Why does outlining my day in advance help so much?

[epistemic status: Hypothesizing. Pretty stream of consciousness. I’m rereading Thinking, Fast and Slow right now, and that has clearly been influencing my thinking.]

Advance outlines

More than a year ago, I read Cal Newport’s Deep Work: Rule’s for Focused Success in a Distracted World. Overall, I wasn’t that impressed with it: it seemed to be mostly fluff. There was one practice that I picked up from that book however, that made the time cost of reading it (actually, listening to the audiobook) worthwhile.

Newport recommends outlining your day, hour by hour, before the day starts. This outline is not intended to be a ridged schedule however: you’re allowed to deviate from the plan. However, if you do decide to change what you do in a given time block, you have to put that on the outline, and also reschedule the rest of your day in light of that change.

(It’s possible that I’m misremembering the actual procedure that Newport recommends. I think that his version has two side by side columns, one with a pre-made outline and the other to be filled in with how you actually spend your time? What I do, at least, is fill out a new column every time I make a decision to deviate from my schedule outline. It looks something like this:


In practice, I often don’t keep this up for the whole day. For the day shown above, “writing” ended up turning into a debugging meeting with a friend/collaborator, alternating with writing, and then going home to pack. [2] )

Outlining my day in advance like this has a pretty large effect on “how well my day goes” overall, my subjective sense of my own focus and productivity. The effect is not as large as waking up early and doing Deep work [3], but it is larger than the effect of a 20 minute meditation. My guess is that the effect is larger than regular exercise, but I’m much less sure of that. (All of these are eyeball’ed subjective estimates. It’s quite possible that my affect heuristic is failing me here, if my subjective sense of wellbeing does not correlate well with my actually getting things done and moving towards my goals. I really need to figure out some better metrics for my own effectiveness.)

A priori, it’s a bit surprising that writing a schedule that I’m not even going to stick to would have such a large effect. Why would this be?

I don’t know. But here are some hypotheses. These aren’t mutually exclusive. For all I know they all apply. I think at least some of these point at interesting psychological phenomena.


Hypothesis 1: It causes me to load up my goals and priorities in some kind of short term memory or background awareness. 

This might be subtle; I don’t know. There’s a thing about having my goals “loaded up”, or at hand to me, not far from my thoughts. Sometimes (like after a workshop, and before I have had time to orient) I don’t have my goals loaded up. I’m not taking actions to hit them, and I’m not experiencing any anxiety about them. I might spend the morning (or the day) doing whatever random thing, because I’m something like not tracking / not paying attention to / not primed to pay attention to / not remembering the things that I care about and want to accomplish? [I should probably study this experience more, so that I have a better sense of what’s going on.]

I think that one of the things that’s happening is that the outlining activity causes me to “load up” my goals in short term memory.

Hypothesis 3: It clarifies time scarcity and tradeoffs

There’s a temptation (for me at least) to act as if there’s infinite time. “I do want to write today, but I’ll do it later.” That kind of postponement feels costless, but it really isn’t. Something has to give. The procedure outlined above gives me a much more visceral sense of the scarcity of the time resource, and forces me to confront the tradeoffs. (For instance, I didn’t do math on July 1, I met with Diva instead. But that was a conscious choice.)

Being aware of the limits on my time supports me in spending it well. I’m less apt to waste time if I’m viscerally aware of what that actually costs.

Hypothesis 3: It allows me to rehearse my day / set TAPs / biases later decision moments

There’s something magical about walking through my day in some detail that, for instance, just making a todo list of three or four priorities, doesn’t do.

In order to schedule in blocks like that I have to visualize how my day will go in at least a little detail. And I think that future-pacing my day like that makes it easier to execute.

I’m not quite sure why this is. It might be something like that walkthrough lightly sets some TAPs, and particular, TAPs for transitioning between tasks.  For instance

TAP: Finish meeting with Ben -> walk over to my desk, take out “How to Prove It” and start reading the introduction).

Note that my current procedure does not have me visualizing the scene in detail like that, or explicitly setting TAPs. But maybe something like that is happening subliminally, as I think about how long I need to do a task and where I’ll be at that time of day, etc.

Another model in this vein (or maybe another frame on the same model) is that scheduling introduces a bias or directional tendency to my decision points. Throughout the day, I have a small hundreds number of moments when I need to determine my next action. Those moments include when I feel like getting up from writing to pace, or if I should go make food right now, or if I’m going to sit down to work on that python script I was writing, or if I should do Focusing on that thing in my belly.

Such decision points inherently entail ambiguity. Furthermore, there are really a large number of factors to take into account: my energy levels, what I feel like doing, if I have enough time to make progress on a thing, the nature of the tradeoffs between the various good things that I could do etc. I have policies and TAPs for making some of these decisions (one wants to live a choice minimal life-style), but most of these moments still entail some level of ambiguity and cognitive effort. And the more of the decision that falls to my current less reflective self, the more likely I am to follow a path of least resistance: taking a break instead of finishing this post, or doing something good but not crucial.

I think having rehearsed the decision in advance takes some of the load off, there’s a sort of echo of having already chosen, I’ve carved a shallow rut, so that the thing that my more reflective self decided was best to do at this time is the path of least (or less) resistance.

Interestingly, this maybe the same mechanism as hypothesis 1, except where Hyp 1 is about loading up goals, Hyp 3 is about loading up task-transitions. And the mechanism in question is starting to look suspiciously like priming.

Let’s clarify that claim explicitly: the main reason why prescheduling works is that it briefly puts my attention on my goals and the tasks to achieving them. This leaves a kind of mental “residue” [4], those goals and actions are more cognitively available. And therefore, those actions are given higher decision weightings at ambiguous decision points. [Plus, it makes time scarcity feel real. (Hyp. 3)]

Next steps

I’m not sure if any of that was even coherent, or if it is, if I’ll think that this is correct in a week.

After writing this, it seems like the natural next thing to do is goal-factor. Is there a way that I can get all the benefits of this procedure more cheaply? If I find a strictly better procedure, that’s a win. If I find a procedure that hits some but not all of the benefits, that would give me more data about the physiological structure in this area.



[1] I was nocturnal for this day because I was transitioning in advance for a Europe trip.

[1] I can easily check, because I separately track all my time in Toggl.

[3] I find that my day goes better the earlier I wake up, and that this trend is robust all the way up to as early as 3:00 AM. It’s really amazing to have long blocks of uninterrupted work time, while it’s dark and the rest of the world is sleeping. Unfortunately, this has the obvious tradeoff of making it hard to  meet with / spend time with other humans.

[4] I believe this is a technical term used for the cost of attention switching?

3 thoughts on “Why does outlining my day in advance help so much?

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