I'll admit, I'm one of those perpetually upbeat people at work who when you ask "How are you?" I respond (in earnest), "I'm living the dream!" Most people think it's awesome and I get a lot of positive feedback. Every now and then people express annoyance with my response ("Oh, must be nice." or "Not me!"), but I generally just ignore them and go about my day. But this one guy is really bothered by it. So much so that he has said to me, "One day I wish you'd stop with your positive attitude about everything and just respond honestly." I was so baffled by this borderline hostile remark. This guy has way more money than I probably ever will (he talks about his money situation pretty openly with the people that he considers his friends at work -- how I managed to make that list I'll never know), but he can't seem figure out that he could just retire and go off and do whatever would make him happy. He's sort of pieced together that I could be FIREd (I prefer the SWAMI lifestyle), but he can't seem to wrap his head around the fact that he could be doing the same thing. If he ever decides to actually engage me in conversation like a normal human being maybe I'll let him in on my secrets, but until then, I'm just gonna let him be cranky.