This is so inspiring! I feel like I'm in a similar situation slowly heading in the same direction. My girlfriend left me (amicably) to travel by moving around to seasonal jobs. I have the nice education, full time job and own a house. She wasn't impressed by this. And I don't feel happy. I thought I was ready to settle down (I'm 43), but that isn't for me anymore. I went on my first bike tour with a friend last summer, taking a week to ride from Pittsburgh to DC. I want to do more tours!
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While I felt I had a good life, when looking back it just dont make sense to me anymore. I guess we keep changing and sometimes the changes are so drastic that we can seem like a different person. Awesome to hear you already have done a tour! It is addicting!
I have a friend who retired, then went on his first tour. He went out for a year and racked up 16,000 miles traveling to Montreal, Key West, California, Alaska, then back to Buffalo.
http://buffalonews.com/2017/09/20/gallery9137/
http://marfapublicradio.org/blog/west-texas-talk/casey-zmich-cross-country-cycler-trucker-and-nomad/