The ideal time to sell your stocks is when you need the money. Long-term investors should have a strategy centered on a financial goal and a timeline for achieving it. That means it should include a plan to start tapping your investments and using the cash you’ve accumulated when the time is right.
That also means that deciding when you should sell a stock has very little to do with what the stock or broader markets are doing at any given moment. Unless you’re day trading and looking to turn a quick profit—which is much riskier than long-term investing—you don’t even have to worry about watching day-to-day price movements.
If you’re second guessing whether you should hold onto a losing stock, think again about why you bought it in the first place and decide whether anything has fundamentally changed. If not, a dip in the price might actually be a good time to buy more.
Stock Sales and Capital Gains Taxes
If you do decide to give your broker the sell order, be sure you understand the tax consequences first. If the stock price has gone up since when you first bought it, you may have to pay capital gains taxes. Gains on shares you owned for a year or less are subject to the higher ordinary income tax rate, up to 37%, depending on your income. Shares sold after more than a year get taxed at the lower long-term capital gains rate of 0% to 20% in 2020.
If the price has gone down, you can use the loss to offset gains you may have earned elsewhere in your portfolio. For example, let’s say one stock you own fell by $10 a share. If you own another stock that gained $15 a share, you can sell both stocks and owe taxes only on the $5 a share difference. But watch out for the wash-sale rule: Once you take advantage of this tax benefit, you cannot buy back the stock you sold at a loss, or any similar stock, for 30 days.