The Roth Conversion Rule Almost Nobody Explains Correctly (4 Scenarios That Make It Simple)
Stay Wealthy Retirement Podcast
Taylor Schulte, CFP®
4.7 • 678 Ratings
🗓️ 19 March 2026
⏱️ 19 minutes
🧾️ Download transcript
Summary
Now that the One Big Beautiful Bill Act has made the 2017 tax rates permanent, more retirees are taking a fresh look at Roth conversions.
But there's one rule that even reputable sources struggle to explain clearly—and the confusion can lead to costly mistakes.
In this episode, I'm simplifying the Roth conversion 5-year rule and sharing:
→ Why the rule is so confusing (and what most people get wrong)
→ The fastest way to determine how the rule applies to your specific situation
→ 4 real-world scenarios so you can see exactly how it works
If Roth conversions aren't a fit today, I'm also sharing one simple step everyone can take right now to make future conversions much easier.
***
📝 GRAB THE ROTH 5-YEAR FLOWCHART (PDF)
Want to apply what you learned in this episode to your unique situation?
Subscribe to the Stay Wealthy Retirement Newsletter and I'll send you my freshly updated Roth 5-Year Flowchart (PDF).
It's a simple guide to help you navigate this tricky rule step by step.
***
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***
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Transcript
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| 0:00.0 | For nearly a decade, Roth conversions came with a built-in sense of urgency. |
| 0:04.5 | Convert now before tax rates go up. |
| 0:06.7 | But that framing changed when the one big beautiful bill act made the 2017 individual tax rates permanent and kept the larger standard deduction in place. |
| 0:15.9 | So while the old deadline is gone, the opportunity is not. |
| 0:19.5 | In fact, for many retirement savers, the case for evaluating |
| 0:22.5 | this strategy may be even stronger today. But as more people revisit it, one question keeps coming up |
| 0:28.7 | again and again. How exactly does the Roth conversion five-year rule work? This is where a lot of |
| 0:35.3 | smart, well-intentioned retirement savers get tripped up, |
| 0:38.1 | and I don't blame them. The rule is nuanced. It's confusing and it's often poorly explained |
| 0:43.7 | by very reputable sources. So in this episode, I'm going to simplify the Roth Conversion |
| 0:48.8 | five-year rule, show you the easiest way to determine how it applies to your situation, |
| 0:53.6 | and walk you through four simple scenarios to how it applies to your situation and walk you through |
| 0:55.0 | four simple scenarios to bring it all to life. And be sure to stick with me to the end, because |
| 0:59.9 | even if Roth conversions are not a good fit for you today, I'm going to share one simple step |
| 1:05.3 | everyone listening right now can take that will make future conversions a lot easier. |
| 1:10.3 | And finally, to compliment today's |
| 1:12.1 | episode and further help avoid confusion, I'll be sharing a one-page flow chart with all |
| 1:17.3 | Stay Wealthy newsletter subscribers this week. If you want to copy, just follow the link in the episode |
| 1:22.4 | description or head to you staywealthy.com forward slash email. |
| 1:30.5 | Welcome to another episode of the Stay Wealthy Retirement Show. |
| 1:35.1 | I'm your host Taylor Schulte, and every week I tackle the most important financial topics to help you stay wealthy in retirement. |
| 1:37.6 | And now on to the episode. |
... |
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