I want to start by talking about the emotional experience of working with a todo list. 

The biggest hurdle todo faces is that the emotion you generally experience when you look at your todo list is shame. This is bad because it makes you uncomfortable with the tool and makes you want to avoid it — you don’t want to look at it because engaging with it makes you feel bad, so you don’t use it, or you wait until it’s too late, you avoid it, etc. etc. 

The key to fixing this is coming up with a todo system where the emotional experience is pride. This way you often want to look at your todo list, you enjoy the experience of working with it, you approach it, you seek it out, etc.

To help describe ways we can do this, I’m going to go over some of the pen-and-paper todo systems I’ve used and describe how I think they fulfill the goal of making the emotional experience of working with your todo list one of pride rather than of shame.

Example #1: Digital Painting Calendar

Back in 2017, I was trying to learn digital painting. I was enjoying keeping up with it, and so I set myself a soft goal for myself of trying to do some digital painting (even if only 10 minutes) almost every day.

To keep track of this, I printed out a single-page calendar for the year, and simply marked off every day where I did some digital painting. By the end of the year, I was so proud of this that I saved an image of the calendar, reproduced below. I think I have the hard copy somewhere, even. This was such a positive experience that looking at it STILL makes me proud, even years later: 

Why did this work so well? I think there are a couple reasons.

First of all, the goal was low-commitment (any painting at all). This encouraged me to start painting often, and 10 minutes often turned into 3 hours. But this is a feature of the goal, not the todo system.

The goal was also simple. This helped the todo system, because it made it very easy to determine whether I had “earned” the right to check off each day. 

The scope of this todo system also has some great features. Because the scope is a year long, as soon as I missed one day, I knew that there wasn’t a chance of me getting 100% on the full year, which made it feel lower-stakes, while still being important. Early failures made the stakes not feel catastrophic, which decreased the threat and sense of shame. Incidentally, I think this is a strong argument against the use of daily streaks in todo apps. Streaks are a threat, not encouragement.

The calendar is also naturally split up into sub-units. There are 12 months and about 52 weeks. This means each week and month could also stand alone for success (or failure), keeping the local stakes high enough to be engaging while still avoiding feeling catastrophic. You’ll see that I completed several weeks perfectly. I also tried (and failed) to do every day in April, then tried (and succeeded) to do every day in October. Having these “local stakes” increased the chances for feeling proud of an accomplishment while keeping the total stakes low in terms of failure. I feel good that I 100%’ed October, but I don’t feel bad at all that I missed a bunch of days in December.

I also think this system works well because it covers just ONE of the tasks that I had on my mind then. I did other things in 2017, but this document doesn’t even try to cover those aspects of my life. I wasn’t overwhelmed when looking at it, and it forms a nice historical document that isn’t cluttered by unnecessary context.

Finally, I think this system works well because it pushes back against what I’ll call “the Tetris Problem”. This is something we will come back to again and again. Namely, the Tetris Problem is:

In this todo system, however, both errors and accomplishments are equally and fairly presented. There’s also some value in the fact that they are presented as fact (did I do painting this day or not), rather than as a judgment.

Example #2: Trello

I mostly don’t like Trello, but one thing it gets right is the combo of cards and checklists. 

When you have a checklist of 10 things, as you burn through it, the checklist fills up. One day 3/10, then 5/10, then 9/10. When you hit 10/10, it gets bold or changes color or something, I don’t remember. 

The important thing is that this turns Tetris on its head. In this system, accomplishments pile up, and errors are nowhere to be seen. 

Another nice feature is that accomplishments pile up at multiple levels. Completed checkboxes pile up in a list. Completed lists pile up in a card. Then, when the card is all finished, you get a final rush when you drag it to the “completed” pile. 

Importantly, the accomplishments don’t disappear until you manually choose to put them behind you. This is a critical difference from Tetris! With Trello, you bask in your accomplishments for as long as you want — until you say, “this was good but I’m ready to put this chapter of my life behind me, let’s move on to some new projects!”

Though this makes me wonder, should a system have a “trophy case” rather than a “completed” deck? A good point of comparison might be the “run complete” screens from recent hit video game Hades. Every time you successfully escape from hell, the game shows you a bunch of stats about your last run and you can bask in the success as long as you want. This seems like a nice feature.

Example #2.5: Trello Mimic on Paper

I copied this approach a little back when I was teaching, except I used a pen-and-paper approach rather than Trello. 

