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John Urban

John Urban spent his career in enterprise software. He co-founded GT Nexus, a supply-chain network acquired by Infor in 2015. When he retired, he ran into a gap: plenty of tools project your finances out over decades, but almost none help you decide what to actually do this year, with taxes in mind. He built RetireSmartIRA to close that gap, a retirement tax-planning app for people managing Roth conversions, RMDs, IRMAA, and the handful of thresholds that quietly decide how much of their savings they keep. He lives in Northern California with his wife, Kathy. When he isn't modeling tax cliffs, he's usually spending time with old friends, reading, following Bay Area sports, or looking for a good bottle of wine.

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Forum Posts

Don't Let a Roth Conversion Trigger a Penalty

33 replies

AUTHOR: John Urban on 7/8/2026
FIRST: Michael1 on 7/9   |   RECENT: Grant Clifford on 7/13

Comments

  • Lou, Thank you. The comments are always the best part. John

    Post: Widow Tax

    Link to comment from July 27, 2026

  • Rick, Thanks, that means a lot given how much time you've spent in this exact material through TaxAide. Please do run with your own piece. I approached this as a snapshot comparison on purpose, so a different lens on the same problem is a good thing, not overlap to avoid. Your last point is the one I keep turning over. Everything in my article treats the year after death as the whole story, but two mechanics keep pushing the picture past that year. RMDs force larger withdrawals every year the survivor ages, since the IRS divisor keeps shrinking, so the tax bill can climb for a decade even if the portfolio never grows. And IRMAA runs on a two-year MAGI lookback, so a new widow's Medicare premium for the first year or two is still riding the couple's old joint income, before the single-filer numbers show up. Year one and year three can look nothing alike, for reasons that have nothing to do with markets or spending. I'm sure there's a lot more to think about as you develop your article. I look forward to reading it when you're done. Best, John

    Post: Widow Tax

    Link to comment from July 27, 2026

  • Sanjib, Yours is a great catch. My analysis assumed nothing about an extension. I ran 2026 law as it stands, a snapshot rather than a projection, and you correctly point to the limitation in that. I reran the middle couple under post-2028 law rather than guess at the impact. You're right about the direction, though the number lands a bit higher than your estimate: about $6,800, not quite under $6,000. The reason it doesn't fall further is that the couple's lost deduction sits in their 22% bracket while the survivor's smaller lost deduction sits in her 24% bracket, so the rate difference eats into the savings the raw dollar amounts would suggest. One piece is untouched either way: the $2,885 Medicare surcharge in that example. IRMAA runs on MAGI, not the deduction, so it doesn't move when the provision sunsets. Thank you for reading the article so closely. I always look forward to the additional insight that comes out in these comments! Best, John

    Post: Widow Tax

    Link to comment from July 27, 2026

  • Thanks for pulling that McQuarrie quote out. I'm a longtime admirer of his work, and that paper is what pushed me to run the dollars instead of the rates. It's worth noting where his sentence indicts my own piece. I kept tax dollars at the center and left the postmortem reduction in expenditure as an aside rather than a number. Dan Smith made the same point elsewhere in this thread. Two readers landing on it in one morning tells me I underweighted it. Your marginal versus effective distinction is the sharper version of what I was reaching for. Effective rate is a reporting statistic, useful for describing what happened. Marginal rate is the decision variable, the only one that tells you whether the next dollar converted is worth converting. My article argued against being frightened by a rising effective rate. You're supplying the part that comes next: when you actually act, use the marginal. The long-term care point is the best addition anyone has made here. Qualified long-term care costs are deductible medical expenses above the 7.5% AGI floor, so a survivor paying for help with activities of daily living can end up itemizing well past the standard deduction the couple used to take. That reverses the largest single piece of the harm I described, for the household least able to absorb it otherwise. I didn't have it in the frame and I should have. Your default of planning for whichever spouse is likely to be alone longest is a sound way to hold a question nobody can answer, and close to where I ended the piece. Thanks also for the Zweig article. McQuarrie and Bernstein together is reason enough to mark March 2027 down.

    Post: Widow Tax

    Link to comment from July 25, 2026

  • Thanks. That's the takeaway I most hoped would land, and you've said it more plainly than I did. The widow tax is rarely the problem. The lost income is the problem, and the tax code is a secondary effect that sometimes runs the other way. Your 50% survivor pension is the clearest version of it. Half a pension gone is a far bigger number than any bracket change, and with less income to tax, the bill itself can fall even as the rate on paper rises. That's my affluent couple arriving by a different route. On the framing, you're right and I hedged. Widow tax is the phrase in circulation, so I used it in order to argue with it. Financial change is the better label.

    Post: Widow Tax

    Link to comment from July 25, 2026

  • Thanks Dan. The expense side is the leg most of these analyses skip, and your examples are the right ones: one Medicare and supplement premium, one car, a grocery bill that drops even if it doesn't halve. That offset is real, and it's why I wanted to keep lost income, spending and tax on separate lines rather than bundled under one label. 

    Post: Widow Tax

    Link to comment from July 25, 2026

  • Thanks Heidi - Your comment made me laugh out loud!

    Post: Widow Tax

    Link to comment from July 25, 2026

  • Thank you Chris&Steve!

    Post: Widow Tax

    Link to comment from July 25, 2026

  • Thanks Dave, I really appreciate your comment.

    Post: Widow Tax

    Link to comment from July 25, 2026

  • Snak123 - You clearly have and use strong planning and analytic skills. Thank you for sharing your process and insight!!!

    Post: Widow Tax

    Link to comment from July 25, 2026

Widow Tax

John Urban  |  Jul 25, 2026

THE WIDOW TAX is sold to the wrong households. It gets pitched to affluent couples as the reason to convert to a Roth or buy life insurance. The pitch says that when one spouse dies, the survivor files single, lands in a higher bracket, and gets clobbered. I ran the numbers for three couples at three incomes, and at the comfortable end the widow tax often costs nothing, or even less than nothing.
The real cost lands lower down,

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A $30,000 Mistake

John Urban  |  Jul 4, 2026

IF YOU’RE IN YOUR early 60s and retired, you probably have a lot of financial questions on your mind. The next few years may be among your lowest-income and lowest-tax-paying years. Your salary and bonus years are behind you. Social Security and required minimum distributions from your IRAs and 401(k)s have not started yet. You are hearing advice about doing Roth conversions during this low-tax window, and the arguments are compelling. You may also be thinking about consulting or part-time work to stay active and bring in some income.

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