What are the technical indicators to cash out half a position? One of the toughest things for any kind of investor is selling, but when you have a profit, it's easier. Look at daily or hourly charts, and compare the stock to the index like the TSX. Is a deterioration about to happen? Then again, something could remain overbought and keep rising. Also, sell if a stock reaches more than 10% of your portfolio. The hardest thing is to hold on if a stock keeps rising. Investors are more likely to sell their winners and keep their losers.