Wow, what a well written post. That was a great read.

I had similar experiences growing up so I can understand where you're coming from. At this point, I'm 33 and every single one of my friends back home, minus one of them, has:

1. A serious girlfriend or wife
2. A full-time job
3. Kids, or planning on having them in the next year
4. A house and a mortgage

Meanwhile, I left the USA and sold everything I owned to live in Thailand which seems completely wild to everyone I know back home.

Here I don't have to worry about money while I'm building things, but that comes at the exact cost you mentioned: isolation.

I think the trick is to join meetups of people in similar situations. I tried joining "nomad" meetups in Bangkok a few times but got tired of it because of the friendship churn: meaning, those type of meetups just have people who are hopping around to a new city every week and aren't going to be long term friends.

I found a new one focused on people who are living here long term, and I'm going to give that a try, but it's definitely not easy.

Keep on keeping on!