When I born...
See intro for short answer. This is a more philosophical piece on "how it came to be".
I don't think anyone expects themselves to become homeless by choice. If you told me when I was 16, that in precisely 6 years I'd be doing this, I'd look at you, blink several times, and walk away —but here I am.
It's uncanny, but only more so because it makes enough sense; when I was 16 I had an intense existential crisis that really defined a large part of my life; I wanted to know what I supposed to do, and I didn't know.
I wish someone told me it was okay to not know, and even for a long time, as long as I was trying to know, making an effort to find out, it would be fine, it didn't have to be more agonizing than it already was, but society (friends and family) don't make it exactly easy to do this.
There's a lot of external pressure to "figure out who you are" and decide on your life, but it's impossible. I've spent a disproportionate amount of time looking for myself, and it was never well accepted; family thinks something is wrong; friends give hesitant looks because they're not even sure if you're the same person anymore, and you yourself don't even know who you are and everything is hell.
Soul-searching requires a definite amount of ridiculousness; when I went to Canada to pursue Overwatch as a pro gamer, it was actually one of the most embarrassing moments of my life. Of course, you might say, "no one cares!" And it's true, and it's also not true. People hold their opinions inside them, they don't tend to speak them, but that's what makes it all the worse!
Those opinions are important because it helps provide perspective that's inaccessible from within the individual. One of my friends, during a conversation, gave me a confused look when I told her that my major was CS&B and that I didn't like the Philosophy classes at UCLA.
"Really? I thought you would have minored in Philosophy at least..." she replied, and it took a moment of reflection, but it dawned upon me that she was right, everything that I'd done in my past was characteristic of what a philosopher would do (hint: think a lot, and if you're a good philosopher: live out your thoughts), and this thought comforted me because it helped me tell other people who I was, and I didn't have this before; I just told people I was me (accurate, but alas, not helpful).
See the difficulty in soul-searching isn't actually figuring out what you're like / who you are, it's very easy —just stop doing everything then see what you like to do, it's how children behave and children know who they are, and that's probably the closest state of what we actually want to do, but the difficulty comes in trying to find a fit in society —what do you tell society that you are?
Unfortunately "philosopher" doesn't have a formal career path except in academia, so for me, I have to find merit in a different path, but the point is still the same: the clarification of who you are is not for yourself, you know who you are already (just stop thinking about it), but to tell other people who you are has some difficulty attached it —and to find a way to express this through work is even more difficult.
The best way is to forget yourself —by focusing on the work, everything becomes more honest, "you" becomes an inherent part of the work, yet that doesn't mean the work isn't difficult —it takes time to find the right way to be yourself under the constraints of work; that molding of the "you" to become conducive to good work is a process.
Anyhow, I digress, how did I become homeless? Well, I'm a "philosopher" —and so at every step of the way I ask myself to simply follow my philosophies, what I believe.
I believed learning was important and dropped out of college because I wasn't learning.
I believed I needed to be alone for a while and left to Canada to do that.
I believed I should not delay on writing any longer, so I thought of the conditions in which I would be able to write.
My beliefs have changed over time —but the importance is in following them as they exist in the present, regardless of how they change.
And they have led me here because I've always lived like this —only I didn't know this because it was natural and therefore escaped any reflection, and it took another person to help me see it. In the same way I think everyone can come to know what they want to do, but it requires living and doing enough, so that it becomes clear to someone else —then have them point it out. To live and do without knowing what you're living and doing... requires a leap of faith.
Here's a great explanation of this from Leo Tolstoy:
"When Levin thought about what he was and what he lived for, he found no answer and fell into despair; but when he stopped asking himself about it, he seemed to know what he was and what he lived for, because he acted and lived firmly and definitely; recently he had even lived much more firmly and definitely than before.
Returning to the country in the middle of June, he also returned to his usual occupations. Farming, relations with the muzhiks and his neighbours, running the household, his sister’s and brother’s affairs, which were in his hands, relations with his wife and family, cares about the baby, the new interest in bees he had acquired that last spring, took up all his time.
These things occupied him, not because he justified them to himself by some general views as he had done formerly; on the contrary, now, disappointed by the failure of his earlier undertakings for the general good, on the one hand, and, on the other hand, too occupied with his thoughts and the very quantity of things that piled upon him from all sides, he completely abandoned all considerations of the common good, and these things occupied him only because it seemed to him that he had to do what he was doing – that he could not do otherwise.
Formerly (it had begun almost from childhood and kept growing till full maturity), whenever he had tried to do something that would be good for everyone, for mankind, for Russia, for the district, for the whole village, he had noticed that thinking about it was pleasant, but the doing itself was always awkward, there was no full assurance that the thing was absolutely necessary, and the doing itself, which at the start had seemed so big, kept diminishing and diminishing, dwindling to nothing; while now, after his marriage, when he began to limit himself more and more to living for himself, though he no longer experienced any joy at the thought of what he was doing, he felt certain that his work was necessary, saw that it turned out much better than before and that it was expanding more and more.
Reasoning led him into doubt and kept him from seeing what he should and should not do. Yet when he did not think, but lived, he constantly felt in his soul the presence of an infallible judge who decided which of two possible actions was better and which was worse; and whenever he did not act as he should, he felt it at once.
So he lived, not knowing and not seeing any possibility of knowing what he was and why he was living in the world, tormented by this ignorance to such a degree that he feared suicide, and at the same time firmly laying down his own particular, definite path in life."
—Leo Tolstoy, Anna Karenina, p. 530
I took several leaps within my life, and all of them became defining in ways that I didn't understand at the time, but it was just me being me. The greater problem isn't that it's hard to be yourself —the problem is it's hard to do so when society has a seemingly infinite number of ways to oppress and stifle this "individual" will. Just try your best, and don't be homeless forever. 😬
Unfortunately the solution probably isn't as simple as just removing societal oppression, but it is one of the key ideas. I'm still thinking more about this topic, it's tricky —it really is because society has its benefits, and it's benefits come from its oppression, so to remove societal oppression is at the same time to remove the benefits.
Just think of it as "your greatest strength is your greatest weakness" —this is almost always true because the design of a strength has the requirement that it's forced into a specific direction, and that directioning always leaves with it it's absence in the opposite direction.
We can't destroy society, but we also don't want it to exist in the exact same way as it is. But what is society? It is compromised of individual people, so what I'm really saying is we can't "destroy people", but we don't also want them to exist in the exact same way as it is. You see? The problem is that "you can't change people", and even if you could, it would be unwarranted because it forces a person to be what they are not, thereby invalidating the solution —the real solution seems to lead to an all encompassing love, but this has been preached for millions of years to no avail... it is difficult.