vihart

Stuff Like Lists: Cognitive Tools for Doing Things (Maybe Even Good And Meaningful Things!) (Patreon)

Published:

2025-07-01 03:59:24

Edited:

2025-07-01 06:09:45

Imported:

2026-10

Content

Introduction

Sometimes I feel like every checkmark I make on my to-do list is a tiny act of violence against myself. If there were ever a feeling of accomplishment, a rush of dopamine, a sense of satisfaction in getting things done—as if the number of things I’ve done makes any impact on the number of things I haven’t done which is and will always be infinite—it lost its pleasure back when I was manipulating myself into doing too much for too little reason, back when I still felt an innate sense that effort and accomplishment were highly correlated with both each other and with a life well lived.

To-do lists are, in my view, a technology. I mean in the sense that writing is a technology, that deductive reasoning is a technology. These things were invented or discovered or something’d by people. No one is born knowing how to make a to-do list.

Like any technology, cognitive tools can be used to empower or to manipulate. When used for things that in your heart you know matter to you, each checkmark on your list can add to your trust in yourself and to your hopes for what you can accomplish in the future. When used for things you feel pressure to think you should do, but really it’s more about desperately filling up space in your life and trying not to look like a failure, each checkmark can chip away at your trust in yourself to make meaningful choices about your life.

At least, that’s how I feel about to-do lists, sometimes.

This post is about tools like lists. Mental technologies for the organization and execution of tasks, things anyone with the right know-how can use to amplify their ability to plan stuff and do the stuff they planned. It’s also about the pitfalls of those tools. They can make powerful allies or powerful bullies.

I've divided it into 4 sections, which I recommend not trying to read all at once.

1. Motivation: exploding to-dos, a scroll, and a zine

Recently, when I was taking on the task of uploading a backlog of videos, each of which would come with its own list of sub-tasks, I found it much easier and more interesting to start thinking about to-do lists in general as a subject of technology research. To-do lists are a tool we take for granted, and I wanted to make the invisible aspects visible to myself. Why do they work? When don’t they?

It’s certainly more interesting to think about these things than to actually do the list of things I was trying to make myself do.

Usually, a list should make the tasks in front of me easier to mentally manage. But I found myself really unwilling to make time for my video uploading project when I thought it was going to look like a thousand item checklist:

I knew that a lot of the items would go by fast, and that many would take a predictable 2 or 3 minutes. It adds up, but it's an approachable project to do in a month.

But I also knew that there were some to-do list landmines in there. You know, items that look like normal solid ground, quick and easy to get through, but once you touch them they explode and expand into subtasks and complications until your day is destroyed.

Uh oh, a video was about current events, about a politically sensitive topic, 10 years ago? And it's gonna look like it was published today? Suddenly the to-do list explodes.

Lists are a tool designed for trust and reliability. We’re supposed to feel safe with our list. We're supposed to have faith that if we just do what it says, the things will get done.

But once you know there might be to-do list landmines hiding in your list—and especially if you start experiencing the explosions—it’s reasonable to be afraid of touching it ever again.

Ten years ago, when I was doing my first mass upload to Vimeo, I had this same problem. And so I organized it in a bit of a different way.

Meet the 2015 video to-do scroll:

I printed this out and had it taped to my office wall so that I could track my progress as I moved 100+ videos from youtube to Vimeo. It’s absurdly long, but as a physical object that absurdity becomes part of its charm. Engaging with this list is a physical feat. And very comfortingly, the physical object is contained and finite, unable to explode the way the digital version might.

Technology-wise, the scroll is functioning like a to-do list. I’m going through an ordered list of videos, checking them off one after the other, making different kinds of markings to represent different sub-tasks done. But there’s the important distinction that this isn’t a list that came from my head. It’s not something I made up or figured out. It’s a literal print-out of digital reality.

The to-do list, as a technology, is magical exactly because it lets us take things from our head that don’t exist as a convenient ordered list in the real world. It lets us work with things that don’t already have their own organized entry into the archive of our lives. But sometimes that’s not necessary, and in this case I was able to use a representation of the task that keeps the meaning and context of the task.

So I’d planned to do something like the scroll again, and as I let my hands work I ended up with something a little different than I’d originally intended.

I printed out the thumbnail view and thought I’d just mark up that print-out, but some videos were looking heavier than others in terms of task-weight. And people were asking for specific favorite videos to get uploaded, so I wanted to prioritize those. I started cutting out the thumbnails and glueing them into organized sets, and before I knew it I had a video uploading zine.