Unfortunately I don’t have pictures, but the general idea was this. I pinned a 8.5 x 11 piece of paper to the wall in front of my desk, where I could easily see it every day. Then, what I did is I scoped out all my teaching duties for the semester in a bunch of vertical checklists. I don’t remember the exact numbers, but something like, there were 12 weeks of lectures, 5 major assignments, 3 exams, etc. Each got a checkbox, and as I hit each milestone, I would check it off — one week down, one exam graded, etc.

This wasn’t quite as exciting as Trello for some reason. It didn’t make me feel proud, but it certainly didn’t make me feel shame. I didn’t have any problem looking at that list, and it gave me a good sense of progress as I slogged through some of the dumb-ass grading they made me do lol. I think I would have liked it more if I had felt better about the classes at [SCHOOL REDACTED], but I did not!

I notice that like the digital painting calendar, the scope of this was pretty long-term. I think that is part of what I mean when I focus on accomplishments piling up — it’s not enough for them to just pile up, they need to stick around for a while. It’s also useful if accomplishments produce ephemera, like the calendar, or like these checklists.

A semester may not even be a long enough scope! As a teenager, I mostly thought about tasks in terms of weeks and quarters. When you’re young, your life is explicitly structured around these short-term horizons. But as an adult, I am already starting to think about progress in terms of years, even decades. 

Compare also to the traffic stats interface provided by WordPress for this here blog. Normally we look at traffic per day, but we can immediately zoom out to look at weeks, months (seen below), or even years at the click of a button. With this, we can appreciate a greater scope whenever we want, and it can be nice to see how far we’ve come.

Example #3: Post-its in College

A long-term sense of accomplishment is important, but when we talk about todo, we also need day-to-day elements.

The best todo system I ever used in my life was in college. At the beginning of every week, I took seven post-it notes, one for each day, and wrote out my major milestones for that week. As I went through the week, I would check each off in turn, adding and removing tasks as needed. 

I don’t have any photos, but here’s an artist’s impression: 

At the end of the week, I would pull all seven off the wall and replace them, which was always incredibly satisfying. I felt like I had slaughtered the week every time. 

I do worry that a digital system will never be as satisfying as physically checking boxes and peeling post-its off my dorm room walls. But Trello for all its failings did give me some of that, so I’m optimistic. Probably the thing to do here is to look to the world of game design, to the concepts of game feel, AKA “juice”. Need that screen shake on my checkboxes!!! 😛 

If this system was so great, why don’t I still do it today? Strangely enough, I think it comes down to a few simple factors. In college, I always had only one desk, which was in my room. Ever since then, I’ve generally had one home desk and one work desk, and even that small amount of separation is enough to kill this system. In college, my desk always faced a blank white wall, perfect for hanging post-its. These days, my desk generally faces a window, to reduce eye strain. Trade-offs, man!

There’s also the fact that, when most of my todos were clearly tied to classes and student groups, it was easier to plan a whole week in advance. These days, my schedule is actually a bit too flexible.

Either way, this was a great system and I think there are a lot of lessons here.

The first thing you’ll notice is that, as before, accomplishments pile up. Every week, I knew what I had accomplished so far that week. Even if I missed a task on Monday, if I managed to get to it on Tuesday, I could go back and check it off Monday’s list.

Planning for the week helped keep me from carrying a todo from day to day. These days I still use post-its, but only one at a time. If I don’t finish a task today, I add it to the post-it for the next day. But this is a bad habit, and stressful too. It encourages me to carry many tasks in my working memory (and/or the paper equivalent), rather than spacing them out across seven post-its.

With the old system, I would have put the task at the point in the week when I thought I would be able to accomplish it. I didn’t get to it that day (which did happen sometimes), I would be able to see that it was overdue. This helped give it a naturally higher priority, and made for a clear indicator of just how overdue it was.

It also helped conflate personal and professional accomplishments. Now you may say, why would I want to conflate these? Isn’t it better to treat them differently? Well, I worry that too many people try to keep their work and their personal accomplishments separate, when both are controlled by the same limited resource — time. Having “get groceries” on the same list as “finish term paper” was a nice structural acknowledgement of the fact that both tasks trade on the same resource. I think it kept me from feeling bad when I didn’t get any “work” done in a given day. Hey, those personal chores were important! They were on the list!

It also helped that post-its are small. This reflects the limited time in a day and kept my ambition focused. I could only ever list a few tasks, so I figured out what I really needed to finish each day. It encouraged me to break up big projects into reasonable pieces, each only a couple of hours long, so I could check off a piece of the project on a given day. 

