I'm lucky enough to have hit the one-year mark in June working as a web developer, and I couldn't be happier with it. It's come with some very nice fringe benefits; namely, the ability to work with a great team from the comfort of my home in Miami. I get pretty sweet weather, and the chance to work on my tan should I want to (still haven't).
This past year also gave me the chance to trip on many of the pitfalls that come with working remotely. You might be thinking I'm crazy for saying this, but working remotely, for all of its benefits, comes with its own set of baggage.
Don't get me wrong -- I subscribed to 37 Signals' manifesto well before I got my current gig. Working remotely was always the dream, before and after I ventured into web development. That being said, in my first remote job, I've come to learn that there be monsters in these depths.
You can't beat the flexibility of working remotely, right? You get to work from anywhere with an internet connection, and you can basically set your own hours. Well, typically, remote workers need to overlap at least half of their time with that of the main office, but you generally get to make it your own. Got kids in class? You can pick them up from school knowing you won't get wrung out for leaving your desk! Need to step outside for a bit? Cool! Out for lunch? That's fine - so long as someone knows you're away from the keyboard, you're good.
But when you start to feel like you could be using that flexibility for an extra-long lunch break? Watch out, because that extra 15 minutes can turn into an extra 45 minutes fast, and for any number of reasons. Remote work gives you some freedom, but you have to manage yourself. Keeping to a schedule seems easy enough, but it's not hard to get tripped up by something innocuous like traffic or other people.
With all the additional freedom can come additional sources of distraction. Being able to work from wherever you like is the other half of that flexibility, but it opens doors to other distractions. Working out of a cafe can be awesome, but you never know when a busker might come in and start playing 'Sweet Home, Alabama' on a rusty guitar. Even at home, the distractions can be plentiful. Especially so when you have kids.
If you can work from home and not mind any additional distractions, then kudos to you. Otherwise, make sure you find a place where you can enter a sort of 'flow-state' with minimal distractions. Some situations don't allow for it as easily, but try and get the consoles, comics, fidget cubes, or whatever might distract you away for at least eight hours. If you live with other folks, be it family or roomies, make sure to have an agreement that you won't be bothered as much. Obviously not one set in stone, but at least let them know that if you're working, you're working.
Also, don't forget about the biggest distraction of all, the one staring you right in the face right now. Your computer and the Internet, with all of its wisdom, has to be the biggest distraction of all! There are tools to help with this sort of thing, but they are only that. It's up to you to use them.
When you begin to work remotely, you might or might not notice a fine line between what's work and what's home. It can vary from person to person, but it's still an important realization to make. If you don't notice it, it can have an effect on your relationships with family and with work itself. One of the easiest pitfalls is to feel like you should keep pushing and giving it your all. It's a commendable sentiment, but it also defeats the purpose of working remotely: better work-life balance. Managing yourself also means managing when you're done, and when you can do that, you can make time for your personal goals and relationships.
This is probably the biggest 'gotcha' for me. Being at home with my wife and kid all day, I can end up working well past my personal work schedule before I realize what little time I have left in the day for them. Yeah, we get to have lunch together, but what's one hour compared to a whole afternoon or evening?
Now, I welcome you to take all of this with a grain of salt. Your situation and results working remotely will likely vary a bit from mine, but these are definitely things that can sneak up on you if you get too comfortable. I would recommend working remotely to anyone, but in the end, you have to be able to manage yourself well.