Stock Basics: 5 Scenarios When Selling Stocks Makes Sense

Hint: It has nothing to do with the market, and everything to do with your personal circumstances.

Ask legendary investor John Rogers Jr. about his biggest challenges, and the story he tells is about selling stocks, not buying them. The chief executive of Ariel Investments earned huge profits on newspaper stocks in the 1990s, and by the mid 2000s Ariel had become the largest shareholder in McClatchy Corp., owner of the Miami Herald and the Sacramento Bee. Even as warning signs mounted—the company carried high debt levels and profits were declining—Rogers held on, hoping for a turnaround. But the stock plunged, and in 2009 Rogers’s Chicago-based fund company sold McClatchy shares for just pennies on the dollar. “We drank the Kool-Aid,” he says. He adds, “Selling is far more difficult than buying.”

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Kathy Kristof
Contributing Editor, Kiplinger's Personal Finance
Kristof, editor of, is an award-winning financial journalist, who writes regularly for Kiplinger's Personal Finance and CBS MoneyWatch. She's the author of Investing 101, Taming the Tuition Tiger and Kathy Kristof's Complete Book of Dollars and Sense. But perhaps her biggest claim to fame is that she was once a Jeopardy question: Kathy Kristof replaced what famous personal finance columnist, who died in 1991? Answer: Sylvia Porter.