This time around, all of the music had been removed from the original CD cases and put in little brown envelopes, with hand-written titles on the envelopes in almost illegible handwriting. That's why I couldn't find the songs.
On one hand, I don't know what keeps triggering this dream. My definition of success has changed so much since the days I worked in radio, and it has nothing to do with money or fame. Back in those days, I was pretty insecure about being "successful" in the biz, compared to today where I don't feel that pressure as a programmer.
On the other hand, the new thing I remembered was that I was most worried about letting my boss down. I could imagine Matt, one of my program directors, sitting me down and telling me he didn't need me anymore, because I wasn't providing a quality show. I can't figure that one out, unless it's some metaphor for something else. I haven't had a boss since the radio days that I was worried about pleasing.
I wish I knew why I kept having this dream, and why it upsets me.