It is impossible to know when it is the best time to jump. There are too many variables to know and there is no solid way to know the interaction between them.
There are courageous leaps that arise from desperate acts. Yet most of the time there is lull in your senses and there is sometimes no catalyst until it is too late.
You have to take risks but you can measure the risks. The simple action of planning is something extra. It may end up hurting and that sucks. The preparation lets you know ahead of time and it sucks a bit less. However the chance of something different that can improve your life is possible.
Just making the day a bit different that can cause a tiny positive benefit may make your world immensely better. Because that single variable can cause many interactions that snowball into something incredible. Hold on tight plus breath. Now leap with purpose and a plan.