:)
I'll pass on the Gabriel.
I really don't have a problem! I am always playing one thing that leads to another thing that leads to another thing. . . .90% of what I listen to is jazz and Brazilian music. . . and it's really easy to move from one to the other following sidemen or vocalist or featured soloist etc. And I've become very interested in classical music the last few years and so there's lots to grab and be intrigued by along those lines (I'm especially blessed to do that here in my parents' home, my dad has many many classical recordings).
I leave my collection pretty chaotic, not organized very well, and I find when looking for something in particular I need to go through so many other recordings that I end up with a little stack of what to play next! It's a great system. When I married a few decades ago I made a concerted effort to battle perfectionism and anal-retentiveness inherent in me, as my wife was far less particular and orderly than me in many ways, and as a result I find a lot of joy in this sort of free-wheeling listening and storage.
Happy listening! Right now on headphones via iTunes on the laptop:

A beautiful group of Jobim tunes performed sort of chamber music style, recorded in Jobim's studio in his home.