No one ever wants to become a hobo or a homeless street person. But hey, it apparently happens! So if you've currently got a few bucks - but know you're going to be homeless soon, here is some homeless advice (via Reddit).
First off, ya gotta buy the following items:
A decent razor. Since you might not have access to electricity, and because you'll be out in the mean streets, be sure to get an old-timey Straight-Edge Razor that you can also use as a weapon.
A decent backpack. Go for comfort - you might want something with a waste strap. Or consider something military-y like this bad boy.
A quality pocket knife. For cutting apples. And skinning cats. Maybe one like this knife - just because it looks like a hobo knife.
A military cot (keeps you dry and relatively un-bit).
A pull up bar. Sounds stupid, but hangers are free and the quickest way out of homelessness is 5 nice unwrinkled shirts. (Of course, you'll need a doorway for this. And normally those are found in homes. Which you won't have one of.)
If at all possible, a phone able to access the internet. Forget service, it's nice if you can get it but not a necessity. If you can pick up a smartphone with a cracked screen for cheap, that's your lifeline. That's craigslist jobs and email your resume office jobs and google maps and lots of other really good stuff. Recharge and surf at McDonalds or Starbucks or whatever is close.
Rope. NOT to kill yourself - life is never that bad. Rope is just good to have around. Small gauge stuff can be used to hang bags of water, put up a tarp if you run across one, replacement shoe laces, repair a busted backpack, hell I even built some make shift shelves with rope and trashed lumber.
A gym membership. If you can afford it a gym membership is a good fix for a hot shower. Not every small town has a gym, sometimes they can get expensive, sometimes they're just too far away, but it's definitely worth investigating.
If you don't have a phone and can't get your hands on one, libraries are great. You need a verifiable address to get a membership, but memberships last a while. Provided that you smell and look decent (once again, gym showers and hygiene), you can use the library computers to aid you in your job-hunting, as well as finding places to stay. If you have no idea where to start looking for a job, library staff will often be happy to help (provided they're not super busy that day).
And finally, regarding hygiene: If you stay clean shaven, wash with soap in near by rivers, and brush your teeth, no one has to know - and life is 10 times easier.
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