On the first page I have the requested and favorite videos which I wanted to get up first. Then, I knew my vimeo page was difficult to navigate, and I needed to start making playlists for things, so that task went along with the pi day videos which are the most obvious first candidate for a playlist.

For each printed thumbnail I can make whatever notes and progress markings are needed for that video. If nothing complicated happens, it doesn’t need a 12 item checklist. I can work in parallel, making partial marks for when videos start uploading or transferring, and I can work on whichever set of videos feels approachable for the time I had that day, focusing on one page at a time.

I can finish my day knowing “I got the symmetry videos done today” and have a sense of what that looks and feels like, rather than having to trust my motivation to abstractions like “I got another 8% of my giant list done, which means if I just keep going I will have accomplished something by the end of the month, and my reward will be more to-do lists for next month and the cycle will never end and everything is meaningless.”

To-do lists are not the only mental technology for the organization and execution of tasks. Just as with hammers, when you’re good at wielding a to-do list, everything starts to look like an item that can be to-done. Choosing the right tool for the job, rather than finding jobs for the tool, is extra important when the job is living your life.

2. Reminders Without Words: Dots, strings on fingers, objects-out-of-place

Most photos you see of cave paintings are the artistic-looking ones that make compelling thumbnails and magazine spreads. But there’s also plenty of human markings on cave walls that are just dots, lines, or other abstract symbols. For example, here’s a photo from the Niaux Caves in France (by the Bradshaw Foundation, that I found in this article about Genevieve von Petzinger’s work categorizing geometric symbols, https://www.bradshawfoundation.com/geometric_signs/index.php ):

There’s no consensus on what these markings mean. Maybe they’re the meaningless scrawling of a child, maybe a communication between nomadic peoples, maybe they’re doing their taxes. People are inventive, and there’s no reason an individual drawing dots in one cave has to do them for the same reason as other people anywhere else.

I’d be surprised if some ancient dots on some cave wall somewhere wasn’t just a particular prehistoric person’s personal reminder of: “oh yeah, I gotta go do that dot thing today.”

A better known classic is tying a string around your finger. I tried and failed to look up the actual history of this. The earliest I could find is reference to a bible passage about remembering certain teachings: “Tie them to your fingers, write them on the tablet of your heart.” (see https://biblehub.com/proverbs/7-3.htm )

It’s unclear to me whether this passage is referencing an existing literal real-life practice of tying strings/ribbons around fingers to remember things, or whether it’s being used as a metaphor. Presumably the part about writing things on your heart is not to be taken literally, but I’m not a bible scholar.

String-around-your-finger types of reminders, whether or not the literal thing, are reminders that don’t tell you what it is that you have to remember. In practice, for most people, often just knowing you have something to remember is enough, as long as it’s just one thing and it’s important. And it has the benefit over to-do lists in that you don’t need to first remember to refer to a to-do list.

Wearables, including clothing, are often used to serve as a reminder of an intention or attitude. Style choices can contain much more information than a simple string, about what you’re intending to remember through your day or evoke in your own mind. (We won't go into the deep problems with the fashion industry, but clothing is still a pretty amazing wearable technology that includes cognitive features.)

Also in this category I’ll put environmental augmentations, like putting an object in your way or out of place. I’ve never heard a formal name for this, but I know anecdotally that I’m not the only one who does things like put the alarm somewhere different when there’s something important I need to remember first thing in the morning, or toss something where it’ll be on my way on the floor when I’m leaving my bedroom.

There's something about an object-out-of-place that says "there's a reason for this, and you can figure it out if you think about it."

I revel in these ideas that seem so simple, at least simple enough that people re-invent them all the time, and yet there’s so many subtle prerequisites. Objects out of place, as reminders, don’t work without a sense of object permanence. They require capacities for planning and forethought. They require having control over our lives and our environment, with a certain amount of stability and safety, such that we can expect things will be as we left them. They require a developed ability for prospective memory, and to be able to intentionally link mental and physical experiences in a way that augments prospective memory.

To me there is something fundamental, something almost magic, in the act of taking a thought bouncing around inside a human mind and embodying it in something physical, something external. It’s such an iconic form of embodied cognition. Of thinking not just with your mind but with your body and the world around you.

