Cameron Zabko, CFP®
When you’re recently widowed and still adjusting to life without a partner, there’s no easy way to face new financial realities. It can feel like you’re stuck between the responsibilities of maintaining your consulting income and the gripping worry that you’ll be penalized in taxes simply because you now file as a single individual. This is where strategic Roth conversions may open new possibilities. By moving some of your traditional IRA or employer retirement plan contributions into a Roth IRA, you can potentially reduce your long-term tax exposure, sidestep Medicare premium surcharges, and help create a more streamlined income for the decades ahead.
At Westhollow Wealth Management®—where we’ve dedicated our practice to guiding widows through times of complex transition—we know firsthand that it’s not just about crunching numbers or juggling new tax brackets. It’s about finding a plan that helps you avoid lying awake at night, worried you’ll outlive your resources. If that fear sounds familiar, see our guide on preventing outliving your savings during market downturns. Roth conversions are one of the tools that can help shield you from the so-called “widow’s tax penalty,” and this article explains why that matters so much for someone with a large pre-tax portfolio.
When one spouse passes away, the surviving spouse will typically shift from filing taxes jointly to filing as a single taxpayer. Single filer tax brackets are noticeably narrower than those for married couples—so even if your household income doesn’t drastically change, the percentage you pay can rise sharply. This is sometimes called the widow’s tax. You can learn more about why acting early helps in our article on starting partial Roth moves early to avoid the widow tax penalty.
If you previously filed a joint return, you likely had more space in each tax bracket. Once you’re single, that same household income fits less comfortably into a compressed bracket. Social Security taxation, required minimum distributions (RMDs), and your W-2 or consulting income can all combine to push you into a higher rate. The result: you end up paying more in taxes on the same or even lower income than before.
Medicare premiums may also climb if your modified adjusted gross income (MAGI) exceeds certain thresholds. Known as IRMAA (Income-Related Monthly Adjustment Amount), these surcharges raise your monthly Part B and Part D premiums if your MAGI surpasses approximately $106,000 in 2025 as a single filer. For a deeper dive into how IRMAA and cost-of-living adjustments interact, read our insight on 2026 Social Security COLA vs. Medicare costs. With your W-2 or consulting income alone, you may already be flirting with a higher IRMAA bracket—even before considering other income. That’s where a Roth conversion strategy takes on new importance.
Often, the best Roth conversion window arises before you must start taking RMDs. For many people, the SECURE 2.0 legislation pushed RMDs to begin at age 73. That gives you a potential 15+ year runway if you’re under 60 now. Additionally, tax provisions in place today are set to expire or adjust in the coming years, with potential bracket changes occurring after 2025. This puts a lot of moving pieces on your radar.
A strategic partial Roth conversion plan seeks to “fill up” a particular bracket intentionally. Let’s say you’re comfortable staying within the 24% bracket as a single filer. In 2025, the 24% bracket might top out around $197,300 in taxable income. If your taxable income (after deductions) sits below that threshold, you can convert an amount of your IRA into a Roth—enough to use that “headroom” effectively, but not so much that you push yourself into higher brackets or risk incurring large IRMAA surcharges. Coordinating your conversion amounts in collaboration with your tax professional is the best way to ensure you do not convert too much.
It’s one thing to understand that Roth conversions help mitigate future tax bills; it’s another to realize you can and should take action while you’re still working. Your current income can complicate this scenario, because you can’t simply turn off your W-2 or consulting income to create the perfect tax scenario, nor do you want to. So how do you work around it?
First, consider how many more years you intend to work at that same level. If you foresee retiring or cutting back significantly in your early 60s, that will open years with comparatively lower income. Those years often become prime opportunities for bigger conversions, since your taxable income is temporarily reduced. You might coordinate starting Social Security later—such as at age 70—to keep your baseline income low, freeing more space for conversions. For help deciding when to start benefits, review our widow’s guide to claiming survivor benefits at 60 vs. 67. The trade-off is you’ll pay taxes on each year’s conversion from your existing cash or taxable account, which keeps your Roth assets growing tax-free.
Second, it’s wise to map out your cost of living and see if you can temporarily live off your reduced income without drawing from your IRA. If you can pay the conversion taxes from a separate brokerage or savings account, you effectively maximize how much actually goes into your Roth IRA, allowing those funds to compound tax-free over the next decade or more.
A structured, multi-year approach makes a world of difference. Imagine creating a calendar and a schedule that covers the rest of your 50s and early 60s, then marking down anticipated income, any pension payments, and projected Social Security timing. Here’s how that might unfold:
1. Estimate Your Future Income StreamsProject your income for the rest of your working years. Factor in any expected drop in workload. If you have other sources of income—like rental properties or a pension—include that. Then decide when you’d prefer to start Social Security. If you can hold off until 70, your checks will be larger, and you’ll keep your taxable income lower in your early and mid-60s, but this isn't always feasible.
2. Fill Up the Target Tax BracketTake your projected income each year and see where it places you in the tax brackets. If you aim to stay within 24%, calculate how much additional room that bracket allows before you hit the top. That difference can guide how much you convert. Because you file single, you’ll likely run into narrower brackets than you realize. Make sure to consult your tax professional.
3. Watch the IRMAA ThresholdsFor single filers, IRMAA surcharges have multiple tiers, with the first threshold typically around $106,000 in MAGI for 2025. If adding a significant Roth conversion to your consulting income starts pushing you past $133,000 or $167,000 in MAGI, your monthly Medicare premiums can rocket up. Moving $30,000 or $40,000 from a traditional IRA to a Roth might be doable, but $70,000 or $80,000 could move you deep into IRMAA territory. Balancing how much you convert every year against how much IRMAA might cost is critical.
