5 Years From Retirement? Here's Your Complete Pre-Retirement Checklist

Five years sounds like a long time. In retirement planning terms, it moves quickly — and the decisions made during this window shape every year that follows. Whether you are targeting retirement at 60, 65, or 67, the checklist below applies. Work through it systematically, and do not wait until the final year to address items at the top.

Income and Savings

1. Calculate your projected monthly retirement income from all sources: Social Security, pensions, annuities, and portfolio distributions. Know the number before you retire, not after.

2. Maximize contributions to tax-advantaged accounts. If you are 50 or older, catch-up contributions allow you to add an extra $7,500 to a 401(k) and an extra $1,000 to an IRA in 2026.

3. Stress-test your savings rate. If you retired today, would your assets sustain your planned lifestyle for 30 or more years? If not, identify the gap.

4. Identify any pension decisions that need to be made. Lump sum versus annuity elections, survivor benefit choices, and timing decisions often cannot be undone.

Social Security

5. Create or update your Social Security account at SSA.gov and review your earnings history for errors.

6. Model different claiming scenarios — at 62, at full retirement age, and at 70 — and understand the permanent impact of each choice on your monthly benefit.

7. If you are married, coordinate claiming with your spouse's benefit to maximize the survivor benefit.

Healthcare

8. Understand when you become eligible for Medicare — age 65 — and plan accordingly if you are retiring before that date. COBRA, marketplace coverage, or a spouse's plan may bridge the gap.

9. Review Part B enrollment windows. Missing your Initial Enrollment Period can result in permanent premium penalties.

10. Estimate your out-of-pocket healthcare costs in retirement, including premiums, copays, and dental and vision expenses that Medicare does not cover.

Tax Planning

11. Map out your tax situation in retirement. Which accounts are taxable, tax-deferred, and tax-free? Do you have a plan for drawing from each efficiently?

12. Evaluate whether Roth conversions make sense in the years between retirement and when RMDs begin. This window is often the most tax-efficient time to convert.

13. Review your capital gains exposure in taxable accounts. Positions with large embedded gains may need to be managed carefully to avoid a large tax event.

Investments

14. Reassess your asset allocation with a retirement income lens — not just a growth lens. Sequence-of-returns risk means that early retirement losses matter more than later ones.

15. Establish a cash reserve or income bucket sufficient to cover 12 to 24 months of expenses, reducing the need to sell equities during a downturn.

Legal and Estate Planning

16. Confirm your will, durable power of attorney, and healthcare directive are current and reflect your current wishes.

17. Review beneficiary designations on all retirement accounts and insurance policies. These override your will.

18. Consider whether a trust is appropriate for your estate and discuss with an estate planning attorney.

Insurance and Risk

19. Evaluate your long-term care coverage. If you do not have a plan for potential care costs, develop one before you retire — options and pricing are more favorable when you are younger and healthier.

20. Review your life insurance needs. Coverage that made sense during your working years may no longer be necessary — or it may be more important than ever, depending on your survivor benefit situation.

At The Protective Wealth Group, we guide Tampa Bay pre-retirees through this entire process. If you are within five years of retirement, the time to start is now — not the year you plan to leave work.