Maybe it's just a 'me problem'. I don't know why, but my mind works like this. Even if the prize is high and the price is to pay is low, I won't risk it. It's totally my opinion, so people can have different opinion on this. But for me, it is what it is. Can't help it. I guess it is a default thing for me 
I do understand where you're coming from. It's a safe approach in a way.
But, as they say, by not taking any risks in life, you're unlikely to ever go bankrupt but you're also unlikely to ever get rich. So it's probably good to have some sort of decision-making approach that is based more on a cold calculation than feelings.
This topic discusses a dye roll, but it's just a simple example that can be transferred into other areas of life (i.e. whether or not to take a particular business opportunity etc.).