4. Pay Taxes from Non-IRA SourcesIf you must dip into your IRA itself to pay the taxes on the conversion, it shrinks what ultimately makes it into the Roth. Additionally, taking a larger total from your IRA can push you into even higher brackets. If you can fund the tax bill from a separate account (for instance, a brokerage or a bank account), you preserve more of your converted assets, which then grow tax-free. This will also help you avoid IRS penalties caused by taking money from an IRA prior to age 59.5.
5. Re-assess AnnuallyLife events happen: changes in project workloads, unexpected inheritances or gifts, or market shifts. One year you might convert $20,000, and the next year $50,000. The point is to make a habit of reviewing your numbers around tax time and adjusting accordingly. Many widows find that consistent annual check-ins keep them from running into big surprises later.
There are a few pitfalls nearly every working widow should keep on the radar. The first is ignoring IRMAA altogether. If you haven’t looked closely at how your overall modified adjusted gross income is calculated for Medicare, you could find yourself paying substantially higher premiums, negating some of the tax savings from your conversion.
Another potential mistake is waiting until you’re 65 or beyond to think about conversions. By that point, Social Security might have kicked in, or maybe your income from work slows only to be replaced by RMDs—both of which raise your taxable income further. Acting earlier often gives you more room to spread out conversions over multiple years at lower brackets.
Additionally, be cautious about claiming Social Security early if you plan a large conversion. Conversions increase your taxable income, and an early Social Security claim can create a “tax torpedo,” where you suddenly find more of your benefits taxed at higher rates. That money can be better protected by timing each piece of the puzzle carefully.
While every situation is personal, consider a broad illustration using real-world constraints. Suppose a widow has income of $140,000 annually identifies a two-year window where she reduces her business projects to an income of $90,000, starting around age 62. In those years, she isn’t drawing Social Security yet, her other income is minimal, and her standard deduction offers more breathing room. Now she can convert enough IRA funds to remain in, say, the 22% or 24% bracket without crossing an IRMAA tier that would substantially raise her Medicare premiums later.
Across those two years, maybe she converts a total of $80,000 to $100,000. She pays the tax bill out of cash in her savings account so that the full amount moves into her Roth. By the time she turns 73 and RMDs begin, her required distributions from her remaining traditional IRA are substantially smaller potentially reducing her future tax burden. Plus, every dollar she siphoned into the Roth continues to enjoy tax-free growth.
Roth conversions don’t just improve your own financial clarity in retirement; they can also simplify things for your children or beneficiaries. While inheritors of a traditional IRA must take distributions (within 10 years after inheriting, under current rules) and pay income tax on those withdrawals, a Roth IRA often leaves them free of the tax burden on those same distributions.
It’s easy to feel overwhelmed by the swirl of future RMDs, new tax brackets, and potential Medicare IRMAA surcharges. You’ve already endured immense loss and might still be figuring out how to navigate unfamiliar territory. But you don’t have to tackle this alone. With a thoughtful plan, you can execute a series of partial Roth conversions that align with your consulting income, your Social Security timing, and your long-term vision for retirement. These steps can serve as a form of stability when so many other things in life may feel unpredictable.
If you’d like a personal roadmap on how to manage these tax thresholds, preserve more of your hard-earned savings, and escape the sting of the widow’s penalty, reach out to Westhollow Wealth Management. We walk you through each step—from calculating bracket “headroom” to safeguarding your IRMAA status—so that you understand the “why” behind every suggestion. Ultimately, the goal is to bring peace and predictability to a future that might otherwise seem daunting.
Ready to begin? Schedule an intro call at a time that works for you and let’s discuss what your next steps could be.
Am I too young to worry about Roth conversions in my 50's?
Not at all. In fact, late 50's is a prime age because you have several years before required minimum distributions (RMDs) begin, and possibly before you go on Medicare. By starting earlier, you spread out tax liabilities, potentially avoid big hits later, and keep more of your savings sheltered for retirement.
What if my income changes drastically from year to year?
You can adjust your conversion strategy annually. The key is to monitor your actual taxable income each year so you don’t accidentally land in a higher bracket or trigger a costly Medicare premium hike. Flexibility is part of what makes partial Roth conversions so powerful—no single year’s plan is set in stone.
Should I convert everything to Roth?
In most cases, it’s more efficient to do partial conversions spread over several years. Converting everything at once might push you into a higher bracket or dramatically boost your IRMAA premiums. Keeping some funds in a traditional IRA may also provide extra tax flexibility—especially if you plan charitable contributions and can use pretax dollars strategically.
How do I pay taxes on the conversion?
If possible, pay them from a separate bank or brokerage account rather than from your IRA. That way, the full converted amount goes into your Roth to grow tax-free. Using the IRA itself to cover taxes typically means a smaller amount actually ends up in your Roth—and it might increase your taxable income in the process.
Does my income level mean I can’t do a Roth conversion?
There’s no upper income limit for converting existing IRA funds to a Roth. While you can’t make direct Roth contributions if your income is above certain thresholds, the law still allows you to convert. The key challenge is determining how much to convert each year without losing out to higher taxes and IRMAA surcharges.
At Westhollow Wealth Management®, we understand how the uncertainty of widowhood can scramble even the best-laid financial plans. With the right guidance, you can navigate single-filer brackets, Medicare thresholds, and future RMDs in a way that preserves and grows your nest egg. That kind of clarity brings peace of mind, letting you truly enjoy the next chapter of your life—and whatever it may hold.
