The short answer: it doesn’t for a VERY long time. At least that’s my experience and the experience of those I talk too.
I’m asking this in a self-reflective way because my perception of how difficult it is for me and other people’s perception about how I’m rolling are quite different. I feel like I’m terrible, too slow, too late and yet other people say I’m rolling really good. I think it’s encouragement but the hard thing about BJJ is it just doesn’t seem to get any easier.
You start off as a White and think that once you get your blue the problems you are having will be solved or at least easier. The thing is…it doesn’t and you find out that even white’s cause problems to Purples from time to time. Jiu-Jitsu is relative especially during the years until your black; you will always be training with people of better and equal skill. Until you get past that hurdle that’s a very long time where Jiu-Jitsu doesn’t feel easy.
Once you can roll very relaxed and adaptive to the situation then I think Jiu-jitsu may become a bit easier. So enjoy rolling and leave your ego at the door – otherwise that’s doing to be one bruised ego after 10 years of jiu-jitsu training.