Well, I could not refer to one or two special moments right now. Would have to think about it.
But more generally speaking:
I started all this bullshit
pretty late in my life, being about 40. Before I began being interested in the normadic / vagabond lifestyle (and began reading and posting here), I had no idea about it. You could imagine me as some kind of nerd, programmer, being depressed about his life and so on.
I had no idea about living on the streets, hitching, squatting or whatever.
I could not imagine me sleeping in some doorway a few years ago. (And if, I would have seen it as a horror I would be forced to do because no alternative.) Heck, even walking through city centre of my quite hometown at night made me feel anxious.
Well, then I started traveling a bit as a backpacker. That was a huge step for me, since before I did not even go on vacation really. Then I met a few squatters/travellers/punks and was invited to the first squat like place I ever experienced. And so one thing came to another. Finally, end of 2015 I quit my job and went on the streets and I don't regret it.
What made it worth for me?
First of all, the
freedom. To be able to do what you wanna do, without considering this and that and another thing. Without obligations. Just doing what the gut feeling tells you is okay.
Then,
not being afraid of being brokle, having only little money or no money at all. Experiencing the feeling that "it's only money" and not such important. Because
the road provides.
Letting go of contraints everyone has living a normal, "socially acceptable" life. (Mostly meaning working in a treadmill and spending lots of money for consumption and paying bills and taxes.) I mean, before I would never have imagined myself sitting somewhere playing harmonica or spanging for some change. Then I did and surprisingly I liked it. Also letting go of other more personal contraints. (I was always anxious about what people would think of me, would not share drinks and food - meaning drinking from the same bottle, eating from the same pot - even with close friends and basically would not do anything "you are not supposed to do")
Last but definitely not least
: Making friends. Of course I had friends before. Like fellow students you spend some time together with. Going to movies, having barebecues and so on. Just normal. But travelling and living on the streets I met a few people who really became close friends. Much more intense that what I ever experienced before.
So yes, that is - in short - what I can think of at the moment.