There’s another element which is also critical, but harder to explain. Nonetheless, I strongly believe it to be true. Having these limited post-its encouraged me to 1) do everything on my list as soon as possible, and 2) filled me with energy and a feeling of freedom afterwards. The same experience is described by Sasha Chapin:

And echoed in the responses: 

Whatever the reason, this is definitely a real phenomenon. In college, I churned through my requirements with astonishing speed — and then continued working really hard at whatever I was interested in.

This may have something to do with what Scott Alexander has called infinite debt (see also here). Your school/work/personal/whatever obligations — your schedule obligations — are in some sense infinite. You can always come up with new things to do. Like the moral equivalent, this can make your todo list feel really bad and overwhelming. This makes for bad designs — you don’t want to look at your todo list and feel like “your work will never be done, you’ll never be good enough.” Ouch.

In contrast, by scheduling finite goals for each day, you can give yourself the sense of being on track — not discharging all of your schedule debt, but discharging all your schedule debt for that day. After that point, you’re free for the rest of the day! 

This works even better with my post-its-for-the-week approach. By scheduling out the major milestones for the week, when you finish your tasks for a day, you’re not just on track for the day, you’re on track for the week! 

This can even give rise to a feeling that is so powerful and vicious I can only describe it as “bloodthirsty”. Since your schedule debt is effectively infinite, you normally have no chance of catching up, let alone getting ahead. Scheduling out the day is better because you can catch up and be on track, but you still can’t get ahead. But if you mark out your milestones for the week, you can actually get ahead of schedule. If you finish your work for the day, and you feel energized (which you often will!), you can get that bloodthirst and chew through the tasks for later in the week! That makes you feel more accomplished, and it also gives you more free time later in the week, leading you to get even further ahead — it’s a positive feedback loop! 

The trick here is making each day’s set of tasks accomplishable in the 24 hours you have. But you should be doing that already. If you do this right, you feel great, you’re more productive than ever, and you get “bonus time”!

Example #4: The Modern Hybrid

Right now I am using something that is kind of like the pen-and-paper Trello checklist approach described above, but I’ve added a few features that I think are important. 

This fills a different niche from the post-its (and you could probably use both). Rather than daily organization, this is the near-term scope of 1-3 months or so. 

There are two-long running goals I’ve had for my todo organization, which I’ve struggled with, but I think these todo lists are starting to approach it nicely.

The first I’ll call “families”. This is simply a recognition that, while all tasks trade on time, different tasks belong to different classes or families. You have your personal list, your chores list, your work list, your hobby list, etc. Personally I find it very disorienting if I don’t keep track of which task goes in which family — or worse, if I don’t know how many families of tasks I have going on at all! This makes my todo list feel infinite, and as we covered before, infinite bad! 

So on the subject of families, you’ll see that my checkboxes are broken up into different sections, so I know how many families I have and what task belongs to which. I think any todo list worth its salt will break things up visually — possibly by color or shape, but even better is to be broken up spatially.

My ideal software would let me slide around tasks and families on the page much like I do when laying it out with pen and paper. This is another thing Trello approaches with its spatial organization, but you could certainly go a step or two further.

Families also serve my second goal, which is a clear representation of dependencies. Tasks within a family often have a clear priority structure and sometimes even have literal dependencies, where one thing has to come before another. 

I’ve always really wanted a good way of representing dependencies, but actual graphs/connections and so on never worked for me. But in this notebook system, simple layout alone seems to work pretty well. In my first two passes (above), dependency is roughly indicated by a combination of left-to-right and top-to-bottom, like English reading direction. Things lower on the page and further to the right are generally lower priority and/or depend on things above and to the left of them.

Below is my most recent version, which instead uses top-to-bottom alone to indicate dependency. Each column is a family, and vertical order approximately indicates priority and dependency, with items higher in the list being higher priority and being requirements for lower items. 

I say “approximately” because it turns out, you don’t always need to indicate dependency explicitly. A todo list is a memory aid, not a memory replacement. I can remember what the dependencies are — the vertical organization just makes it easy for me to think about it, compare across families, not worry about tasks I haven’t reached yet, and so on. 

Having a quick visual shorthand for dependencies is useful and saves time. Actually bothering to map out all the dependencies tends to look cluttered, and does not save time at all.

In conclusion:

To make you feel pride rather than stress or shame, the ideal features of a todo system are something like:

1. Accomplishments accumulate
2. Long-term scope to see the arc of your success
3. Multiple levels of scope to get sense of reward at multiple scales
4. Recognize that tasks and events all compete for one resource — time 
5. Limit your daily tasks and get “Bonus Time”
6. Clear visual families & dependencies, probably through spatial organization