With something as simple as a string around our finger, or an upside-down bottle on my kitchen counter, our environment becomes part of ourselves, part of our thinking mind.

3. Containing Multitudes: dopamine menus, habit trackers, nails and hammers

It’s easy to forget what you’re supposed to remind yourself of when there’s a lot of things, or when the things don’t have the kind of weight where they stick out in your memory. This makes to-do lists amazing at organizing piles of little things that don’t really feel like they matter individually. Which is a double-edged sword, because life is full of things that might not really feel like they matter individually but that are parts of a meaningful whole, but it’s also easy to use to-do lists to fill life with lots of little things that genuinely don’t matter.

If your list isn’t of things you intend to do all in a row one after the other, but includes long-term things, optional things, or aspirational things, a to-do list might not be the best format. Luckily there’s plenty of other neat tools you can use to bully yourself into doing a lot of little tasks all the time, or maybe even doing things that are actually good for your brain!

A "dopamine menu", or originally "dopamenu", is a recently trending tool that puts lists of optional activities into a menu style, organized into categories. It's intended to offer alternatives for scrolling or other mindless addictive internet consumption.

According to my internet searches, this idea was invented by Jessica McCabe in this video on How To ADHD in 2020 ( https://www.youtube.com/watch?v=-6WCkTwW6xg ). Here's one page from her original example:

Feature-wise, it’s similar to a to-do list or habit tracker in that when you find yourself asking “what should I do now,” you don’t have to start from scratch figuring out all the things bouncing around in your brain. You front-load that introspection and decision-making once, externalize it, and now when you need a recharge and don’t feel like using your forebrain you can pick something that looks appealing without having to think of it from scratch or vet it for worthiness.

But the meaning and context is quite different from to-do lists or habit trackers, because these are meant to be fun things that recharge you and make you feel good, rather than chores you have to force yourself to do.

In practice, I have no idea whether anyone has ever once looked at their dopamine menu to use as recommended, after creating it and posting it on social media. I tried making one and I like it a lot as an art object, but haven’t found it practical as a tool. It might be more of a creative and intention-setting activity than a functioning technology. Or it might be more of a conceptual art exercise, where it’s not important whether the menu gets literally used as a menu. It’s hard to tell with highly instagrammable internet trends. Maybe I’m just bad at using this particular tool.

Either way, the conceptual nature of it appeals to me. It’s almost the opposite of the pitfall I see with some of these other technologies, where the mental and conceptual aspect of the technology can start to get phoned in while the day-to-day use of the pen-on-paper part of it takes over.

Which brings us to habit trackers.

Habit-trackers are a cognitive technology that allow for reoccurring tasks and optional tasks, usually spanning a week or month. Unlike a to-do list it’s not necessarily mandatory that you do all the things every day. Over time you can create a visualization of what you’ve done when.

These days I mostly associate habit tracking with the Bullet Journal trend, which was started by Ryder Carroll in 2013 and is still going strong. The visual part of a habit tracker can be stylized a number of ways, and the visual appeal is part of why people find it motivating and why it spreads online so well. I’m just gonna paste an image search for “bullet journal habit tracker” to give a taste to the uninitiated.

It just makes you want to journal and conquer your entire life, seeing such pretty pages! But equally important to the visuals is the invisible mental part of the tool, the part where in your head you’re telling yourself “I like seeing this evidence that I did all this stuff last week, and so I know that even if I don’t feel like doing this right now I’ll thank myself for it later. I can see my effort over time adding up.” Or, conversely, “Oops, I can see I haven’t been doing this thing that matters to me. What can I change to prioritize it better?”

When people get into habit trackers or daily to-do lists or other things inspired by bullet journaling, I often see people adding tasks for the technology rather than using the technology to better organize tasks they had previously prioritized as important. When you have a fun new technology toy it’s natural to want to play with it, adding brand new hobbies and lifestyle choices at the same time as trying a brand new habit tracking tool that makes every habit look like a nail.

Get up at 5am. Meditate for 10 minutes. Eat a perfecly-portioned meal-prepped breakfast. Go on a 20-minute run. Take a 3-minute cold shower. Journal for 5 minutes. Read nonfiction for 15. Now you’ve got a full twenty minutes to practice drawing, or piano, or whatever other brand new creative hobby you imagine a better version of yourself would find fulfilling, before starting your work day.

