"When do you stop playing risky?"
Never! If you are the kind of person who enjoys playing risky, double-edged chess, you should never change your style. What changes is your ability to assess risk more accurately and to avoid taking stupid risks. You may abandon some of the unsound gambits that worked OK when you and your competition were weaker, but your attitude never has to change
Agreed. Risky chess is fun if that's what you like.
I became more risky when I stopped caring about my rating and results (winning/losing) -- instead, caring about playing an interesting game and having fun.
Don't fear risk, just learn how to do it better.
I am playing for pretend points so I don't care how risky it is. Now if there was money involved I would hire someone smarter than me to play for me.