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Retirement Planning

Roth IRAs and Taxes

Is your Roth IRA a tax strategy or a tax trap? Robert Braglia American Financial & Tax Strategy discusses Roth IRA's.

By Robert Braglia May 13, 2026

Roth Accounts
Robert Braglia Robert Powell CFP® — Co-founder, finStream.tv; Editor, Retirement Daily at TheStreet
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Key Takeaways

  • Don't rely on online Roth conversion calculators without scrutiny—they make unfounded assumptions about your future tax bracket (which could change in 20-30 years) and assume current tax laws will remain unchanged
  • Only convert to a Roth in low-income years ('free Roth conversions')—such as after a job change, sabbatical, or business sale when your tax bracket is temporarily depressed
  • Account for the opportunity cost of taxes paid upfront: if you're using money sitting around to pay conversion taxes, that money should otherwise be invested and earning returns, not sitting idle
  • Beware of marketing motives behind Roth conversion advice—much of the push comes from financial institutions wanting to move your assets to them rather than from genuine analysis of your situation
  • Consider the full equation including heirs: even with the loss of stretch IRAs, paying taxes 30-50 years early involves too many unknowns; spouses can delay distributions further, making the calculation even more speculative

Is your Roth IRA a tax strategy or a tax trap? Robert Braglia American Financial & Tax Strategy discusses Roth IRA's.

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