It seems like everywhere you turn these days, someone is talking about Roth conversions.

Financial advisors are promoting them. Financial publications are writing about them. Social media is full of people explaining why you should be converting your traditional IRA to a Roth IRA. Even some tax professionals seem convinced that Roth conversions are something just about everyone should be doing.

And I get it. The concept sounds pretty appealing. Pay taxes today, allow your investments to grow tax-free, and potentially avoid paying income taxes on qualified withdrawals in the future.

What's not to like?

Well, potentially quite a bit.

Over the years, I've received countless questions from people who have heard about Roth conversions and want to know whether they should be doing them. Often, the question isn't whether a conversion makes sense for their particular circumstances. It's more along the lines of, "How much should I convert?"

That's putting the cart before the horse.

A Roth conversion isn't automatically a good financial decision simply because it creates tax-free retirement assets.

Like most things in financial planning, the answer to whether you should convert is: It depends.

And it depends on a lot more than your current income tax bracket.

Let's Start With What You're Actually Doing

When you convert money from a traditional IRA to a Roth IRA, you're generally choosing to pay income taxes today on money that otherwise would have been taxed when withdrawn in the future.

In other words, you're voluntarily accelerating a tax liability.

That might be a smart decision. It might also be an expensive mistake.

The fundamental question is whether paying those taxes today puts you in a better financial position than paying them later.

If you're paying taxes at a lower effective rate today than you reasonably expect to pay in the future, a conversion may offer meaningful benefits.

But what if you're paying taxes at a higher rate today than you would have paid later?

What if your retirement income turns out to be lower than anticipated? What if you never need to withdraw much of the money? What if your investments don't perform as projected?

And here's another question that doesn't get nearly enough attention:

What could you have done with the money you're using to pay those taxes?

Because that money has value, too.

The Tax Bill Is Real. The Future Benefits Are Projections.

Let's say you're considering converting $200,000 from a traditional IRA to a Roth IRA.

Depending on your circumstances, the additional federal and state income taxes could be substantial.

That tax bill isn't hypothetical. It's real, and it's due.

The anticipated benefits, on the other hand, depend on a series of assumptions about the future.

What will income tax rates look like in 10, 20, or 30 years? What will your taxable income be? How long will you live? How will your investments perform? Will you be married or single? Will your beneficiaries face higher or lower tax rates than you?

We can model these possibilities. We can make reasonable assumptions. We can run different scenarios.

But we cannot know the answers.

In my June 2025 whitepaper, Why Quantifying the Value of a Roth Conversion Is So Challenging, I discussed the importance of evaluating the break-even point—the point at which the projected financial benefits of converting outweigh the upfront tax costs.

That remains an important consideration.

But there isn't one universal break-even calculation. The outcome depends on how we account for the tax payment, investment growth, future distributions, tax rates, and the alternative of leaving the money in the traditional IRA.

And if the anticipated benefits don't materialize during your lifetime, the conversion may have provided little or no financial advantage to you personally.

That doesn't necessarily mean the conversion was a mistake. It may have accomplished other objectives.

But those objectives need to be understood before making the decision.

Your Tax Bracket Is Only Part of the Equation

One of the more common Roth conversion strategies involves converting enough money each year to fill a particular income tax bracket.

There can be merit to that approach, particularly during the years between retirement and the beginning of Social Security benefits or required minimum distributions (RMDs).

But simply filling a tax bracket isn't necessarily an optimal strategy.

A conversion can affect much more than your federal income tax bracket.

Depending on your circumstances, it may increase the taxable portion of your Social Security benefits, trigger higher Medicare premiums through income-related monthly adjustment amounts (IRMAA), affect certain deductions or credits, or create additional state income tax liabilities.

For someone purchasing health insurance through the Affordable Care Act marketplace, additional taxable income may also affect eligibility for premium tax credits.

These interactions can make the actual cost of a conversion considerably higher than the advertised marginal income tax rate.

And what about the years ahead?

Perhaps you're currently married and filing jointly, but eventually one spouse will be filing as a single taxpayer. That could create a legitimate reason to consider conversions today.

Or perhaps you're planning to relocate to a state with lower income taxes. Paying taxes now in a higher-tax state may make little sense if those same distributions could be taxed more favorably later.

The point is that tax brackets don't exist in isolation. Neither should Roth conversion decisions.

Are You Planning for Your Retirement or Your Heirs' Inheritance?

Here's where I think the conversation gets particularly interesting.

One of the arguments frequently made in favor of Roth conversions is that they can leave beneficiaries with tax-free assets.

And that's true under current law, assuming the applicable requirements for tax-free distributions are satisfied.

But let's think about what that actually means.

You may be choosing to pay substantial income taxes during your lifetime so your children or other beneficiaries won't have to pay those taxes after you're gone.

There's nothing inherently wrong with that.

Some people have more than enough money to support their retirement lifestyle and genuinely want to maximize the after-tax inheritance they leave behind.

For those individuals, Roth conversions may be an appropriate estate and tax planning strategy.

But what about everyone else?

Should you voluntarily reduce the money available for your retirement so your heirs can potentially receive a larger after-tax inheritance?

Maybe.

But maybe not.

I've worked with plenty of people whose primary objective isn't to die with the largest possible investment portfolio.

