October 14, 2016
Forget todo lists. Use an online calendar with recurring events instead. Explicitly allocate time for good habits and be specific about how to spend the remainder of your time. Have places where you record stuff for later (e.g. notes, things to read, etc) such that you can do so without a big interruption. Schedule time to review all those places regularly and get them to “inbox 0” each time.
We can not solve our problems with the same level of thinking that created them. – Albert Einstein
Have you ever deleted your todo list and decided to start fresh? Have you wanted to re-evaluate your todo system and what software to use?
Dumb solutions to a smart problem beat smart solutions to a dumb problem. – ME
There is a lot of todo list software out there. My theory is that each time some creative person thought their todo system sux, they also thought the usual creative thing: I'll make a better one! The rest of us use existing project management software and complain about it.
Later, when there is too much stuff and you're stressed out and this and that, you bankrupt your todo list and re-evaluate. Meanwhile, the creative types are stuck dogfooding their new software. Remember kids, never write software.
So, everyone gets this piece right. There is a problem with your todo list system.
The problem is that it is a system for the wrong thing.
It's like being stuck in the woods, running in circles to stay warm and thinking you need a better system to run. You don't need a better running system, you should make a fire.
Building an awesome bridge when you need a house is dumb regardless of how good the bridge is, even though both can provide shelter.
The first principle is that you must not fool yourself and you are the easiest person to fool. – Richard Feynman
I like asking the following question whenever I encounter a new idea, discipline, tool, system, or whatever. Is this for self-delusion or for self-honesty?
Fool me once, shame on me. Next time use a fool proof tool, but you're still cool, fool. – ME
That's the problem with todo lists in a nutshell. They are a tool for self-delusion.
The cost of adding something to a todo list is ~0. A todo list with 3 items may be longer than one with 20. The todo list hides how long the tasks take and how they may get blocked. A todo list doesn't give good feedback. 
At best your todo list is aspirational. 
Todo lists sux.
: I don't mean to knock self-delusion too hard. Self-delusion is bona fide useful. Very useful, very often, even. Just not always. That's one for a different essay.
: Even if you kept all the history of your todo list, analyzing that teaches you very little.
: Some very-productive people are very good at keeping their aspirations attainable and doing other meta-cognitive things. Todo lists may work for them. I suspect they don't spend too much time reading about productivity on the internet.
Don't rely on motivation, rely on discipline. – Jocko Willink
That's basically the point, but I really like mixed-proverbs, so…
Relying on motivation is planning to fail. – ME
Motivation is great when you are motivated. The problem is timing. When motivation strikes and how long it lasts is unpredictable. As soon as your mind encounters something interesting you'll get motivated by that and demotivated to do what you were doing. Further, it is possible to go for long stretches feeling demotivated about everything. I'd argue that's the common case. It seems to be the case for me.
Don't make me think. – Steve Krug
Todo lists were invented to serve a good goal: freeing your brain from tracking what needs to get done. That way you can use your brain for what you need to do instead of for tracking it.
Fool me once, shame on me. Think twice, shame on me. It ain't no use in thinking twice, but it's still alright so long you write it down, honey babe. – ME
Some people advocate no todo list and keeping it all in your head without fear of forgetting stuff. Whatever you forget was not important. That probably works for some and probably within a narrow scope. For example, not having a todo list for a side-project may work well. But, your life is a lot more complicated than a side-project.
I suspect those who suggest this approach for avoiding todo lists actually have much better systems in place. It just happens that saying “I don't have a todo list” is way shorter than “I have 35 redundant productivity systems and none of them use the todo list abstraction.”
Either way, writing things down is good because it frees up your brain and that helps you focus.
Cognitive load sux.
I understand there's a guy inside me who wants to lay in bed, smoke weed all day, and watch cartoons and old movies. My whole life is a series of stratagems to avoid, and outwit, that guy. – Anthony Bourdain
Discipline, probably, has some bad connotations in your mind. Probably about being forced to do things you don't want to do.
Habitually good is way better than occasionally great. Optimize for the long term. – ME
What if I told you that you can put a positive spin on discipline? It is not a drill sergeant calling you maggot and demanding 50 pushups. It is calling yourself by your favorite name and pampering yourself into doing 50 pushups.
Discipline is doing the things you want to want to do.
