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The Free Financial Advisor
The Free Financial Advisor
Brandon Marcus

Should You Pay $25,000 in Taxes Today to Avoid a Bigger Tax Bill in Retirement?

Should You Pay $25,000 in Taxes Today to Avoid a Bigger Tax Bill in Retirement?
A Roth conversion can create future tax flexibility, but paying $25,000 in taxes today only makes sense when the current cost fits the larger retirement plan – Shutterstock

Paying $25,000 in taxes today to potentially save more money on taxes decades from now sounds a little like volunteering to get punched before the fight even starts. Yet that strategy can make sense for some retirement savers, especially when it involves converting money from a traditional IRA to a Roth IRA. The catch sits in the details, because paying a giant tax bill now does not automatically create a giant tax savings later.

A Roth conversion essentially moves money from a traditional retirement account into a Roth account, and the untaxed portion generally counts as income in the year of the conversion. That can hurt today, but qualified Roth withdrawals can avoid federal income tax later, and the original owner of a Roth IRA does not face required minimum distributions during their lifetime. So when does paying $25,000 now actually make sense?

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