The Stock That Got Away

I bought about 100 shares of Yahoo! when it debuted via its initial public offering (IPO) in 1996. I think it was around $30 back then. After a few months, I sold at roughly the same price because I needed some money to buy a house. Stupid me. Then again, stupid me in retrospect. Who knew?

- R.B., Rising Sun, Md.

The Fool Responds: You're right. There is no way to know which of your holdings will be the most stellar performer until you're looking at them in a rearview mirror. That said, you can improve your odds by keeping up with your holdings regularly - evaluating how strong their financial health is, along with their growth prospects and competitive position. When you need money, sell the holding in which you have the least confidence. Yahoo! shares have risen more than 16-fold for its earliest investors who hung on - that's enough to have turned $5,000 into more than $80,000. Think about your home, though - its value has probably increased considerably, too, boosting your net worth.

Do you have an embarrassing lesson learned the hard way? Boil it down to 100 words (or less) and send it to The Motley Fool c/o My Dumbest Investment. Got one that worked? Submit to My Smartest Investment. If we print yours, you'll win a Fool's cap!