At Hill Investment Group, we’ve found that when a few clients ask similar questions, many more are likely thinking the same thing. To better serve you, we’re introducing our “Hey Hill” newsletter series—addressing common client questions and sharing our perspective.

To submit a question for a future post, email us at service@hillinvestmentgroup.com

Is a Roth IRA Conversion Right for You?

Roth IRA conversions can be a valuable, but often misunderstood tool in long-term financial planning. When thoughtfully timed and executed, they may provide tax advantages, increased flexibility, and legacy planning benefits. But like most financial strategies, they’re not one-size-fits-all.

So how do you know if a Roth conversion might make sense for your situation?

What Is a Roth Conversion?

A Roth IRA conversion means moving money from a pre-tax retirement account—such as a Traditional IRA—into a Roth IRA. You’ll pay ordinary income taxes on the converted amount in the year of the transfer. From that point forward:

• Your investments may grow tax-free inside the Roth
• You can make tax-free withdrawals in retirement (if IRS rules are followed)

In essence, you’re trading a tax bill today for the potential of tax-free growth and withdrawals in the future.

Who Might Want to Consider a Conversion?

A Roth conversion may be worth exploring if:

• You expect to be in a higher tax bracket later
• You can pay the tax bill from non-retirement assets, leaving your retirement funds intact
• You’re in a temporarily low-income year (e.g., early retirement, career break, or sabbatical)
• You’re planning for heirs—Roth IRAs aren’t subject to required minimum distributions (RMDs), which may make them attractive in legacy planning
• You don’t need the money soon—the longer Roth funds grow tax-free, the more powerful the benefit

How It Can Support Your Long-Term Plan

When aligned with your overall strategy, a Roth conversion can:

• Reduce future RMDs and lower taxable income in retirement
• Diversify your tax “buckets,” giving you flexibility in how you draw income
• Potentially ease your heirs’ future tax burden by leaving them tax-advantaged assets
• Help you build more predictable after-tax income over time

It’s a classic example of playing the long game—something we believe in deeply at Hill.

When It Might Not Make Sense

A Roth conversion isn’t ideal for everyone. It may not be the right move if:

• You’d need to use retirement funds to pay the conversion tax
• You’re already in a high tax bracket and expect it to be lower in the future
• You’ll need access to the converted funds within five years (each conversion starts a separate 5-year clock for penalty-free withdrawals)

The Bottom Line

Roth conversions can be powerful, but the decision is nuanced. The tax rules are complex. The upfront cost can be significant. And timing matters.

That’s where we come in. Through our advisory relationships, we help clients model the long-term impact of a Roth conversion—year by year—so they can move forward with clarity and confidence.

At Hill, we don’t just focus on what’s smart today. We help you make decisions that align with your long-term goals and legacy.

Thinking about a Roth conversion? Let’s explore whether it’s a fit—for your plan, your family, and your future.

Book a time to talk.

Disclosures:

Hill Investment Group is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. The information provided is for educational purposes only and should not be construed as personalized investment, tax, or legal advice. Roth IRA conversions involve complex tax considerations and may not be appropriate for all investors. Consult your tax advisor or financial professional before implementing any financial strategy. Investing involves risk, including the possible loss of principal. Past performance is not indicative of future results.

Continuing on in the tax management series, this month we’ll look at account sequencing during wealth accumulation and retirement withdrawal periods. The basic questions are:

1) When accumulating funds, what accounts (tax-deferred, taxable, etc.) should be funded first?

2) When withdrawing funds, in what order should funds be withdrawn?

Individual circumstances may constitute different strategies, but the following examples demonstrate two common approaches. The first is based on someone in the accumulation phase who pays taxes in the highest bracket, and the second is a retiree in the withdrawal phase who will leave behind some amount of inheritance:

Following logical strategies for adding and withdrawing funds ensures that you accumulate and retain the maximum after-tax amount possible.

Next month, we’ll look at matching investments with the most appropriate account types.

With our investing philosophy, by and large, we recommend a set it and forget it mindset as it relates to your investment plan, which generally doesn’t benefit from excess activity. Tax planning, on the other hand, offers more frequent opportunities to actively add value (even above and beyond the extreme tax-efficiency of the investments themselves).

Here are three examples:

1. Guiding the sequence of additions to your various accounts during your career and, likewise, ensuring that withdrawals are taken in proper order from those accounts in retirement

2. Matching the right type of asset (equity, fixed income, real estate) with the appropriate account registration (be it taxable, tax-deferred, or tax-exempt)

3. Making creative suggestions based on our understanding of your situation and goals (i.e. IRA contributions, Roth conversions, charitable giving)

As the CPA on the team, I can assure you that we all work together to minimize the impact of taxes on your portfolio and maximize opportunities to leverage tax planning. Tax sensitivity is one of the things that helps us support you in your goals.

Watch in future newsletters for detailed discussions on each of the items listed above.