Updated September 2026
Most retirement advice is written for people who are decades away from retiring: start early, diversify, let compounding do the work. That advice is sound, and largely useless once you are within ten years of the finish line. At that point, the questions change. It is no longer about how much you can save. It is about how you convert what you have already built into an income that lasts, without giving away more to taxes and market timing than necessary.
This is the checklist we walk clients through in the decade before retirement, roughly ages 55 to 65, when the decisions made carry outsized weight on everything that follows.
1. Get Specific About Your Number
Vague retirement savings goals do not hold up under real planning. "A comfortable retirement" is not a number. What matters is a realistic projection of your annual spending in retirement, adjusted for the fact that spending rarely stays flat. Healthcare costs tend to rise. Travel spending often front-loads in the early retirement years and tapers later. Housing costs may drop if a mortgage is paid off, or may not, if you plan to relocate or downsize into something more expensive.
Build the number from your actual life, not a rule of thumb. A rule of thumb tells you where to start looking. It does not tell you whether you are on track.
2. Maximize Contributions While You Still Have the Room
The final working years are also the years with the highest contribution limits, and that is not a coincidence. For 2026:
- 401(k), 403(b), and most 457(b) plans: $24,500 in elective deferrals
- Age 50+ catch-up: an additional $8,000, for $32,500 total
- Super catch-up, ages 60-63: an additional $11,250 in place of the standard catch-up, for $35,750 total
- Traditional and Roth IRAs: $7,500, or $8,600 with the age-50 catch-up
If you are between 60 and 63, the super catch-up window is worth paying attention to. It applies only during those four ages and only if your employer's plan permits it, and it disappears once you turn 64. For high earners, note that catch-up contributions above $150,000 in prior-year wages must now go into the plan on a Roth basis rather than pre-tax, a change that took effect in 2026 and requires some recalibration if you were counting on pre-tax catch-up contributions to manage current-year income.
3. Model Your Social Security Claiming Strategy Now, Not at 62
Full retirement age is 67 for anyone born in 1960 or later. Claim before that and your benefit is permanently reduced. Delay past it, up to age 70, and your benefit grows by roughly 8% for every year you wait. The difference between claiming at 62 and claiming at 70 can amount to hundreds of thousands of dollars in lifetime benefits, depending on longevity and the rest of your income picture.
The right claiming age depends on more than the benefit calculation alone. It depends on your health, your spouse's benefit and claiming strategy, whether you plan to keep working, and how Social Security income interacts with the rest of your tax picture. This is not a decision to make in the year you turn 62. Model it now, while you still have time to adjust the rest of your plan around it.
4. Plan the Healthcare Bridge to Medicare
Medicare eligibility begins at 65. If you plan to retire earlier, you need a coverage plan for the gap, whether that is COBRA, a marketplace plan, or continued employer coverage through a part-time or consulting arrangement. This gap is also where a Health Savings Account, if you have access to one through a high-deductible health plan, becomes especially valuable. Contributions made in these final working years, left invested rather than spent, can become a dedicated, tax-free fund for exactly the period when healthcare costs tend to climb.
5. Use Lower-Income Years to Your Advantage
If you retire before claiming Social Security, or if your income dips during a business transition, those years often represent your best window for converting pre-tax retirement funds to Roth at a favorable rate. Once converted, those funds grow tax-free and are never subject to required minimum distributions. Partial, systematic conversions over several years, timed to avoid pushing you into a higher bracket or triggering Medicare surcharges, can meaningfully reduce your lifetime tax bill. This is a strategy worth modeling well before you retire, not improvised once you are already there.
6. Shift How Your Portfolio Handles Risk
The math of investment losses changes once you start withdrawing from a portfolio instead of contributing to one. A market downturn in your final working years, or in the first few years of retirement, can do outsized damage if you are forced to sell depreciated assets to fund living expenses. This is often called sequence of returns risk, and it is one of the more overlooked threats to an otherwise sound retirement plan. Reviewing your asset allocation and building in a cash or bond reserve to cover near-term spending needs, rather than relying entirely on portfolio withdrawals, is a standard part of de-risking this transition.
7. Stress-Test the Plan Against What You Cannot Control
A plan that only works if markets perform as expected is not a plan. Before you retire, it is worth modeling what happens if markets underperform for the first five years, if inflation runs hotter than projected, or if you or a spouse needs long-term care. These are not pleasant scenarios to plan around, but finding out whether your plan survives them now, while you still have time to adjust, is far better than finding out after you have already left your paycheck behind.
8. Review Beneficiaries and Estate Documents
Retirement accounts, life insurance policies, and annuities all pass according to their named beneficiaries, regardless of what a will says. It is common, particularly after a job change, a remarriage, or simply the passage of time, for these designations to fall out of date. The decade before retirement is a natural checkpoint to confirm that your will, powers of attorney, healthcare directives, and account beneficiaries all reflect your current wishes.
Bringing It Together
Each of these items works in isolation. They work far better coordinated. A Roth conversion changes your income for Medicare surcharge purposes. Your Social Security claiming age changes how much you need your portfolio to produce in the early retirement years. Your asset allocation shift should account for when you plan to claim. This is the coordination problem we help clients solve in our tax planning and broader retirement income work.
Frequently Asked Questions
Q1: Is ten years really the right window to start this checklist?
Ten years gives you enough runway to actually act on what you find, particularly around Roth conversion windows and Social Security modeling. Starting later is still worthwhile, but the further out you start, the more options remain available to you.
Q2: I max out my 401(k) already. What else should I be doing?
Maximizing contributions is necessary but not sufficient. Claiming strategy, tax bracket management, healthcare bridge planning, and portfolio risk all matter independently of how much you have saved, and none of them are addressed simply by contributing the maximum.
Q3: How is this different from a general financial plan?
A general financial plan covers your full financial life across every stage. This checklist is specific to the small number of decisions that are time-sensitive and difficult to reverse in the final working decade, which is why they deserve focused attention on their own.
Related Reading on the MJT Blog
- Is a Roth Conversion Right for You?
- Tax Planning Strategies That Actually Move the Needle
- A Real Financial Plan: What It Includes, Why It Matters, and Where Most People Fall Short
- Maximizing Your Health Savings Account: A Strategic Tool for Retirement
Conclusion
The decade before retirement is not the time to coast on a plan built years earlier. It is the time to get specific: about your number, your claiming age, your tax exposure, and your portfolio's ability to withstand a bad few years right when you can least afford one. Getting these decisions right does not require predicting the future. It requires working through them deliberately, while you still have room to adjust.
Ready to build your own decade-before-retirement plan? Contact us today to schedule a consultation.
