I lived in a van for about nine months while traveling around Japan.

I lived primarily off savings, though I worked for three weeks at a beer garden over the summer, two weeks washing dishes at the Sumo in Tokyo and did some consulting work here and there for previous clients.

Once you find your groove it's easy. For me, it was 1) from about 6pm try to find a place to shower, then a place to park. 2) spend about an hour planning the next day's activities. 3) get into some sake, read some comics, then sleep. 4) wake up early enough and move on so that no-one notices you just camped there overnight. Head into town and start sight-seeing.

Fortunately it was 2007 when I came to Tokyo to look for "proper" work and there were all these jobs supporting these people working in something called "sub prime mortgages"...

I was 27 at the time. Still here almost 10 years later though I live in an apartment now. Next month I'll be heading back to Australia to work on a few projects and the thought is a bit daunting. It was much easier at 27 to quit the job and pack it all up, but I think having the experience under my belt makes it easier the second time around.

Second time around will be more like what you describe above, the "quit your job and into the unknown." My tips (as much for you as for me) from doing it once are 1) less is more when it comes to luggage. If I didn't have to work I'd probably go entirely bagless (see: Scottevest) or close too it. 2) A lot of it comes down to a few simple requirements that need to be taken care of every day. Once you have these under control your mindset changes in ways that could fill a blog post on their own. 3) For many hiring managers, a year traveling on your CV is poison. That's their shortcoming, not yours. 4) Consider doing "local" jobs while traveling. I was working and being paid minimum wage but loved every moment of it, and I still keep in touch with my colleagues from those experiences (I've since worked at a bean-sweets factory and a hot spring resort, another stint at the Sumo, and there was a hotel somewhere in there too). 5) The more food prep you're prepared to do the more you can save. If I knew there was a market nearby I'd be up at the crack of dawn jostling with the old ladies for discounted local produce. I learnt and employed time-tested methods for preserving food (salting, spicing, fermenting, drying, etc) or bought from markets pre-preserved (I spiced and dried some meat hanging in my car one time while on the freeway with my windows open. The drag probably cost me more in fuel than I saved by being able to buy the discounted meat lol). I had several go-to meals, and became a master of one-pot cooking. Worst case I would go without, or spend a buck getting some cheap calories from the convenience store. 6) Talk to people. Everyone has a problem they need solved, and you might be the person to solve it. Maybe one thing leads to another and you have a source of income for a while, or more. All of my part-time jobs above bar one came from introductions from people I had spoken to or worked with along the way. Often you can bring a unique perspective, or worst case you learn something yourself.