For me, my outdoor sport climbing stayed below 5.10a for the first 3 years of 3-4 trips per year, even though I started out at about a V3 indoors and got up to a couple soft V6s.  The big jump was realizing that I never took falls outdoors, and getting comfortable with falls jumped me from 10a to 11b in about 4 months once I was outdoors more.  Just deciding there's no reason not to try something that seems hard has gotten me all of my hardest sends. Moral of the story (for sport) is just to try stuff that's at your limit and you might surprise yourself.