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The Roth series · By Rich LoPresti, CFP®

If you believe in the Roth, why are you still feeding the IRA?

The gap years after you retire are a great time to convert. But if you're still working, you don't have to wait for them to start building your Roth.

The short answer. A lot of people tell me they plan to do Roth conversions once they retire. Then they keep putting every paycheck contribution into their pre-tax 401(k). That's adding more money to the exact problem they're planning to solve later. While you're still working, there are three ways to start the Roth now: switch some or all of your 401(k) contributions to the Roth option, make Roth IRA contributions if you qualify, and consider a smaller conversion before you retire. Each one costs some tax today, while you have a paycheck to cover it. Each one also gets money growing in the Roth sooner, and gives that growth more years to work. Accelerate the Roth. Slow down the growth of the tax-deferred bucket.

Stop adding to the problem.

Think of your savings as three buckets: taxable (your bank and brokerage accounts), tax-deferred (your 401(k) and traditional IRA) and tax-free (your Roth). Most people I meet in their fifties have nearly everything in the tax-deferred bucket, because that's what the 401(k) enrollment form defaulted to thirty years ago.

That bucket has a tax bill built into it. Every pre-tax dollar you add, and every dollar it grows, is taxed when it comes out, on the IRS's schedule once required withdrawals begin. If your plan is to spend your gap years converting that bucket to a Roth, every new pre-tax dollar you put in today is one more dollar you'll have to convert later.

And waiting has a cost of its own: years of growth that could have happened inside the Roth, where qualified withdrawals are tax-free, happen instead inside the account you're trying to shrink.

Three ways to start while you're still working.

MoveWhat it costsWhat to watch
1. Switch to Roth 401(k) contributionsYou lose the deduction, so your taxable income goes up by what you contributeYour employer match usually still goes in pre-tax. The contribution limit is the same either way
2. Make Roth IRA contributionsContributions go in after tax, with no deductionIncome limits apply. Some people use a "backdoor" Roth, which has its own rules if you hold other IRAs
3. Do a smaller conversion before you retireThe amount converted is added to that year's taxable incomeSize it to the room left in your current bracket, and pay the tax from cash

1. Switch your contributions to the Roth side.

Most 401(k) and 403(b) plans now have a Roth option. Same plan, same investments, same limit. The only difference is when you pay the tax. Pre-tax gets you a deduction now and a tax bill later. Roth gets you no deduction now and, if you follow the rules, no tax later on the contributions or the growth.

Yes, your take-home pay goes down a little, because you're no longer getting the deduction. But you're working. You have a paycheck to absorb it, and this is usually the easiest time in your life to pay that tax. You don't have to go all in, either. Plenty of people split their contributions between the two.

And for higher earners over 50, the choice is partly being made for you: starting in 2026, catch-up contributions for people whose prior-year wages were above a threshold have to go in as Roth anyway. That rule covers the catch-up only, not everything else you contribute.

2. Add Roth IRA contributions if you can.

If your income is under the IRS limit, you and your spouse can each contribute to a Roth IRA, even if one of you isn't working, as long as you file jointly and have enough earned income between you. It's a smaller amount than a 401(k), but every dollar of growth on it can come out tax-free.

There's a quieter benefit, too. The five-year clock for tax-free Roth growth starts on January 1 of the year you first put money into any Roth IRA. Getting that clock running while you're working means it's long finished by the time you need it. A Roth 401(k) has its own clock; it doesn't start the Roth IRA's.

If your income is too high, a "backdoor" Roth, a non-deductible IRA contribution that's then converted, may be an option. It doesn't work cleanly if you already have money in a traditional IRA, so check that before you try it.

3. Start converting a little before the gap years.

You don't have to wait for your last paycheck to do a first conversion. In some working years there's room left at the top of your current bracket. A year with a smaller bonus, a spouse who has already retired, or a few months of retirement in the year you leave all create room. A modest conversion can fill that room without moving you up a bracket.

The bigger conversions still usually belong in the gap years, when the rate is lower. But starting small gets money into the tax-free bucket sooner, and gives it more years to grow there.

Put the right things in the Roth.

How much you move matters. What you move matters just as much.

How I think about the three buckets

Accelerate the Roth. Slow down the IRA.

Tax-free (Roth): your longest-term, most growth-oriented money
Grow
Tax-deferred (401(k), IRA): steadier assets, like bonds
Slow

An illustration of a general approach called asset location. Bar lengths are not projections, and growth-oriented investments carry more risk, including the risk of loss.

Qualified Roth withdrawals, growth included, are tax-free, so in the plans I build, the longest-term, most growth-oriented investments go there. Bonds and other steadier assets can sit in the tax-deferred bucket, where slower growth means a smaller tax bill waiting at the end. That's the opposite of what one blended fund in every account does, and I explain why in One fund got you here. Spending it takes a plan.

When pre-tax still makes sense.

I believe in the Roth, but this isn't all-or-nothing, and I wouldn't tell you it's right for everyone. Pre-tax contributions may still be the better choice if:

For most people the answer lands somewhere in between: some pre-tax, some Roth, and a plan for which bucket gets spent when. That flexibility, having money in all three buckets before you retire, is the real goal.

Bring it back to your plan

Four questions worth asking

  1. Does my 401(k) have a Roth option, and where are my contributions going today?
  2. Have I ever opened a Roth IRA? When did my five-year clock start?
  3. How much room is left in my current tax bracket this year?
  4. Which of my investments would I most want to never pay tax on again?

What this article does not show.

Worth being explicit, because an article like this can imply more than it should.

Part of a series on the Roth. Start with The Roth isn't a tax break. It's a steering wheel.

Try it on your own dates

Is this worth a look for you?

Two minutes, eight questions, nothing saved. Or map the years between your last paycheck and your first required withdrawal.

Take the two-minute check →   Map your conversion window →

The timing

Why the years right after the paychecks stop are often the cheapest time to convert.

Read the article →

The objections

Paying the tax, the five-year rule, and "my accountant says don't."

Read the article →

The survivor's bracket

What happens to the tax bill when one spouse is left filing alone.

Read the article →

Still working? Start the Roth now.

An hour is enough to look at where your contributions are going, how much room is in your bracket, and how to start building the tax-free bucket before you retire.

Talk with Rich →

Sources: IRS Publication 590-A and Publication 590-B (IRAs and Roth IRAs); IRS 2026 inflation adjustments for tax brackets and standard deductions; Social Security Administration, Medicare Premiums: Rules for Higher-Income Beneficiaries; Connecticut Department of Revenue Services.

Educational content written by Rich LoPresti, CFP®, drawing on recurring planning conversations. It is not a client case study, testimonial or individualized recommendation. Roth 401(k) and Roth IRA contributions are made with after-tax dollars. Qualified Roth distributions require a five-year holding period and age 59½, death or disability. Roth IRA contributions are subject to income limits. Roth conversions are taxable in the year they occur and cannot be recharacterized. Employer plan features vary. Consult a qualified tax advisor. Retirement Approaching provides retirement-planning education. Advisory services are offered through Milestone Asset Management Group, LLC, an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. No investment result or tax savings is guaranteed.