Phillip Smith

Tips for living & working remotely

This could be a unique time in history for work nomads and digital drifters

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When my partner, Tania, said “I’m booked for a one-week assignment in Israel, it would be great if you could join me,” I reminded her of my commitment to try to fly less by spending at least four-weeks wherever I land. Unfazed as always, she called and rearranged her return flight from Tel Aviv, and we started making plans to leave Mexico and to live and work from the Middle East for a month.

I find it challenging to write about living and working remotely without feeling a small bit like one of those people trying to sell a 4-hour work week-esq nomadic lifestyle that “anyone” can have. I don’t believe it’s possible for everyone; in fact, it’s probably unlikely if a person is socially or economically disadvantaged in any number of the typical ways. That said, if your advantages in life make it possible for you to consider, I highly recommend it right now for a few reasons:

  • Flight costs may be stable for now, but the quality of service and comfort does not seem to be improving.
  • We know more know about the impact of flying on the environment than ever before. Flying less (or not at all) may be the only viable choice in our lifetimes.
  • Who knows how geo-politics are going to play out over the next few years: could be better, but likely worse. As is said, “Why put off until tomorrow what you can do today?”

Beyond all of my fear mongering, the reality is that the logistics of living and working remotely have improved to the point that it’s possible for successful companies to be almost entirely “virtual,” with no office to speak of. That’s a pretty amazing thing when you think about it.

Five years ago, when I started my own personal nomadic experiment in 2009, there was a bit more research and planning necessary to unplug from a comfortable existence in Toronto. AirBNB, for example, founded in 2008, was still under the radar and described by the NYTimes as “a novel housing service that is a cross between and Craigslist.” Now commonplace, travel companions like the Apple iPad were still a year away from announcement.

In 2014, however, the ecosystem around remote living and working has exploded. There are new Web sites dedicated to the topic. There’s a large selection of tools vying for the attention of people on the go. It’s easy to find places to work and people to meet just about anywhere in the world. It’s possible to have an entire offline copy of Wikipedia at your fingertips, not to mention maps and guides of every kind.

Here are just a few of the improvements since 2009, which made the last four weeks in the Middle East both enjoyable and very productive:

Research & intel

When I left for South America in 2009, there was ample info available to me – if I wanted to add the weight of several dead-tree information delivery systems (aka “books”) to my otherwise light load. The Kindle was announced about a year before the trip and I knew a couple friends who owned one, but it was more than $400 and the “whispernet” service didn’t work outside of the US, making it a questionable investment at the time. It wasn’t until almost 2010 that the Kindle became generally available to Canadian market, and – as mentioned – in 2009, the iPad was still a rumour.

Today, I can carry an almost unlimited number of travel guides, offline maps, and books of all sorts, and the combined weight of my iPad Mini 64GB ($329) and refurbished Kindle Touch ($50) is less than a pound. Travel is changing for the better and at an incredibly rapid pace.

I could ramble on at length about all of the great resources available today, but I’ll limit my recommendations to these three:

More than these, you can also typically find your favourite travel guides available to download as a PDF, iBook, or Kindle book, e.g., Lonely Planet, Rough Guide, and so on. For deeper research, look for a Facebook group about the location in question. I started one in Oaxaca that’s grown to more than 400 knowledgeable members. Great places to uncover local intel and meet new people.

Living & working

Before I arrive at a destination, I typically like to have accommodations sorted out. Craigslist had always been my go-to place for hunting for affordable “vacation rentals,” and Vacation Rentals by Owner was also worth a quick look. Today, I start with AirBNB: where one can “rent unique, local accommodations on any budget, anywhere in the world.” From there, there’s usually a number of Web sites with local listings (like the useful Casa San Telmo in Buenos Aires) that are worth a look too; I usually ask about these sites in a local Facebook or Couchsurfing International group.

Since late 2012, I’ve traveled with a Ninja Standing Desk ($159, weight 4.5 pounds), making it possible to set-up an ergonomic workspace just about anywhere I am: apartment rental, hotel room, etc. However, that doesn’t mean that it’s not nice to get outside of my routine and work with people elsewhere. Thankfully, the idea of co-working spaces has continued to grow since 2009 and now there are usually a few options in a city of any size.

