To-Do lists are the productivity tool, universally known and used. Yet, it’s not all rosy. For many people - including myself - it seems to be very hard to maintain and use a to-do list productively. They are very easy to abandon, easily forgotten.
Why is that?
This post tries to identify the common problems with to-do lists, but it is neither a rant nor a dunk. I will try to describe specific problems, for example why it sometimes feels like work to even look at our to-do lists. A lot of the experiences described will differ from person to person. I am sure you will find a grain of truth in most of them - however, maybe not in all. For all the mentioned problems, I will offer thoughts and solutions in the latter part of this post. Since I am not trying to hand out a death sentence but to expand the ways to-do lists can be understood, this post is likely valuable even if you love to-do lists.
Problems
The intro out of the way, let’s get to it. Why don’t to-do lists work?
Problem #1: Choice Fatigue
The proverbial kid in the candy store paralyzed by the overwhelming choice is not just a cute trope, it underlines a common psychological phenomenon: Choice Fatigue. When the human brain is faced with too many choices (and we are not talking that many to trigger this), it just doesn’t choose anything. It’s overwhelmed.
To-do lists are basically always either so short that it was kind of useless to even write them down or so long that the choice of which item to do next is indeed overwhelming. So what do we do when Choice Fatigue sets in? We opt to choose nothing, walk away from the situation and avoid it in the future. In the case of to-do lists: We do none of the items, put the list away and avoid looking at it as much as possible.
Problem #2: Dread
Another, less subtle problem also related to length or volume of the to-do lists is just the feeling of dread just looking at it, not even trying to pick a next item: This might be fear of failure, a feeling of impossibility due to the sheer volume of work, or a reliving of past failure to get things done.
Obviously, this leads to the very same avoidance behavior described above.
Problem #3: Arbitrary Order
The core problem here is that to-do lists are ordered quite arbitrarily, possibly by the order the items came to your mind while writing it down. This is not ideal for getting through the items - ideally you would have the items ordered in such a way that they slowly ease you into flow, or apply principles like “Eat the biggest frog first”. What’s the chance that the order of to-do items on your lists is like that? Of course, it’s possible to change the order of the items - especially if you have a digital list. Which brings us to the next (potential) problem.
Problem #4: Overengineering
Overengineering means solving a problem in an overly complicated (and thus, time- and energy consuming) manner. This is not an inherent problem of to-do lists - quite the contrary - but very easy to do once you start, say, ordering your items. And prioritizing them. And color-coding them. If the aforementioned actions actually help with doing the things on the list, then this is a very acceptable cost! Even if the customization is not strictly necessary but fun to do, fair enough. I will talk about this in a later section.
There are however two problems with overengineering: On the one hand, it’s quite easy to cannibalize too much time of actual doing by planning to do. What is an acceptable ratio of planning vs. doing? Hard to say, and very easy to justify spending way too much time organizing to-dos. On the other hand, do realize that the dread and choice fatigue mentioned above are not really gone, no matter how much organizing and sorting you do. Thus, you might face the very unpleasant situation of having put a lot of effort into your to-do list, and then still avoid looking at it ever. Doubly painful.
Problem #5: Bad items
Another problem which I want to discuss briefly is not related to the list as a whole, but to specific items. These may be items that are too big, ambiguous, outdated or missing a pre-condition. I will talk about them briefly later, but this problem is described and discussed very thoroughly elsewhere (see for example SMART goals).
Problem #6: Out Of Sync
The problems described above and the resulting avoidance of the to-do list create a spiral: You look at your to-do list less than needed, so it reflects less and less what you are actually doing, did do and have to do. What mostly happens next is that you start living your life without updating the list. You think of things you ought to do, but just keep them in your head. You start to-dos without having them on the list. You finish to-dos and don’t cross them off.
Gradually, this makes the list less and less valuable, because after some time, what help is it even? “Organizing the list” even becomes another unpleasant to-do, and it’s probably not even on the list.
Solutions
Still here after all this negativity? Great. Now I want to switch to a more positive note and offer some solutions, thoughts and ideas to fight the problems above. As usual, there is no single silver bullet and I don’t have all the answers, but I am convinced that most of the problems above are preventable to a significant degree.
You Only Need One Item At Once
A lot of problems with to-do lists stem from the fact that you always see the whole list. An important realization is that this is actually rarely necessary - it might be useful if you, say, try to get an overview on how you spend your time, but for adding, completing and getting your next task seeing the whole list is completely counterproductive. So, how do we hide everything but the next task?
The sad truth is that most tools just straight up can’t do this. But there are ways. Sometimes there is a feature or extension which helps, like this browser extension for Trello which displays the next item for a given task. If you are working on physical paper, you can get creative: Craft a stencil with a small window to only look at one to-do item at a time. Or put your to-dos on paper cards, stack them and only ever regard the first card on the stack.
