Is it better to realize the loss and buy back in at the lower price or just hold it?

I'm not a big fan of hypothetical questions. It depends on what you're trying to optimize for, i.e. taxes or total return. Most investment advisors would tell you "don't let the tax tail wag the investment dog."

There's an opportunity cost to selling with the intent to buy back in at a lower price. What if it recovers as quickly as it dropped? What if it drops further?

Time in the market generally beats timing the market. If you liked the stock at $150 and intend to hold it indefinitely, you should love it at $100 and consider buying more instead of selling.


Adding my comment to the answer:

You can't realistically assume that you're selling and buying at the same price.

Even if you did, what's the point? If you're selling/buying near instantaneously the loss will be disallowed due to the wash sale rule, which prohibits selling an investment for a loss and replacing it with the same or a "substantially identical" investment 30 days before or after the sale.

If you wait long enough, it's virtually impossible to buy back in at the same price. At a minimum, you're crossing the bid-ask spread.

Answer from 0xFEE1DEAD on Stack Exchange
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Cabot Wealth Network
cabotwealth.com › daily › stock-market › when-to-sell-stocks-at-a-loss
When to Sell Stocks at a Loss - Cabot Wealth Network
April 1, 2025 - ... If you’re a momentum-driven growth investor, your approach should be similar to that taken by Cabot’s growth advisories: Be patient. Let your winning stocks keep winning. Take partial profits on the way up. That way, you’ll never have ...
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Seeking Alpha
seekingalpha.com › article › 4110314-about-the-i-never-sell-my-stocks-rule
About The 'I Never Sell My Stocks' Rule (NYSEARCA:SPY)
September 28, 2017 - Join Seeking Alpha, the largest investing community in the world. Get stock market news and analysis, investing ideas, earnings calls, charts and portfolio analysis tools.
Discussions

capital gains tax - Is it better to realize a loss and buy back into a stock at the lower price or just hold it? - Personal Finance & Money Stack Exchange
And if you're thinking of holding ... you'd never owe capital gains tax... ... In the US, it's also a wash sale if you buy replacement shares within 30 days before realizing the loss. ... @njzk2 in the US you can't use a wash sale to claim a capital loss, but when you do finally sell the stock, you can include ... More on money.stackexchange.com
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November 10, 2022
Never selling shares - Bogleheads.org
It never dawned on them that they could simply sell shares to get the needed income. Hi APC, You are absolutely correct if holding VTI as all stock. But OP's Dad is not holding all VTI. So his Dad's investments yield at least 4%. His Dad has done well and his investments are still doing well. As Taylor always reminds us there are many roads to Dublin. "Success is going from failure to failure without loss ... More on bogleheads.org
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stock markets - It's not a loss until you sell? - Personal Finance & Money Stack Exchange
When buying stock, there is a widespread saying, namely It's not a loss until you sell. This implies that the price at which you bought is relevant. However, I think that once I have bought the sto... More on money.stackexchange.com
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November 8, 2019
What is your opinion on never selling at a loss?
This is an emotional strategy, and thus, inherently atrociously bad. Your buys and sells should be based on what you know about the stock and the market. If something goes bad, and you think it will get worse, bail. Sell whether it’s green or red. If something is red but you believe you can wait it out for what you believe will ultimately be green, then hold it. Another way to look at it… ever been in a bad relationship that went on for too long? Now imagine holding on to one FOREVER. More on reddit.com
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Reddit
reddit.com › r/stocks › what is your opinion on never selling at a loss?
r/stocks on Reddit: What is your opinion on never selling at a loss?
October 8, 2020 -

I got tired of getting the Wash sale mark next to some of my stocks because I sold at a loss, or sold a portion of it while it was down from the day before (even though my total gain was still green), and buying back the same or similar stock within 30 days. So I don't sell anymore if it's in the red, even if it's down a penny.

Would this hurt me in the long run? I feel like I did miss out on some opportunities to invest in other stocks with the same capital because I refused to sell. I wonder if avoiding wash sales is worth this loss of opportunity.

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Is it better to realize the loss and buy back in at the lower price or just hold it?

I'm not a big fan of hypothetical questions. It depends on what you're trying to optimize for, i.e. taxes or total return. Most investment advisors would tell you "don't let the tax tail wag the investment dog."

There's an opportunity cost to selling with the intent to buy back in at a lower price. What if it recovers as quickly as it dropped? What if it drops further?

Time in the market generally beats timing the market. If you liked the stock at $150 and intend to hold it indefinitely, you should love it at $100 and consider buying more instead of selling.


Adding my comment to the answer:

You can't realistically assume that you're selling and buying at the same price.

