The Doc Project

12 tips on writing great to-do lists (from a guy who's bad at writing them)

Producer Tom Howell sets out to learn why he has such a hard time getting things done and how to-do lists can make or break your progress.

From bitter experience, Tom Howell set out to learn how to write a to-do list that might actually get done

The pile of unfinished to-do lists has been dubbed "Hopeless Mountain." (Submitted by Linda Besner)

While re-organizing my home office to make room for my girlfriend to move in, I found 20 years' worth of old to-do lists in various notebooks and on loose papers.

This has prompted some thoughts on the practice of list-writing, such as: "I am really bad at making to-do lists," and "Why is it so hard to be an adult?"

Here is a typical to-do list from my accidental archive.

(Tom Howell/CBC)

That one is also a shopping list, obviously, but the open borders between categories of tasks, shopping, life ambitions, and general aspirations accurately illustrate my list-writing incompetence.

During one period, I think around 2005, I apparently abandoned bullet-listing altogether and tried writing my to-do lists as paragraphs. I don't remember why this was supposed to help.

(Tom Howell/CBC)

Some of the lists reveal the frustration of other sectors of my psyche, which begin uttering retorts at the main list-making personality. "How?" they whimper. Or, "Now!" they bark.

And at other times, I have switched up the technology. For instance, chalk.

(Tom Howell/CBC)

"Tax prep" is a pretty common item throughout the archive of to-do lists, since one of the consequences of my struggle with personal organization is that I am always somewhere between six months and a few years behind on my tax returns.

It's hard because dragon drugs and yeast are so much more urgent, for reasons I surely don't need to explain.

But I didn't come here just to complain about myself at you.

I came here to offer the tips I have picked up during the course of a wide-ranging search for help, and answers on what's been going wrong with my to-do lists over the years. This search has taken me into conversations with masters of the self-employed worker game, with clinical psychologists, and with some new friends I made at the Canada Revenue agency along the way.

To-do list to-dos

Here is a collection of my findings, for your consideration: 

1. Items on a to-do list should take about 15 minutes or less to complete.

2. The list should not exclusively contain things you don't want to do. (Put some fun stuff in there, too.)

3. Lists ought to lead toward a specified goal, such as a reward.

4. The list-making tone should not be condemnatory or angry.

5. One's ego must sometimes be cajoled as one might cajole a defiant teenager.

6. If you work from home, it may help, before beginning the list of tasks, to get dressed, leave your house, walk around the block, and re-enter the house as if arriving at an office.

7. It is easier to do things for others than for yourself, especially if those others will suffer from your failure to perform a task. You must be able to picture their suffering in order to empathize, so try to be specific and visual here.

8. It is totally okay to use the suffering of others as a motivation for one's own productivity; please stop questioning this point.

9. Do not put a date at the top of the list.

10. Do put a date at the top of the list, and write estimated times next to each task.

11. Become comfortable with a life full of contradictions.

12. Number the items on your list.

That's my interpretation, anyway. 

'I thought I did; I guess I didn't' — the to-do list song

Instead of Tom tackling his to-do list, he spent a whole weekend writing a song to illustrate his to-do list foibles. It works great as a ringtone, or even as a soundtrack while you write your own list. 

Click here to download. 

I wish all of you who have read this article the best of luck with getting through your next to-do list.

If you need further encouragement, listen to the radio documentary that lies behind all this. 

This episode originally aired in Sept. 2018. Listen to Tom's documentary by clicking the Listen link at the top of the page, or download and subscribe to our podcast.

Tom Howell
About the Producer

Tom Howell is a panellist on Because News, CBC Radio's comedy news quiz. He also jointly presents an ongoing series of documentaries about Canadian PhD students, called Ideas from the Trenches. His semi-fictional book about the English language is The Rude Story of English.

This documentary was edited by Acey Rowe.