I'm from Canada and have been a full time expat since I'm 19 (32 now). I've lived in Hong Kong, China, USA, Dominican Republic and now Turkey. I never really planned anything, I just visited places and eventually decided to stay longer than expected. I'm lucky that I can work from home and made some lucky investments. For me, the most difficult is dealing with bureaucracy like getting visas and bank accounts. Another difficult part is not having many close friends nor many people I can relate to. I also sometimes envy people who identify to a culture and have their important life choices made for them. I have a lot of analysis paralysis / paradox of choice regarding that. But overall, I'm very happy with my trajectory.