When I got to college, I learned a lot about computing fairly quickly, before I even stepped into my first computer science course.

During my first year, a friend-of-a-friend needed help recovering a lost file. At their dorm, I stood behind them as they opened their MacBook.

“Where was the file before it was missing?” I asked.

“Usually I just see it here…” they gestured to some windows in Pages. The urgency of the situation became more clear: they’re working on a paper that’s due soon.

“Alright, open Finder.”

Silence… then, “What?”

“Open Finder…”

“What’s that?”

“Where all your files are?”

“Oh, I didn’t know that’s what that was called.” They closed all their open windows, revealing a desktop that must have had hundreds of files, all overlapping, all over the place. It was like an episode of Hoarders, but the digital equivalent. No less frightening. We just opened the front door, and got our first glimpse at what’s inside.

“Whoa. What’s going on here?” Shocked by what I was looking at, I was curious to understand.

“This is how I get to my files?”

“You just keep them all on your desktop? How do you ever find anything?”

“Yeah that can be annoying sometimes…” they said, in a sort of assumed, shared complaint — “computers, eh?” kind of way.

“Click the blue smiley icon at the bottom of your screen.” Finder opens.

“What’s this?”

We found their file by opening the desktop folder in Finder and sorting by recently updated. Stoked by this “new” feature on their computer? Not so much. “That’s complicated?” they said of the Finder window, and sure enough, when I checked in some months later, they were still at it with the piles on the desktop, dragging files off of others to find one that’s currently needed, and keeping the most important ones in little holes where fewer files piled up.

Delighted as we may be with our graphs of items, our backlinks and transclusions, and any other means of organizing our things or calling them up in different views for different purposes, if we’re looking at all of personal computing, we cannot ignore what many would do when they just want to be done with what they’re working on. And if we’re being honest, we have to admit: we do it too.

When we’re in a rush, don’t want to be working on our present task, overburdened, or multitasking — basically, when we’re experiencing much of human life — we take the path of least resistance, even if it looks to others like a far less efficient path. Sometimes, it’s the path that requires you to learn nothing new; the most familiar. Sometimes, it’s the one that requires the absolute fewest clicks, even if it means saving a file in an obscure place. Sometimes, it’s propping up an earlier path of least resistance, going to greater effort in order to co-locate misplaced items together.

It isn’t good enough for our systems to be capable of beautifully perfect organizations; we will find their messiest allowable state at some point. We will be in a rush, we will click the easiest button, we will fall to the system’s defaults some percentage of the time — whatever they may be.

How might our system’s defaults keep us organized? How can we get as many of the helpful organizations available in an itemized, graph-based OS for free? How can we put the most effective ways of using such a system on the paths of least resistance?

An itemized system intentionally breaks down the boundaries of today’s apps and their data siloes. With all of your items in one system, and all capable of being referenced from any and many other items, the messy desktop could get a lot worse.

In the next lab note, I’ll cover some ways that I’ve tinkered with how an itemized OS could help. But until then, I’m curious to know: have you seen any promising directions?

Notes

[1] Part of this story I left out: When I said to open Finder, they actually opened Spotlight first, guessing that might be what I was referring to as "Finder" — that was interesting!