I've been doing the same for 9 months now. I've travelled round the whole world, had a fantastic time, and wrote a book for O'Reilly as I went. It's been the best year of my life. In fact, it turns out that writing books is one of the best ways to do this - as it's very flexible and a successful book will just about cover traveling costs. What most people don't realize, is how cheap it is to do this.
As always though, everything is best in moderation. I'm yearning to be back in the startup/technology scene - and I will be come September. I'm sure that'll I'll do another trip like this in my twenties though (I'm 21 now).
One thing I'm certain of is that my expenses for a trip like this when I was 21 would have been much lower than for a trip like this now.
I've sadly grown accustomed to fancier meals (restaurants over ramen) and softer beds (hotels over hostels). It would be a lot of mental work to keep my expectations down and readjust them to what they were in my student days.
Yes, hostels through most countries, but hotels in Asia. I live pretty cheaply, but I've actually eaten out every night of the trip. I love the minimalistic lifestyle, having 100 things and living out my bag - I hope I never lose that.
I could stay in pretty nice hotels for the price of the rent I pay for the Helsinki flat. Most interesting cities are nowadays so expensive to have a home in, that hotels simply start sounding like an affordable alternative. And even more so if you want to stay in cheaper countries
There are several books about it. Off the top of my head... 4 Hour Work Week touches on it, Vagabonding by Rolf Potts has a version for lower-skilled workers, and Life Nomadic by Tynan is a free pdf.
As always though, everything is best in moderation. I'm yearning to be back in the startup/technology scene - and I will be come September. I'm sure that'll I'll do another trip like this in my twenties though (I'm 21 now).