Working remotely: How to find a job that allows you to go on a vacation
Working remotely may seem like a unicorn a concept that would be magical and amazing, but likely doesn't exist but non-traditional work arrangements are becoming more common every year As more and more large businesses realize they can save buckets of cash while making their employees happier by allowing them to work from home (or Costa Rica), they're slowly integrating such arrangements into their company documentation.
At the moment, however, you may be better off working for a smaller company or startup if you're looking for a remote work situation, especially those in the tech sector, as these are the ones that tend to be experimenting most with geo-non-specific employment as a way to stay competitive.
You should keep a few things in mind when you're looking for the right kind of remote employment position. First, make sure that the work you're doing, and the company you're doing it for, doesn't impugn upon your ability to enjoy traveling the way that you want to travel. It would be great to find a job you enjoy doing that will allow you to work from wherever you want, but that same job is fairly pointless if you have to be connected to your computer or a phone 20 hours a day.
Second, make sure that you'll be able to go the places you want to go with the pay you'll be receiving. The worst thing that could happen would be to find you overseas while struggling to dig yourself out of a money pit. Avoid starting to travel until you've dug yourself out of debt, but if you manage to put yourself back in debt while on the road, and your job isn't paying you enough to pay that debt off, you're going to need a new strategy.
Finally, make sure that you'll have the freedom to travel, not just to work from home. I know one person who took a job working from home, and she assumed that this meant she could work from anywhere, so she took off without telling anyone at the office. It wasn't until she found herself fired while traveling through South America that she realized there was a miscommunication from the company she was working for, and they were horrified at the idea that one of their employees would try to pull such a stunt. Clarify everything before you take a job, so that you can be sure to keep it while on the road.
On the same topic of communication, make sure you know what your company will be paying for, and what you will be responsible for taking care of some companies will hook you up with room and board and internet access anywhere you go, while others will only pay your salary and nothing else. Either arrangement has pros or cons, so make note of everything and plan your travels accordingly.
If you do happen to find yourself with a remote work situation that allows you to travel, do your best to over-deliver whenever possible, and show your employers that not only is this a good arrangement for you, it's good for them as well.