Even if you did, what's the point? If you're selling/buying near instantaneously the loss will be disallowed due to the wash sale rule, which prohibits selling an investment for a loss and replacing it with the same or a "substantially identical" investment 30 days before or after the sale.

If you wait long enough, it's virtually impossible to buy back in at the same price. At a minimum, you're crossing the bid-ask spread.

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If you're asking about taxes, you'd need to specify a country. If you're in the US (based on your profile), you'd have a wash sale unless you bought the shares back more than 30 days later in which case you wouldn't be allowed to deduct the capital loss. So in the US, unless you want to exit the position and stay out for more than 30 days before buying the shares back, you're better off holding the shares.

If you are willing to stay out of the position for more than 30 days, then it can be reduced to a math problem. But you'd need to make guesses about things like what the capital gains tax rate will be when you sell, what discount rate to apply to get the present value of future cash flows, etc. And if you're thinking of holding the shares until you die, potentially you'd never owe capital gains tax...

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Charles Schwab
schwab.com › learn › story › 4-reasons-to-sell-your-losers
4 Reasons to Sell Your Losers | Charles Schwab
If you don't want to sell your ... Regardless of whether an investment has lost or gained value, you should never keep it if it no longer fits your strategy....
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CNBC
cnbc.com › 2020 › 03 › 22 › why-long-term-investors-should-never-sell-stocks-in-a-panic.html
Why long-term investors should never sell stocks in a panic
March 23, 2020 - While it might seem counterintuitive to sit back and relax while stocks post swift and steep losses, for investors with longer-term time frames it typically pays to wait it out. Looking at data going back to 1930, Bank of America found that if an investor missed the S&P 500′s 10 best days in each decade, total returns would be just 91%, strikingly below the 14,962% return for investors who held steady throughout the ups and downs.
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Merrill
ml.com › articles › when-to-sell-investments.html
Reasons to Sell a Stock (And Reasons to Hold)
July 1, 2024 - Selling an investment at a loss may be easier to accept when you know the loss can be used to offset capital gains and may reduce your tax bill. “But don’t sell an investment solely for tax reasons,” McGregor says. Even if the investment has hit a rough patch, consider its prospects and the role it plays in your portfolio. It may be a good idea to talk with both a tax professional and your financial advisor before selling. The share price of a stock shouldn’t be viewed in isolation when considering whether to sell.
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Investopedia
investopedia.com › investing › selling-a-losing-stock
10 Reasons to Sell a Losing Investment Before It's Too Late
November 6, 2025 - Selling a losing position early, while there is still market interest or when you don't need liquidity as much, can help avoid more significant losses, especially in volatile or declining markets.
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Bogleheads.org
bogleheads.org › board index › us investors › investing - theory, news & general
Never selling shares - Bogleheads.org
The point of buying them is to eventually sell them, not hoard them. just got finished reading Meir Statman's Finance for Normal People and he talked about how the little old ladies were crying at the Con Edison shareholder meeting when the board eliminated the dividend during the oil embargo crisis. These widowers had never sold shares, but only lived off the dividends. It never dawned on them that they could simply sell shares to get the needed income. Hi APC, You are absolutely correct if holding VTI as all stock.
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University of Florida Warrington College of Business
warrington.ufl.edu › home › news › faculty & research › investors less likely to sell losing stocks when entire portfolio is at a loss
Investors less likely to sell losing stocks when entire portfolio is at a loss - UF Warrington College of Business
August 5, 2025 - “People find it painful to sell a losing stock, leading to the disposition effect,” explained Baolian Wang, Bank of America Associate Professor at the University of Florida Warrington College of Business. “In this case, individual investors will be more likely to hold on to the stocks that have performed at a loss yet sell stocks that have gained value.”
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I Will Teach You To Be Rich
iwillteachyoutoberich.com › home › blog › personal finance › when to sell stocks: the only 5 reasons to sell (ever)
When to Sell Stocks: The ONLY 5 Reasons To Sell (EVER)
April 28, 2025 - That way, you’re not cashing out during a dip and making a loss. If your goal is less than five years away, you should set up a savings goal in your savings account. For more information on that, check out our article on sub-savings accounts. If you’ve invested money for a longer-term goal and you’ve achieved it, sell and don’t think twice. That’s a great investing success, and you should use the money for whatever your original goal was. You earned it, after all. The stock market can be unpredictable; just take the madness of GameStop, for instance.
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U.S. News
money.usnews.com › home › investing
When to Sell Stocks at a Loss | Investing | U.S. News
February 23, 2024 - The point is that if a stock's fundamentals have not changed, the mere fact that a stock is down is not a reason to dump it. Conversely, if a company's big-picture outlook does change, you may want to rethink your position. This article takes a look at four fundamentally important things to track: earnings, revenue, debt and dividends. If these four indicators are deteriorating, then selling for a loss may be justified.
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Investopedia
investopedia.com › articles › stocks › 08 › capital-losses.asp
The Art of Cutting Your Losses
June 30, 2024 - Therefore, looking at the major indexes tends to overstate the resiliency of the average stock, which does not necessarily bounce back. In fact, many companies never regain their past highs and some even go bankrupt. By avoiding selling a stock at a loss, many investors do not have to admit to themselves that they've made a judgment error.
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LinkedIn
linkedin.com › pulse › timeless-wisdom-warren-buffett-why-you-shouldnt-sell-your-vishwkarma
The Timeless Wisdom of Warren Buffett: Why You Shouldn't Sell Your Stocks
September 4, 2023 - The stock market is known for its volatility, and short-term fluctuations can lead to impulsive decisions that may result in losses. Buffett's approach of 'buy and hold' encourages investors to stay focused on the fundamentals of the companies they've invested in rather than reacting to market noise. By committing to keeping your stocks forever, you minimize the temptation to sell when the market takes a dip or panic when it soars.
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Quora
quora.com › If-people-advise-to-never-sell-stocks-then-what-is-the-point-of-having-it-if-you-won-t-get-any-money-in-return
If people advise to never sell stocks, then what is the point of having it if you won’t get any money in return? - Quora
When people say `never sell stocks` they don’t mean `never sell`. In fact buy, hold and rebalance by definition means selling from the winners to the losers once a year. It just means hold onto it until you need the money.
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Medium
medium.com › @FIREmansblog › how-to-never-lose-money-in-the-stock-market-7ea17826c426
How to NEVER Lose Money in the Stock Market | by FIREman's Blog | Medium
December 15, 2023 - But, as long as you never sell your shares, you’ll never lose money. In fact, those that pull their money out of the stock market in response to a crash are actually likely doing the worst thing possible. After a major correction, shares are often priced well. The adjustment has already been made, so it’s too late to avoid further losses.
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Bankrate
bankrate.com › investing
How To Know When To Sell A Stock For A Profit — Or A Loss | Bankrate
September 23, 2025 - Markets rise and fall for a number of reasons in the short term, creating potential opportunities for true long-term investors. A stock that is attractively priced can always become even more attractively priced, and that’s a reason to buy, not sell. There is never a shortage of things that markets and traders worry about.
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White Coat Investor
whitecoatinvestor.com › home › search archives › why ‘you don’t lose money until you sell’ is bunk
Why 'You Don't Lose Money Until You Sell' Is Bunk | White Coat Investor
June 10, 2025 - That’s why it’s called REALIZED gains and losses. Having the belief that you don’t lose until you sell which, if it prompts people not to sell, is an ENTIRELY psychological issue. If I have a stock I bought at $100 and it declines to $10 and hold it, then in 15 years goes to $300, there is NO gain or loss until sold – I have NO realized gains or losses.
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"It's not a loss until you sell is a rationalization that people use to negate reality.

