Hey, I can relate to this a lot. I'm 20 and I dropped out last year. I come from family of teachers and professors, so that was weird, but my parents and most of my grandparents are dead so they can't really say shit. I love the free life, and I'd love to travel like you, I just need to learn languages and get money first. I read a lot, and I think you might find something consoling in Hesse, particularly Siddhartha, or a book like the Tao Te Ching. Western philosophy isn't there for comfort, but to challenge and to provoke further uncertainty, at least in my opinion, so it makes sense that it didn't provide you with what you were looking for. I think Eastern philosophy and poetry might. Maybe look at the School of Life's videos on Matsuo Basho and Wabi-sabi?

I'm going to follow you because I'm interested in what you're doing and I'd love to see pictures of your travels, particularly non touristy sections of the cities you visit. Now, I don't want to self promote, but I guess I will. This isn't about that though, I swear. I actually want to see what you think about this video my friend and I put together, because it's my attempt at sort of taking a stab at the existential anxiety of modern life and figuring out how to build a system or mindset that helps one live comfortably. Here's the link: