Currently a 9-5er(more like a 7-7er) dreaming of one day travelling around for next to nothing. Just saving up for a base of operations to keep all of my hard earned shit, before eventually hitting the road on a custom built vehicle that can move like a car but legally pass as a "bicycle" to law enforcement. Train hopping is definitely a bucket list item, but I currently have no pressing need to do it, and currently won't given the risks entailed. If a legitimate need ever arose, I'd certainly give train hopping a try.
My childhood was mixed, varying from working poor to very brief periods of being lower middle class. I spent a large portion of it living in the hood. I discovered anarchism at a young age, printing out the Jolly Roger and Anarchist Cookbook from my grandmother's dot matrix printer and a floppy drive when my age was in the single digits, but never really lived the life so to speak. I studied well in school and earned scholarships for college, still wasn't able to avoid student loan debt, spent my 20s still living in the hood to pay it all back off once I found a "good" job instead of getting out of the hood(but a different hood multiple states away where I found the job), and today have gotten myself a lower-middle-class income minus any debt. I still live like I'm poor, still live in my parents' basement in the hood, and just stack everything, so that one day I will no longer need to work for money in order to meet my needs and won't need to constantly rely upon the good will of others as so many living on the road must do. I want to be self sufficient as much as possible, and then just disappear from "society" while helping out anyone I can along the way.
I've been homeless before, but not due to lack of money. I've refused to get government-issued identification after biometrics became incorporated into the issuance process, and for a period, it was impossible to get someone to take my money in exchange for rent, cash in hand. They wanted to do all of this background check, credit check BS, one of the potential landlords even wanted to digitally fingerprint me with a handheld device(I told them to fuck off), and I basically didn't exist to some of these systems and/or had nothing but my name in others. So I camped out in bandos, with a five-figure amount of savings in the bank, using my workplace shower located in the gym in the mornings to keep clean, until two formerly homeless friends that I had helped out got into a place and offered to me a chance to split the rent with them. We stayed together for years and I kept stacking my money, until an ailing parent prompted me to move back home.
I also used to dumpster dive for food. I hate wasting food when so many people are doing without. But where I am at, that is getting harder to do, and today I buy almost 100% of my food(especially given my limited time availability at the moment). I'd like the land to try to grow/raise my own food, but I'm not there yet and don't want any debt. A permaculture system set up would be ideal.
I'm approaching 40, and I don't think it will be ever too late to live on the road, at least regarding chronological age. The key to making this viable is keeping my health in good condition. I've taken good enough care of myself that I still pass as a late teen or early 20-something to complete strangers, so I shouldn't have any problem blending in with any younger gutterpunk crowds I may encounter. People are completely clueless that I'm almost an old man. An obvious advantage is that younger ladies won't know any better either.
