Have you ever bought something when, at the time, you were unsure whether it was a wise use of money, only to find out over time that it was one of the most useful things you’ve ever purchased? Conversely, have you ever bought something that you were sure was worthwhile, only to question your wisdom in hindsight?
When I was a poor grad student living in Michigan, I needed something warm to wear running. Yeah, I used to run. A lot. It somehow took me years to notice that I was fat and not very fast and that running wasn’t that fun. Anyway, I made $8 an hour as a TA in the finance department, but some of the first-year students would get together and pay me like $25 an hour for private sessions. Felt like big money, so after a few of these, I dropped $80 on a windbreaker at the running store. I even paid full price. And promptly began wondering whether it was worth it.
I would have got my money’s worth at three times the price. I wore that windbreaker running in bad weather, I keep it in my camelback if I’m going to mountain bike in rain or wind, and it’s also a nice, light outerlayer to wear on the climb when backcountry skiing. Both pocket zips are now broken, there’s a tear on the chest from colliding with a gate post during a night ride (repaired somewhat crudely with tent repair tape), and it’s got an aroma that will never, ever completely wash out. But I still wear it and will until it’s in shreds.
On the other hand, a few years ago I decided I needed alpine ski boots that really fit. So I spent a good chunk of money and countless hours at a bootfitter trying to accomplish that. The Langes I bought are still not completely comfortable, but I’ve given up on doing anything else. Given the return in comfort and performance on my time and money, not the best use of resources.
Alternatively, my touring boots were purchased on steepandcheap for 67% off retail, and after getting the liners baked by someone who knows what he’s doing (Rob at SLC REI, if you’re wondering), they’re as comfortable as slippers. I don’t even think about my boots in the backcountry anymore.
Problem is that my steepandcheap boot experience was such a pleasant one that I’m now addicted to backcountry.com’s one-deal-at-a-time sites and have five desktop alerts going off all day, every day. In the last week or so, I’ve bought a pair of sandals, a shirt, and some sunglasses, none of which were planned or budgeted. I think I may have a problem. Then again, probably better the money's spent here than where some of my neighbors are spending it.

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