I'm in my mid-40s, still 20+ years out from retirement age. Original vandwelling plan was to hit the road from Maine at the end of the summer and head to warmer climates for the winter, FL, AZ, SoCA, etc. This was when I was still a full time bicycle mechanic. When it gets snowy and cold in ME winters, bike shop hours get cut way down and cycling is in-season in warmer places. Figured I'd be a migrant mechanic, following seasonal employment. Spring and Fall, while mobile, look into WWOOF (
http://wwoof.net/) opportunities between North/Summer and South/Winter stints. I can also fit a basic bicycle workshop in my van, so there would be opportunities on the road for mobile bike repair anywhere I decided to stop for any length of time -- I see lots of bikes strapped to RVs...
However, things change and a former employer I made contact with regarding a reference on my resume offered me my old job back. More pay (met my "sell-out" price), less hours/responsibilities, something I didn't hate doing -- publishing production management. However, this is a 4-5yr commitment, so migrant traveling has been tabled indefinitely. I still do PT bike work over the weekends to keep skills sharp and to receive employee discount on bikes, bike parts... And while I'm currently working out of the Newburyport MA office, we have an office out on the West Coast in SF.
I discussed my vandwelling situation with my boss and a longing to get mobile. Was pleasantly surprised when he offered up the office shower toward hygiene needs, and agreed with a plan I'd been scheming on ever since I took this job back -- hitting the road in the Winter and heading out to vandwell in SF for a couple months before returning to the East Coast. There's also an outside chance that I could turn freelance project production management into a portable job as well.
This past weekend was the last weekend the bike shop is open on Sundays, cutting my PT hours there in half, but through the Fall, I'm getting back in with my ex-in-law's beef farm as a meat cutter, and will be learning slaughtering as well. ...Which could be useful as a skill to bring to the table in possibly WWOOF situations; meat cutting is also a great skill for potential seasonal grocery work.