I usually hold a few months unless something turns against me badly... I like to buy stocks that have been beaten down and are trading at or below book value. If I think they could go bankrupt, buy calls and puts, so there's a lot of upside, but I still make money if it goes to 0. I use the technicals (RSI + Bollinger + MACD + Stochastics) as pretty reliable indicators over a stretch of time... selling the calls when overbought, unless I think there's more upside and vice versa with puts. If there's more upside and it's overbought, hopefully sell half my position to cover the cost of all contracts and let the rest ride out as profit.