It's hard not to LIKE Guillebeau; he's just so damn earnest. But this book suffers from the same dynamic that motivational speakers engender; post-talk letdown. Some meals consist of a number of tasty morsels, but not much actual nutrition. You're hungry almost immediately afterward. So it is here.
First the positive stuff: Yup, this will get you in the proper mindset for examining your priorities, needs and goals. (But, what self-help book doesn't?) It's encouraging to hear how the author has "made do" (and then some, apparently) with an unconventional approach to "making a living", while actually managing to have some fun. He's perhaps the ultimate paradigm for getting paid for play. An inspiration or model for others? Perhaps.
The book starts out as if it will really lead up to something, but peters out; a promising "let's get our thinking in order" platform kind of trails off into a series of vignettes concerning his quest to visit every country on earth, ramblings on "world domination" (his rather loose construct for living live on your own terms) and numerous appropriations from a number of other self-help guide authors (Seth Godin, Tim Ferriss, Chris Brogan, etc.) If cheer-leading is what you're looking for, this book never relents. If you want more, you'll be disappointed.
In sum, this is what I call a 'booklet' - a couple of core ideas that have been expanded and expounded on enough to fill several hundred pages. (Seth Godin is a master of churning out an endless series of flabby brochures of this kind.) EVERYTHING in this book is available for free on Gillebeau's blog. As much as I like Guillebeau and admire his feisty way of making a living, I can't avoid observing that a BIG part of this book is pure filler. On the other hand, if you want to get a (quick) handle on why Guillebeau's blog is so damn popular, this is probably as good a way as any. (Just don't expect to start issuing world orders right away.)