I quit my job for a year and did this with my wife. We didn't work while traveling -- it would have been too hard / distracting. This might sound odd, but traveling takes as much time as a real job -- the amount you spend just figuring out where to go next and what to do is significant. If you want to work while travel then your best bet is to taking a break from travel and live somewhere for a little while. It's not a bad way to go but it's not what we did.

One interesting thing is the amount we spent for a year of travel was slightly less than the amount we spent simply living at home. If have saved enough where you can spend a year without salary then you can afford to do it.

A few recommendations -- don't plan ahead. You can't. Just plan the first place you want to go to and go from there. You'll have ample time to figure things out and be open to changes in plan. A corollary to this is that if you plan on spending less than 5 months traveling then you may not be able to travel quite that way. It takes a few months just to get into the swing of things.

Lastly, don't stretch your budget thin just to hit an arbitrary length of time. Spend what you need to and leave a few months earlier. You won't enjoy yourself if you have to scrounge for every dime. I'd see people stay in super nasty places for $5-10 / night in places that had simple, clean, and comfortable places for $15 / night.