Ask Yourself These Essential Questions Before Selling Stocks

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For me, it’s much easier to buy a stock than sell one. Not least because there’s a lot of FOMO involved in selling. When I sell an investment that’s performed well, I worry I’m missing out on bigger future gains. If I cut my losses on something that’s lost money, I’m left with an annoying doubt I should have waited longer.Alert: highest cash back card we’ve seen now has 0% intro APR into 2026
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Click here to read our full review for free and apply in just 2 minutes. If you’re looking to sell some of the stocks in your brokerage account, first answer the following questions to help you avoid seller’s remorse.1. Why do you want to sell?It’s easy to let emotions drive your actions when investing. Especially at times of volatility when it looks like the value of your nest egg is plummeting. If you want to sell purely because the price has gone up or down, reconsider.As a long-term investor, it’s important not to make decisions based on price action alone. That isn’t to say you should never sell — just that it’s good to take a beat and avoid knee-jerk trading. Perhaps you need the money. Or you’ve lost confidence in the company. Or you’ve found an asset you think will perform much better. Those are all good reasons to switch things up.Click here to learn more about how the best brokerages make it easy to buy and sell stocks. Not only can you find stock brokers that charge zero commissions on many trades, but some will also offer access to expert research and charting tools.2. Does your investment thesis still hold?I’ve learned the hard way that I always need to put my “why” in writing when buying stocks. It makes a huge difference when deciding whether to hold or sell. For example, let’s say you invest in a cybersecurity company. It has a strong position in the market, invests heavily in research and development, and you trust the management team.But there’s a glitch in the technology. Several big clients pull their business. The CEO quits. Suddenly, your investment thesis doesn’t seem so valid. You sell.What about a different scenario? The company reacts quickly to remedy the glitch and doesn’t lose many major clients. It improves its software. The share price falls but you think your rationale still makes sense. You hold.3. Is your portfolio still in line with your investment goals?If you’re a buy-and-hold investor, it’s tempting to leave your investments untouched for years. But a portfolio is a dynamic beast — and so are your needs. It’s a good idea to check in with your investments roughly every six to 12 months.Think about whether your goals have changed. Perhaps your risk tolerance isn’t what it was. Maybe your life circumstances have changed and you’re now planning on getting married, having kids, or buying a house. Or not doing any of those things. As your life focus shifts, you might also need to tweak your portfolio.Equally, you’ll likely want to reduce risk as your retirement gets closer. You’d potentially increase your holdings of safer assets like bonds and lower your exposure to riskier assets like stocks as you get older. A diversified portfolio that’s suitable for your level of risk tolerance is central to successful investing.On the other side, perhaps your investment goals and strategy remain the same, but the value of your assets has shifted. Maybe you had some AI-focused stocks that performed exceptionally well and your portfolio is now overly weighted toward tech. You might rebalance things to reduce your exposure. Some investors also use robo-advisors to keep things balanced.4. What are the tax implications of selling?Generally, if you sell a stock for a profit, you’ll have to pay tax on the gains. Exactly how much depends on what type of account you use, what you’re selling, and how long you’ve held the investment. If you sell stocks at a loss, you may be able to use that to offset any gains.One big exception to this is if you’re using a tax-advantaged account such as an IRA or Roth IRA. Before you sell, work out how it might impact your tax bill — and if necessary get financial advice on how to best manage it.Every investor needs to learn when to sellIt takes discipline to hold on to stocks during the rough times, though it helps if you have a clear investment rationale to lean on. That can help you know if it’s a short-term issue that will pass or a bigger problem that will damage your investment’s long-term potential.As with most things in life, there’s rarely a definitive right or wrong. We have to make the best decisions we can based on our circumstances and the information we have.Alert: highest cash back card we’ve seen now has 0% intro APR into 2026
This credit card is not just good – it’s so exceptional that our experts use it personally. It features a 0% intro APR for 15 months, a cash back rate of up to 5%, and all somehow for no annual fee!
Click here to read our full review for free and apply in just 2 minutes. We’re firm believers in the Golden Rule, which is why editorial opinions are ours alone and have not been previously reviewed, approved, or endorsed by included advertisers.
Motley Fool Money does not cover all offers on the market. Editorial content from Motley Fool Money is separate from The Motley Fool editorial content and is created by a different analyst team.The Motley Fool has a disclosure policy.”}]] [[{“value”:”

For me, it’s much easier to buy a stock than sell one. Not least because there’s a lot of FOMO involved in selling. When I sell an investment that’s performed well, I worry I’m missing out on bigger future gains. If I cut my losses on something that’s lost money, I’m left with an annoying doubt I should have waited longer.

