I liked this idea from James Clear: “If you’re always right, you’re not learning. If you’re never failing, you’re not reaching… if you’re always winning, you’re undershooting your potential.”
It pairs well with an idea out of the Warren Buffet and Charlie Munger investment playbook: “Avoid placing bets you can’t afford to lose.”
The challenge is developing a muscle that can intuitively, analytically, and objectively discern the difference between bets. It takes a lifetime of practise, and it never gets easier.