The OP statement / question seems best suited for the young.
When I was younger, I was more of a risk taker. Some were foolish risks, but some were calculated risks, like changing jobs when hearing of a new opportunity that seemed promising. I'm glad I took the chance to advance my career when I could, instead of staying where I was without moving forward.
These days I'm more inclined to only take necessary risks. I recently moved my IRA accounts to a different bank for good reason. I get annual estimates on home insurance and review health plans, then change companies, if I believe there's an advantage. But taking major risks, like putting my home up for sale, or starting a new relationship - probably not. This isn't a time in my life to chance big blunders, if I can possibly avoid them.