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. The app and his free Roth conversion and RMD calculators are at The app and his free Roth conversion and RMD calculators are at: https://www.retiresmartira.com 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.

Forum Posts

Taxes 34 Don't Let a Roth Conversion Trigger a Penalty StartedJohn UrbanJul 8, 2026 First replyMichael1Jul 9 LatestDerek Shuttleworth2 months ago

Comments

Rick, thanks for the mention, and for running your own numbers. Most people never do that part, and your article does a great job of showing why it's important.
Post: Widow’s Penalty Redux
Link to comment from September 26, 2026
Hall, thank you. That's kind of you to say and it is much appreciated!
Post: Widow’s IRA Choice
Link to comment from September 15, 2026
Gary, thank you. You are right about the framing. Nothing here depends on which spouse dies first. It works the same way for a widower. Your second point is where I have to disagree. Only a surviving spouse can take the account as their own. A child, a sibling or anyone else cannot, so there is no choice for them to make. Most of them have ten years to empty it instead. The exceptions are narrow: a disabled or chronically ill beneficiary, a minor child of the owner, or anyone less than ten years younger than the owner. That last category quietly covers a lot of people who leave an account to a sibling or a friend of similar age.
Post: Widow’s IRA Choice
Link to comment from September 13, 2026
Casey, thank you. Good question. What the surviving spouse does with an inherited Roth account is important too. Leave it as inherited and they have to start pulling money out once the deceased spouse would have reached RMD age. Make it their owned Roth and they never have to pull money out, and can leave it to be inherited by the kids as a Roth. The kids then have ten years to empty it. In either case, money withdrawn from a Roth is generally not taxed.
Post: Widow’s IRA Choice
Link to comment from September 13, 2026
This is exactly the right way to do it, and a good example for all of us. You held the account as a beneficiary while that kept a distribution off the table, then took it as your own at the point where switching cost you nothing. And you did it with only a one-year age gap, which is the part worth noticing: it was worth checking even when the difference looked too small to matter.
Post: Widow’s IRA Choice
Link to comment from September 12, 2026
Both figures are the required distribution for that year, not the tax. Inherited, Single Life table at 76: $480,000 divided by 14.1 = $34,043. Taken as her own, Uniform Lifetime table at 76: $480,000 divided by 23.7 = $20,253. Same balance, same birthday. The only difference is which table she is on.
Post: Widow’s IRA Choice
Link to comment from September 12, 2026
Bill, both of those are right, and both get less attention than they deserve. Thank you for sharing them. Your point that there is no time limit on assuming is the one I would add to the article. It is what lets a survivor under 59 and a half leave the account inherited and take it as her own later, and it is the same move behind the delay in the exchange with Michael1 above. The article told people to choose. The better answer in those cases is to choose in sequence.
Post: Widow’s IRA Choice
Link to comment from September 12, 2026
Joan, Yes and the sequence matters. It is the reason this works for a spouse and nobody else. A beneficiary cannot convert an inherited IRA. The Code denies rollover treatment to a beneficiary of an inherited account and then defines inherited so that it expressly does NOT include a surviving spouse, which is what leaves this route open to her. So the account has to become hers first, and then it converts like any other IRA of hers. Section 408(d)(3)(C).

You have spotted what makes that one year different. A joint return is generally available for the year of death, so a conversion made that year runs through joint brackets. From the following year the survivor is filing single. Same income, narrower brackets.

One constraint, and William Perry raised it above: any required distribution for the year has to come out before the conversion, including your husband's own year-of-death RMD if he had reached his starting age. An RMD cannot itself be converted. Section 408(d)(3)(E).

The awkward part is practical rather than technical. The window closes on December 31 of the year someone dies, which is the worst possible time to be working out conversion sizing. Your question is a really good one because the answer highlights that the Roth conversion discussion belongs in the conversation you have while it is still hypothetical, alongside the own-versus-inherited decision.
Post: Widow’s IRA Choice
Link to comment from September 12, 2026
Sole beneficiary is the case the article assumes, and it matters more than it looks: it is the precondition for both options being open. They are not alternatives. Inherited describes how the account stays titled. Sole beneficiary is her status, and it is what keeps both routes available. If she is the sole beneficiary with an unlimited right to withdraw, she can take the account as her own, and as sole beneficiary she can instead leave it inherited and delay the start of distributions until the end of the year you would have reached your own RMD age. Treas. Reg. 1.408-8(c)(1) and 1.401(a)(9)-3(d). One thing to check: she needs to be named directly rather than through a trust, which fails the test even when she is the trust's sole beneficiary. As for which is better, that is the article plus the exchange with Michael1 above. Usually taking it as her own, unless you are young enough that leaving it inherited would defer the start for a meaningful stretch.
Post: Widow’s IRA Choice
Link to comment from September 12, 2026
Yes, and thank you for the catch. Those are the required distributions, not the tax. I should have written "must take" rather than "owes", and I will ask for the wording to be fixed, so future readers aren’t confused
Post: Widow’s IRA Choice
Link to comment from September 12, 2026

Widow’s IRA Choice

John Urban | Sep 12, 2026

WHEN A HUSBAND dies, his widow inherits his IRA. Somewhere in the paperwork of the months that follow there is a decision to make, and nobody presents it to her as one. She can take the account as her own, or she can leave it titled as inherited.
Taking it as her own means filling something in. Leaving it means doing nothing, and the IRS tells custodians they may assume that is what she wants.

Roth Conversions and Taxes

John Urban | Aug 8, 2026

EVERY ARTICLE ABOUT Roth conversions says the same thing: pay the tax from taxable money, not from the IRA.
That is good advice if you have taxable money.
Plenty of retirees do not. Their savings sit almost entirely in a traditional IRA, built from years of 401(k) contributions and a rollover at retirement, with little brokerage money and no cash reserve worth naming.
For them, “pay from outside money” is not advice. It is a condition they do not meet.

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,

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.