Replying to Risk vs reward

At what point does risk out way reward for you guys? For example you have a big cliff you have been eyeing up or a new trick you want to add to your bag. At what point do you feel that it may not be worth it. I am having a bit mental battle about high dive at revelstoke, it is a feature that I have wanted to give a go for a while but I struggle with the battle of is that one hit worth the potential pain and suffering or time off work If it does not go well. I don’t think it’s out of the ball park for my skill level as I think I have grown into a pretty technically proficient skier it’s just that chance that’s constantly in the back of my mind.

anyways what is the breaking point for y’all and if you don’t have one what goes through your mind before a big move?