Well and also, look at what did work out for them. for instance if someone is 50 years old and 'played it safe' for 30 years, yet is living a very boring life. You might find that 'playing it safe' is something you don't want to do.

Also, it doesn't matter if things fail, or if you're doing something wrong. You are gonna be wrong about stuff anyway, you are definitely gonna fail at stuff. Yet, if you choose to not be wrong, or never fail, you will never learn, never grow, and hardly be happy.