The Roth Conversion Decision Framework

Should You Convert to a Roth IRA? The Answer Depends on Your Numbers.

Roth conversions can be one of the most powerful retirement tax strategies available—but converting too much, too soon, or in the wrong year can create unnecessary taxes and costly consequences.

The Roth Conversion Decision Framework gives you a practical, repeatable way to decide whether to convert, how much, when, and when to stop.

Instead of relying on rules of thumb like "convert as much as you can while tax rates are low," this book walks you through a six-stage decision process built around your income, tax brackets, Medicare, Social Security, healthcare costs, state taxes, timeline, and legacy goals.

Updated for 2026 rules, including the $6,000 senior deduction, 2026 IRMAA tiers, the return of the ACA subsidy cliff, and the 2025 law that made today's tax brackets permanent.

Inside this book, you'll discover:

• The Six-Stage Roth Conversion Framework: Assess, Map, Model, Decide, Execute, and Review.
• How to Find Your Conversion Headroom before crossing a higher bracket or other key threshold.
• How to Compare Strategies: no conversion, moderate, and larger conversions side by side.
• The Tax Traps That Can Change the Answer: RMDs, IRMAA, Social Security taxation, ACA subsidies, the senior deduction, state taxes, and filing status.
• How to Pay the Conversion Tax, and why the source of the payment matters.
• When NOT to Convert: when waiting, converting less, or skipping a year is the better decision.
• 37 Real-World Decision Scenarios covering early retirement, marriage, widowhood, divorce, large IRAs, inherited IRAs, legacy planning, and more.
• Built-In Worksheets: Decision Scorecard, Headroom Worksheet, IRMAA, Social Security, ACA, Survivor and State Tax Checks, Tax-Funding Decision, Annual Range, Stop Test, and Annual Review.

BONUS: The Roth Conversion Planning Kit (free download, no sign-up)

• The Roth Conversion Planner (Excel): a 13-tab workbook that runs all six stages on your numbers, including a True Marginal Rate Ladder showing the all-in cost of each additional $5,000 converted.
• Annual Thresholds Reference Sheet: current brackets, IRMAA, Social Security, ACA, and RMD figures, updated as new figures are published.
• Fillable Worksheet Pack: every worksheet in the book, plus a Conversion Log and one-page Decision Summary for your CPA.
• Conversation Scripts: what to say to your CPA, advisor, custodian, and Social Security.
• Calendar, Age Timeline, Scenario Finder, and Heir Handoff Packet.

Printables come as PDFs and editable Word files.

Whether you're approaching retirement, recently retired, or already taking income, this book replaces guesswork with a year-by-year process you can revisit as your circumstances change.

Don't ask only, "Should I convert?" Ask the better questions: How much? When? Why? And when should I stop?

Your numbers should drive the decision—not someone else's rule of thumb.