They want to enjoy their retirement. They want to travel. They want to spend time with their families. They want to help their children or grandchildren while they're still around to see the benefits.

Maybe they'd rather take the entire family on a memorable vacation than spend that same money paying taxes on a Roth conversion.

Maybe they'd prefer helping a grandchild with college expenses or helping their adult children purchase a home.

Or maybe they simply want the financial freedom to enjoy the retirement they've worked decades to achieve.

Those are perfectly legitimate financial objectives.

In fact, for many people, those experiences and opportunities are far more meaningful than leaving behind a larger investment account.

And yet, when we focus exclusively on minimizing lifetime taxes or maximizing the value of an estate, we can lose sight of those priorities.

The objective of financial planning isn't necessarily to leave the most money behind. It's to use the money you have to accomplish what matters most to you.

Sometimes the Best Roth Conversion Is No Conversion

That's not a particularly exciting headline, especially in a world where financial strategies are often presented as opportunities you can't afford to miss.

But sometimes doing nothing is the better decision.

Consider someone who has accumulated substantial retirement savings but expects to remain in a relatively modest income tax bracket throughout retirement.

If converting today requires paying taxes at a higher effective rate than future withdrawals would likely incur, what's the advantage?

Or consider someone who intends to leave a significant portion of their traditional IRA to charity.

Qualified charitable distributions (QCDs), when available, and the generally favorable tax treatment of retirement assets left directly to qualified charities may make converting those assets unnecessary or counterproductive.

What about someone whose retirement resources are more limited?

If paying the conversion taxes requires withdrawing additional money from retirement accounts, reducing financial reserves, or sacrificing planned retirement spending, the decision deserves careful scrutiny.

And sometimes a conversion simply doesn't produce enough projected benefit to justify the cost, complexity, and uncertainty.

There's no rule that says you must convert.

And there's certainly no prize for having the largest Roth IRA.

When Roth Conversions Can Make Sense

I don't want to leave the impression that I'm opposed to Roth conversions.

I'm not.

I've recommended them when the circumstances supported doing so.

For example, conversions may be particularly attractive when someone experiences a temporary reduction in taxable income, such as the years immediately following retirement and before Social Security benefits or RMDs begin.

They may also help reduce future required distributions, provide greater flexibility in managing taxable retirement income, or address the potential tax consequences for a surviving spouse.

For families with substantial retirement assets, conversions may be an effective way to manage the tax burden ultimately passed to beneficiaries.

And some people simply value having a portion of their retirement assets in accounts that can provide qualified tax-free distributions, even if the projected financial advantage isn't overwhelming.

That's a reasonable objective, too.

But here's the distinction:

A Roth conversion should be the result of a financial planning analysis, not the starting point.

The right question isn't necessarily, "Should I do a Roth conversion?"

It's, "What am I trying to accomplish, and would a Roth conversion help me accomplish it?"

If the answer is yes, then we can evaluate when to convert, how much to convert, and how to manage the resulting tax consequences.

Sometimes that means converting a relatively small amount annually.

Sometimes it means taking advantage of a particularly favorable tax year.

And sometimes it means leaving the traditional IRA alone.

Don't Confuse Paying Less Tax With Having More Money

This is another distinction I believe deserves more attention.

People understandably dislike paying taxes. Nobody wants to pay more than necessary.

But minimizing taxes isn't always the same thing as maximizing financial well-being.

You can construct a strategy that reduces future income taxes and still end up with less money available to spend during your lifetime.

You can create a larger after-tax inheritance while reducing the financial flexibility you enjoy during retirement.

You can even execute a technically successful tax strategy that accomplishes very little toward your actual personal objectives.

That's why I believe financial planning needs to look beyond tax savings alone.

We should be evaluating the potential impact on retirement income, liquidity, investment assets, surviving spouses, beneficiaries, charitable intentions, and, perhaps most importantly, the lifestyle someone wants to enjoy.

Tax planning is important.

But it's only one component of financial planning.

The Bottom Line: It Depends

I realize that "it depends" isn't the answer most people want to hear.

They want to know whether Roth conversions are good or bad. Whether they should convert $50,000 or $100,000 this year. Whether they should convert before tax rates change.

Unfortunately, financial planning doesn't lend itself to universal answers.

A strategy that makes tremendous sense for one household may be completely inappropriate for another.

Even within the same household, the right decision can change from year to year.

What I find troubling about much of the Roth conversion discussion is the assumption that converting is inherently beneficial and the only real question is how aggressively to pursue it.

That's simply not true.

Roth conversions involve trade-offs. They involve assumptions about an uncertain future. And they involve paying real money today in anticipation of benefits that may or may not materialize.

Most importantly, they involve personal choices about what you want your money to accomplish.

If your priority is maximizing the after-tax wealth you leave your heirs, that may support one approach.

If your priority is maintaining financial flexibility and enjoying your retirement years, it may support another.

Neither objective is inherently right or wrong.

Your money should serve your objectives. Your objectives shouldn't be sacrificed to accommodate a tax strategy.

And when it comes to Roth conversions, sometimes the smartest decision is to convert. Sometimes it's to convert less than you originally planned.

And sometimes it's to do nothing at all.

It depends.