I was told that spending time in the office was optional when I started working at Agape Red. Although my first reaction was to ignore the perk, and treat my new job like any other traditional 9-5, it didn’t take me long for cabin fever to set in.

As a consultant for Agape Red, any quiet place with high speed internet access can become my office. A bug fix on a pier in San Francisco. Code deployed from a bus in Austin. Client meetings from an apartment in Memphis. It’s all Omaha to me. Just without the whole Omaha part.

Now, nearly a year after starting with Agape Red, I’ve inadvertently cut almost all ties to Omaha, a city that’s been home for nearly 20 years. This includes both ending my year-long relationship, and saying goodbye to a few user groups. At this point in my career, I have travelled over 12,000 miles across North America, and have a few international trips in the works for later this year.

With a backpack full of essentials and my laptop, I’ve learned to take full advantage of the freedom to work from wherever I want.

How I Wound Up in Canada

There are trips that happen in the moment, and others that require more diligent planning. My upcoming trip to Kuala Lumpur, for example, has been in the works for quite sometime. The decision to go to Canada, however, was formed with a little help from Google Maps. It was around 5:15PM and I had just finished working from home for the third day straight. I had to get out. I pulled up Google Maps and there I saw the promise land, Winnipeg, Manitoba. Canada, the 51st state.

With a fresh passport in hand, I got in my car determined to make it to Canada in time for our morning stand up meeting. By 2AM I reached the border. 2 hours later, after having my car searched, my background checked, and interview with a couple border patrol agents, I made to Winnipeg.

Things I Learned About Our Neighbor to the North

This was my first of three trips (six by this end of the year) to Canada this year, which amounts to nearly a month of total time spent traveling around.

Canada is very similar to America, some things are better, and some are worse. Internet, for instance is widely available, but 4G still feels like a new thing, and I was often unable to get it, even in a larger city like Montreal. The best internet coverage I received up North, was better than the best in the states (Google fiber aside). In one instance I was able to get 15 mb/s up and 20 mb/s down. In a coffee shop.

If you have a phone that which works internationally, like an iPhone, you’ll have a couple of options for cell service. I stick with Fido, it’s one of the cheapest carriers for prepaid and it’s under the Rogers umbrella. Rogers is more or less the AT&T or Verizon of Canada.

If you use T-Mobile in the US, you are able to roam for free in Canada. I have had a hotspot with T-Mobile for a while, but bringing it up north was terribly slow. You technically get Rogers 3G (Bell from time to time) but I’ve experienced faster EDGE speeds. Bottom Line: You can count on coverage, not on speed.

Regus and Liquid Space have many options available nationwide for coworking. If you find yourself working from a coffee shop you can get by with some pretty good internet. In the States, we’re blessed with some really fast internet, courtesy of Google, at any Starbucks. However, unless your goal is to lose clients, avoid Starbucks. Bell – the AT&T of fast food internet providers- is not a bad internet provider, per say. For some reason, they really seem to throttle it at Starbucks and McDonalds. Winnipeg, Montreal, and Toronto I had the same experience where it could take around two minutes to load the homepage of the New York Times.

Also, don’t be fooled by Second Cup. Naively, during my first visit to Canada, I expected it to be a local coffee shop. But it’s a chain which has locations on every corner of most major cities. It is, in essence, the Starbucks of Canada, and the internet is pitiful. If you have an Edge connection on your phone, I would suggest using that instead.

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Tips and Tricks to Finding Success in Canada

All of the information until this point has been applicable to almost all of the major cities in Canada. I still have a few things, however, that I want to note city by city.

Winnipeg

Where to stay

Osborne Village

Unlike the other cities on the list, Winnipeg is very much a city where people go to raise a family (outsiders perspective). But Osborne Village is a real happening place with cafes and pubs you might find resembling Greenwich Village in New York or SoCo in Austin.

Where to work

Remember my rag on Second Cup? Winnipeg was my first journey to the Canadian coffeehouse. Unfortunately I didn’t get a good sampling of many coffee shops or coworking places. However there’s plenty to choose from in Osborne Village.

Toronto

Where to stay

Trinity – Bellwoods

This location is near the University of Toronto meaning a bunch of places to study/work are real close. Little Italy and Little Portugal are neighbors of Trinity-Bellwods meaning a lot of good eats for your lunch break. Staying on AirBNB in this neighborhood is pricy, but doable.

If you’re looking for a little more relaxed area, Leslieville or The Beaches provides a nice friendly experience, though not close to a lot of places you’ll want to be.

Where to work

I like the Regus in downtown Toronto, it provides a great view of Dundas Square (Think Times Square but friendlier). Dineen Coffee is an exceptional coffeehouse, especially being in a major downtown area, which provides fast internet and is right across the street from the Regus.

B Espresso bar is far from Trinity-Bellwoods, but a beautiful spot with great coffee, very laptop friendly.

Not far from B Espresso is Cafe 260, cozy certainly fits the shop. The man who I presume to run the place is very friendly.

Aroma Espresso bar has a large number of locations across Toronto that provides pretty good coffee and reliable internet.

Montreal

Where to stay

Mont-Royal – Plateau

Coffee shops galore, a bunch of restaurants, and the best poutinerie in all of Canada. A couple spots here on AirBNB for $40 or less a night. A number of grocery stores in this area makes it overall a very affordable stay.

Where to work

For coworking, Espresso Space was a great option located in the Plateau. Run by a company which has open seats. A good chunk of the people there have work or have background in development or design. Naturally they have a free-to-use espresso machine in the kitchen.

Cafe Torrefiction was my favorite coffee place, very fast internet and great coffee. Usually it was quiet enough for me to accept a call inside.

Cafe Plume is just steps away from the Espresso space, great espresso, previously a no Laptop zone (according to Foursquare reviews), I found it very welcoming to my digital nomad lifestyle.

Cafe Neve was a nice place to work as well, the internet was pretty unreliable, so I stuck to working here on the weekends when I didn’t need to be available for a meeting.

Cultural Notes

One thing to keep in mind with Canada, tipping rules are the same as the US. Generally when staying more than an hour, I suggest tipping one or two bucks and you won’t get any trouble about staying there the better part of a morning.

Canada is very English, the province of Quebec being the exception. People will often approach by saying “Bonjour, Hello.” Most people will be pleased to find you trying to speak French, but will swoop in with English when you’re struggling. If someone starts speaking French, simply say “Sorry, I can’t speak French” or “Desole, mais je ne parle pas francais.” I rarely found a person under 50 who couldn’t speak conversational English.

A note on food, pick up a Canadian favorite, Coffee Crisp, the greatest candy bar ever. Also, milk can be purchased in bags, for whatever reason.

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