Risks? Big question

 When it feels scary to jump in, that is exactly when you should jump. Otherwise, you end up staying in the same place your whole life. This is a dialogue by Oscar Isaac from the movie "A most violent year".

Well, I have a different opinion. I'd rather advise taking calculated risks rather than a naive intuition-based random walk. Maybe, like a Gradient descent where you take each calculated risk to minimize your distance from your target.