Point A to Point Z: the how-to of vagabond-working

Travelling, I meet a lot of new people. Invariably, I have the same conversations with them, over and over again, at least until we get past the formalities of who are you, why are you here, what do you do… The conversation usually goes something like this:

Me: “I run my own business, so I pretty much work from anywhere I have internet.”

New Stranger Friend: “Oh my! That’s so cool! You’re so lucky!”

Me: “I know. It’s something I’ve been wanting to do for a whole three years, so I’m lucky I’ve been able to make it happen! I’m extremely fortunate.”

By and large, once people stop fawning over how lucky I am (depending on how magnanimous I’m feeling, I’ll either agree with them wholeheartedly or make a pointed comment about how I worked like mad to make this happen), they invariably start wondering how it all works.

Really, sometimes I’m sort of amazed things haven’t totally fallen apart for me yet. I’ve been doing this vagabond thing fairly permanently for the last year and a half, in which I’ve spent five months in Canada, and my business hasn’t suffered in the least for it. In that time, I’ve been to eighteen different countries, taken innumerable flights, trains, ferries, and buses, and crossed borders back and forth countless times. In all that, I’ve only taken five days of real, honest-to-goodness “time off”, when I was in the Amazon. Through it all, I’ve been working and (for the most part) I’ve managed to stay on top of running a business while running all over the world.

The second most popular phrase I hear from strangers is “How do you do it?”

I run my business in a highly unorthodox manner, I’ll admit. I wrote a business plan once six years ago. I wrote it in two hours and haven’t looked at it since. I tend to eschew a lot of common business practises, and I stopped doing any legitimate attempt at marketing years ago. My business probably shouldn’t survive, according to all common wisdom.

Graffiti in Granada
If my ‘business plan’ were a picture, it would look something like this. Maybe with Munsch’s ‘The Scream’ and a bit of Kadinsky thrown in for good measure and messiness. Graffiti in Granada’s old maze-streets.

That said, here’s how I make it work for me.

1. You need a reliable friend at “home.”

For me, this is my roommate-cum-househusband. I’m not sure I could do this thing I’m doing without him. (Thanks again, Dan!) Most of my clients still pay me by cheque, and having nine months’ worth of cheques piled up in a post office box is simply not a viable solution. Before I left for Argentina, I went and chatted with my bank, and they signed my househusband on to my business chequing account—I think he can only deposit money, but I trust him inherently. I invoice my clients in batches, so that all cheques are due either on the first or the fifteenth of the month. On those days, Dan counts up all the cheques that have come in, sends me a report of who’s paid and who’s outstanding, and cashes them. My business account is linked to my personal account, so I can transfer money back and forth when required using my online banking.

Oh, and it’s pretty vital to have a personal account that doesn’t charge you for foreign ATM withdrawals, because that will eat up your money faster than you can imagine. North America tends to be very card-friendly. Everywhere else (especially South America and Southeast Asia) you’ll be operating almost solely on a cash basis, unless you’re going to pricey restaurants all the time. Food stands don’t take MasterCard.

2. Technology is your new best friend.

When I started this trip, I was travelling with two laptops: my Air, which I bought with as much memory and power as I possibly could, and an old and impressively beaten-up Macbook Pro I called “Lazarus” after he was revived from the dead two weeks after I poured scotch all over him. A lot of people told me I was crazy to be travelling with two laptops, and lugging the extra weight around was a pain, but it got me out of a few scrapes.

Ultimately, my business is dependent on my having access to a computer. Rentals and internet cafés don’t suffice in this regard: I need all my fonts, files, and applications, and I need to have enough processing power to do my work relatively quickly. Every day I’m computerless, I’m losing money (and esteem). In some parts of the world, Apple stores either don’t exist or will respond much, much more slowly to service requests. I’ve hurt computers in Argentina, in Mexico, and in Spain, and every time I did, I was grateful to have my old beaten-up machine with me. (I actually mailed the machine home to save on weight just before I left Thailand, hedging my bets that I’d be alright in Europe, and I only lost a few days due to the Spain Incident.)

It’s important to have as many failsafes in place as possible, in case the worst happens. Statistically speaking, the longer you travel, the more likely it is that the worst will, in fact, befall you. I carry a teeny tiny little external hard drive with me and plug it in on a regular basis so that all my files are backed up. I use Dropbox to back up anything super-vital or super-current. Basically, so long as I’m connected to the internet, it’s extremely hard for me to lose data.

And of course, internet is vital. It always surprises me that the countries that seem more developed often have lousier access to internet. Ultimately, you can never really be sure until you get there. One of the first things I do in a new country is buy a SIM card for my phone and load it with data. Most of the time, this at least affords me immediate access to email (helpful when dealing with weird time zone displacement issues) and the ability to tether my computer to my phone for (sometimes snailishly slow) internet access anywhere within the country. (Being able to text and phone people within the country without paying a fortune is just a bonus.) Surprisingly, coverage, price, and quality of service is much better in Cambodia or Mexico than it is in Spain, where I usually can’t even make a Skype call over 3G (and have no way to pay for faster speeds). Keep an eye out for cafés and bars that have free wireless (FourSquare is useful in this regard, as you can search for “wifi” and find the password out in advance). Make sure your laptop can handle being sans-power for a while. (Power outlets are ridiculously difficult to find in some countries.) Whenever I find a good place to work, I tend to go back there frequently.

