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" ... If you have a taxable brokerage account with a lot of embedded capital gains that you will be forced tap during retirement to pay for your outrageous living expenses, then realize those gains in as low a bracket as possible. If you are married and your adjusted gross income is below $96,000 (after deductions and exemptions), you can realize these gains all day long up to this income threshold and pay no taxes at all. Or, if you are paying 15% on your capital gains now but see that you will be crossing the $250,000 borderline and it feels like you are going to lose your mind when the Obamacare 3.8% surtax starts to bite, then recognize more capital gains today rather than paying 18.3% tomorrow. The worst tax case applies to married couples filing jointly with over $466,950 in income, who will pay 25% on their capital gains (even more if there are state taxes). If that is what you see in the crystal ball, start recognizing these gains sooner, right to the toppermost of any bracket below this. ... "