zslastman comments on Positive Queries - How Fetching - Less Wrong
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Also a chronic loser of keys. In addition to what's been suggested below - are your keys heavy enough? MIne have, e.g., a bottle opener and a usb key on them, and a very thick ring. The bottle opener in particular makes it difficult for them to slip out of a pocket, and the whole thing is heavy and noisy enough that a) it makes a lot of noise when dropped b) I can easily check for it's presence by patting my pants. Getting into the habit of doing this whenever leaving a location has saved me a lot of hassle.
Fellow pants-patter here. Also, before bed I get my tomorrow-pants set up with keys, wallet, etc. before throwing the current ones in the laundry pile. More generally, strong habits can compensate for much in the way of weak memory.
I solved this a slightly different way: I found a very thin wallet (more of a flat coinpurse, really) and put my keys and a couple other cards in it. This makes it heavier (which helps) and sit cleanly in my back pocket; checking that it's there doesn't even need a pat. In theory, this increases the potential loss if I do lose my keys, but increasing the stakes also makes me check more often. (I'd found this previously when I bought a semi-expensive mechanical pencil instead of a box of new ones, and proceeded to keep track of it for longer than it had taken me to go through a box of 12.)
It also has other benefits: I keep my money in a separate, garden-variety wallet, but always keep at least $25 in the key-wallet for a bus ticket or short cab ride home, which is a nice hedge to have.