Every year for Christmas I end up getting a large amount of cash from various family members. I always end up feeling conflicted about how best to use the money. I'm a frugal type of guy. I don't like making large purchases, and even when I buy things that I know I'll use and enjoy, I still tend to have buyer's remorse about spending the cash. I know that stuff won't make me happy, I've proven this to myself time and again, so when I do spent large amounts of money of stuff, I always feel conflicted.
I don't like the way that my brain functions when I have that extra money sitting in the bank account post-holidays. I get into consumer mode, where I feel like I need to spend it, either to honor the wishes of the givers, or simply to get rid of it so it will stop weighing on my thoughts. I end up spending far too much time thinking about the things I could buy, weighing options, etc. It starts to consume my thoughts.
10 months out of the year, I am good at not spending money on frivolous things because I can simply tell myself "it's not in the budget" and be completely content with that. Except, for a couple of months a year, it is in the budget. Part of me wants to just give it to charity and be done with it, but another part of me doesn't want to part with it. I don't like the greedy part of myself, even though I want to give in to it.
This year I'm trying to decide between buying wood working tools (a new hobby of mine), or more/nicer bike commuting gear (some merino layers and better lights for the winter, especially), but the time spent trying to decide what to buy, and how best to maximize the money is starting to drive me crazy.
How do you handle these sorts of windfalls?