Anyone in late thirties leave it all behind to go to Japan?

I am a 37 year old living in Wisconsin USA, I have a pretty good job as a project manager. Every day I think about wanting to go back to Asia, I taught ESL in Korea only for 1 year when I was 23 and 24. Later I went to Thailand to get a CELTA certificate and I worked there for a while but as a writer. I don’t have any kids or a mortgage or a spouse or anything, I just worry about taking such a massive hit in income. Has anyone later in life left their comfort zone to do this? Did you have success?