Your 60s are not a countdown to retirement. They are the decade when everything you have built starts to come into focus, and the decisions you make now will shape what the next 20 or 30 years actually look like. In more than 35 years of working with pre-retirees and retirees in Pasadena, I have seen that the families who enter retirement with the most confidence are almost always the ones who spent their 60s preparing intentionally, not reactively.

This checklist gives you a clear, age-by-age framework for the decade ahead. Think of it as a guide, not a weekend project.

Ages 60 to 62: Build the Foundation

The early part of your 60s is about getting organized and honest about where you stand.

Get a clear picture of your finances. Pull together your account balances, pension estimates, and Social Security projections. If you have not logged into ssa.gov to review your earnings record and projected benefit, start there. It takes 10 minutes and tells you a lot.

Maximize retirement contributions. In 2026, workers 50 and older can contribute up to $31,000 to a 401(k), including catch-up contributions. Under SECURE 2.0, workers ages 60 to 63 are eligible for an enhanced catch-up that allows even more. IRA contributions are capped at $8,000. These limits are worth using consistently.

Start projecting your retirement expenses. Many people underestimate what they will spend in retirement, especially in the early years when they are active and traveling. Build a realistic picture that includes healthcare, housing, and family support, not just basic living costs.

Make a Plan for Long-Term Care. It may (or may not) be too late to get a good price on insurance, but you should still be thinking about what kind of care you may want/need, how much it could cost, and who you can lean on as you near end of life.

Review your tax situation now. Your early 60s are often your highest-earning years and frequently the last window before Social Security and Required Minimum Distributions (RMDs) add to your taxable income. Strategic Roth conversions can be especially valuable in this window.

Ages 63 to 65: Navigate the Medicare Transition

Medicare is one of the most confusing transitions retirees face, and getting it wrong can be expensive.

Understand your enrollment windows. Most people become eligible for Medicare at 65. If you are not yet receiving Social Security, you need to enroll during your Initial Enrollment Period, which runs from three months before to three months after your 65th birthday. Missing this window can result in permanent late enrollment penalties on your Part B premium. You can find enrollment timelines and details at medicare.gov.

Know how Medicare interacts with employer coverage. If you or your spouse is still working and covered by a group health plan, the coordination rules are nuanced. In some cases, delaying Part B enrollment makes sense. In others, it does not. Get guidance specific to your situation before making any decisions.

Learn the difference between Original Medicare and Medicare Advantage. Original Medicare paired with a Medigap supplement offers broad provider access and predictable out-of-pocket costs. Medicare Advantage plans are often lower-cost upfront but come with network restrictions. Neither is automatically better; the right choice depends on your health and priorities.

Develop a Social Security claiming strategy. The difference between claiming at 62 versus 70 can be as much as 76% in your monthly benefit. The right age depends on your health, your spouse’s situation, and your other sources of income. For many people in their late 60s who are still working, waiting makes sense, but not always. Run the numbers before you decide.

Plan for IRMAA. Medicare premiums are higher for individuals above certain income thresholds, based on your tax return from two years prior. If you expect a high-income year at 63, it may affect your Medicare costs at 65. This is worth planning around in advance.

Ages 66 to 69: Optimize Before the Finish Line

This is often the most consequential window in pre-retirement planning. You are close enough to see the finish line, but you still have time to act.

Get serious about Roth conversions. The years between retirement and the start of RMDs at age 73 are a prime opportunity to convert traditional IRA funds at favorable tax rates. Converting now means paying taxes on your terms, rather than having RMDs push you into higher brackets later.

Revisit your asset allocation. Your investment mix at 68 probably should not look the same as it did at 48. Retirees today may spend 25 to 30 years in retirement and need their portfolios to keep pace with inflation. The balance between growth and stability should shift deliberately, not by default.

Update your estate plan. Beneficiary designations on IRAs and 401(k)s override what your will says. Review everything: wills, trusts, powers of attorney, healthcare directives, and beneficiary forms. If your family situation has changed in the last few years, this is overdue.

Ages 70 to 73: Get Ready for RMDs

Understand when RMDs begin. Under current law, Required Minimum Distributions start at age 73. The IRS RMD page explains the rules in detail. Missing an RMD carries a significant penalty. If you have multiple IRAs, you can aggregate the total and take it from any combination of accounts. 401(k)s require separate calculations.

Consider Qualified Charitable Distributions. If you are charitably inclined and over age 70½, a QCD lets you direct up to $108,000 per year (the 2026 limit) directly from your IRA to a qualifying charity. This satisfies your RMD and keeps the distribution entirely out of your taxable income. It is one of the most tax-efficient strategies available to retirees who give regularly.

Watch how your income streams interact. Once Social Security and RMDs are both in play, your taxable income can increase significantly, potentially pushing you into higher brackets and triggering IRMAA surcharges. Understanding how these interact is exactly the kind of planning that pays for itself.

Pasadena-Area Considerations

California’s state income tax is among the highest in the country, and unlike some states, California does not offer favorable treatment for retirement income. IRA withdrawals and Social Security income are generally taxable at the state level, which makes Roth conversions, withdrawal sequencing, and tax-efficient investing even more valuable here.

California has no estate tax, which is a planning advantage. However, Proposition 19, which took effect in 2021, significantly changed the rules governing the transfer of real estate to adult children. If your home is part of your legacy plan, this deserves a conversation with your advisor.

Finally, the cost of living in the greater Pasadena area is real. Retirement income projections that work elsewhere in the country may need to be revisited here.

Red Flags to Watch For

A few patterns can quietly derail an otherwise solid plan. Watch for these:

• Delaying action because retirement still feels far off. Even at 60, five years go faster than you expect.
• Underestimating healthcare costs. Even with Medicare, out-of-pocket expenses can be significant.
• Working with an advisor who earns commissions on what they recommend. This creates a conflict of interest that can be hard to see and costly over time. A fee-only, fiduciary advisor’s compensation does not depend on what you buy.

The Bottom Line

Your 60s are a remarkable window. The key is being intentional about the decisions you make along the way, rather than waiting until retirement is weeks away.

At Mission Street Wealth Planning, we have been helping families in Pasadena and throughout Greater Los Angeles navigate exactly these decisions since 1989. If you would like to talk through your own pre-retirement checklist, we would love to hear from you.