What's a holiday rep? He's in the US, which isn't full of companies offering cheap one-week charter trips to some foreign country.

And while I do get tired of telling people that their romantic ideas of moving to another country are going to be difficult to fulfill unless they have a good deal of money or choose countries according to their accessibility, I don't think it is a good idea to tell people there are lots of jobs to be had when it just isn't true. It is, I think, even less true for Americans.

One option would be to apply for a working holiday visa to New Zealand or Australia, the only countries where Americans have that option. There are also lots of volunteer opportunities for those who are willing to pay, but the OP doesn't give the impression he has a lot of money to spend on expensive programs.