Ryan Singer

June 14, 2021

13. Beyond to-dos

When work is turned into tickets, our brains shut off. In ticket-land, the work is a given, and it's just a matter of "doing it." This is true for any traditional to-do software.

The thing is, when smart people tackle work, they actually do work on the work to figure out what the work is. They do it in their heads or on paper next to their laptop or on a whiteboard — not in some to-do app. That's because traditional to-do tools are made to account for work, not figure out what the work is.

One of my pet projects has been turning the tools that super effective people do in their heads into patterns we might implement in software. Here are some examples I've been prototyping.

The first is affinitizing — which is like categorizing except you don't have any of the categories in advance. It's a way to chunk things up by likeness and let the categories emerge. Today I sat down to do a bunch of code and UI implementation on a project I'm wrapping up. (It's an unconventional workflow for inviting someone on another account to share data.)

First I just dumped everything I had in my head that I thought I had to do. I made an explicit "WIP Dump" box for this on the left. Then on the right, I made a set of unnamed boxes for groupings.

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By dragging and dropping, I narrowed those down to a smaller number of groups (corresponding to scopes in Shape Up).

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I named one of them "Acceptance" — work related to accepting an invitation to share. The rest didn't need names.

Looking inside the "Acceptance" group, one piece of work I had dumped was very fuzzy. So I reached for another tool: unpacking. This is the opposite of aggregating. It's digging inside of one thing to get more things out of it.

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Zooming back out, all of those unpacked pieces went back into the Acceptance box:

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Now that the work was broken into separate scopes, it was easier to dive in. But I knew I wouldn't get everything done. Today was the last day I had budgeted time to finish the feature. So instead of "doing" everything, I added another alternative: "cutting." Some stuff just wasn't going to make it into release.

Here are the boxes segmented to show a hard day's work and non-work. Finished stuff moved down into the grey "Done" box, and cut stuff moved into the dotted "cut" area.

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Another tool I often reach for is the interrelationship diagram. This is for sequencing: figuring out what to work on first, second, etc.

I had a couple hours set aside to kick off a research project. There were a bunch of tasks swimming in my head. To settle on what to do, in what order, I first dumped everything, and then drew an interrelationship diagram.

Like in the affinitizing example, I dumped whatever was in my head into a box on the left first:

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Then arranged the items on the circle, and drew arrows to show which things are inputs to which other things.

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Here's where it gets a little mathy. Each of these tools can be used on the others. I didn't feel like I was getting warmer yet (it still looked like a tangle of random things) so I reached for the affinitizing tool. The arrows just followed the tasks as I dragged them into the boxes.

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This time I found it helpful to name the boxes. Naming can boil things down that were formerly complicated into a few words, giving handles for the things I'm thinking about.

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Now that the boxes are named, I could simplify by running interrelationship again at a higher order. This is applying the same process (think of it like a function) but taking the outer boxes as inputs instead of the inner boxes.

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This last picture was simple enough that my brain finally relaxed. "Okay — I'll set up the Calendly event, compose the recruit email, send that for review, and ... while waiting on that ... start on the last recruit steps and pick the email tool for blasting."

These tools demonstrate the difference between merely accounting for work vs. working on what the work is. From dumping what's in our heads, to hardening it into pieces of real work, to sequencing and making decisions about what's in and what's out given the interdependencies and time pressure.

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I'm not sure what this is yet, but I'm sure it's something beyond to-dos.





Thanks to Bob Moesta and Greg Engle for teaching me the affinitizing and interrelationship methods.