I just saw this, thank you for the super encouraging reply! While I've never been poor, I come from a place where the thinking is very narrow and I've been super lucky to get out and have a chance at living on my own terms.

Your idea of starting an online diary is also very interesting - I'll definitely consider doing everything in public. I'm just a bit paranoid about putting my (sometimes opinionated) thoughts out there for future employers to see. Maybe it can be a strictly advice, wins and losses.