If you’re within five years of retirement and most of your savings are sitting in a traditional 401(k) or IRA, there are specific tax moves available to you right now that won’t be available once you retire. Some close the day you hand in your badge. One closes the year you turn 64. One closes the day you enroll in Medicare. Some opportunities change or narrow after retirement, and others require earlier evaluation to remain flexible.

I’ve been building retirement plans for about 30 years. In that time, the most consistent thing I see is people arriving at retirement having never taken these five steps — not because they weren’t capable of doing them, but because I’ve observed that these considerations are often overlooked. That’s what this article is for.

These are not obscure strategies. They’re available to most high earners with significant pre-tax savings. The challenge isn’t access — it’s awareness and timing.

Most people in their late 50s and early 60s are at or near the highest earnings of their career. Marginal tax rates may be relatively high. At that level, contributing to a traditional pre-tax 401(k) still makes strong mathematical sense for many people — you’re avoiding tax at a 32% marginal rate today and will pay at a much lower effective rate in retirement.

Here’s how that math works. The following is a simplified hypothetical illustration for educational purposes only. A married couple withdrawing $240,000 per year from a traditional IRA in retirement doesn’t pay 22% on all of it. They pay 10% on the first tier, 12% on the next, 22% on the remainder — but the standard deduction shelters the first $32,200 before any of that begins. The result: approximately $35,000 in federal tax on $240,000 of income. That’s a 14.6% effective rate. Saving at 32% marginal while working and paying at 14.6% effective in retirement is a real advantage.

But this calculation has a limit. The pre-tax strategy wins when your effective rate in retirement is meaningfully lower than your marginal rate today. The problem is that if your traditional balance is already large — say, $2 million or more — continuing to pour money into pre-tax accounts makes a future problem larger. Required Minimum Distributions at 75 could force more income than you actually need, potentially pushing you into higher brackets and triggering Medicare surcharges. In that case, shifting some or all new contributions toward Roth starts to make sense, even in a high bracket today.

The key question isn’t “what’s my bracket now versus later?” It’s “what will my forced income look like at 75 if I keep doing what I’m doing?” Without modeling, this decision may be made without full visibility.

Most people know about the standard catch-up contribution for those 50 and older. Fewer know that the SECURE Act 2.0 created a significantly enhanced catch-up for a very specific four-year window: ages 60, 61, 62, and 63 only. At 64, you revert to the standard amount permanently.

Here are the 2026 numbers:

*415(c) combined limit includes employee deferrals + employer match + after-tax contributions. All figures 2026.

The difference between the standard catch-up and the super catch-up is $3,250 per year — but at a 32% marginal rate, that’s over $1,000 in annual tax savings on contributions alone, before compounding. If you’re in this window right now and contributing the same amount you were at 55, you may not be fully utilizing allowable contribution limits.

Most people think they’re limited to the standard employee deferral limit when contributing to their 401(k). They’re not — if their plan allows it. Many employer plans permit after-tax contributions that can fill the gap between your regular contributions plus employer match and the IRS combined 415(c) limit. Those after-tax dollars can then be converted to Roth immediately — either inside the plan or rolled to a Roth IRA.

Because the money was already taxed before it went in, no additional tax is due when executed properly. No income test. No pro-rata complications. The result is Roth money at a scale you could never build through direct Roth contributions.

Here’s how this looks in practice for someone in the age 60–63 super catch-up window:

Step one is simple: call your plan administrator and ask whether after-tax contributions are permitted. Not all plans allow this. But if yours does and you’re not using it, this is one of the most valuable things you’ll learn from this article.

The Health Savings Account is the only account in the tax code offering all three tax advantages simultaneously: contributions are deductible, growth is tax-free, and withdrawals for qualified medical expenses are completely tax-free. A traditional 401(k) gives you the deduction but taxes withdrawals. A Roth IRA gives you tax-free growth and withdrawals but no deduction upfront. The HSA gives you all three — making it, dollar for dollar, the most tax-efficient account available for healthcare costs in retirement.

But the window closes when you enroll in Medicare — typically at 65. Once Medicare begins, you can no longer contribute, though you can continue spending existing balances tax-free on qualified medical expenses. These last working years are your final opportunity to build the balance.

Most people drain their HSA on current-year medical costs. A more powerful approach: contribute the maximum, invest the balance in low-cost index funds, pay current medical expenses out of pocket — and keep your receipts. There is no time limit on reimbursing yourself for past qualified medical expenses from an HSA. You can pay out of pocket now and reimburse yourself years later, effectively using the HSA as a tax-free reserve you deploy strategically in retirement.

One additional advantage worth noting: qualified medical withdrawals from an HSA generate zero MAGI. Unlike IRA withdrawals or Roth conversions, HSA medical distributions don’t affect your IRMAA calculation. In a retirement where managing MAGI is one of your most important annual tasks, that’s a meaningful planning advantage.

Here is something most people don’t know — and that surprises nearly every client when I show it to them for the first time.

Spending $120,000 or even $150,000 per year in retirement often isn’t enough to reduce your traditional IRA balance. At a 6% growth rate, a $4 million balance generates $240,000 in growth per year. Spend $150,000 and the account still grows by $90,000 annually. The balance at 75 is larger than the balance at 65 — even with significant spending. Add the contributions you’re making in these final working years on top of that, and the trajectory is steeper than most people expect.

This is why the RMD problem is so insidious. You aren’t actively doing anything wrong. You’re spending reasonably, contributing diligently, growing your investments. And the result is a forced income event at 75 that can push your tax bill higher than anything you faced during your working years.

The Math Behind Two Real Scenarios

Let me show you what this actually looks like. Both scenarios below assume a hypothetical individual starting at age 60, retiring at 65, with 6% annual investment growth and no Roth conversions during retirement. Born 1960 or later, so RMDs begin at 75 under current law. All numbers are illustrative.

The Tools to Manage It

Once you’ve modeled your trajectory, you have three primary levers during the years between retirement and RMD age:

Roth conversions during early retirement. This is one of the most powerful tools. Converting pre-tax dollars to Roth during the low-income window before Social Security and RMDs stack up directly reduces the balance that will generate forced distributions at 75. Size conversions carefully — staying below IRMAA thresholds and accounting for all income sources — but every dollar converted is a dollar that never becomes an RMD.

Drawing from taxable accounts for spending. Using your brokerage account for living expenses rather than your traditional IRA keeps the pre-tax balance lower and preserves more room below IRMAA thresholds for Roth conversions in the same year. One caution: capital gains from appreciated positions count toward MAGI even at a 0% income tax rate. Coordinate carefully.

Retiring slightly earlier. This is a frequently overlooked consideration. Even one or two extra years of retirement before RMDs begin means more spending drawing down the pre-tax balance, more Roth conversion room, and a lower starting point at 75. It doesn’t always solve everything, but it consistently moves the needle more than people expect.

The Window Is Time-Limited

These five moves share a common thread: they’re all time-limited. Some close the day you retire. One closes the year you turn 64. One closes at Medicare enrollment. And the RMD modeling you do now shapes decisions you’ll be living with for 20 years.

The hardest part isn’t executing any one of these strategies. It’s seeing them all together — understanding how they interact with each other, with your Social Security timing, with your IRMAA exposure, with your heirs’ tax situation. That’s not something a rule of thumb can solve. It requires a real model built around your specific numbers.

The next article in this series covers the five moves that belong in the first five years after you retire — which is where everything you did in the working years actually pays off.