Here are my usual go-to sites:

Rates vary, but it’s usually worth giving each space a phone call to arrange a time to drop in. Typically, the first day is free.

For the time-zone challenged

Once I’ve got home accommodations sorted and have an idea of the co-working options, the next step for me is to set up a routine that ensures I’ve got enough non-interrupted work time to give 110% of my attention to client commitments. Working remote for me means being more attentive to the people I collaborate with, not less.

One of the aspects of working in various countries around the world that I’ve actually enjoyed more than expected is exploring working at different times during the day. For example, the Middle East is 8-10 hours ahead of where most of my clients are currently located. So instead of starting my “work day” at the usual 11AM, I started it at 2PM to have the most overlap with the east and west coast of North America.

This schedule let me have the mornings to explore, at the expense of working a bit later and having client calls after dinner. When you have to add other time zones into the mix (like a recent call with participants in San Francisco, New York, Tel Aviv, and Cape Town), it can get a bit confusing. I’ve witnessed some friends struggle with this at first, but the essential tools that I rely on here are:

  •’s international meeting planner: I use it so much that I keep it running in a Fluid app.
  • MailHub or something similar: I use MailHub to schedule e-mails to go out at specific times, and to set follow-up reminders. There are lots of tools for this. Find one that works for you.
  • A good calendar that does a good job with multiple time zones: I use BusyCal and don’t know how I’d live without it.

Phone calls & meetings

Once I’ve got a work schedule sorted out, the next thing on the list is managing client communications. Luckily, I’m a pro at this now. I started back in 2009 with the company DIDWW: they provided inexpensive DID numbers for any city where I had a client, and let me route that number to a local number in Buenos Aires. It was a straightforward no-frills service, but it worked well enough.

These days, I’ve greatly increased my monthly investment in phone-based communications because speaking with people on the phone is a critical part of good relationship building when face-to-face meetings aren’t possible.

Though expensive, I rely on these three services exclusively:

  • RingCentral: Costly, but thorough. All the internet-based calling features you’d want, local and toll-free numbers, number porting, and an iOS app that keeps getting better (SMS support, etc.). Can’t recommend it enough.
  • PhoneTag: I’ve been using this inexpensive service to transcribe my voicemails to text for more than seven years now. It just keeps working.
  • Calliflower: Reliable Canadian conference call solution with great features and a local number in almost every major city in the world, as well as Skype and SIP options. It’s my go-to for almost four years now.

There are lots of other options out there for both VOIP/IVR systems – even more if you don’t need a Canadian number, or if all your clients are based in the US – but I’m happy to pay for these services because they’ve proven their worth to me over several years of day-to-day use.

Travel distractions

Last but not least, when I’m not working or relaxing or exploring, there are often those long, uncomfortable times when I must move between one destination and the next (and, honestly, I hate that part!). I got lucky on my recent flights back to Toronto – all exit row seats, no baggage problems, and so on – but that doesn’t ever make it “enjoyable.”

To get through those times, I rely on:

  • Safari Online Books: I can’t recommend this service enough. Every technical and programming book that you’d ever want, often before they’re published, in the palm of your hand, and offline too. Well worth the $472.89 that I invest every year.
  • Instapaper: Obvious, but if you’re not using it, you should be. I send all the articles from a handful of sites directly into Instapaper, then catch-up while on the plane, train, or automobile.
  • Video Download Pro: Not great, nor even good, but it does the job. Download videos from the Web to an iPad for offline viewing. Great way to watch those software demos that I never have time for.

Honestly friend, there’s never been a better time to try living and working from another city, country, or continent, and there may never be as good a time to do it again. It’s not possible for everyone, but if you think it might be possible for you, I assure you that the rewards – actually living in another culture, hearing and speaking another language daily, and avoiding the Polar Vortex – greatly outweigh the risks.

Got your own nomadic working or digital drifting tips? Shoot me a note on Twitter or drop them in the comments below.


Hi, I'm Phillip Smith, a veteran digital publishing consultant, online advocacy specialist, and strategic convener. If you enjoyed reading this, find me on Twitter and I'll keep you updated.


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