My own productivity app, kaado.io, was actually built around this very principle. It can be used to organize different kind of productivity needs (to-dos, habits, learning, …) but crucially only ever shows exactly one item to do next, preventing Choice Fatigue as well as the dread of the overwhelmingly long list seen all at once.
Limit Overengineering
When you work your list one-by-one, you have an opportunity to fix the overengineering problem: Allow yourself to split up tasks, prioritize them, color-code them - but only the to-do item that is next in your list.
Say for example you cross of an item - nice - but then the next one kind of feels to big and hard to attack. You are then allowed to for example add a note with how to start this specific task, or even destroy the item and split it up in several smaller items. You are not allowed to go spring-cleaning your whole list, derailing your productive session!
It is also helpful to have a process in place in case you can’t or don’t want to do the due item right now. This will happen - remember Problem #3. If you are maintaining a stack of physical cards for example, allow yourself to put cards back at the bottom of the stack. Be aware however that you are walking a fine line, Choice Fatigue is just around the corner!
To prevent this foe from taking over, it’s helpful to set rules. For example: “When I put a card to the back of the stack, I say the reason why I did so out loud”. You could also make a commitment to always edit a to-do item before pushing it to the back of the list. Or make some tiny action towards getting it done, like placing the letter you have to send closer to your front day.
Having some habit like this is invaluable, but hard to build. A good process is easy to do, but it will probably be very easy not to do. Thus, regular introspection and analysis is needed. Are you cheating and putting items to the back silently? However, if you are not, you are actually also solving Problem 3, because kinks like cards that can’t be started etc. are slowly getting ironed out.
Recognize Leeches
Leeches is what the learning tool Anki calls flash cards whose contents you just can’t memorize. They leech of your learning time without adding any value.
The same principle applies to some to-do items: If you have a system where you only see one item at a time (recommended!), these are the ones you always skip. If you have a system where you see your whole list, these are the lines of text you try to not read.
Every time this happens, a bullet is added to the magazine of the voice in your head who is calling you a failure, because you didn’t do the thing, again! Of course, this makes it more unlikely that you attack the item next time ‘round, because you just want it out of sight as soon as possible. A dangerous cycle! It can make the to-do list as a whole deeply unpleasant to interact with. And these leeches sneak up on you, they are often trivial little action items which you just won’t do.
Recognizing these is very valuable, and I wish more tools would support this feature out of the box.
Make It Obvious
A core tenant of habit building described in the glorious Atomic Habits is the principle of making things you want to do obvious. This applies here as well, in multiple ways. Items should be obvious, as in, clear in their goal, clear in how to start them and clear in when they are done.
For the list itself, the same principle holds. If it’s physical, keep it in an obvious location near you. If it’s digital, have it automatically start when your computer boots. If it’s an app, consider enabling push notifications. If it’s a webapp, there is the New Tab Override Extension allowing you to always load your to-do list in each new tab you open.
Make It Fun
Last, but definitely not least is making the usage of your to-do list pleasant (this is also mentioned in Atomic Habits - I told you it’s a good book). This is related to the previous point - you shouldn’t have to get up to know what the next item is, and you should not have to go through a multi-step sign-in process either.
But even apart from that, some to-dos will just be unpleasant. And their unpleasantness will rub off to the general look & fool of whatever tool you are using. So you do need to counterbalance that. Aesthetics help: Use an app you consider good-looking, use quality paper to write on. Gamification helps: Keep a score of things done, reward yourself for x items done. Habitica is a good choice if you interested in the latter.
Another idea is to put pleasant items on your list. Ever considered explicitly putting “book a massage” or “watch an episode of trash TV” on your to-do list? Of course, this only makes sense if you have a working system which exposes you to one item at a time only. Otherwise, it is likely you will only do the pleasant items on your list. The underlying principle here is a variant of Variable Rewards, a psychological concept stating that a system is most pleasant to use when you sometimes get no reward, sometimes a big one, and sometimes a small one. This effect is well documented, but even if you don’t subscribe to the theory, it is just more interesting to get a fun to-do item once in a while then to know that it’s always going to be dreary, boring or exhausting. Kaado.io allows you to randomly intersperse quotes, art, memes or other entertainment in between to-do, habit and learning cards.
Making It Fun might sound silly or even childish, but I can’t recommend it enough, personally. It does not have to be gaudy - even an intermezzo of “take a short walk” or a picture of visualized goal of yours in between the other to-do items can make a huge difference in terms of long term motivation.
Summary
You reached the end! There is not much more to say - the purpose of this post is neither to glorify or denounce to-do lists, but to offer thoughts on their shortcomings, potentials and possible improvements. If I could answer the question of why to-do lists often do not work very well despite their popularity even a little bit, I have succeeded here. I hope you could take something away, and please do share your experience with managing to-dos.