While Westcoast has some great points, it's not as black and white as the picture he is painting. You can create a career on your computer these days. No doubt about it.
If you want to do it responsibly, though, build at least some semblance of an income before you leave. You can hunker down in your home town for a couple weeks to a month working and not going out to do this. That'll also prove your ability to ignore distraction.
Then once you're abroad, work on a regular basis. 5 days a week. Preferably 8 hour days. Maybe more. Maybe a little less as you can afford to. Treat it like a real job. Or a real business.
Also, as he mentioned, you don't want your lifestyle choice to leave you with zero professional skills. It doesn't have to.
Always be studying some new skill that you can leverage. There's such an abundance of online training programs for a variety of high-value professional skills (most of which are growing in demand, I might add), that it's preposterous to think you couldn't constantly update your arsenal to become more and more relevant in today's workplace.
You can also gain real-world experience in these things by applying them as you learn them for both yourself and clients. That's a resume with real-world results to show - something most employees do not have. If you can produce that, and especially back it up with numbers, trust me, you can find a real job if you want it.
My work has not only taught me a lot and led to plenty of $60 - $100/per hour work but has also led me to quite a few traditional salary job offers, some remote and some not. I don't bother keeping a resume but I assure you if I wanted to slap one together at any time I could find a "real job" within a month, and probably in far less time.
One guy I met online and worked with for years leveraged his freelancing to get in with one of America's top companies in a very lucrative industry. He did this quickly and easily. As in one day waking up and deciding working for himself wasn't working and he wanted to see what it was like to work for a big corporate and then within a couple weeks was in a top level marketing position.
And then moved from that job into working at Amazon. He's put me in touch with his recruiter, who works with many other name brand multinationals and has invited me to put together a resume as he thinks my experience could definitely be a solid stepping stone. One job lead he threw my direction was for another company name that has definitely passed across the lips of every person on this forum.
I've got a part-time salary (could be full-time if I wanted it) offer on the table right now from a friend who just secured big funding for a very promising social media startup, and it includes some interesting profit-sharing options. Earlier this year, I turned down a 20 hour per week position with a Swedish tech company making $40 an hour.
I get these offers all the time, and I don't even pursue them. Why not? Perhaps stupidity and shortsightedness, sure. Perhaps laziness, sure.
But my point is imagine if I did. Imagine if I not only did but did so with a clearcut gameplan to keep moving from one bigger and better position to the next. For a career-conscious person, I assure you this can all be done.
Now maybe I'm not the best person to be giving career advice as my own financial situation could be a lot better than it is and should be. I can agree with that. This isn't because the opportunities to stack cash aren't there; I just haven't been very good at maintaining my schedule over the years and I've suffered for it.
So yea, it's easy to waste it too. One way to look at that is to say not everyone is cut out for it, and maybe that's true for me. I'm more inclined to think, on the other hand, that my career path (that's what I see this as) is one that moves from lower income and less security towards higher income and more security (as well as more freedom) as I mature and develop my focus.
For one, thing, I find I get better about staying on track for longer periods of time as I get older. So like many people, I assume this means my income will also go up as I age, only for different reasons than they do for others.
I also work on book projects on the side, and considering what I do to create my income (marketing and PR, essentially), it's not that much of a long shot to assume I can eventually create a decent income out of this in the next decade. With the off-chance of something going big and making me some real money.
Not smart to depend on that, but I don't need to because I have my current business either way (similar to the track proposed in the book, "The Education of Millionaires").
All these observations of my personal track are irrelevant though and probably don't paint the best picture. My real point is that the option to make it into something far more substantial is definitely there. Hell, some of the guys who ran with info I offered on freelancing on this forum built the equivelant of an entry-level corporate salary (but with location freedom) within a month or so and are off the ground and running. Others have matched my $100/hour rates and even surpassed them.
My suggestion? First, don't follow my bad example.
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Second, don't think of it as a vacation! As others have mentioned it, give it a year or two. Work your ass off at whatever it is you're trying to accomplish, keep your eye on the ball, and give yourself deadlines within which you have to make a certain amount or accomplish certain things. If you reach those deadlines and haven't done shit, get off the boat and go to plan B.
Seems reasonable and responsible enough to me. Don't forget - for every person who has built the kind of life they want to build, there have been hundreds standing right there to tell them they were doing the foolish, irresponsible thing...
As sound as WestCoast's advice and financial acuity is (you can definitely be a winner following his lead), a matter of a year or two isn't going to make it that difficult to jump back into the traditional business world if things don't work out. Yes, it will be difficult to focus and make it work as planned. Yes, you can lose and waste a couple years. Yes, changing course will take an extra push of effort and going without.
But a temporary detour before you get started isn't going to stall you up that much.
And at least you can say gave your dream a shot.
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