Much TODO About Nothing

For the longest time, during the pre-smartphone days, before there were all manner of task-tracking and note-taking apps, I carried around an 8.5" x 11" sheet of paper in my pocket along with a little pencil (stolen, err borrowed, from my local library). The paper was folded in half 3 times so it was about the size of a billfold, and on it was written my near-term TODO list. And without fail I completed almost everything I had on my list every day. And every night I would write out the next days TODOs on a clean panel of the sheet of paper (using about 1 sheet per week), and repeat this cycle, with 90-100% completion, daily. The system worked gloriously for nearly a decade.

And then I switched to a smartphone. And TODO lists become longer. And slightly more abstract. And way more ambitious. The formatting was off the charts, but I felt I was getting less and less done every day. This went on for about 5 years, with my TODO list being a braindump and me using a variety of other tools (GMail, Outlook, JIRA, stickies) to actually manage short- and long- term tasks. Because my TODO list had become a catch-all blob, it was hard for me to focus on the top n things that really mattered each day. Moreover, it was (too) easy to tack items on and I was getting less and less done daily; and the feeling of getting less done every day compounded my waning confidence in getting things done, period.

So I switched up the structure a little bit. About 7 years ago I started bucketing my TODO list into 4 areas:

ibrahim @ibscribe

revamping my todo list: (1) today (2) tomorrow (3) every day (4) some day

I’ve gotten really good at making "everyday" TODOs a habit now, which is why I don't need to put that at the top. I keep "today" short and prioritized so that I can actually accomplish things. And "tomorrow" is an exercise in pushing from "today" and pulling from "some day". Periodically, I sift through "some day" and just drop altogether. This approach has been working pretty well, both personally and professionally.

But lately, in my more Luddite-like moments, I wish I could set aside the smartphone. As much TODO prowess as it gives me for my GSD lifestyle, it also comes with all sorts of notifications and reminders and interruptions and distractions. Strangely, or predictably, I miss the sheet of paper and the little pencil.

And I can't shake the feeling that I got more done back then. And was more efficient too. I've been mulling over why that might be the case, and I've arrived at a counter-intuition conclusion: the smartphone has nearly eliminated any friction in my task management routine, but it was precisely that friction that forced me to prioritize and focus. Having to rewrite a TODO list from scratch every day meant a few things, implicitly:

1. it felt weird to rewrite the same task daily, so I would either finish it or convince myself (usually correctly) that it wasn't a priority - my smartphone TODO list easily becomes a stale pile of task laundry

2. I was limited to 1/8 panels of the folder letter-size sheet of paper - the TODO list had to be finite, even with my chicken-scratch handwriting - my smartphone TODO list goes on for many page scrolls

3. in order to add something, I would have to drop something, or write sideways (which drove me nuts) - my smartphone TODO list is a little too accommodating when it comes to piling on

4. I could only add to the bottom - my smartphone TODO list allows me to introduce new items for "today" and interrupt any flow I'd conceived the night before

Now, I know what you're thinking. Can't I just aggressively prune my smartphone TODO list daily and achieve the same results? Maybe, with discipline, but more often than not, I know I don't have to; it's already pre-populated for every day with the things I haven't gotten done, whereas before I was starting with a blank panel on a sheet of paper unless I explicitly put something on there. And that is the biggest psychological difference now in my view; starting fresh daily is a different mindset than picking up where you left off yesterday.

So I'm seriously considering going Luddite and returning to physical vs. digital. Hopefully the local library still has those little pencils.

Would love to hear from readers about their TODO list hacks…

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further reading / references

• A Brief History of the To-Do List and the Psychology of Its Success

• the Zeigarnik Effect explains why we remember uncompleted tasks

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childish drawing / interpretation