Being a Clever Investor Isn't Always Smart

Practical Investing

Being a Clever Investor Isn't Always Smart

I'll save a little more in taxes than I "lost" on my tax-inspired trades, but I'm not sure that the savings were worth all the angst.


I've made a few transactions in the Practical Investing portfolio over the past few months, and I thought it was time for an update of the good, bad and indifferent results.

See Also: The Biggest Mistakes Investors Make

First, the good. As I mentioned in my June column (The Power of Reinvested Dividends), I bought additional shares of Seagate Technology (symbol STX) at the end of March because I thought that the stock, then selling at 11 times projected earnings and boasting a generous dividend yield of 4.2%, was undervalued. Shares of Seagate, which makes data-storage devices, had been beaten up because of concerns about soft personal computer sales. I bought 118 shares at $52.94 per share on March 27, bringing my total Seagate stake to an even 600 shares.

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A few weeks later, Seagate announced earnings that beat analysts’ estimates. The stock popped and, as of May 1, it was selling for $60. In barely more than a month, I had a 13% gain on my latest Seagate purchase. I remain optimistic about the company’s prospects and continue to hold the stock.

Next, the indifferent. In my May column (Pruning My Pricey Stocks), I reported that after reviewing my portfolio, I concluded that Johnson & Johnson (JNJ) was overpriced. I sold the bulk of my JNJ stock at about $103 (keeping just one share to make it easier to follow my former holding). JNJ shares, now at $100, have essentially been in a holding pattern. Though it saved me a few bucks per share to get out when I did, the difference is unremarkable.


Finally, the bad. In my April column (How to Make Your Losing Investments Pay Off), I described what I thought would be a clever strategy for making lemonade out of an energy-stock lemon whose share price had plunged along with the price of oil. The stock in question was Stone Energy (SGY), an oil-and-gas producer that had sunk from $50 in April 2014 to as little as $12 in January. Because I was in the midst of preparing my 2014 tax returns, I began to eye the tax benefit I would reap if I sold my Stone shares at a $4,800 loss.

The problem with my idea was Uncle Sam’s “wash sale” rule, which prevents you from claiming a loss if you repurchase a stock within 30 days of its sale. That means that if you want to sell for the tax benefit, you run the risk that the stock could surge while you’re out of it. One way of dealing with that risk is to replace the stock with a similar company. But that idea also has shortcomings because even companies in the same industry can perform differently.

I thought I’d found a brilliant solution. I would sell Stone and use the proceeds to buy SPDR S&P Oil & Gas Exploration & Production ETF (XOP), an exchange-traded fund that tracks—you guessed it—energy-exploration stocks. I figured that if oil prices began to recover, the ETF’s holdings would benefit to roughly the same degree as Stone.

There were just two problems with my plan: The index isn’t perfect, and neither am I. When Stone started shooting up in late March, I lost my cool and reversed the trade, selling the ETF and buying back the stock. The trade had effectively cost me $642—the additional amount I would have had in my portfolio had I simply held on to Stone. I had waited the necessary 31 days, so I’ll get to use that $4,800 loss when I figure my 2015 taxes; it will likely cut my combined federal and California income tax bill by about $1,100. So, yes, I’ll save a little more in taxes than I “lost” on my supposedly clever trades, but I’m not sure that the relatively modest savings were worth all the angst and effort.

On the bright side, my column is all about teaching by example. This, dear readers, was an example of me doing something silly so that you won’t have to. You’re welcome.