Nope, not a typo. Discipline is doing the things you want to want to do.
Want to want is different than want. I want a pint of ice cream and a pack of cookies after eating 2000 calories worth of steak and pizza for dinner every day. I want to want to be in good shape when I'm young and have low probability of cancer and heart disease when I'm old.
Anyway, since discipline is such a bad word, let's just use another one: habits.
People often treat habits and productivity as separate issues. Strategies for habit building can be a deep topic of self-exploration, but I'll just link you to one post about habit-building that you should read at some point. 
Here is a cop-out way to show you that habits and productivity are basically the same issue. Your mental habits dictate everything you do. And I really do mean everything: how you learn, your emotional responses, how you behave, how you write code, how you do math, how you eat, how you walk – everything gets processed by your mind. Okay fine, you can't control things like your heartbeat with your mental habits, but that's about where it stops. Your productivity is, to a good approximation, what you do. See? The same.
That's a cop-out because it is true but not useful. It is really hard to actually observe your mind working. It's especially hard to observe what mental habits you have, let alone change them (possible, but a lot of work).
How to build habitual activities you want to do is more approachable and helps a lot. This is the gist:
1) Build one habit at a time.
3) Start small. Determine what a minimal time commitment is. That is, find the least amount of time you can spend on the habit which will bring the desired benefits. For a lot of things, e.g. meditation or getting started with a musical instrument, this is about 15 minutes. For some other things, e.g. getting in shape, it is more like 60 to 90 minutes. For some others it'll be only a couple of minutes e.g. brushing your teeth. Know why this number is what it is for your habit. Timers and clocks are your friends, they reduce cognitive load.
4) Explicitly allocate that amount of time for your new habit. Schedule it for when you'll be able to do it. Think of it as having an important meeting. Make a recurring event on your calendar, set reminders, the whole nine yards. The CEO of your mind will scold you in front of all of you if you miss this meeting.
5) Only worry about showing up at first. i.e. don't worry about how to best use the time, at first. Remove as many barriers to showing up as possible. Go to town with this. If the way to go to the gym daily is to eat 2 donuts before and 2 donuts after, so be it. Really pamper yourself into showing up.
6) When you feel like showing up is no problem, start worrying about making good use of that time. At this stage it is okay to start trying to remove some of the things you were using to pamper yourself if they are detrimental in some way e.g. start eating only 1 donut before and after the gym.
7) Get bigger. When you start feeling intrinsic motivation, allocate more time and figure out good ways to use it. This step is optional for a lot of habits, since you get most of the benefit from just doing the minimal thing e.g. brushing your teeth does not require this. You know you are at this step when you go to the gym on its own right, not because of the donuts, but because you want to go to the gym. It may take a long while to get here – think months or years. This is when the habit has set in.
For example, if you are trying to learn the guitar, first, allocate the time – put it on the calendar with the adequate reminders. Then add a journal for “guitar” in Way of Life. Then start showing up: pick up your guitar for 15 minutes when you are supposed to. It doesn't matter what you do so long you have your guitar in hand for 15 minutes. Once you are doing it regularly, make good use of time: get a guitar method and start going through it during your 15 minutes. As you start getting good, allocating more practice time will be easy if you want to – it'll start feeling good to play. That's intrinsic motivation. Boom. You now play the guitar.
Good habits are awesome.
: Do read Leif's post. It is really good. Just not right now. Use a bookmarklet for saving…uh… maybe just leave the tab open.
: Only a little bad instead of VERY bad is super important. You don't want to feel like it is all hopeless as soon as you miss your habit for a few days.
Don't tell me what you value, show me your budget and I'll tell you what you value. – Joe Biden
Would love to talk values, Joe. I can make 2p-4p ET next tues or thurs, send me a calendar invite?
Don't tell me your priorities, show me your calendar. – ME
Good systems for self-honesty have the following features: they capture all the necessary information and not too much more, they make tradeoffs explicit and clear, and they provide feedback i.e. it is easy and useful to analyze later.
What time-management tool has all of those features? An online calendar.
Explicitly scheduling your habits and the things you want to want to do won't be enough, but it's a start. Start there. This will provide some feedback immediately: you will see at a glance how many hours you have available. You will also see at a glance whether you can afford to add one thing or how adding that one extra todo just doesn't fit unless you sacrifice sleep, or this activity, or that meeting with Joe. Sorry Joe.
