I got this question as a comment on an older post today, and I wanted to bring it up for everyone to see.
I have dreamed of doing what you are doing, and I wonder if it could be possible for me. I DO have my passport, after all! My fear is having no pension or health care or other things like that for the future. How do you deal with these issues? Do you have any ideas or encouragement for me?
Yes, I have ideas and suggestions for you! And lots of encouragement.
I’ve been self-employed for 20 years and continue to work on the road, so my situation with healthcare, pension, etc. is the same whether I’m at home or traveling. I have to provide my own. It’s actually easier for me to save for retirement, since I can live so cheaply, and traveller’s health insurance is MUCH cheaper than health insurance back home (but probably not as comprehensive in case of a major illness).
People who prefer the security of a traditional job would want to work for an employer remotely. I know several people who work from home in the States, but the time difference and occasional internet issues would be a problem for them, I think. You’d need a lot of flexibility. Craig was working remotely for his company back home, and internet connectivity was his #1 issue on the road.
The other thing some people do is take a “career break” — a full year off from work. It’s more common in Europe than in the US, but I’ve met Americans who’ve done it. They’re essentially quitting their job for a year and hoping to find a new one when they get back. If they were valued employees with strong skills, had a good relationship with their employer, and gave plenty of notice, it’s sometimes possible to come back to the same job.
There’s a group called “Meet Plan Go” that offers lots of support and advice for people who are interested in career breaks, including hosting local meetups where people who’ve successfully done it come and answer your questions. I went to one of their events in St. Louis while I was making up my mind, it was wonderful. Here’s their website: http://meetplango.com/
The advantage to a career break is that you can focus on travelling all the time. I have to travel very slowly and accept that I can’t Do All The Things because I’m not on vacation. Of course, the disadvantage is that you have to save up money before you go, and look for a job when you get back.
Good luck to you!