Since end of November 2013 I put myself into the position of working while traveling. It all sounds like a peanut butter or a piece of cake. At the end of April 2014 I found out for myself that it’s not even an little piece of cake. Here’s why:
You are barely or never in the moment. Nothing is worse and more frustrating, especially for fellow travelers, to have one person not paying attention. Because when you work on a project while you are geographically at the beach in the Philippines, you won’t be able to cope with both things — enjoying / relaxing and working — if you don’t keep them separated.
Don’t be rushy while you travel and work. Make sure you can stay in one place for a while, a week or so, so you can adjust and build up a little routine for your working hours.
It’s not healthy and prevents you, the by default distracted person, to stay sane when you think about projects (work) while you are at the most beautiful places in the world.
Clearly distinguish work and travel. You can work for 6 months, and travel for the other 6. You can travel for 3 months and work for 9 months. Or you can just work your way all the way through 2, 3, 4 or 5 years while you take your little breaks every three months or get 1 year off every 7 years like Stefan Sagmeister (from Sagmeisterwalsh) does.
But you don’t wanna merge both — just like a distinction of work and personal leisure time is crucial. Things will merge into each other anyway. Your effort must be put into reducing it [the merging process] to a sane level.