Ian Daniel Stewart

Some thoughts on how to push back against the gravity of “going it alone” when working remote or in an all-distributed company.

I have several friends at work who love the Zelda game series from Nintendo. And I played the first few games growing up so the video-game-famous quote from the first game, “It’s dangerous to go alone! Take this.” has been stuck in my head for years now. So maybe it’s no surprise that the other day while thinking about what it’s like to work in an 800+ person fully-distributed company where everyone is working “remote” I realized that there’s a high chance that this sort of sums up what I think is one of the most important survival mechanisms or truisms for that kind of work.

Here’s the idea broke down into two principles.

1. Remember that it’s dangerous to go alone.
2. Gear up when you go it alone.

Be careful about letting people go it alone and make sure you’re armed to the teeth whenever it looks like you might be.

Remember that it’s dangerous to go alone

This first principle should be pretty obvious but I find it surprising how often we (as in humans in general) tend to forget it. Going it alone kind of sucks. You wind up bearing the burden of what will likely wind up being more and more increasingly complex decisions. It’s all on you. Sometimes it means you can move faster but remember, it’s dangerous.

Here’s an example from outside of the world of Zelda.

“… pairs of people working together can make better decisions than the better member of the pair working alone.”
— Neuroscientists Uta and Chris Frith

Let’s reverse that, let’s say you’re a pretty smart person and make great decisions on your own. You’re missing out on making even better decisions when you’re not pairing up with someone. (Also, there’s a high chance you’re not as smart as you think you are — or maybe you’re even smarter than you think! Self-awareness can be tricky and your smarts are situational.)

Recently at work we’ve been experimenting with pairing up design leads with tech leads, or business leads with tech leads, to run projects. And experimenting with small groups of three designers leading design teams for products. We’ve found this to work extremely well.

As I look back on the first fruits of these experiments it’s seemed like unusually rapid progress has been made on complex problems with work that stretches across multiple teams, divisions, and even products. I like to think that this pairing has helped with that.

Inside our distributed design team for WordPress.com we try and work similarly. We take advantage of video calls to bring people together in the same way. A weekly “show and tell”, bi-weekly “team times” where we talk about how we work or share knowledge, pairing during video-based “working sessions” (remote control with Zoom is especially cool), and in general, just trying not to let anyone get stuck out there on their own on important projects.

Gear up when you go it alone

Note that in the Zelda game the intrepid hero Link is going it alone. He’s getting that sword because it’s dangerous out there. What’s the sword you’re going to bring with you when you go it alone? Like Dr. Seuss says, “Whether you like it or not, alone will be something you’ll be quite a lot.”

The short answer is, I don’t really know yet, but it’s something I’m always trying to figure out. I think it looks a lot like just taking care of yourself.

• Journal
• Meditate
• Exercise
• Eat right
• Get outside
• Take real breaks away from work

The truth is that we need partners, we need guides, and we need friends. Lean on your relationships and networks at work. Ask for some help once in a while. Take care of yourself.

And be creative. I love this tweet from my colleague Alison Rand.

Distributed work often means not being able to properly catchup with a colleague after a long week and exhale. Finding meaningful ways to include that into your rituals is key to reflection and constructive feedback.

— Alison Rand (@alisonrand) November 30, 2018

Distributed work is a different kind of work. That means taking the time to think creatively about new rituals and new ways of communicating with people.

I know that things like this can seem obvious but it also seems like they’re surprisingly easy to forget. I see people forgetting it all the time. Working in an all-distributed team means I can sit in my home office in the middle of Canada and work with people from all around the world. It also means I have a responsibility to make that work as well as it can for myself and my colleagues.

In other words, it’s worthwhile to be conscious about it.

Also, I’d love to hear about how you make your situation work for you if you work remotely or in an all-distributed company! Send me an email or leave a comment below.