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, starting now, because several of these items require years of lead time to execute properly. Waiting until the final year before retirement to address tax strategy, healthcare coverage, or Social Security claiming is like studying for a final exam the night before — technically possible, but the results will reflect the lack of preparation.

Income and Savings

1. Calculate your projected monthly retirement income from all sources: Social Security, pensions, annuities, and portfolio distributions. Be specific — not a rough guess, but actual numbers based on your current balances, projected growth, and planned withdrawal rates. Know the number before you retire, not after. If there is a gap between what you need and what your income sources provide, the next four years are your window to close it.

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. Over five years, maximizing catch-up contributions alone can add over $40,000 to your retirement savings before investment growth — and if your employer offers matching contributions, the effective return on those dollars is even higher.

3. Stress-test your savings rate. If you retired today, would your assets sustain your planned lifestyle for 30 or more years under different market conditions — not just average returns, but also poor sequences? If not, identify the gap and determine whether it can be closed through additional savings, reduced spending expectations, or a later retirement date.

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 once made. These are among the most consequential and irreversible financial decisions you will make, and they deserve careful analysis rather than a quick selection on a form.

Social Security

5. Create or update your Social Security account at SSA.gov and review your earnings history for errors. The SSA occasionally misses reported earnings, and correcting errors now protects your future benefit calculation. Your online statement also provides benefit estimates at ages 62, full retirement age, and 70.

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. The difference between claiming at 62 and claiming at 70 can be as large as 76 percent in monthly income, and that difference compounds with every future COLA adjustment for the rest of your life.

7. If you are married, coordinate claiming with your spouse's benefit to maximize the survivor benefit. The higher earner's claiming decision directly determines what the surviving spouse will receive — making this one of the most important joint financial decisions a couple makes before retirement.

Healthcare

8. Understand when you become eligible for Medicare — age 65 — and plan accordingly if you are retiring before that date. The gap between early retirement and Medicare eligibility can be expensive. COBRA coverage typically lasts 18 months, marketplace plans are available but premiums vary significantly based on income, and a working spouse's employer plan may offer the most cost-effective bridge.

9. Review Part B enrollment windows carefully. Missing your Initial Enrollment Period can result in permanent premium penalties — a 10 percent surcharge for each 12-month period you were eligible but did not enroll. For Wesley Chapel and Tampa Bay residents who move to Florida from states with different healthcare marketplaces, understanding the enrollment timeline is especially important.

10. Estimate your out-of-pocket healthcare costs in retirement, including premiums for Parts B and D, Medigap or Medicare Advantage plan costs, copays, and dental and vision expenses that Medicare does not cover. A common planning estimate is $6,000 to $8,000 per person per year in total healthcare costs during retirement, though individual circumstances vary widely.

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 type in a tax-efficient sequence? The order in which you tap different account types can affect your tax bracket, your Medicare premiums, and how long your money lasts.

12. Evaluate whether Roth conversions make sense in the years between retirement and when RMDs begin. This window — often ages 62 to 73 — is frequently the most tax-efficient time to convert, because your income may be lower than during your working years and lower than it will be once required distributions begin. A well-planned series of conversions during this window can save significant taxes over a multi-decade retirement.

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 in a single year. For retirees in the 0 percent long-term capital gains bracket, strategically harvesting gains during low-income years can reset your cost basis and reduce future tax liability.

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, and a portfolio that was appropriate during your accumulation years may carry too much volatility for a period when you are withdrawing rather than contributing.

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. This buffer is one of the simplest and most effective ways to manage sequence risk — it gives your portfolio time to recover without forcing liquidation at the worst possible moment.

Legal and Estate Planning

16. Confirm your will, durable power of attorney, and healthcare directive are current and reflect your current wishes. Florida has specific requirements for these documents, and documents drafted in another state may need to be updated to comply with Florida law after a move to the Tampa Bay area.

17. Review beneficiary designations on all retirement accounts and insurance policies. These designations override your will regardless of what the will states — an outdated beneficiary listing a former spouse or deceased relative can direct assets contrary to your intentions. This is one of the most common and most preventable estate planning errors.

18. Consider whether a trust is appropriate for your estate and discuss with an estate planning attorney. Florida's trust laws are relatively favorable, and instruments like the lady bird deed can simplify property transfer without triggering full probate. For retirees with blended families or specific distribution wishes, a trust provides control that a will alone cannot.

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. The average cost of assisted living in the Tampa Bay area exceeds $4,000 per month, and a multi-year stay can deplete savings quickly without adequate planning.

20. Review your life insurance needs. Coverage that made sense during your working years — when you were protecting dependents against the loss of your income — may no longer be necessary. Or it may be more important than ever, depending on your survivor benefit situation, estate planning goals, or whether you are using life insurance as part of a long-term care funding strategy.

At Protective Wealth Advisors, we guide Tampa Bay pre-retirees through this entire process — not as a one-time checklist, but as an ongoing planning relationship that ensures each item is addressed thoroughly and in coordination with the others. If you are within five years of retirement, the time to start is now — not the year you plan to leave work.