I had learned the core Java language years before and I knew Java was "enterprise", so I figured that might be a good spot to start, so I bought a book on J2EE development with GlassFish, downloaded all the appropriate SDKs, and after multiple days of spending nearly every minute I could on it, I got something not quite as good as something I could have whipped together in ColdFusion (or Railo/OpenBlueDragon) at the time.
I thought that maybe I was just stupid, and I suppose the jury's still out on that, but shortly after that experience I found a Django tutorial series on YouTube and went through that, and felt like I was productive almost immediately. I was able to build "real" stuff in a matter of a few hours instead of days, and it didn't feel like it was more chaotic than the stuff I had done with J2EE. I then did a similar experiment with Rails, and had the same effect: me being an idiot is not solely to blame for me not really grokking J2EE. Eventually I learned Node.js and did that for a few years, until I was able to (thankfully) transition out of "web development" entirely.
Personally, while I'm sure the Glassfish server, and maybe J2EE has its merits, I don't think they're worth the headaches I went through to try learning it. Java has plenty of cool frameworks now (e.g. Play, vert.x), but I've never even tried using those with Glassfish.