I think most of us have a lot of frustrations about various things, so to me that's the first thing I would look at regarding sleep issues. The guy getting exactly what he wants sleeps well.

More specifically, I'll have trouble falling asleep and then start thinking about what's not good in my life, and I'll often sit up then and there, crack open my laptop, and take some action to at least be closer to making the thing better (writing an email to get the ball rolling, or just reflecting about ways to interpret whatever the issue). I then usually feel more satisfied and can sleep, though I may lose an hour or two doing this.

My point is take a hard look at what isn't going as well in your life as you'd hope.