A No-Name Loss

I'm not even sure of the name of my dumbest investment. It was one of those tech stocks — a search engine, I believe. It's still in my portfolio. Selling it would be admitting I made the mistake to begin with.

— Greg B., McLeansville, N.C.

The Fool Responds: We've all got regrettable moves in our investing histories. It's best not to let them linger too long, though. Many people hang on to imploded stocks because of a small hope that they might surge one day, regaining dollars lost. Others hang on out of some sort of pride. But consider the alternative. For one thing, by selling, you'll generate a capital loss, which you can use to offset a capital gain, thereby owing less in taxes. If you have no capital gain, you can deduct up to $3,000 from your income per year, carrying forward the remainder of the loss. And finally, you might recoup your loss, but the better way to do so is to move whatever money you have left in the loser into a stock in which you have a lot of confidence.

Do you have an emb arrassing lesson learned the hard way? Boil it down to 100 words (or less) and send it t o The Motley Fool c/o M y Dumbest In vestment. Got one that worked? Submit to My Smartest Investment. If we print yours, you'll win a Fool's cap!