When to Sell

Adam M. Grossman

U.S. STOCKS ARE DOWN almost 19% so far this year. The broad bond market, surprisingly, has also lost money, sliding almost 11%.

At times like this—when the headlines are almost all negative—the standard advice is to avoid panicking and stay focused on the long term. I agree with that, and indeed the data are clear: Investors who attempt to time the market with “tactical” trades often suffer whipsaw. But that doesn’t mean we should bury our heads in the sand. There are at least four situations in which it might make sense for investors to sell during a down market.

1. Cash flow. The first—and most obvious—reason you might sell stocks is to meet cash needs. In general, I recommend that investors hold at least three years of expenses in cash or bonds, if not more. But what if your portfolio wasn’t structured that way before the market dropped, and you find yourself with insufficient cash and bond holdings to meet upcoming expenses? It might seem like an unpleasant prospect to sell now. That’s understandable. Ideally, we would only sell when the market is strong. Nonetheless, I wouldn’t hesitate to sell.

Yes, the market is down. But relative to past downturns, things really aren’t so bad. The S&P 500 is off 18% in 2022. While that might sound like a lot, that’s relative to a high point—and comes after more than a decade of almost continuous gains. Compared to just three years ago, for example, the S&P 500 is up 37%, and bonds are down only 3%. Unloading investments at today’s prices is hardly a fire sale. If selling some shares at today’s prices would help you to build a cash reserve, I wouldn’t hesitate. You could then sleep easy, even if the market dropped further.

2. Suboptimal holdings. In my view, there are four types of investment that are less than ideal. First are highflying investments—things like speculative technology stocks. Second are stocks or funds that simply have a lackluster outlook. Unlike highflying stocks, lackluster ones probably won’t drop too much. Instead, the risk is that they simply won’t gain very much. Many banks and old-line industrial companies fit in this category. Third are high-cost mutual funds. On average, funds with higher expenses have underperformed funds with lower expenses. The fourth category includes private funds, where transparency and liquidity are generally low. As I’ve noted before, publicly traded stocks rarely go to zero. But I’ve seen private fund investments lose all their value more than once.

If you hold investments that fit any of these categories, my advice would be to look for a way to get out. When the market is high, such an exit might carry a tax cost. But with the market lower today, you might be able to exit a suboptimal investment with little or no taxable gain. The proceeds could then be reinvested immediately into investments that are more promising or less risky. The nice thing about a swap like this is that you wouldn’t be a net seller while prices are low and you wouldn’t be changing your asset allocation. Instead, you’d simply be upgrading your portfolio.

3. Tax losses. Even if your portfolio isn’t saddled with suboptimal holdings, market downturns offer another potential benefit. Tax-loss harvesting is the strategy by which an investor sells an investment and then immediately purchases a replacement with the proceeds. That provides a valuable and flexible tax benefit. First, the investor could use that loss to offset capital gains on other sales. If there are no gains, up to $3,000 of the loss could be applied against ordinary income, such as wages. To the extent that there are unused losses beyond that, those could be carried forward to future years.

Here’s what makes tax-loss harvesting so powerful: When you do a swap like this, you can collect the tax advantage without substantially changing your portfolio. Under IRS rules, you can’t sell an investment just to book the loss and then immediately buy it back. In fact, the rules say that you can’t buy back anything that is “substantially identical.” Otherwise, it’s called a wash sale and the tax benefit is voided.

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You can, however, buy back an investment that’s similar—just not identical. Suppose, for example, you own a fund that tracks the S&P 500. If you sold that, you’d have several options for replacing it. You could buy a total stock market fund. That sounds like a different investment, but it has an overlap of more than 80% with the S&P 500, so its performance shouldn’t be too different. While the IRS has never precisely defined its “substantially identical” litmus test, most advisors agree that a swap like this wouldn’t run afoul of the rules.

Alternatively, you could swap into a fund that follows a large-cap index other than the S&P 500. Vanguard, for example, offers a fund that tracks the CRSP large-cap index (symbol: VV) and one that tracks the Russell 1000 large-cap index (VONE). If you were to compare the historical performance of these two funds to an S&P 500 index fund, you’d find them to be very similar—but not identical.

