Investors often have outsized positions due to appreciation and large pre-tax retirement accounts. You may be looking to reduce portfolio risk and protect gains now, while also aiming to reduce your future income tax burden. Roth conversions and harvesting capital gains are two effective financial strategies that can achieve these goals; however, they accelerate income tax costs. There are current tax consequences associated with each strategy, and the issue becomes whether to accelerate ordinary income, capital gains, or a combination thereof.
You may struggle to choose the optimal balance between Roth conversions and harvesting capital gains. This flowchart will help guide your decisions. It includes: