This post is part of a series on the various ways I've used pen and paper in my life. To learn more about it, check out the introduction, or view the "ink and paper brain" category for other posts.

Digital tools strive for a frictionless ideal. Armed with modern technology’s hypermobility, connectivity, and sheer capability, we’re constantly designing and using tools that reduce the friction of our mental lives. When a thought crosses my mind at work, I can pick up my phone and speak to it, telling it to remind me when I’m home to pay my credit card bill, and when it detects that I’ve returned to my home address, it will deliver my note-to-self with a gentle buzz. By making “smart” devices, we reduce our own cognitive burden.

Taking A.P. Physics tests in high school, I longed for the simplicity of a frictionless world, but in the way one longs for magic powers, with the recognition that my wild fantasies would never be anything but fantasies. Friction may be frustrating when it adds three steps to your calculations, but it also serves a purpose; friction keeps our cars on the roads, our glasses perched on our noses. As Doug Lane indicates in a recent blog post, whether we’re talking about the physical world or the psychic one, a certain amount of friction is necessary to keep the system functioning. The trick is managing it.

I have roots on both sides of the analog-digital schism; after all, I’m using pixels to talk about ink. I spent years trying to come up with a task list strategy that worked for me, providing just the right amount of friction without slowing me to a halt, and the search bounced me from analog to digital and back again. My Hipster PDA was one of my earlier attempts at an analog solution.

Before college, I hardly ever kept a central to-do list, relying mostly on my memory and scattered reminders in my binders to stay on top of my deadlines. That ceased to be tenable in college, however, so I began exploring my options, and found the Hipster PDA. Originally a stack of index cards held together with a binder clip, my version eventually evolved into a pad held together with Levenger Circa discs.

The Circa system doesn’t use binder rings or wire coils. Instead, it holds pages together with plastic discs, which slot into special mushroom-shaped punches. Because of the shape of the punches, pages—or in my case, index cards—can be freely removed from the discs, reorganized, and slipped right back on, without damaged edges and without having to pull a binder ring apart. It was near-digital flexibility with an analog tool.

This appealed to me. Digital task lists, like all digital tools, typically have the advantage of flexibility. If an important task is being pushed to the bottom of my list, I can reorder it with a click. I can filter my to-do items based on categories, tags, and other forms of metadata, allowing me to focus only on what’s relevant. While nothing in the physical realm can exactly replicate that infinite flexibility, the Hipster PDA, in both its original binder-clip form and my Levenger Circa modification, came close.

That said, if I wanted a digital solution, I would have found one. I used the Hipster PDA because task lists are one realm where analog tools clearly win out over digital for me. It’s a matter of feedback. Clicking a checkbox on a screen feels nowhere near as satisfying as the physical act of crossing a task out on paper or erasing it from my dry-erase board. Any digital task list that doesn’t include big, clickable checkboxes may as well be dead to me, and even among those that do, there has to be a considerable amount of rewarding feedback for me to buy in. The only application I’ve found that comes close is HabitRPG, where marking off my completed tasks earns me virtual gold and experience points–and as rewarding as that is, I often just stick to my paper lists.

I expected that the flexibility of the Hipster PDA would make it my ideal analog tool, but I was mistaken. It never quite worked for me, in part because, in my quest for perfect organization, I gave myself far too much work. The system I had designed for myself contained way too much friction. I kept a separate to-do card for each class, a sound principle that in practice meant endlessly shuffling a half-dozen cards and inevitably forgetting the right ones on my bulletin board when I left for class. What’s more, I never codified a system for capturing information, meaning that when I wanted to record something, I often faced the additional cognitive burden of deciding how best to record it.

I gave up on the Hipster PDA by the end of my first year at Whitman, but I would later return to the idea of a paper-based to-do list. I just had to find the right way to manage the friction.