Does it hurt when you sell at a loss?

I've been into this audio hobby for 30 years, and I am afraid to actually tally up the money I have spent, as well as the money I have lost when I have either sold or traded in equipment. I'm sure there are other hobbies and habits that can cost quite a bit, but I have to wonder, when I see a Linn CD12 up for sale for 11k, does the original owner actually lose 9k in the process. How does everyone justify this behavior, or are we trapped psychologically somehow?
Thanks I would appreciate some feedback.