Good q. I've been remote working for years, and been really successful. It isn't for everyone, and I tend to put in more hours than perhaps in the office (but I have no commute!)
I think getting building a reputation for good work, and then working to line up remote friendly work - be it a full time gig, or putting together a mix of work. I also try to use traveling to my advantage- offer to speak at meetups as you travel... so you can promote the company/your work/you as an integral part of your travel.
Then comes the scary part. Setting a deadline, and going. Putting everything in storage, renting the house and booking the flights :)
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