medigap supplement or Medicare Advantage before your coverage start date.

2. Plan Your Social Security Timing

You can claim as early as 62 or delay until 70 for an 8% annual increase past Full Retirement Age (67 for those born in 1960 or later). Coordinate with your spouse if you are married — the higher earner delaying often maximizes lifetime household income.

3. Review All Insurance Coverage

Life insurance needs change in retirement. If your mortgage is paid off and children are independent, you may need less — or different — coverage. Confirm beneficiary designations on all policies, retirement accounts, and bank accounts are up to date.

4. Build a Retirement Income Plan

Map out your guaranteed income (Social Security, pension, annuities) against your estimated monthly expenses. The gap is what your savings must cover. Consider whether a fixed annuity or income annuity makes sense to shore up guaranteed income.

5. Prepare for Healthcare Costs

Fidelity estimates a 65-year-old couple will spend $330,000 on healthcare costs in retirement — not including long-term care. Build healthcare expenses into your retirement budget and consider whether long-term care insurance or a hybrid life/LTC policy makes sense.

6. Update Your Estate Documents

Review your will, powers of attorney (financial and healthcare), and beneficiary designations. If you do not have these documents in place, now is the time to work with an estate attorney.

Approaching retirement? Wisler offers free consultations to help you navigate Medicare enrollment, life insurance, and retirement income options — all in one conversation.