Yep, I think that planning and being aware of what's happening it's the key to know where to sell. For example, no one is telling you that certain stocks are going to crash, but certain indicators can tell you that indirectly.
It sounds like the gist of what you are saying is, "Don't worry too much about selling". I don't know if that helped me too much though. I still feel like I have no real idea of when to sell (yes, when I make a profit, but a profit of how much?). Just making a profit isn't the aim, else this would be easy. The aim is to make as high a profit in every transaction as possible and when you sell should be closely related to maximizing the chance of that.
I am cautious by nature and I do think that it protects me when it comes time to make a decision like this. I have been right several times doing it but glad I waited on other occasions.
You sell whenever the you feel satisfied. Is the current price, whether high or low, worth the chance of it getting higher or lower, for YOU?
If you need the money, you need to sell, that's to start with. If you don't need the money you can wait and make a more rational decision, sometimes waiting a couple of years can mean a huge income and all you have to do is wait.
For me the best time to sell is when I have managed to get back the money that I put in. Ideally if I put in say $100 I would sell when my stock has risen and then now worth $200. I would basically take out the hundred dollars that I put in and let the rest of the stock make more money for me in the long run. That's the basic rules that I go by. Sometimes this may be a bit different and it really depends on my financial situation but on average this is pretty much how I work.
Obviously knowing when to sell is the whole point at the end if the day, we are all in this game to make a profit right? In an ideal world, we all want to make a profit on our initial investments, but that isn't always going to be the case. So knowing when to cut your losses can also be just as important aswell.
