Whenever I start to feel my worldview shrinking, instead of thinking expansively and looking outwards, there’s a passage from David Foster Wallace’s famous “This Is Water” commencement speech that speaks out to me:
“And the so-called real world will not discourage you from operating on your default settings, because the so-called real world of men and money and power hums merrily along in a pool of fear and anger and frustration and craving and worship of self. Our own present culture has harnessed these forces in ways that have yielded extraordinary wealth and comfort and personal freedom. The freedom all to be lords of our tiny skull-sized kingdoms, alone at the center of all creation. This kind of freedom has much to recommend it. But of course there are all different kinds of freedom, and the kind that is most precious you will not hear much talk about much in the great outside world of wanting and achieving…. The really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day.”
In particular the way he describes how we become “lords of our tiny skull-sized kingdoms” manages to always viscerally snag the fragile fabric of my reality, like the prickly side of a velcro strip. It wakes me up. Because it’s so easy to fall asleep and run on our default settings.
One of the benefits of knowing how to speak machine is to condition ourselves to remember that the more simple minded and predictable we become, the more easily we fit into a default model.
That’s because in general, the core operating model for computational products is to nudge us into operating within narrower sets of predictable behaviors so that we can be tracked more easily. It’s akin to when Little Red Riding Hood wonders why The Wolf, disguised as her grandmother, has such big eyes. “The better to see you with, my dear,” the Wolf answers. When we are easily understood by machines, our digital environment will feed our inputs in ways that can shift our realities with a high degree of effectiveness. How? We are presented with either what we love with all our hearts. Or we are presented with what we love to dislike or, even worse, hate.
During this pandemic, when many people who are fortunate enough to work from home can fully center themselves geo-spatially, their skull-sized kingdoms have grown a little bigger — to the sizes of their homes. I’m one of these people. And instead of having random encounters in the physical world that play a major role in reshaping, tweaking, and tuning my reality, I feel like I’ve become like my aging parents. Their entire sense of reality has primarily developed within the size of a bedroom, and it’s been powered by a television set for over twenty years. For those who are healthy and were wealthy enough to travel before the pandemic, it was possible to sustain and grow a broader view of the world, in ways that we had a little more control over. It certainly doesn’t feel that way now, at least for me.
Keep in mind that whenever I was in Silicon Valley, I kept hearing this term “remote work” and wanted to learn more about it. So in 2016, I jumped at the opportunity to work at what was then the world’s largest all-remote tech company: Automattic. I wound up working there for three years, and was able to fully absorb and understand the wisdom of Matt Mullenweg, the founder of the Automattic and a key proponent of the “distributed work” movement. I was able to observe his two key arguments as truths that could play out at scale — something I thought could never happen. The first was you needed everyone to work all-distributed for it to work within an organization; otherwise there would be a kind of “caste” system of those who were on-premise versus off-premise. The second was that there needed to be a shift from synchronous work activities to asynchronous ones; otherwise you could never manage across many time zones and the work-life imbalances that result from distributed work. Today you can visit any VC or tech guru who has “remote work” and listen to them essentially parrot what Matt has been saying for the last decade.
Does this mean I’m “pro” distributed or remote work? Not really. Like all disruptive paradigms, it’s better for a few things, but it’s not a panacea for digitally transforming businesses overnight.
A few business functions, e.g. customer support and certain kinds of software development, can definitely get done better by distributed workers than a forced on-premise workplace norm. But for any job or function that requires a Dweckian “growth mindset” and the ability to inspire organizations in whole, or in part, to prosper beyond their own wildest dreams, it’s definitely not enough. At least that’s the conclusion I’ve come to, having lived the “remote life” for longer than most leaders out there.
Why do I think I might be right? Frankly I don’t know. I haven’t swiped through a recommended article or related video on the topic yet. I figure if I write enough about it, then my skull-sized kingdom will be rewarded by it soon enough. And I’ll feel terrific to be right. Or I’ll feel reviled when I’m told that I’m wrong. In both cases, I’ll be back here to see what cards the computer (or the Internet) deals me. Although I love the convenience of it all, I’m still looking forward to the post-pandemic future, when I can take my card game into places where I can feel a broader range of cognitive discomforts that extend well beyond having a stationary brain that can be targeted ad infinitum. I love my parents but I’m not ready to be like them. Not yet.