Advanced Roth Conversion & Retirement Tax Planning
Reducing lifetime taxes in retirement requires more than filling up a tax bracket.
For many high-income retirees, the window between retirement and Required Minimum Distributions presents an opportunity. But converting too much can increase Medicare premiums. Converting too little can create larger tax exposure later.
The question isn’t whether to convert. It’s how much, and when.
As a fee-only fiduciary and Chartered Financial Analyst (CFA) Charterholder, Certified Financial Planner (CFP®), and Enrolled Agent (EA), my work integrates investment strategy with multi-year tax modeling. Roth conversions are evaluated within the context of your broader retirement income plan, not in isolation.
Schedule Roth Conversion AnalysisHow Roth Conversion Decisions Should Be Made
Most conversion decisions fail because they focus on the current year.
A proper evaluation considers:
- Future Required Minimum Distrbutions (RMDs)
- Social Security timing and taxation
- Medicare IRMAA thresholds
- Federal and Californa tax brackets
- Portfolio growth assumptions
- Estate planning considerations
Rather than making a single large conversion, many households benefit from a deliberate, multi-year strategy designed to smooth taxable income and reduce long-term exposure.
The goal is not to minimize taxes this year. It is to minimize taxes over retirement.
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Example
Consider a recently retired couple in their early 60s with $1.8 million in traditional IRAs.
They planned to convert aggressively before RMD age.
After modeling multiple scenarios:
We identified a conversion ceiling that avoided higher Medicare premiums.
We coordinated conversions before Social Security began.
We reduced projected lifetime taxes by smoothing income across years.
The result was not simply “convert more.” It was a structured schedule aligned with long-term tax efficiency.
Who Is This Designed For
This planning is best suited for retirees or pre-retirees who:
Have significant traditional IRA or 401(k) balances
Are approaching or recently entered retirement
Expect meaningful taxable income
Want coordinated tax and investment strategy
If you’re looking to execute a transaction without broader planning, this may not be the right fit.The result was not simply “convert more.” It was a structured schedule aligned with long-term tax efficiency.
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