A week or two ago, I lost my Topeak bike tool on the lake front path, it fell out of my messenger bag when I left the zipper open on the pocket it was in. I actually *heard* it fall to the pavement, but it didn't even register with me that something fell out of my bag, until the next day. So I bought another bike tool.
Fast forward to today, I went to TJ's this morning for coffee and other breakfast essentials, and my bag was so full of stuff that I just put my u-lock in my back pocket on the way home, which is usually not a problem. Well, my lock fell out of my pocket on Diversey, just west of Southport. I felt it fall out, of course, so I stopped and looked for it. Should be easy to locate, right? I could not find it at all! I kept looking under parked cars, in the middle of the street, everywhere, it's like it just disappeared. Damn.
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Sorry man. We've probably all had similar streaks of entropy. I've managed to lose TWO entire panniers over the last twenty years of bike commuting. (Way less likely now that I'm rolling Ortliebs) That is such a pain - both times I had to replace a lock and pump and took kit and of course the bag!
You could use bluetooth stickers. They're pricy, but finding your U-Lock would have paid for them.
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