ROTH CONVERSION STRATEGY WORKBOOK

A Question-Driven Framework to Determine Whether Roth Conversions Are a Tax Arbitrage—or a Costly Mistake

Educational content only. Not financial, tax, investment, or legal advice.

WHO THIS WORKBOOK IS FOR

This workbook is designed for individuals and households who:

Are age 45–75
Have significant pre-tax retirement balances (401(k), IRA, SEP, SIMPLE)
Expect future income from Social Security, pensions, or RMDs
Want to reduce lifetime taxes, not just this year’s bill
Suspect Roth conversions might help—but don’t want to guess

This workbook does not assume Roth conversions are good.

It is built to determine when they help and when they hurt.

HOW TO USE THIS WORKBOOK

Answer every question honestly

“Not sure” = risk

Complete annually and before:

Retirement
Social Security claiming
Medicare enrollment
Large income events

Scoring

🟢 Green — Modeled, documented, understood
🟡 Yellow — Discussed but not stress-tested
🔴 Red — Not evaluated or misunderstood

If a Roth decision is red, do not execute it.

PAGE 1 — ROTH CONVERSIONS ARE A TAX TRADE, NOT A FREE LUNCH

A Roth conversion is a voluntary acceleration of income.

You are choosing to pay tax now instead of later.

Foundational Questions

Do I understand that Roth conversions are irreversible?
Do I know my current marginal tax rate?
Do I know my expected future marginal tax rate?
Do I know why a Roth conversion might help me specifically?
Do I know why it might hurt me?
Do I understand the opportunity cost of paying tax early?
Do I know how conversions affect Medicare premiums?
Do I know how conversions affect Social Security taxation?
Do I know how conversions affect my surviving spouse?
Do I know what happens if tax laws change?

Scoring: 🟢 🟡 🔴

PAGE 2 — CURRENT TAX POSITION & BRACKET CONTROL

Before converting anything, you must know where you are today.

Questions

Do I know my marginal federal tax bracket this year?
Do I know my effective tax rate—and why it’s less relevant?
Do I know my state marginal tax rate?
Am I close to moving into a higher bracket?
Do I know how much “room” exists in my current bracket?
Do I know what income pushes me into surtaxes (NIIT)?
Do I know what income triggers Medicare IRMAA?
Do I know how conversions stack on top of other income?
Do I know which deductions or credits phase out?
Do I know which income sources are temporary vs permanent?

Scoring: 🟢 🟡 🔴

PAGE 3 — PRE-RMD CONVERSION WINDOW ANALYSIS

The most valuable Roth window is often after retirement but before RMDs.

Questions

Do I know when my RMDs will begin?
Do I know the projected size of my first RMD?
Do I know my expected tax bracket once RMDs begin?
Do I have a low-income window before RMDs?
Do I know how many years that window lasts?
Am I still earning W-2 income during that window?
Am I delaying Social Security during that window?
Am I using that window intentionally—or wasting it?
Do I know how much pre-tax money could be converted safely?
Do I know what happens if I wait too long?

Scoring: 🟢 🟡 🔴

PAGE 4 — HOW MUCH TO CONVERT (NOT ALL OR NOTHING)

The question is rarely “Should I convert?”

The real question is “How much, and at what tax rate?”

Questions

Do I have a defined target tax bracket for conversions?
Do I know how much income fits into that bracket?
Am I converting up to a ceiling—or guessing?
Do I understand diminishing returns of higher-bracket conversions?
Do I know how partial conversions affect future RMDs?
Do I know how conversions affect capital gains taxation?
Do I know how conversions affect Medicare premiums?
Am I coordinating conversions with tax-loss harvesting?
Am I converting annually—or sporadically?
Do I have a written conversion framework?

Scoring: 🟢 🟡 🔴

PAGE 5 — MEDICARE IRMAA & HIDDEN SURCHARGES

Roth conversions can quietly increase Medicare premiums.

Questions

Do I know the current IRMAA income thresholds?
Do I know Medicare uses a two-year lookback?
Do I know how conversions affect MAGI?
Have I modeled Medicare premiums with conversions?
Do I know how long IRMAA surcharges last?
Do I know the dollar cost of triggering IRMAA?
Am I converting too much too close to Medicare?
Do I know which conversions are “worth” the surcharge?
Have I considered spreading conversions to avoid spikes?
Do I know when IRMAA stops being relevant?

Scoring: 🟢 🟡 🔴

PAGE 6 — SOCIAL SECURITY & ROTH INTERACTION

Conversions and Social Security are tightly linked.

Questions

Have I modeled conversions before Social Security begins?
Do I know how conversions increase Social Security taxation?
Do I know how provisional income works?
Am I accidentally turning 0% income into 85% taxable income?
Do I know whether delaying Social Security creates more conversion room?
Do I know how conversions affect survivor benefits?
Have I coordinated claiming strategy with conversions?
Am I stacking conversions on top of benefits unnecessarily?
Do I know which income should happen first?
Have I tested multiple claiming + conversion scenarios?

Scoring: 🟢 🟡 🔴

PAGE 7 — SURVIVOR & WIDOW(ER) TAX PENALTY

Many Roth conversions are justified by survivor tax risk.

Questions

Do I know the survivor’s future tax bracket?
Do I know how quickly brackets compress for single filers?
Do I know how RMDs affect the survivor?
Do I know which income disappears at first death?
Do I know which income remains fully taxable?
Do I know how Roth assets help survivors?
Am I converting to protect the survivor—or just myself?
Do I know the survivor’s Medicare cost impact?
Do I know how long the survivor will live on this plan?
Does the conversion improve the survivor’s cash flow?

Scoring: 🟢 🟡 🔴

PAGE 8 — MARKET TIMING VS TAX TIMING

Good Roth strategies focus on tax timing, not market predictions.

Questions

Do I understand that lower markets reduce conversion cost?
Am I waiting for “perfect” market timing?
Do I know how volatility creates conversion opportunities?
Am I converting during high-income years unnecessarily?
Do I know how tax-loss harvesting pairs with conversions?
Do I know when not to convert?
Am I letting fear delay rational action?
Am I over-converting during market highs?
Do I know how conversions affect portfolio allocation?
Is tax timing driving decisions—not headlines?

Scoring: 🟢 🟡 🔴

PAGE 9 — ROTH CONVERSION RISK HEAT MAP

Area	Green	Yellow	Red
Current Tax Bracket	☐	☐	☐
Pre-RMD Window	☐	☐	☐
Conversion Amount Strategy	☐	☐	☐
Medicare IRMAA	☐	☐	☐
Social Security Interaction	☐	☐	☐
Survivor Tax Risk	☐	☐	☐
Market vs Tax Timing	☐	☐	☐
Lifetime Tax Outcome	☐	☐	☐

Rules

Red = do not convert yet
Yellow = model further
Green = execute deliberately

PAGE 10 — ADVISOR MEETING AGENDA (ROTH-FOCUSED)

Ask directly:

Why is a Roth conversion right for me?
What tax rate am I locking in?
What future taxes am I avoiding?
How does this affect Medicare?
How does this affect Social Security?
How does this help the survivor?
What happens if tax laws change?
What happens if markets disappoint?
What assumptions matter most?
What happens if we do nothing?

FINAL PAGE — EDUCATIONAL DISCLAIMER

IMPORTANT DISCLOSURE

This workbook is provided for educational and informational purposes only.

It does not constitute financial, tax, investment, or legal advice.

Roth conversions involve complex tax tradeoffs and irreversible decisions.

All strategies should be evaluated with qualified professionals before implementation.