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Just for a couple of months in Southeast Asia; but I met a lot of real travelers along the way. The person who really impressed me was a (very young) woman who'd spent four months backpacking and travelling in India, all on her own on a miniscule budget. She really knew how to take care of herself.
Anyway, it's pretty easy to hook up with other travellers, but they won't always be there, or wanting to head in the same direction that you do. And it's fairly daunting to face a new and strange country all by yourself, if you haven't already had solo travelling experience.
So before you do this, I'd first ask if you've at least spent a month or two on the road in countries where you don't speak the language and the culture is strange to you. If you have, great. If you haven't, you should do so: for the experience, to find out if you'd actually enjoy this, and to get a better idea of how you'd like to travel and what kind of things you want to find on the road.
That said, the one predictable thing is that things _won't_ go as you expect. That can be good or bad, but you should be ready for it :-).
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