'With All Due Respect, This Makes No Sense' – Suze Orman Explains Why This $1.6 Million 401(k) Rollover Plan Could Backfire

In a recent episode of her Women & Money podcast, Suze Orman took a firm stance on a complicated retirement strategy proposed by a listener.

A 56-year-old retiree, Gina, sought Orman's advice on rolling over $1.6 million from her pretax 401(k) into a Roth IRA over ten years without tapping into her liquid savings to cover taxes. Her company's benefits advisor had recommended a series of steps that seemed, on the surface, like a viable plan to avoid an immediate tax hit. Orman, however, didn't mince words in her response: “That's absolutely crazy.”

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Gina's approach, as advised by her company, involved rolling over $100,000 from her pretax 401(k) to a Roth 401(k) and then from her Roth 401(k) to a Roth IRA. To cover the taxes owed on the conversion, she planned to withdraw $40,000 from her 401(k) and have her company withhold 100% of that amount for taxes. If too much was withheld, she anticipated receiving a refund; if too little, she expected to owe a manageable amount.

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The rationale behind this strategy may have been to minimize the upfront tax burden, but Orman quickly pointed out its fatal flaw: taxes. When converting funds from a pretax 401(k) to a Roth account, you move money from a tax-deferred status to one where taxes must be paid upfront. “That's not a rollover,” Orman emphasized, “that's a conversion ... so guess what? My dear Gina, you owe taxes from that point in time.”

One key misconception in Gina's plan is the belief that she could somehow lessen the tax impact by moving funds between different retirement accounts. Orman clarified that this isn't possible: “Like, what have you avoided there?” Any conversion from a pretax 401(k) to a Roth IRA triggers a taxable event in the year the conversion takes place and no amount of shuffling between accounts can bypass that reality.

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Moreover, Orman warned that if Gina’s Roth IRA hadn't been open for at least five years, even funds from a Roth 401(k) could face taxes on earnings when withdrawn. This added complication makes Gina's plan unnecessary and potentially harmful regarding unexpected taxes.