My to-do list addiction as a high leverage meta-habit

Over the past 4,093 days I’ve completed 43,736¹ to-do’s.

Creating my to-do list habit 11 years ago when I was deeply struggling to understand my place in the world, and then re-committing to it mid-PhD (even more strugs) a few years later was one of the primary moves that pulled me out of the downward spiral I was in and put me on the path I’m on today.

Since then I’ve completed an average of 10.7 to-do’s/day. After switching to Todoist and starting my company ~three years ago, I’ve completed an average of 21.2 to-do’s/day. And over the last three months since going through CBTi (and also doing a round of ketamine therapy + beginning somatic therapy) my daily average has increased to 30.1 to-do’s/day, which is some of the clearest evidence I have of the efficacy of these interventions.

My to-do list is one of my most valuable keystone habits and it plays a pivotal role in nearly every aspect of my life. The reason for this, I believe, is that used correctly a to-do list can become an incredibly powerful meta-habit—i.e. a habit that makes it easier to create other habits.

To-do lists as meta-habits

“Civilization advances by extending the number of important operations which we can perform without thinking about them.”

–Alfred North Whitehead

The basic idea here is simple. Habits are a useful tool to complete actions without the use of willpower, other than the initial expenditure necessary to create the habit. To-do lists are a special sort of habit by which we can often easily create certain other new habits with only a nominal amount of extra willpower, by leveraging the habitual nature of completing to-do list tasks.²

This obviously doesn’t always work, but if implemented correctly it can be a powerful strategy to easily kickstart the creation of many new habits.

A few habits I’ve built effortlessly this way

• lots of boring logistics stuff like changing my sheets, replacing my tooth brush, checking credit card charges, staying on top of races or conferences I’m interested in, experimenting with various diet/health interventions, replacing air filters, resurfacing books I want to read or podcasts I want to listen to, etc
• drinking more water
• eating more fruit
• doubling my protein intake—went from ~60 g/day -> 120 g/day just by adding a twice daily reminder for protein intake
• building a daily gratitude practice
• starting a weekly stretching routine
• staying in touch with grandparents more frequently
• collecting and reviewing writing ideas (like the idea for this blog post!)³
• setting up various kinds of personal knowledge base reviews—e.g. a ~bimonthly review of all of the best fundraising or recruiting advice I’ve received
• becoming a better friend—e.g. when I know a friend is struggling one of the first things I do is set a twice-weekly reminder to reach out to them for hangs, support, or just check-ins
• becoming better at delegation—I keep this quote as a monthly recurring to-do to remind me to prioritize effective delegation: “By working longer hours you can get 20% or even 40% more done, but with effective delegation you can get 10x or 100x more done.” –Jonathan Swanson
• sharing my gratitude for others with them
• setting aside deep work time to think about important problems
• generally fighting entropy
• starting a monthly volunteering practice
• doing one thing each day that scares me
• staying on top of the scientific literature—11 years of browsing my research RSS feeds first thing every morning, then pushing usefully interesting articles to my to-do list to read later has helped me acquire a vast breadth of scientific knowledge
• collecting, reminding myself of, and implementing various lifestyle design choices I’d like to try
• rereading a handful of my favorite articles, inspired by this Ben Kuhn tweet
• checking for new biotech IPO’s to potentially invest in
• sharing my Kindle highlights on Goodreads every week (more people should do this plz)
• the meta-meta-habit of being more focused with what goes on my to-do list and gets prioritized by setting up a weekly reminder to prune extraneous tasks

My last week in to-do’s

What I’ve done well

Most people overestimate what they can do in one year and underestimate what they can do in ten years.”

–Bill Gates

“Your mind is for having ideas, not holding them.”

–David Allen

The very best thing I’ve done in regards to my to-do list habit is just to stick with it, using basically the system, for over a decade.⁴ The sum of many small, habits, optimizations, and knowledge intake can accrete into something wonderful over a long enough time period.

I’ve been religious about one of the central ideas espoused by David Allen’s GTD system which is to move actionable thoughts to your to-do list as quickly as possible. I can’t emphasize enough how important I think this is for good mental hygiene (at least for a certain type of brain). For me the ability to move future-actionable thoughts out of working memory quickly has freed up a ton of mental energy for all sorts of more interesting thinking. This, in conjunction with the habit of always writing down and reviewing any ideas I have,⁵ has been the key to my scientific creativity. We all only get a limited amount of thinking energy over our lifespan. Why waste it on remembering things that a computer could do for you?

I’ve also done a decent job of not falling into the trap of only having to-do’s that look exactly “task-like”—e.g. many of my to-do’s are simple open-ended problems such as “spend five minutes thinking about how you can move 10x faster” or “think about first principles approaches to living a good life”.

Finally, this habit has been extremely useful to keep me moving towards the goal when I’m tired, unmotivated, or depressed. In times like these I can almost always find small but useful to-dos with which to retain my forward momentum, and this has helped pull me out of many negative feedback loops more quickly than otherwise.

Obvious pitfalls

The most obvious pitfall is the risk of over-systematization and bias towards completing tasks at the expense of all the joy, romanticism, and serendipity that actually make life worth living. Relatedly, there’s a common “eyes bigger than your stomach” phenomena where having a place to capture to-do’s effortlessly can lead one to creating significantly more tasks than are feasible or worthwhile to complete.

I’ve definitely fallen prey to both of these, and still do to some extent. My best advice here is just have a very high bar about what goes on your to-do list, and to set up a weekly meta-habit to ruthlessly prune ones that don’t spark joy, aren’t truly important, etc.

Another common and related failure mode is to bias towards completing easy, close-ended tasks at the expense of more important, harder, open-ended ones. My solution to this has been to just break down the latter type of tasks into much smaller and more actionable chunks such that they have roughly the same activation barrier as the former. In practice this means that instead of having tasks like “write an executive summary for your company” I’ll instead make a ~daily recurring task to “spend five minutes working on your executive summary”.

Lastly, I’m not convinced that having a to-do list at all is a required ingredient for a happy or productive life. There are plenty of examples of people who have achieved both without anything more than their mind as their productivity tool.⁶ This is only weak evidence, but it does shift my priors away from believing in the power of to-do lists slightly.

My system

My system is pretty simple, I’ll write more about it some day but here are a few of the key pieces:

• Every usefully actionable thought I have goes directly and immediately into my to-do list, tagged with a date and a specific project/life area. If I don’t have time to think about how it should be categorized upon entry I just leave the project untagged (defaults to #Inbox) and put the date as today so there is a bias to categorize it correctly soon.
• Projects are usually fairly large buckets so I don’t have to think to much about where things go, e.g. Work, Health & Fitness, Things To Do, Learning & Self-Improvement, and Media.
• Tasks also get a priority from P1 to P4. P1 = important, urgent, ughy, P2 = recurring reminders, P3 = important but not urgent, and P4 = everything else.
• I’ve also started using sections and/or other projects recently in Todoist to put things that I know I want to come back to at some point, but don’t have an exact date for. Usually for things like this I’ll create a ~quarterly reminder within that section to check to see if any of the contents have become relevant.
• On desktop I use the quick-add shortcut (for me ⌃⌥A) religiously, and on iOS I have a quick-add widget set up on my home screen. The goal is to be able to add to-do’s as quickly and seamlessly as possible.
• I also have an IFTTT integration set up to copy any iOS reminders -> Todoist, so that I can easily use Siri to add to-do’s as well. This is most useful when I’m in bed about to fall asleep and some thought comes up that I want to write down.
• Day to day I run my life off the Today view, organized by priority and sorted by project.

Notes