Not only that, looking back on your calendar will be an accurate record of how you spent your time or at least of what you meant to do.
So, that's a start, but not the whole thing.
If you are anything like me, you'll still have to fight yourself to actually do what your calendar says to do.
Doing as the calendar says can be hard because your mind interrupts the task at hand with other stuff that either is or seems important. This adds cognitive load, which sux. You want to eliminate that as much as possible. So, I suggest having one or a few simple systems for unloading things that you want to come back to later. Usually a simple text file with notes or a physical notebook is the best way to start. The most important aspect here is that it be very quick to dump whatever you don't want to be thinking about into it. Keep your systems as simple as possible until you really understand why complicating them would make them better.
Don't your notes then become a todo list?
They will if you fail to keep them in check. Here is where it all starts coming together. Feedback!
Regular feedback is very important. Have a regularly scheduled meeting with yourself, during which time you review your notes and calendar, and clean up everything. Ideally you'd empty your notes during each session. “Inbox 0” for everything. And guess what? Having these sessions is just another habit that you build and schedule in your calendar.
I have had good results with this system. 
Between having regularly scheduled time to practice guitar, actually practicing guitar, and keeping a good progress log, you might actually learn to play the guitar. When it seems that you aren't progressing fast enough it will be easy to realize things like “i've only put in 2 hours of practice in the last 4 weeks, let's try to do better next week” instead of thinking “i've been playing guitar for months now and i still sux, i'm so musically untalented :(”
Self-honesty is awesome.
: Also, once you are in the habit of using your calendar, it'll seem more natural to schedule time to do something than to add a note about doing it. As your various systems develop into being useful, the natural way to unload things from your brain will become more obvious and your notes will be the target less often. Eventually your notes will start becoming ideas and thoughts instead of todos, or to-reads, or to-whathaveyous. I think this is how Buddha did it, he used vim.
: My details, in case they are useful: I have weekly, monthly, and yearly reviews sessions scheduled. Each review session has a set agenda (lowers barrier) and they are related e.g. “review goals for the month” is an item in the weekly session's agenda. I keep my priorities for the week visible in a sticky on my desktop which I review and throw out after each weekly session (redundancy, they are on my calendar). Weekly and yearly sessions are similar. In addition, I keep notes and logs for all the activities that I want to want to do. The logs are simple: date, time spent, and brief notes. Logs could also serve as a seinfeld calendar, but I find that it is best to keep those separate. Seinfeld calendars are about whether you do it, the log is about making good use of the time and having good feedback. I have 8 daily habits that I track with Way of Life. And a few text files for things I want to read (reading is one of my Way of Life habits, and gets scheduled), movies I want to watch, and the catchall: notes. I have been using this system (or at least some similar version) for several years.
Do what you're told, and everything will be all right. – Norman Jewison
The most glaring problem that remains to be accounted for is the one of not doing what your calendar says to do.
No. – ME
And that one has been the hardest for me.
Some things that seem to have helped are: lowering my caffeine consumption, drinking less, exercising daily, waking up early, and meditating daily. But I'm not sure about any of them having really helped.
It's more likely that the habit of doing what your calendar says to do needs to be built like any other habit. Since this is what you have to do constantly, it is hard to track and train it like the other habits. Furthermore, it probably takes a long time to settle in.
I seem to have the mental habit of saying “No” to anything someone (including myself) tells me to do. The further down the hierarchy of mental-habits a certain habit lives, the harder it is to modify. So it goes.
Or it may be that good systems are hard and my systems still sux.
Or it may be that human minds will always resist doing what they are supposed to do because we evolved to survive an environment without Seinfeld, calendars, or todo lists. Who knows?
But I do know that having the calendar, and the reviews, and the habits, and the tracking, and writing notes, and – they have all added up to me feeling better about how I spend my time. Not self-delusionally better. Self-honestly better. I do more of the things I want to want to do now that I have my systems than before having them. I don't use a todo list.
And done! I just wrote a blog post!
Thanks to Nathan Collins, Michael Hueschen, and Nathan Schucher for helping me flesh all of this out and to Janet Choi for improving many drafts.
Discussion on /r/DecidingToBeBetter. I'll be reading and responding to comments there.