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When you sell investments that you hold outside a tax-sheltered retirement account, such as in an IRA or a 401(k), taxes should be one factor in your decision. If the investments are inside retirement accounts, taxes aren’t an issue because the accounts are sheltered from taxation until you withdraw funds from them.

Just because you pay tax on a profit from selling a nonretirement-account investment doesn’t mean you should avoid selling. With real estate that you buy directly, as opposed to publicly held securities like real estate investment trusts (REITs), you can often avoid paying taxes on the profit you make. (See Chapter 12 for more information.)

With stocks and mutual funds, you can specify which shares you want to sell. This option makes selling decisions more complicated, but you may want to consider specifying what shares you’re selling because you may be able to save taxes. (Read the next section for more information on this option.) If you sell all your shares of a particular security that you own, you don’t need to concern yourself with specifying which shares you’re selling.