One of my children is an overthinker. It can be challenging encouraging someone who is sometimes paralyzed by so many "what-if's." I definitely see benefits from thinking things through before you act , but truthfully alot of who I am has been shaped by diving in, thriving when things go well and learning when they don't.
Yep, that is part of "living" life. If you overthink you never really "do" much. Spend too much thinking about it...