Money and Values asks the question Are you naturally frugal or not? Penny, the author, seems to be frugal to the point where it costs her more money to "re-buy" a product after the first has failed. I have to say that I've probably been guilty of this more than a few times.
My biggest problem is that I can't stop my mind from adding up wasted dollars. My fiancee and I just moved in together, so naturally we had two of everything, two dining room tables, two beds, two microwaves, etc. The overlap is incredible. So what do we do with two of everything? There's the Ebay option for some of the smaller stuff. There's Craigslist, but it seems like I have to relist everyday for any interest. And when there is interest, everyone is looking to give you less than 10 cents on the dollar. There's also Freecycle to just give it away. It just kills me to not get good value for something that's still good quality.
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