An UNREALIZED loss results from holding onto an asset after it has decreased in price, hoping that asset price will eventually recover. Selling the stock converts it to a REALIZED loss.

For example, if your 100 shares of a $50 stock goes to $10, you have lost money. You just haven't realized it yet. If you think otherwise, will your broker allow you $5,000 of margin borrowing when the stock is $10? Nope. Even your broker recognizes the LOSS and will base a possible margin loan on the current value of $10.

Or suppose you bought the $50 stock on 50% margin. When it drops below $33.33 and violates the minimum margin requirement of 25%, will your broker say, "No problem mate, it was once worth $50 and there was no LOSS"? I think not.

Making or losing money is based on today's stock price. Realizing that gain or loss occurs when you sell the stock.

Here's an extreme example. Do you think that anyone who bought Enron or Lehman Brothers (and rode it down) says: "I didn't lose money because I didn't sell the stock."?

A more realistic way to think about this is that whenever you buy something, your money is lost (you gave it to someone else). At a later date, you may recover some of it, all of it, or even a profit, when you sell it to someone else who then gives you their money.

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Your money is lost when you buy a stock, and gained when you sell it. In the sense that it is no longer liquid or legal tender in exchange for other goods.

You should think of investing in this way so you are only ever willing to invest what could be lost forever (although it is extremely unlikely a diversified investment would lose all or even most of its value)

Historically, yes, the stock market beats inflation. But in ideal settings buying low and selling high is good, and selling before any continued drop and then rebuying is better than holding.

You should remember ITS NOT A GAIN UNTIL YOU SELL IT (and it must be at a higher value than you initially paid)