Expert: Dr. Joseph de Beauchamp - 8/29/2005

Question
I need to sell some stock.  I have 3 choices, with all of the stocks being purchased in the 1980's and I would make the same (pre tax) amount selling each:  1.  sell a stock that is peaking (I would have a considerable cap. gain tax) or 2. sell a stock that has a cost basis equal to its current value(though I have continually reinvested so I have many more shares than originally purchased) or 3.  sell a stock that I will take a pretty big loss on (it is a tech stock that is slowly coming back, but a big loos none the less).  
  I am in a lower tax bracket, own a small business, and have taxes (fairly minimal) due each year.  I hope this gives you enough information to give me some advice.  Thanks very much.

Answer
Jennifer,

I never recommend holding a stock on the issue of taxes.

I base the decision on holding a stock on the following question:

"Would you buy this stock today at this price?"

IF the answer is "NO", then sell today at market. If the answer is "YES", then explore your answer as to why you feel this way  --you might have a false positive response here. If "Maybe", then sell.

Dr. Joseph de Beauchamp