Planning for Single Retirees — Part 3: Tax Planning and Roth Conversions
Big Picture Retirement®
Devin Carroll
4.7 • 545 Ratings
🗓️ 2 February 2026
⏱️ 33 minutes
🧾️ Download transcript
Summary
The tax planning process doesn't change for single retirees—but the margin for error does.
In this episode, we explain why taxes behave differently when there's only one tax bracket, no spousal coordination, and no survivor window to clean things up later. We discuss why IRMAA thresholds hit sooner for single filers and how small income decisions can have outsized consequences.
We walk through a simple framework that focuses on understanding your income baseline, where your assets are held, how Medicare premiums factor into tax decisions, and why time horizon matters more when there's only one lifetime to plan around.
This episode isn't about squeezing out every last tax advantage. It's about protecting flexibility, avoiding irreversible mistakes, and building a plan that works without a backup.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
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Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
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Transcript
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| 0:00.0 | The Big Picture Retirement Show does not provide tax, legal, or financial advice. |
| 0:04.3 | Listeners are encouraged to seek out their own advisors in these areas. |
| 0:10.3 | Hey, everyone, welcome to the Big Picture Retirement Show. |
| 0:13.0 | I'm your host, Devin. |
| 0:14.3 | Today, John's out of the studio again, but I am joined by one of our CFPs here at Carol |
| 0:20.3 | advisory group, Nick Domachowski. Nick, you first time on the show, welcome. Thank you, Devin. Happy to be here. Certainly listen to the podcast for quite some time and happy to be a part of it for a change. First time back in a podcast studio in about five years for me. Yeah, well, welcome back and you picked a good one to make you return to. Yes, sir. You know, I was telling Jeremy, we don't have that many guests here when we recorded last week's episode, you know, for our listeners, they know that, you know, we're not just one of those shows that has, has guest on and they get to pitch their book or whatever their service is. We want to use those selectively, but I do have a very high level of confidence in the team that we've assembled here. |
| 0:58.0 | And having you guys on the show is a pleasure. |
| 1:01.4 | And I think this will be the first of many. |
| 1:04.0 | Now, we've been doing this series on retirement planning for singles. |
| 1:08.6 | And some of the ways that it's different. |
| 1:28.3 | You know, John and I kind of laid some of the foundation in the very beginning, talking about some of the differences between singles and married couples. And we also, you know, we're very careful to define what a single person is. And as John pointed out, that all of us will either be dead or single at some point in the future. 100% chance. |
| 1:29.0 | Yeah. |
| 1:29.5 | Yeah. |
| 1:33.2 | We have enough data to know how this works out, right? |
| 1:39.2 | And so that means that what we're talking about today may not be pertinent for everyone right now, but it very well may be in the future. |
| 1:41.3 | And it's highly likely that our listeners know someone who is single, |
| 1:46.3 | whether that's single by divorce, single by death, or just single by choice. |
| 1:51.3 | So, good information that we're covering here. |
| 1:54.5 | And we've already laid some of the foundation. |
| 1:56.8 | We've talked about social security for single people. |
| 1:59.0 | Now let's get into one of the big core areas of planning for a single person, |
| 2:05.3 | and that's the tax planning component, because this is where things start to change. |
... |
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