The Freedom to Travel Anywhere, Anytime Without Getting Fired

It was the 28th of January this year, early in the morning. My wife had just pushed me out of bed so I’d get ready in time for our flight. It wasn’t at the forefront of my mind, but I was nervous: this was the first time I was going to be working full-time hours without access to my office or my main working computer. Despite all the time I’d spent either freelancing or working from home, the only times I’d ever traveled, I’d left the work at home.

It’s pretty nerve-wracking at first: what if I leave important project files at home and forget to copy them to the laptop or the server? What if the wireless broadband plan I signed up for doesn’t have any coverage in the areas where I’ll be staying? Years of working from my office, my fixed base, had instilled a whole lot of fears in my mind about the idea of not being able to access it.

The truth is, such fears are unfounded. It’s a fear of freedom, especially when you’re not used to it. Don’t get me wrong, I had the option all along — but I’d never exercised it. In this case, I was travelling to Melbourne, which isn’t even leaving the country, and I was only going for two weeks. When I consider that two of the directors at Envato where I work have been successfully remote working around the world for longer than I’ve been working for them, my trip was barely a drop of water in the ocean and there was no legitimacy to my fears.

So I was going to ask the question: have you created the freedom to travel anywhere, anytime without getting fired? But perhaps a better question to start with is: do you have the guts to accept freedom and do something with it?

Cut a Deal with the Boss

Unless you work for yourself, or you’re employed but working from home, the toughest part about obtaining the freedom to work from wherever you want can be the company you work for. Generally it’s a good idea to work up to remote working — don’t start there. Start with telecommuting. Ask your boss for permission to work from home just a day or two per week and once you’re boss is more comfortable with what you’re doing and has seen that you’re doing well — preferably even better — when you work from home, it shouldn’t be hard to convince him or her that you don’t need to come in at all. If it does prove difficult, Tim Ferriss makes some recommendations for convincing managers that telecommuting is a good idea in his book “The 4-Hour Workweek”.

It’s probably best that you work from home successfully for a decent amount of time — minimally a month — before approaching your boss again and letting them know you’d like to travel while working. This could be a harder pill for them to swallow, but if you’ve been doing well from home for a sustained period of time you’ve got some credibility behind your request. You could perhaps offer to start with a two day or five day trip to somewhere relatively close — within half a day’s driving distance to the office — before embarking on any real trips.

Better yet, get out of the rat race! Start a business (whether it’s freelance or otherwise) and make yourself the boss. Sure, it’s still a race, but you’ll no longer be the rat — you can make decisions for yourself, something surprisingly few adults are able to do and many children are disappointed to discover as they grow up.

Synchronize Your Life

Once you’re able to get up and go whenever you want without a horde of managers on your tail, you should take steps to make sure your information resources are truly mobile. That means you need to start focusing on centralizing your files. For many of us who are used to residing in one location, keeping some files on the desktop computer and some on the laptop is not a problem. It’s a bit disorganized, but it’s easy to grab any file you need especially with a decent wi-fi network.

If you want to have the freedom to stay at home one week and run off to New Zealand next week, you’ll need a better plan and system than that. The most important principle of your system shouldn’t actually be labelling and easy rediscovery — though they are still important and deserve attention — but in fact, centralization. You should be able to access your project files for work from anywhere.

There are a variety of solutions out there. You could use Dropbox, which aside from just being a cloud storage and backup service also has cool features like revision tracking. If you use Macs, MobileMe comes with both iDisk (online backup and storage space) and Back to My Mac capabilities. For Back to My Mac to be useful it requires you to keep the home computer on while you’re travelling, which could pose a fire risk and a needlessly high electricy bill.

As for what I did during my travels: I am an anal retentive file-filer, so I just dragged my “Work” folder onto an external hard drive I was bringing along. That Work folder had every single file pertinent to any work I was doing whether as an employee or for my freelance holdouts. At least 75% of my work stuff is in Gmail anyway, so I was pretty safe if I lost the hard drive.

Get Wireless

I bought a 3 Mobile Broadband USB stick with 12GB of data on it. This proved useful in Melbourne and will prove useful again in June when I move interstate and will be without true broadband for a few weeks. My point is that getting wireless broadband is a smart and convenient move whether or not you plan to travel — I did not expect to be moving interstate when I bought mine but it’ll save my life (and my job) when I do get off that plane.

I can’t comment on the offerings in the US or anywhere else in the world other than to say: I hope your coverage is better than Australia’s. If you’re going to metropolitan areas you’ll be right. Remote working as a whole can be iffy in rural areas, because some of them are struggling to get even dial-up connectivity.

Ideally, mobile broadband should be a backup plan. On my trip I was lucky to have wi-fi networks within range most of the time. Try to stay in a hotel, house or tent with its own connection. I should warn that at this time tents don’t usually come with broadband!

Get on a Plane

… or a bike, surfboard, car, bus or pink rollerblades. If you’ve dealt with the human implications, got your files together, got Internet access sorted, then all you need to do is go! Enjoy some freedom. Don’t allow yourself to be imprisoned by geography.