Chalk Talk: Should You Do a Roth Conversion? How to Think About It, and the Mistakes to Avoid
on Oct 12, 2026
“Real Money Questions. Expert Answers”
When:
October 20th, 2026
3:30 pm Eastern; 12:30 pm Pacific
~45 minutes & Q/A included
How: Zoom Meeting
Recorded and available to retrieve for one
month
Cost: Free to ongoing clients; $10 per session for guests
Should You Do a Roth Conversion?
How to Think About It, and the Mistakes to Avoid
Hosted by: Anna Sergunina, CFP®
Guest commentator: Rob Colon, CFP®, EA
Tax Professional: MainStreet Tax Services
Should you convert part of your IRA to a Roth, and is this the year to do it? It’s the question we hear most in client meetings this fall, and many people get stuck debating it while the window for 2026 closes on December 31. Join Anna Sergunina, CFP®, and Robert Colon, CFP®, EA, the tax professional who prepares returns for MainStreet clients, for a practical conversation about how to think through the decision, the costs that go beyond the income tax, and the mistakes we see most often on real tax returns.
Meet Robert Colon, CFP®, EA
Rob is an independent tax professional and trusted partner of MainStreet Financial Planning. With over 15 years of experience in financial planning and accounting, he provides tax preparation and proactive tax planning services to MainStreet clients. As both a CFP® professional and an IRS Enrolled Agent, Rob works closely with our financial planners to help clients make tax-smart decisions that support their overall financial goals.
MainStreet Tax Services: Tax preparation and forward-looking tax planning for active MainStreet clients, built into your Money Roadmap so your planner and your tax preparer are working from the same plan.
Some of the topics we’ll discuss:
- Should you convert at all? The basic trade-off of paying tax now or later, and who pays it later, you or your heirs
- The years when converting makes the most sense, and when it doesn’t
- Costs beyond the income tax: Medicare premiums (IRMAA) and ACA health insurance subsidies
- How much to convert, without overshooting your tax bracket
- The mistakes we see most often
- Next steps, what documents to gather and what professionals to engage
- Your questions, answered live
Disclaimer: This is a broad group session and certain strategies may or may not be appropriate for specific situations. MainStreet makes no claim that all member posted information is accurate or should be acted upon without professional and individual financial planning, tax and/or legal advice.