Another key point about tax-loss harvesting: By immediately replacing the investment you sell with a fund that’s similar, you again aren’t a net seller, so you shouldn’t feel you’re doing something unwise by selling while the market is down.

4. Imbalances. A fourth reason you might sell, even though the market is down, is to correct a significant portfolio imbalance. These imbalances can take many forms. Some investors have a concentration in a single stock. I often see accounts, for example, that have disproportionate holdings in Apple or Amazon. In both cases, these imbalances are the result of great performance in recent years. Nonetheless, a big holding of a single stock represents a significant risk. Imbalances can also find their way into portfolios via mutual funds that are concentrated in certain parts of the market—technology stocks, for example. Similarly, imbalances can crop up on the bond side.

In each of these cases, there might be nothing wrong with any one individual holding. The problem is the risk they present in aggregate. Harry Markowitz, the father of Modern Portfolio Theory, said it best. In his initial work back in the 1950s, he used railroad company stocks to explain the concept of diversification. There’s nothing inherently wrong with railroad stocks, he explained. But if a portfolio consists of only railroad stocks, that’s a problem. Companies in the same industry are often affected by the same economic factors. A portfolio may seem diversified, but if too many of its holdings are concentrated in one area, it may be far riskier than it appears.

“One hundred securities whose returns rise and fall in near unison afford little more protection than the uncertain returns of a single security,” Markowitz explained. If you identify an imbalance like this among your holdings, that’s another situation in which it may be worth selling even when the market is down—and even if correcting the problem will generate a tax bill.

Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam’s Daily Ideas email, follow him on Twitter @AdamMGrossman and check out his earlier articles.

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Kurt Clark
Kurt Clark
23 days ago

Thanks for the informative article. Assuming one had three years cash expenses going into this market downturn and the market treads water for the next 12-18 months are you comfortable reducing your on-hand cash balances to 12-18 months?

I feel comfortable keeping three years cash expenses on-hand but struggle with what to sell (bond funds vs. stock funds) when the market is down.

28 days ago

While technically not selling, doing Roth conversions when asset prices are low is also recommended.

28 days ago

Hey Adam. as always I enjoyed your informative article. I do have a question though on this part of your statement below. My understanding is the same but I thought I could, for example replace BND with AGG (or SCHZ or SPAB). This to me would constitute “similar but not identical”. For example, I can’t buy back BND within 30 days (assuming I sold this at a loss) or replace it with its mutual fund equivalent from Vanguard (VBTLX).

I get the impression in reading what you have below that my assumption is incorrect. Can you clarify please?

In fact, the rules say that you can’t buy back anything that is “substantially identical.” Otherwise, it’s called a wash sale and the tax benefit is voided.

You can, however, buy back an investment that’s similar—just not identical.

Thank you!

Jonathan Clements
Jonathan Clements
28 days ago
Reply to  rgscl

I’m pretty confident that replacing one fund that tracks the Bloomberg Aggregate Bond Index with another would violate the wash-sale rule.

28 days ago

To have a cash reserve of a least 3 years would you sell bond funds? If so, would you sell bond funds with duration of 6 to 8 years or 2 to 3 years first?

Last edited 28 days ago by PAUL ADLER
Kevin Thompson
Kevin Thompson
28 days ago
Reply to  PAUL ADLER

Bond funds have become very precarious these days with tax bills sent out to clients and embedded losses. I am more partial to owning actual bonds being that they mature at par and pay coupons. As for your question, I would consider why you purchased the bonds initially. If they are providing a sustainable cash flow that subsidizes your living expenses then there is really no reason to sell at a loss unless you are trying to harvest those losses and purchase higher yields. Laddering bonds is key at the moment.

27 days ago
Reply to  Kevin Thompson

Your question…

I would consider why you purchased the bonds initially.

My bond funds has all the money to meet Bill Bernstein requirement “if you won the game stop playing“.

Last edited 27 days ago by PAUL ADLER

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