**Give yourself a quota of fails per year to ensure you’re challenging yourself. **
You could give yourself a “failure quota” of 2 or 4 (or whatever) major failures a year, to ensure that you aren’t just repeating what you’re good at. Also it can take the sting out of losing, “hey at least I get to check off a failure”.
If you only stick with what you’re good at, you’ll never learn anything - Elbow Grease by John Cena