Don't make to many plans, travel by yourself and meet people as you go, they will give you the ideas and info you need.

You should be able to get work in places like Oz and Europe, might under the table work, but at lest enough cash to live on. Asia and Sth America...well your cash will go a long way there.

When I backpacked in the 90s I met more then a couple of solo Americans who had Canadian flags on their backpacks....just saying....