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vali comments on Group rationality diary, 1/9/13 - Less Wrong
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For theft: Everything I own that is expensive stays in my backpack, which never leaves my back. I have full weatherproof gear, so I'm not worried about rain either. If anyone enquires about my job history gap, I'll tell them I was traveling.
If you want to change some aspect of your life, like ditching everything you own and walking off into the sunset, all I can say is that you have to want it, and want it bad. At some point I got so depressed and fed up with my life that walking away became easy, because nothing I was leaving behind was worth it. I was too profoundly unhappy about my life to care about little things like where I sleep or if it's raining. It also helps that sleeping in strange places does not bother me overly much, and I live in California, so the weather is rather mild.
How do you plan to not get robbed (backpack and/or bike) while you're asleep? I suppose you will lock your bike somewhere while you sleep, which is probably? reasonably secure for one night at a time. The best way I can think of to prevent backpack theft is to physically attach it to yourself in such a way that moving it will wake you, but even that doesn't necessarily prevent someone from opening and rooting through it.