[ryandrake]

I suppose I have the exact opposite problem: I'll only spend money if I'm getting a thing that I believe I have a chance to resell later and re-capture at least a little of the value--even if it's just pennies on the dollar. And, I avoid buying things new because most things' resale value is gone the moment you walk out of the store. Sometimes I think everything I own I got on Craigslist.

I have a terribly difficult time allowing myself to spend on travel, shows, experiences and so on, because these things leave you with nothing but fleeting memories, and you can't re-sell those later on eBay when you're tired of them. I don't really feel the inherent value of the experience.

[etrautmann]

I used to identify with this, but made a hard switch the opposite way. When I look back on the last 10 years, the things I value are memories with friends. The idea of saving a few bucks to not going on a trip for a "fleeting memory" is crazy to me. That's all we have at the end of the day. I feel so much richer having experiences with friends and family, and the gear and stuff I buy gives me zero satisfaction compared to my honeymoon or another trip, or a nice dinner I hosted with friends.

[Zambyte]

I replied this to the parent comment as well, but I highly recommend journaling about your "fleeting memories". It will help you remember and enjoy your memories for longer.