Useful iPhone apps for travelling: World Travel Guide (WikiTravel offline; great for reading on the place before you land in a foreign place and if you need a phrasebook/guidebook), CityMaps2Go (not as good as Google, but the best offline-maps app I’ve encountered thus far), MetrO (public transit guide for tons of cities), Translate (imperfect translations are better than none), Currency (so you know what you’re taking out of the ATM before you accidentally take $1000), OnTheFly (awesome flight searches), WhatsApp (free text messaging via your data plan), Foursquare (finding places Google Maps won’t recognize, figuring out where to go for dinner). I vaguely remember travelling without a phone, but I think it was harder. In spite of my phone having been stolen twice (Argentina and Thailand) the expense is always worth the value it provides me.

3. Pack light. Stay long.

Working while you travel is different from how most people travel, and you need to take this into account while planning your trip. The first few times I travelled, I didn’t go for very long. (One week in Mexico, hopping around the Yucatan peninsula, followed by five weeks in Europe, where I rarely stayed in a single city much longer than a few days.) That sort of schedule is fine when you’re travelling like a normal person—when you have all day to go exploring and meet new people. But if you’re working as you do it, some days are just going to be a wash. Some days all you’ll see is the inside of the nearest café with wireless. It’s a slower process that requires a major change in the way you look at travel. Personally, I love travelling this way, but it’s not for everyone. For me, travel is more about seeing the way a place works and how people live there, rather than trucking around to every must-do tourist attraction on the list.

The hours of operation of a fruteria in Churriana de la Vega, Andulucía. It reads: ‘Open when we arrive, closed when we leave. Open 365 days a year.’ Spain, especially in the south and especially in smaller towns, has some really strange opening hours, which can take some getting used to. You adjust accordingly.

Either way, where you might stay a place for only a few days doing “regular travel”, you’d probably want to double (at least) that time for work-travel. Staying longer, luckily, opens up your accommodation options a bit more. I tend to use a variety of different methods to find homes and places to stay, but mine are all generally on the budget end of the spectrum. When I’m moving from place to place, I’ll couchsurf and stay in hostels for up to a couple of weeks consecutively, then I’ll splurge on a whole room to myself. My introvert nature can only manage the stress of sharing space with other humans for so long before I start going insane, and I plan for this.

If there’s anything I’ve learned from this trip, though, it’s that it’s much, much easier to buy a return ticket to one city, rent an apartment (or room) there, then do “offshoot trips” from that one home base. You’re a bit more limited in where you can go, and you can’t do some crazy all-the-way-around-the-world thing like I’m currently doing, but you don’t have to worry so much about lugging all of your belongings around, which means you don’t have to strip them down to the absolute essentials (and so you can keep your Lazarus!) At this point, I’m down to a backpack and a carry-on, but I started with a backpack, a tent, a carry-on, and an absolutely massive blue suitcase you could probably hide a person in. Things are always a liability (and even more so when you’re doing budget travel), and it’s nice being able to have them with you (especially if you’re gone for such a long time) without needing to worry about them.

I’ve managed to find some great apartments via AirBnB, both for short and long term. I can usually finagle a discount for extended stays, but I’m still paying more than locals do for rent. CouchSurfing will sometimes have discussion groups for a city, which can be a reliable way of finding a place to stay (especially with roommates) but there are some countries where it’s simply more practical and reliable to pay more for an easy apartment. (For example, my two-bedroom in Argentina cost $800, probably at least triple the “local cost” in pesos. Leases in Buenos Aires required a massive amount of paperwork, a two-year contract, and would generally take months to arrange. For five months, it simply didn’t make sense to go the cheaper route. Of course, since I haven’t had an apartment in Canada for a while, I don’t pay rent for an apartment I don’t use, which makes the financial commitment easier. When I return to Canada, I have vague plans of renting an apartment again, but I’m planning to use AirBnB again to rent out free space while it’s not being used, so hopefully it balances out for me again.

4. Be flexible.

Ultimately, the trick is to find out what works for you. I decided a few years ago that travel was important to me, and I’ve been figuring out a way to make it work for me ever since. This wasn’t a sudden thing; it’s something I’ve manipulated my business and behaviours to suit so that I’ll be able to do what I want to. Every time I take off, I play around with the rules a little bit. I still haven’t quite hit on the perfect formula. I’m not sure I ever entirely will, because the formula needs to take into account the culture of the place you’ll be immersed in, who you’ll be with (if anyone), and what sort of life you want to have outside of the 18 hours a day you’re working. All this will invariably shift, and you need to be able to adapt along with it.

I could go on for ages about this, but ultimately, the short answer to the “How do you do it?” question is this: I just do. It’s not magic, it doesn’t cost a fortune, and it isn’t unattainable. You just figure out how to make it work, and then you do it.