Thoughts on remote working

The last four posts I've written here were strictly about content marketing. In-depth, evergreen, and actionable articles. I just re-read them all, as a matter of fact. And I'm proud of the work I've done structuring my knowledge and experience into useful resources. I still regularly send these posts to people asking me questions about content.

Still, I feel like this blog needs to be more than that. I created it with the firm intention to write my thoughts on many different things: startup culture, remote working, SaaS struggles, SEO & content marketing, being a "non-technical" guy in a world of software and developers, and more.

But I haven't had taken the time to explore these. Things have been crazy at Snipcart. My technical SEO learning curve has been steeper than I'd have thought. Guest blogging has been more dragging than predicted. Feature releases went faster than expected with our new hire. On top of that, we just hit a content homerun (30 000+ views, r/javascript & Echo JS front-page, Codrops feature, non-stop Twitter mentions) with this post on learning vanilla JS over frameworks—the hours of research, ghostwriting, SEO optimization & outreach paid off on that one!

And now, I just got back from a remote working month in the US and BC. I saw friends and family, and discovered cool new cities (Seattle, Victoria, what's up!). Again, I felt blessed to be able to conjugate work and travel. I even wrote a quick love letter to the Internet on Facebook.

But it was mostly a rainbows and sunshine post. And when my designer friend Tony from Osmo sent me this article on the dark side of digital nomadism, I decided I'd dive a bit deeper into the subject here.

First, to paint a more balanced portrait of remote working. Second, to lay down expectations for my upcoming (and biggest yet) remote working trip: 6 months in Chiang Mai, Thailand.

"OMG you're so lucky!"

I've done my fair share of remote working in the last 3 years:

Same time zone cities than our Québec office [Eastern Time Zone UTC-05:00], like Montréal, Sherbrooke, and New-York. Cities with slightly different time zones, like Colorado Springs, Denver, Minneapolis, Seattle, Victoria, Whistler. Other cities with completely different time zones, like Lausanne, Paris, Nantes, Dublin, Siargao, Manilla.

Yeah, I've seen pretty awesome places and met remarkable peeps. But it wasn't all fun and games. I've struggled with quite a few things actually:

  • Asynchronous communication & time zone gaps
  • Mediocre Internet connexions
  • Serious injuries & insurance red tape
  • Missed flights & unplanned expenses, i.e. being broke as hell
  • Long-distance relationships (don't do it)
  • Seeing friends and family live cool moments back home without you
  • Loneliness

The last one hit me harder on my recent trip. Because yeah, spending 40 hours a week alone in coffee shops with little to no social interactions ("would you mind watching my laptop while I hit the bathroom please?") takes a toll on you.

But still, on November 9th, I'm hopping on a plane to give digital nomadism a more serious try. I believe I'm at the perfect place in my life to do that: single, family out-of-town, no time and money-consuming assets (car, house/condo). I'd hate myself for not taking advantage of this epic opportunity many around me do not have.

Before I leave, I want to remember and share what I've learned in my previous trips, and list what I want to get out of the next one.

Lessons I've learned working remotely

  • Internet access is priority #1

The most important part of "remote working" is—drum roll—working. So decent Wi-Fi isn't a plus when working remotely: it's a priority. Grabbing a SIM card with a data plan has also become one of my must-do. Saves you from clueless wandering and Wi-Fi outages.

  • A bit of planning will go a long way

I'm a big fan of not losing my time and money.

Spending half an hour wandering the streets to find some place to get work done? Not gonna fly.

Spending hundreds of dollars on last-minute lodging bookings? Forget that.

When you wake up in the morning, you should already know where you're going to work (try Workfrom), and how you'll get there. And when your rent/check-out date comes up, you should already know where you're going to stay.

  • Flexibility is not a plus; it's a duty

You can't force upon teammates and clients the consequences of your remote-working decisions. If you have a call, try choosing an hour that works for all parties. Impossible? Adapt. Wake up early or fire up your laptop late at night if you have to.

And try to pick a spot that's not too loud for your calls. I've seen background noises run a good meeting and potential relationships to the ground in a few minutes. If you're forced to talk in a noisy environment, master the mute/unmute on your mic. ;)

  • Communication is KEY (duh)

At the office, there's a heavy chunk of real-time feedback you give & receive, without even noticing. In a different country & time zone, lots of these valuable micro-interactions disappear.

So you need to be super proactive with communication. Always be communicating what you're doing and thinking. And of course, share jokes and pictures in appropriate channels. It shows presence and motivation.

Everybody on the team needs to understand how important it is to respond to messages, even if they were written hours ago. And if chat doesn't work, go for email. But keep the discussion going, all the time. Otherwise, you'll kill synergy.

Also, I realized how important seeing live friendly faces really is. I do spontaneous calls in Slack way more often when I'm remote. It reinforces the feeling of cooperation & belonging. It's a good occasion to crack jokes and show teammates around your remote spot!

Oh, and I almost forgot: invest in some good-ass headphones. You won't regret it.

Chiang Mai bound: expectations & objectives

I want to meet new, inspiring people living the digital nomad reality.

There's already an active community of expats and remote workers in Chiang Mai. I'm going to get an insider look at it. To see which types of gigs these people are doing. Where they've been, what they've done. Are they freelancers? Do they share my startup reality? What can they teach me? I'll be on the lookout for answers to all of these questions.

Chances are they'll show me different variations of the life I could live in a remote-centric context.

I want to maintain a steady, healthy work-life balance abroad.

My goal isn't to be "traveling" in Thailand, but living there. I want to prove to myself I can be focused and happy on a long-term basis in a totally foreign country. I want to live meaningful work and personal experiences. Deliver results, and explore in my free time. Maybe I'll fail at it. But I intend to give it a serious shot. I know how easy it is to surrender to the shuffling traveler feet. To pack your things and GTFO when you feel like it, or when you encounter irritants.

To give myself a chance, I'll book long-term stays in comfortable places, and pay for steady co-working offices access.

I want to get to know Thailand and get fresh perspective.

Perspective is invaluable. I'm intent on getting some by diving head-first into a whole new culture, with an open mind, and who knows, maybe even an open heart.

I also want to learn more about Buddhism, and maybe try a meditation retreat somewhere nearby. I've witnessed first-hand the benefits of mindfulness and meditation in the last years. But I've stopped practicing lately. I'm guessing this could be the perfect time to find my way back to it. We'll see.

Finding out what comes next

The underlying pattern of this trip is finding direction. Or at least trying to. It'll give me loads of time, distance, and new insights. I'll use them to think about my life, and where I want it to go.

The way I see it, there are two possible outcomes:

  1. I enjoyed the experience so much that I want to repeat it for the next few years.
  2. I didn't get enough good and happiness out of it, so I start seeking it elsewhere: maybe back home, maybe not.

I do respect many of my friends' decision to opt for the low key, comfortable suburban grind. They're enjoying a whole set of awesome stuff: meaningful and long-lasting relationships, children & family, outdoors, healthy routines, peace and quiet in a cozy home, etc. But I can't get myself to want that. At least not right now. I feel I've got to move. See a little more of this big bad world before settling down, you know?

In any case: I feel good. I feel like I'm moving forward.

I'll be sure to let you know if that feeling changes.

But for now?

Onward, with momentum and new experiences just a few days & miles ahead.

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