372 Easy Steps to Expanding Your Mind

June 30, 2018

It’s a trap, one I fall into often. I’ll be reading Twitter or Hacker News, and come across an article. It’s promising and potentially enlightening, but long, so I send it to Instapaper for reading later.

Each time I do this, I get a sense of accomplishment. “Yeah! Good for me! I decided to read a substantial essay, something that will expand my mind!”

Yet I have accomplished nothing. Nothing has expanded – other than my Instapaper backlog.

Sure, on occasion I’ll have the good sense to read some saved articles instead of the latest bleeps and bloops, and when I do it’s always rewarding. But I like the latest bleeps and bloops. And reading feels like work! I can start tomorrow.

As a result, I do a lot of saving articles, but not a lot of mind-expanding.

So, this spring, I decided the time had come: I would read through my Instapaper backlog by the end of June. I would finally benefit from those thoughtful and insightful articles no matter how much reading it took.

Spoiler: it took a lot.


After turning on the unread badge in Instapaper – and using an advanced setting to let it download my full backlog – I came face to face with my goal: 372 articles. 372 pieces of writing that past-me had delegated to future-me. Well future-me, time to make some coffee.

With my coffee steaming and my toddler napping, I got comfortable and scrolled down, way way down, to the oldest article.

It was from 2009.

Apparently, I once used an early version of Instapaper to save an article from A List Apart on a topic as old as time: JavaScript frameworks. This wouldn’t have been the first article I’d ever saved, but I guess it was the first one I procrastinated reading.

I skimmed the article for old times’ sake, then hit Archive. Progress 1, mind expansion 0.

Over the coming weeks, I diligently worked my way forward in time. The JavaScript article wasn’t the only piece to age poorly. “The bold new world of 3D TV”, ha right. “Why Twitter must reverse its 2012 policy changes,” sigh. “Why Trump could never be elected,” projectile barf.

Before long, I’d learned to cock my Archive finger when I came across a piece about politics or technology news. These links, the bulk of my Twitter and RSS feeds, seemed important when they were new, but a few years later they’re kinda just not. The more urgent a take felt, the less likely it turned out to be an important one. Which is kind of a known thing.


Luckily for me, some of those older articles did stand the test of time. There was a 2010 posting based on a 1988 paper on defensive communication, and how spontaneity, provisionalism, and problem orientation can lead to better outcomes when giving feedback and communicating generally. So that was cool.

Incidentally, this was one of the pieces that aged poorly for another reason: archaic pronoun usage. Prose that I wouldn’t have blinked at 5 years ago sticks out now for strangely gendered pronoun usage, either due to authors flipping between “he” and “she,” or using the awkward “he or she” construct every time they need a pronoun. The singular “they” happened slowly, then all at once.

For every article that aged poorly though, there was a timeless classic. Stories of ages gone by, for example. I loved Nintendo of America’s weird origin story, the story of how NHL ’94 became a masterpiece, and how Starcraft barely worked and originally looked like some kind of acid trip.

I was also pleased to find great stories of great failures – whether it was massive oil rigs losing their way, massively acclaimed studios losing their best staff, or massively funded startups losing their grip. I tell myself I like to read about failures so I can learn from their mistakes, but there’s something more to it. I’m fascinated by the key element of failing at scale: hubris.

Nicholas Carlson spun a brutal tale of hubris in an excerpt from his book about Marissa Mayer and the Fight to Save Yahoo, which was fascinating albeit clearly one-sided. The piece wants you to think of Mayer as hopelessly arrogant, but she sounded to me more like a smart person trying really hard to move a beached whale on an impossible schedule. Fascinating nonetheless.

Hubris is maybe even more interesting when it doesn’t (quite) lead to doom and gloom. I enjoyed learning about Angus Reid and the power struggle at Vision Critical, and the wild way Elon Musk built SpaceX with sheer force of will. Either story might feel like a stretch as a work of fiction.

Remarkably, out of 372 articles I found but a single piece of fiction: the brilliantly written and provocative short story Cat Person. The fact this was one of the best articles in the bunch seems to indicate I should be reading more short fiction.

Beyond the hubris and the stories, I did find a few essays that should help me actually do my job. For example, two articles helped me refine my thinking on our labs projects at Steamclock: Aaron Harris’ Why Toys?, and an article about Teehan + Lax’s Labs program. I also got a good reminder from Rands that leaders need to Say the Hard Thing, and a peek at the culture that being too hard purportedly created at Amazon.

I also learned more about the confidence gap that is an obstacle for many women and marginalized people when building their careers, and the pernicious nature of “Assuming Good Intent” in codes of conduct.

As helpful as those few essays were though, I expected to have saved more solid articles on these topics. Building stronger products and teams is my job – I should be reading about it. Sounds like I need to improve my list of inputs.


Today, I read the the final article. I’d already finished the original 372, but I’d also kept adding new articles, so after roughly 400 articles, I finally finished The Trouble With Johnny Depp. I’m now at Instapaper 0.

So, did all that expand my mind? Maybe. A bit, yeah.

But in a bigger way I feel dumber. It feels as though the world of knowledge and ideas and stories that I don’t know has grown a lot, and the world I do know has only grown a little. Which makes sense – there are a lot more than 400 long form stories and essays worth reading, and it’s going to take a lot more than three months to read them. But I’m willing to try.

Armed with my Save for Later bookmarklet and my Kindle, I’m going to keep on reading. I’m going to expand my mind. I’m going to read those great articles, those great essays, and the great novels too. Yeah! Good for me!

I can start tomorrow.

© Allen Pike. See also Twitter and Steamclock.