Remote Work

It’s been more than two years since I logged out of my corporate 9-5 desk job. I remember the day clearly: it held a mix of anxiousness, excitement, apprehension, and optimism. You name it, I felt it.

The day I walked out for the last time, I felt something else as well – something you might not expect to be a typical response.

I felt guilt.

I felt like I was playing hooky; like I was expected to be at work.

It’s that same feeling as when you skip a period in high school, but you can’t enjoy it because you feel your absence is noted and tangible.

My new life as an entrepreneur felt foreign to me, even though this was my second entrepreneurial venture.

It was exciting but shrouded in all kinds of emotions.

Day One

When I woke up that first Monday morning in my new life, I had no structure. My wife, Kaitlind, reminded me that just because I was self-employed, it did not mean that I could sleep in past 9 am.

I went to my computer. Or worked out. I don’t remember exactly. But I followed the pattern I was accustomed to at my corporate job – sitting at my desk all day doing whatever needed my attention.

With some thought and experiment, I soon developed an intentional routine for my new life. I set aside my mornings for writing, research, reading, discovery, and sometimes putting out potential fires before the day begins.

Following that, I do my task work. The things that I personally need to get done. Finally, I start having phone calls and meetings as the afternoon draws on.

Two years later, that routine is pretty well developed, mixing in working out and meditation where and when I can.

But now, I’m starting a new routine. Only this time, I am not throwing everything out the window and starting from scratch. I’m merely transporting my routine to another country.

Slow Travelling and Working Abroad

My wife and I are fairly newly married; it’s been about 6 months. We live in a furnished condominium in the Distillery District in Toronto.

The unit came furnished because the landlords originally expected to make it into an executive rental suite, but found out it was not as easy as it sounded. We accepted, since the furniture we had was neither complete nor of high quality (reminiscent of our university days).

Our possessions can realistically fit inside of a cargo van. I prefer to live as minimalistically as possible, likely due to the fact that I have moved over two dozen times in my life. Every time you move, you get rid of stuff instead of lugging it to the next place.

We realized that this may be the last time in our life when we will own just our essential possessions. No mortgage, no kids, no car, no jumbo jet. My wife, also a recent corporate ex-pat, was ready for a change, so we took this as an opportunity to put “settling down” on hold for a few more months while we pursued our goals of travelling and working remotely.

For the next while, I will be working full-time on my business, as usual. My clients rarely see me in person, so there should be very little difference to their experience in working with me.

The trains will continue running. I will continue working and being available during North American business hours.

I will not be backpacking nor trying to see it all – I will be working 10 hours a day, as I do now, except from an AirBNB or local coworking space in one of the cities we are planning to visit.

Kaitlind will help out in my business in more ways than she probably knows.  She’s smarter than she even realizes.

The Fear

Any time you tread off the beaten path, you get the Fear. You feel it in your gut.

The upside potential is high, but the downside potential is present too. There’s always a potential downside, even in your safe 9-5. What if you get fired or laid off? That’s worse than losing a client. That’s losing all the eggs and the basket.

Naturally, we are excited, but also a bit nervous. That same feeling of guilt I felt when I left my corporate job to pursue my goals is starting to rear it’s head again in both Kaitlind and I.

Should we be doing this? Are we being selfish? Will people think we are crazy? What will my clients think? There’s never a perfectly solid answer.

The Rationality

At the end of the day, we rationalize through the cumulation of the following factors:

• We don’t have any furniture, mortgage, car payments, nor kids.
• We want to move homes anyway, so why not travel in between places we live?
• Kaitlind wanted to make a career transition, so why not travel and work before hunkering down at her next gig?
• We want to see more of the world before we die. When will there be a better time?
• My business works remotely already. I have clients with whom I have never met or only met once. So, why not work from another country while doing so?
• Since I’m able to work along the way, we won’t use our savings. There is only the “opportunity cost” from losing Kaitlind’s income for a few months, which we hope to offset in a few ways.
• We have saved enough money to have safety nets under safety nets.

The way people work is changing. More businesses are hiring consultants or contractors to keep their labour costs down. They are are finding it more efficient to hire people like me instead of an under-utilized employee or one who tries to do too many things.

I believe I am an example of this change. You could call it “just-in-time” labour and expertise.

Closing Thoughts

One day we are going to die.

It’ll happen when we least expect it (ideally in about 90 years from now).

Will we look back and say, “we should have played it safer. Put our heads down, waited until later to pursue our life experiences.”?

Or will we say, “those were some of the best days of our lives”?

The story is yet to be written, but we placed a bet on the latter.

Now it’s time to sit down and do the work to make it all possible.

Curious about where we will be travelling? I’ll write about it again soon.

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