Alert: highest cash back card we’ve seen now has 0% intro APR into 2026

This credit card is not just good – it’s so exceptional that our experts use it personally. It features a 0% intro APR for 15 months, a cash back rate of up to 5%, and all somehow for no annual fee!

Click here to read our full review for free and apply in just 2 minutes.

If you’re looking to sell some of the stocks in your brokerage account, first answer the following questions to help you avoid seller’s remorse.

1. Why do you want to sell?

It’s easy to let emotions drive your actions when investing. Especially at times of volatility when it looks like the value of your nest egg is plummeting. If you want to sell purely because the price has gone up or down, reconsider.

As a long-term investor, it’s important not to make decisions based on price action alone. That isn’t to say you should never sell — just that it’s good to take a beat and avoid knee-jerk trading. Perhaps you need the money. Or you’ve lost confidence in the company. Or you’ve found an asset you think will perform much better. Those are all good reasons to switch things up.

Click here to learn more about how the best brokerages make it easy to buy and sell stocks. Not only can you find stock brokers that charge zero commissions on many trades, but some will also offer access to expert research and charting tools.

2. Does your investment thesis still hold?

I’ve learned the hard way that I always need to put my “why” in writing when buying stocks. It makes a huge difference when deciding whether to hold or sell. For example, let’s say you invest in a cybersecurity company. It has a strong position in the market, invests heavily in research and development, and you trust the management team.

But there’s a glitch in the technology. Several big clients pull their business. The CEO quits. Suddenly, your investment thesis doesn’t seem so valid. You sell.

What about a different scenario? The company reacts quickly to remedy the glitch and doesn’t lose many major clients. It improves its software. The share price falls but you think your rationale still makes sense. You hold.

3. Is your portfolio still in line with your investment goals?

If you’re a buy-and-hold investor, it’s tempting to leave your investments untouched for years. But a portfolio is a dynamic beast — and so are your needs. It’s a good idea to check in with your investments roughly every six to 12 months.

Think about whether your goals have changed. Perhaps your risk tolerance isn’t what it was. Maybe your life circumstances have changed and you’re now planning on getting married, having kids, or buying a house. Or not doing any of those things. As your life focus shifts, you might also need to tweak your portfolio.

Equally, you’ll likely want to reduce risk as your retirement gets closer. You’d potentially increase your holdings of safer assets like bonds and lower your exposure to riskier assets like stocks as you get older. A diversified portfolio that’s suitable for your level of risk tolerance is central to successful investing.

On the other side, perhaps your investment goals and strategy remain the same, but the value of your assets has shifted. Maybe you had some AI-focused stocks that performed exceptionally well and your portfolio is now overly weighted toward tech. You might rebalance things to reduce your exposure. Some investors also use robo-advisors to keep things balanced.

4. What are the tax implications of selling?

Generally, if you sell a stock for a profit, you’ll have to pay tax on the gains. Exactly how much depends on what type of account you use, what you’re selling, and how long you’ve held the investment. If you sell stocks at a loss, you may be able to use that to offset any gains.

One big exception to this is if you’re using a tax-advantaged account such as an IRA or Roth IRA. Before you sell, work out how it might impact your tax bill — and if necessary get financial advice on how to best manage it.

Every investor needs to learn when to sell

It takes discipline to hold on to stocks during the rough times, though it helps if you have a clear investment rationale to lean on. That can help you know if it’s a short-term issue that will pass or a bigger problem that will damage your investment’s long-term potential.

As with most things in life, there’s rarely a definitive right or wrong. We have to make the best decisions we can based on our circumstances and the information we have.

Alert: highest cash back card we’ve seen now has 0% intro APR into 2026

This credit card is not just good – it’s so exceptional that our experts use it personally. It features a 0% intro APR for 15 months, a cash back rate of up to 5%, and all somehow for no annual fee!

Click here to read our full review for free and apply in just 2 minutes.

We’re firm believers in the Golden Rule, which is why editorial opinions are ours alone and have not been previously reviewed, approved, or endorsed by included advertisers.
Motley Fool Money does not cover all offers on the market. Editorial content from Motley Fool Money is separate from The Motley Fool editorial content and is created by a different analyst team.The Motley Fool has a disclosure policy.

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