You want the Dr who has done the operation 10 times, and learned something each time, and incorporated that into their future efforts. You probably don’t want a Dr who will do their 11th surgery on you exactly the way they did the first.
This is what that saying is about
Fair enough. I guess I am making a bit of a straw-man in that I feel I just don't buy the idea that doing the same thing 10 times over the course of 10 years is somehow worse than doing different things over the course of 10 years. They are signals, and depending on what we are attempting, they just mean different expected outcomes. One isn't necessarily worse than another, but in this case it seems to be implying it is the distinction between Midlevel and Senior.