My instinct is to roll my eyes at these social media extremes, and the whole general attitude. You can live a worthwhile life without being healthy, educated, productive, or good at anything. You can live a meaningful life where you connect with loved ones and with your community, and never succeed in a professional career or creative hobby. You can be a good person even if you drink too much coffee and hate yoga.

But I think it’s still worth trying if you want, if you can avoid buying into the more toxic parts of productivity culture. It certainly seems to work for a lot of people in real life, despite that much of it online is pure performance art.

I don’t think it even has to be that fulfilling to be worth a try. When you have a tool that helps give you power over the parts of your life that are still yours, sometimes hammering all the nails is just what you need in that moment. There is value in rediscovering the strength of a neglected hammer regardless of what you are building with it.

Here is how I feel when I use these kinds of tools:

I can hammer so many nails. Where are they going? Why does everything still feel unstable? Do I need to hammer more nails, or am I just damaging the ground I stand on and tiring myself out?

For myself I’ve found habit tracking effective in the short term, because I’m generally extremely disorganized when it comes to doing everyday normal people things. And from the outside, given my success in my careers, it's hard to argue the results. But ultimately I always find it unfulfilling and burnoutable. I start to feel like my soul has been shaped into a glorified coloring book.

I want to imagine the "habits" will become easier or feel more habitual if I keep doing them for months. In reality, they only ever get harder to keep up over time. I’ve never found that having better habits for a few months here or there has made me a better person or given me a better life.

(I'm not trying to give anyone else life advice here, though. My experiences aren't everyone's.)

How does one find the balance? If you decide to let go and stop micromanaging your life, is that a step toward finding what’s really meaningful? Or is that the way toward apathy and depression?

4. We see meaning where it isn’t, and also meaninglessness where it isn’t.

It’s common enough for people to read meaning into randomness. To think coincidences are fate. To find patterns in small sample sizes that disappear with more data. Because of this, particularly in certain circles, I’ve seen how easy people find it to feel smart about denying the meaning in things, erring all the way to the side of “meaningless until proven meaningful”.

There’s good reasons many people are sensitive to the pitfalls of seeing meaning where there isn’t. The harms done by pseudoscience, superstition, and certain aspects of religion have been well covered by others many times over, to the point that being skeptical is effortless and feels both intelligent and safe.

But you know what’s less well covered? The also absolutely real brain phenomenon that when you look too closely at something you stop seeing meaning when it is there. That sometimes, digging into something until you see the meaninglessness in it isn’t you getting wise, it’s you overloading and hypnotizing your brain into making a cognitive error.

There’s a couple specific flavors of this phenomenon that have been studied, like semantic satiation and jamais vu, that fall into the more general categories of mental fatigue and sensory adaptation.

Semantic satiation is that the thing where if you repeat a word over and over it starts to lose meaning until your brain stops being able to perceive it as having any meaning at all. If you’ve never experienced that, stop and say the word “door” over and over for a few minutes until you get what I mean. As a psychology term, it was coined by Leon Jakobovits James in his 1962 thesis ( https://escholarship.mcgill.ca/concern/theses/c821gp587 . I chose “door” because that’s what psychologist Chris Moulin used in one of his experiments. )

Jamais vu is a more general term for something familiar suddenly looking unfamiliar and divorced from its meaning and context, usually in a way that feels uncomfortable or eerie. It’s spiritually related to deja vu, with both being french loan words. (“Deja vu” translates to “seeing again,” while “jamais vu” means “never seen.” But I haven’t been able to find the origins of the phrase.) As with semantic satiation, it can be induced by focusing too long and hard on something.

I think something like semantic satiation happens whenever we stare at any part of ourselves or our lives too closely and too often. It’s like the opposite of when some strange coincidence happens and our brains see meaning where there isn’t. The phenomenon of semantic satiation proves that with close attention and repetition, our brains can see meaninglessness where there isn’t.

At least I know I often look too closely at myself and see meaninglessness where there isn’t.

This is a post about things like lists, so I won’t harp too long on my more general thoughts on this, but I think the pitfall of seeing meaninglessness where there isn’t is more common and more harmful these days than the opposite pitfall. It’s trendy to associate being smart with knowing everything and believing nothing. We think the more we learn, the more reasonable it is to lose faith in ourselves, the world, and each other. We understand deeply and instinctively that forests cannot exist, because we’ve learned that what we thought was a forest was actually just a collection of trees.

