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Boldin’s Lowest Lifetime Tax Liability Roth Conversion Strategy

This article describes the strategy and compares it to the tax bracket strategy

Nancy Gates avatar
Written by Nancy Gates
Updated today

🔹 Lowest Lifetime Tax Liability Roth Conversion Strategy

Key Objective:

Minimize the total cumulative income taxes you pay over your lifetime.

  • How it works:

    • Boldin projects your income, RMDs, Social Security, and possible Roth conversions year by year.

    • It then finds the Roth conversion schedule that results in the lowest sum of all taxes you’ll ever pay.

  • Key feature: It doesn’t care about year-to-year bracket thresholds — it only cares about the total bill across your lifetime.

  • Result: The algorithm might recommend big conversions early (when income is low), or no conversions at all, depending on what leads to the smallest lifetime tax bill.


How does the Lowest Lifetime Tax Liability Strategy Compare to the Tax Bracket Strategy?

🔹 Boldin’s Tax Bracket Strategy

  • Objective: Minimize lifetime taxes paid by keeping conversions within a chosen bracket.

  • Mechanics: Each year, it recommends converting just enough to “fill” your bracket.

Strength: More closely tied to your lifetime after-tax spendable wealth, even if estate values aren’t maximized.Result: Provides a consistent, predictable conversion pattern, easier to plan for cash flow and Medicare/IRMAA considerations.

🔹 How They Differ

Feature

Lowest Lifetime Tax

Tax Bracket

Main Goal

Minimize total lifetime tax paid

Keep annual taxes inside a chosen bracket

Flexibility

Can recommend uneven or front-loaded conversions

Steady, predictable year-by-year pattern

Estate Impact

May leave larger pretax balances if no conversions are “worth it”

Typically shrinks IRA balances more systematically

Practicality

May create big spikes in taxable income (less comfortable)

Easier to manage IRMAA, cash flow, state taxes

🔹 Which Is Better?

  • Lowest Lifetime Tax strategy → best if your only concern is minimizing your lifetime IRS bill, regardless of estate size or income spikes.

  • Tax Bracket strategy → better if you want steady, predictable planning that balances lifetime taxes with manageability (cash flow, Medicare, state impacts).

Advisors often compare both → Sometimes the “lowest tax” option technically saves a little more in total taxes, but creates big bracket spikes or IRMAA surcharges, so the bracket-filling method feels more practical.

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