Jonathan Cutrell

How Remote First Companies are Antifragile

March 06, 2020

Modern workplaces are being forced to respond with caution as COVID-19 spreads worldwide. As of the writing of this post, over 100k cases have been confirmed.

Many companies are responding by telling their workers to work from home while we figure out what to do next.

I’m intrigued by this as a remote worker; a behavior that is unusual and difficult for a large group of people is a chosen mode of operation for others.

Companies that embrace a geographically distributed workforce already understand this.

Last year on an episode of Tim Ferriss’s podcast, Josh Waitzkin (the subject of the movie Searching for Bobby Fischer) talked about boiling, a technique for practicing foiling (a challenging type of high-speed surfing).

An excerpt from the episode:

Most people, if they’re foiling, you don’t have many chances to train at boils, and when they happen, it’s just catastrophic. It’s a massive wipeout. Now, I did two sessions where I went over 200 boils at top speed. It’s doing tons of reps of boils or tons of steep sections. The learning curve is incredible.

Josh’s choice of surfing into the boil seems crazy at first, but he knows this will result in a much better outcome.

This concept runs deep in antifragile thinking: how can I use the exceptions, difficulties, disorder, etc to become stronger? Instead of simply recovering, or taking the blow - how can we improve as a direct result?

Remote work isn’t the same, necessarily, as boiling. Boiling is mostly an exercise of stress-induced growth, while remote work is a different modality of work, but some similar principles apply.

We don’t choose remote because we are forced into it. We choose it because of the advantages it provides.

The first thing I get on a quick search about remote work studies praises the positive effect of remote work on morale. I tweeted about this and people shared some clear advantages to their personal lives.

Remote isn’t “easy” on day one.

Don’t take me wrong - I’m not trying to preach to non-remote companies that they should change.

Remote work can feel isolating. It isn’t our “natural way” - we lose a lot of bandwidth in communication when we’re representing ourselves through a few words on Slack or a 5 minute Zoom call. This is not easy.

I’m interested in exploring this interesting gap between chosen pathways resulting in antifragility, when the same chosen pathway is a threat when it’s forced.

I’m interested because I want to know what other places we can seek out pathways we otherwise would avoid. What exceptions should we invite? What stress should we use as a pathway towards antifragility?


Written by Jonathan Cutrell, engineering manager at Tesorio and podcast host at Developer Tea. You can follow him on Twitter at @jcutrell.