How and why did you start working remotely?

I’ve always loved traveling, and I think location independence has always been the dream. In 2014/2015 I started to have “the itch.” I had been in Montreal for 4-5 years then. Before that I was in Tokyo for a year, and before that Halifax for a year.

Then it happened. The startup I was working for faced a cash crunch, and had to immediately let a few people go. Myself included. “We can hire you back in 2-3 months,” they said. That was my cue. I already had a one-way ticket to Singapore for my annual trip there; I only had enough miles to claim a one-way and hadn’t bought the return. Within a month, I sold everything I owned, wrapped up my life in Montreal, said my goodbyes, and left.

I had a rough plan. I’d join a company remotely. One that I love. Whose (SaaS) product I loved. Who’s in “growth mode”/just raised a Series A. (I’ve seen too many seed startups run out of money.) Can’t be that difficult, right?

As it turns out, finding a company with all 3 ticks was quite the unicorn hunt. So, I turned to freelancing, and dipping my toes into drop shipping and affiliate marketing.

What are the biggest benefits to working remotely?

Not having to set an alarm! I wake up naturally after I finish my last sleep cycle, which is typically after ~8 hours of sleep. You know how sometimes you wake up feeling very unrested? Your alarm probably rang when you were in deep sleep (stage 3). Not having to set an alarm lets your body cycle through the sleep stages, and wake up naturally.

Setting my own schedule is pretty great too. I have the freedom to attend a yoga class or something in the middle of the day, and take a day off when I want to.

Lastly, but of course, being able to combine work and travel. My overseas rent, and travel expenses amount to less than half of what I would spend at home (geoarbitrage). Not only that, when you’re working a “normal” job, your savings tend to go towards vacations anyway, so this lifestyle makes so much sense. Work from a new city/country, and get to explore it!

What are the greatest challenges to working remotely?

Not being able to commit to anything.

• I was in the middle of a 1 year RCIA program at my church in Montreal when I upped and left.
• It’s hard to stick to a workout routine. Sure, running you can do from anywhere, but if you need weights you need to find a gym, which is a challenge, or rather, time-consuming on top of having to find a place to stay, places to work from… Also some don’t have day/week passes, or they do but are expensive. Or they don’t have AC. #firstworldproblems
• “Eating clean” is hard as well. If you live in a hotel or studio, it probably doesn’t have a kitchen; and it’s hard to find meals of brown rice, whole wheat bread, etc. when eating out. It’s also not feasible to travel around with a bottle of olive oil for example.
• Of course dating is a challenge as well.

What is a remote work pain point, and how do you address it?

Bouncing too quickly is a pain and not very feasible. After learning this lesson I now stay in cities for 1 month. Researching flights, accommodation, sightseeing activities, and cafes to work out from is a pain, and a solution I might explore is outsourcing this to a VA. Finding wifi is a pain in certain countries (like Laos), and my solution is to not go to cities that are not on the Nomad List.

What gear can't you work remotely without?

• MacBook
• Headset
• iPhone
• PacSafe backpack

What apps or websites can't you work remotely without?

Apps:

• Swarm
• Calm
• Google Translate
• Trail Wallet
• WhatsApp
• Google Voice
• MagicJack
• Audible
• Instagram
• Snapchat
• Uber
• Airbnb
• XE Currency

Websites:

• Todoist
• Asana
• Trello

Do you have tips for saving money while working remotely?

In a foreign country it’s easy to feel like you’re on vacation and spend money without thinking, especially if your home currency is much stronger. Keep track of your expenses. At home, I use Mint and have all my bank cards connected to it. In Asia I’ve mostly been using cash, so I’ve been manually inputting all my expenses into the Trail Wallet iOS app.

You can save money on accommodation by house sitting (which I haven’t tried), or by doing WorkAways (which I have). The latter was introduced to me by a South American yoga teacher in Laos. She was teaching yoga and doing graphic design for a really nice resort in Vang Vieng in exchange for accommodation and breakfast (hotel buffet breakfast!). I taught English once, and did marketing and built websites other times.

Would you consider returning to a traditional office job, or are you remote for life?

I’ve been doing this for almost a year now and I already feel tired. Tired from constantly moving, juggling clients… I’m also getting desensitized to beauty from constantly seeing so much of it, which scares me. I love travel and never want to be disillusioned by it. I’m considering slowing it way down. I think my ideal scenario would be to spend 6 months of the year in Canada, and 6 months traveling. I’m trying to make that work, else I’m open to relocating to a tech/startup office somewhere new. Say, Berlin? San Francisco?

How has working remotely impacted your career plans?

Yes. Being in the tech/startup world I always thought I’d either have my own startup, raise money, and exit via acquisition, or, have these 3 types of experiences in the span of my career:

1. Startup
2. Big 4
3. VC

Now, it’s become so clear to me that my goal in life is to do things I enjoy.

How do you stay connected to your professional community virtually?

Whichever city I’m in, I search for “city nomads,” “city expats,” and the like on Facebook, and join those groups. They are great to find out about celebrations, meetups, or events that are going on while you’re in that city, search or ask for information on apartments, etc. (I always ask about yoga and an English Catholic mass), and to meet people.

How do you stay physically active while working remotely?

It can be challenging or time consuming to find local yoga classes and a gym wherever I go, so I don’t always go as often as I’d like. In Da Nang, Vietnam, I lived across the street from a yoga studio, and in Chiang Mai, Thailand, I had yoga in my building, so I went frequently and regularly. In Taipei, Taiwan, I lived near a local gym (with an olympic-sized pool!) so I did workouts with weights regularly as well. The past month in Hualien and now Kaohsiung, both in Taiwan, I’ve been walking and cycling every day as a means of transportation, going for the occasional jog, and doing some of Blogilates’ arms and abs exercises every morning. Also, my Airbnb host in Hualien had a yoga mat, so I did yoga at home. 

How does working remotely impact your diet?

At home I have cornflakes, berries, and skim milk for breakfast every single day. I love this combo and never get sick of it. But since I’ve been nomading in Asia, skim milk and berries are hard to find. That and I don’t often have access to a kitchen. So, I’ve been having fruit like apples and dragonfruit for breakfast at home, and heading to my COTD (Coffice of The Day) for brunch. Which is typically western-esque like eggs and sandwiches. Then I’ll have a local (typically fried and oily) dinner. “Eating clean” is hard while nomading. If you live in a hotel or studio, it probably doesn’t have a kitchen; and it’s hard to find meals of brown rice, whole wheat bread, etc. when eating out. It’s also not feasible to travel around with a bottle of olive oil for example.

How do you cope with feeling lonely while working remotely?

Loneliness is often cited as one of the cons of nomading, if not THE con. There is, however, a difference between being alone and being lonely, and with this nomad life, you’re alone a lot. I found being alone something interesting to explore and experience; I’m often told that I’m an extrovert, but I’ve learnt that I love to spend time alone.

I think this loneliness on the road thing can be dealt with easily, and it’s up to you how “lonely” or social you want to be. I actually have a draft blog post on this, and here are the main points:

• Join Facebook groups of whichever city you’re in e.g., Kaohsiung Nomads, Kaohsiung Expats. You can write a post introducing yourself, and that you’re new to the city, and/or keep an eye out for events posted.
• Join Nomad List’s Slack channel of the city you’re in, and chat with and meet people there.
• Look for events on meetup.com.
• Look for other nomads in the city you’re in via Twitter, or a 3rd party tool like ManageFlitter.

How do you stay in touch with friends and family while traveling?

• WhatsApp
• FaceTime
• Facebook
• Snapchat