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When uncertainty rises in the stock market, panic can set in, and few things fuel anxiety more than war. The inclination to head for the exits is understandable, but fear is a bad reason to sell stocks. There are, of course, instances when it makes good sense to unload shares. We’ll walk you through some of them and share strategies for selling if you decide it’s time to let go.
But first, any moves should be made within the context of an investing plan that considers your risk tolerance, your time horizon and your investment goals, says Jonathan Lee, a wealth management adviser at U.S. Bank. That “becomes your North Star and can help with the discipline around selling stocks.”
Second, try to tune out your emotions. They can get in the way of making judicious investing decisions, says Ekta Patel, head of client advisory services and financial planning at Altfest Personal Wealth Management in New York City. Not only do you not want to sell in a panic, but you also don’t want to be stubborn about holding on. “Don’t fall in love with a stock,” she says.
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Finally, the pros will tell you that there are few hard-and-fast rules about when to sell a stock. “It’s more of an art than a science,” says John Buckingham, editor of The Prudent Speculator. That means in some instances, though some signals are flashing “sell,” you may choose to hold on anyway for other reasons. And that’s okay.
“Like most things in life,” says U.S. Bank’s Lee, “you have to take a mosaic of information and circumstances to make the best investment decision.”
It’s not you, it’s the stock.
When contemplating the sale of a stock, go back to the beginning: Why did you buy it in the first place? Does the reasoning still hold? If not, “you should sell,” says Ross Mayfield, an investment strategist in Baird’s private wealth management division, “and that’s regardless of whether the stock has tripled in price or has been cut in half.”
If you bought the stock for its dividend, for instance, but the company has recently trimmed or suspended its payout, that’s reason to let the stock go. These kinds of corporate moves often point to bigger problems. Walgreens Boots Alliance (WBA) halved its dividend in early 2024, only to suspend it a year later, laden with debt and shrinking cash flow. Investors who got out in early 2024 made out better than those who held on. A private equity firm eventually took Walgreens private in August 2025 —for about half what shares were worth when the initial dividend cut occurred.
Or perhaps you bought a company prized for a certain product, but its sales are slowing. During the pandemic, for instance, sales soared for iRobot’s Roomba, a self-driving vacuum cleaner. But the company failed to keep pace with intense competition, and in 2025 it filed for bankruptcy.
Tune out your emotions. You don’t want to sell in a panic or be stubborn about holding on.
Has a new chief executive arrived? If the old CEO was one of the reasons you bought the stock, that may be a material reason to at least reevaluate the holding, says Baird’s Mayfield, if not shed some of your stake while you watch how the new team fares. The transition to a new chief can be a tumultuous time for companies and their stocks. Starbucks (SBUX) and Under Armour (UAA) have seen significant CEO turnover in recent years; both stocks have lost ground over the past 12 months.
Of course, it’s easy to forget, especially if it was years ago, why you bought a stock. So adopt a practice of making a note of why you’re buying a stock and what you hope or expect to happen three or four years down the road, says Mayfield. You can refer to it later if you need to reassess your investment thesis and whether it has played out as you thought it would.
Actually, maybe it is you.
Sometimes, a good reason to sell a stock has more to do with your situation and your portfolio than the company itself. If your asset allocation is off target, for instance, you’ll need to rebalance your portfolio by selling assets that have performed well and investing the proceeds in assets that have underperformed.
If a single stock makes up a large portion of your portfolio — more than 10% of your stock holdings, say — it’s a good time to trim your shares. “A single stock can move more sharply than the broad market,” says Mayfield, which can rattle your nerves as it impacts your portfolio.
Cash needs are another valid reason to sell a stock. For example, an investor may have aged out of a certain risk-tolerance profile and now needs to reduce the risk in their portfolio or build up cash for an imminent retirement.
Selling strategies.
If you must sell, unload shares in smart ways. There’s no need to sell the whole lot, for starters. “There’s a middle ground,” says The Prudent Speculator’s Buckingham. “Sell a little, keep a little.”
Should you sell over time or all at once? The answer depends on how active an investor you are, for the most part, and the reason you’re selling. If you’re tweaking your asset allocation — raising cash, for example — you can start by trimming some of your biggest gainers and selling a few batches of shares over time. “Dollar-cost averaging your way out is a good way to minimize risk,” says Mayfield.
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Or, if the stock is climbing and you’re whittling a stake to cash in on gains, for example, sell over time, on days the price is up. If you’re cutting back on a holding that’s done well to rebalance your portfolio, on the other hand, it may make sense to sell in one go. But mom-and-pop investors needn’t overthink this part. “Most people do not live to manage their wealth,” says U.S. Bank’s Lee. “They manage their wealth in order to live.”
You do need to be aware, however, of any potential tax bill if the stock you’re selling sits in a taxable account. Profits on stocks held longer than one year are considered long-term and are taxed at a top rate of 20%, depending on your income; short-term gains are taxed as ordinary income. To minimize taxable gains, consider selling shares with the highest cost basis (the lowest gain) first. You can offset any potential taxes on gains by selling shares in another stock at a loss, assuming you have a dud you’ve decided to unload. Line up like gains with like losses (pair long-term losses with long-term gains and short-term losses with short-term gains).
In the end, the question of whether to sell a stock boils down to whether you’d buy the same stock today, says Steph Guild, chief investment officer of Robinhood Strategies, the wealth-management side of online broker Robinhood. “If you’re truly investing for the long term, ask yourself the question, Would I still buy it today? Because not selling is essentially buying it,” she says.
Note: This item first appeared in Kiplinger Personal Finance Magazine, a monthly, trustworthy source of advice and guidance. Subscribe to help you make more money and keep more of the money you make here.
