07/23/2026
Maybe a Roth conversion is not the best
A $300,000 IRA taxed at 37% costs $111,000 to convert to a Roth.
Drop the portfolio 25% first and the same conversion costs $83,250, a $27,750 difference for converting the exact same account, assuming it recovers inside the Roth.
One way to lower the tax cost is converting after a temporary market decline, which is available to almost anyone with a tax-deferred account.
The second technique is genuinely niche. It only applies if you already hold a privately valued asset, like a business interest or real estate, inside a self-directed IRA.
A qualified independent appraisal can apply discounts for illiquidity, lack of control, and minority interest, each commonly running 10% to 40%, before you convert the asset.
Those discounts can stack, which is how a $100,000 private investment can sometimes convert at a fraction of that value on paper.
Neither method is free of risk. A market decline can keep falling, or recover before you act, and the money set aside to pay the conversion tax may have dropped too.
A private asset also needs documentation an appraiser will stand behind, not a number that just sounds convenient. The IRS scrutinizes these.
Would you time a Roth conversion to a down market, or does the uncertainty cancel out the appeal?
*The content shared here is for educational and informational purposes only. It is not personalized investment, tax, legal, or financial advice. Consult a licensed professional before making decisions based on your specific situation.*