Roth Conversions: Pay Now or Pay Later?

2025-08-19

Are you approaching retirement and worried about taxes? In this episode of Advised, we dive into the reality of Roth conversions, IRAs, RMDs, and retirement tax planning—and why so many people experience sticker shock when they first see the tax bill. Too often, retirees hesitate on powerful strategies like Roth IRA conversions because they’re focused only on the short-term cost instead of the long-term lifetime tax savings. Rick breaks down how to make these decisions without fear, inc...

Are you approaching retirement and worried about taxes? In this episode of Advised, we dive into the reality of Roth conversions, IRAs, RMDs, and retirement tax planning—and why so many people experience sticker shock when they first see the tax bill.

Too often, retirees hesitate on powerful strategies like Roth IRA conversions because they’re focused only on the short-term cost instead of the long-term lifetime tax savings. Rick breaks down how to make these decisions without fear, including:

Why writing a big check to the IRS today could save you hundreds of thousands in the future
How Required Minimum Distributions (RMDs) force taxable withdrawals and how to plan around them
Balancing Roth conversions with healthcare premiums, Medicare surcharges, and inheritance planning
Why fees and financial advisor costs aren’t just expenses—they’re investments in value and strategy

Whether you have a seven-figure IRA or a more modest retirement account, this episode will help you see the bigger picture and align your money decisions with your goals, values, and legacy.

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