An object out of place is noticeable, it jogs the memory, it demands action. But when things are where they should be, every day, over and over, they become invisible. We can be looking right at them and not see anything.

Conclusion

Cognitive technologies for the organization and execution of tasks, such as lists and habit trackers, shine when you know what you want to do. If you know what you want to do, you can augment your ability to get it done. But they are not built to be tools for meaning finding or meaning making, so it’s not a surprise that they’re bad at those things.

I think it’s a mistake to spend too much focus on what can be definitively tracked and measured with lots of datapoints and checkmarks, but also a mistake to lose sight of the meaning in those things where it does exist. Our brains can and will make both those mistakes.

I still have no answers when it comes to what to do. Besides spending quality time growing your favorite and least-toxic relationships, and spending time with your community making it stronger. Those are always solid choices that stand the test of time.

The end!

🐌,

Appendix: Further Reading and Background

This post isn’t about more modern tech, but I've got to give a shoutout to M Eilo’s "Prosthetic Memory," an installation which solves the problem of not being able to recall the connection between an externalized reminder and an associated memory by having computer vision do the searching for them: https://www.blinkpopshift.com/project-pages/prosthetic-memory (M is also here on Patreon: patreon.com/BlinkPopShift )

There's probably actual research on the kinds of non-computational memory and reminder tools I'm talking about in this post, so feel free to link me anything if you know it. For all I know there's an established community that studies these kinds of things.

My perspective is heavily influenced by my research lineage through Alan Kay and others, for which the foundational document is probably this:

Doug Englebart's 1962 "Augmenting Human Intellect: A Conceptual Framework" https://www.dougengelbart.org/pubs/augment-3906.html

I was first introduced to the term “Tools for Thought”, influenced by the above. There's a lot of names for cognitive tools, mental technologies, etc, and I'm using them interchangeably in my post, but "tools for thought" was the first for me.

Howard Rheingold's "Tools for Thought" from the 1980s: https://www.rheingold.com/texts/tft/ (and editing to add that he has a Patreon! patreon.com/howardrheingold )

Working at our Xerox Parc-inspired research group, and around Alan, Nicky Case, Michael Nielsen, Bret Victor, Kate Compton, Evelyn Eastmond, and many others, I absorbed a lot more ideas that came from this lineage. See:

Michael Nielsen's "Thought As Technology": https://cognitivemedium.com/tat/

Bret Victor's "Media for Thinking the Unthinkable": https://worrydream.com/MediaForThinkingTheUnthinkable/

Nicky Case's Explorable Explanations hub: https://explorabl.es/ (Nicky is also on Patreon patreon.com/c/ncase/ )

Over time, I became more interested in tools for other aspects of our minds that could do with some augmentation, beyond just learning smart stuff and thinking smart stuff. What about things like meaning, and creativity, and self-expression? See:

Kate Compton's thesis on Casual Creators: https://galaxykate.com/blog/casualcreator.html

Working with M Eilo, Andrea Hawksley, and Evelyn Eastmond opened up my eyes to a whole lot of things about non-computational tools (and everything else) that had been invisible to me. Not just tools for thinking and seeing, but for feeling. This was not my strength in those days, and I would be a different and worse person without their influence.

M Eilo's projects: https://www.blinkpopshift.com/ (and again, on Patreon patreon.com/BlinkPopShift )

The four of us's "One Year of VR Research" from 2017: https://vimeo.com/1076506740

Originally I was interested in the history of non-computational tools and embodied cognition for the purposes of then coming back to see the potential of computation in a new light, particularly for emerging tech like VR, AR, and AI. That's what my research centered around back in 2014-2020.

Somewhere in here we could probably give a shout out to Project Management as a discipline, and tools like Gantt charts (invented by Henry Gantt in the early 1900s), which I know more about than I ever thought I would thanks to my time at Microsoft.

In my later years in tech research, particularly during and after the pandemic when I started getting pulled into more serious work with actual consequences for human lives, I learned that we humans know how to solve many of our biggest problems. We don't need more or better intelligence. We're smart enough, we have the understanding. We just choose not to do it.

Still, sometimes we do collectively decide to add something important to our societal to-do list, and I think it's possible we'll learn to get better at making meaningful choices together and sticking to them. And the tools we need to do that might be the simple ones, the ones so powerful and pervasive that we forgot how to see them.

Okay, now the real the-end! Thanks for reading!