Congratulations if you reach retirement holding a diversity of assets-tax-deferred IRA, Roth IRA, pension, Social Security and a taxable brokerage account. Also condolences, because it's hard to know which assets to use first when you need spending money. Should you withdraw cash from your traditional IRA or sell appreciated stocks in your taxable brokerage first? You're going to have a tax bill either way, since withdrawals from that IRA and capital gains are both taxed. Which is the lesser evil? Or what if the choice is between cashing in stocks that have gained and dipping into your precious Roth, the retirement account that is totally tax-free? The correct answer here is tricky; it depends on whether you are likely to be leaving money to heirs.
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