Now Bliss, it might be a whole lot easier to respond to this if you said what the risks are. I mean this could be a risk of crossing over the M25 by foot at 7am in the morning, or the risk of embarrassed from breaking/knocking something over in a store.
The thing with risk, I think, is it is mainly about your perception. The perceived risk, and the reward for taking it. If you really want that reward and the risk seems likely to run in your favour, then you would run that risk. If their is too much uncertainty of the predicted result of running the risk then you are going to feel that the perceived risk is not worth the reward, especially if that risk is life threatening lol.

Look at a sky diver. They have a parachute and then a back up chute in case the main chute fails. A plan B, so maybe you need to formulate a plan B? or even C, D and E? Lol. Without knowing what the risks are and the reward I don't think I can say anything of much help. However, if you want to start to learn to take more risks in your personal affairs, take up a risky hobby. Start doing "other" risky things and maybe your fear or avoidance of risk will begin to change as you learn to let go of the fear

I hope there is some sense in that...

I kind of agree with handsel, putting it all on paper and see where your thoughts lead you.

Bliss, you said that not taking action/making a decision is a 'bad thing' - it can't be THAT bad, else you would have been prompted into doing something about it - you wont like me saying this, but sometimes the 'comfort zone' isn't all peaches and cream, and yet we stay stuck in that bad place because it is actually easier to just sit there moaning about our lot and doing nothing, just having others reassure us yeah it's bad.....

What I am saying is that if you don't like where you are at, only YOU can change it - take the bull by the horns and as Susan Jeffries said "Feel The Fear And Do It Anyway" - by the way, that is a cracking book that you might find helpful!