The secret life of your to-do list

A seemingly simple productivity tool is far more nuanced than you might think.

A notebook and a pen next to it for a to-do list
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It’s taped on fridges, typed into iPhones, or copied lovingly into bullet journals. It’s the to-do list – a seemingly simple productivity tool that’s far more nuanced than you might think.

The phrase “make a to-do list” is so ubiquitous, it almost becomes unhelpful. That’s because this idea (which boils down to “write something down”) isn’t nearly enough to capture the complexity that goes into organizing your daily goals, feelings, struggles, and tasks into a series of bullet points.

If this feels high-minded, take into account that scientists like Tim Pychyl, a psychologist at Carleton University and the author of Solving the Procrastination Puzzle, have actually studied the to-do list. Pychyl tells me that the to-do list is a useful tool for procrastinators, but it’s far from a panacea.

“It’s not going to solve a procrastination problem, but we do find that people who use to-do lists procrastinate less,” he says.

“Your to-do list is an intersection of you and your context. It’s influenced by your emotions, your expertise,” he continues.

Many of us may end up frustrated with to-do lists if we don’t make them correctly or give them the consideration they deserve. Here are a few things you can do to make that list work for you and not against you.

Digging deeper into to-do lists

When I spoke to Pychyl, he told me that a doctoral student in his lab, Shamarukh Chowdhury, had just completed a study on to-do lists. (It has yet to be published in a journal.) Chowdhury surveyed 300 students on how they made to-do lists and took measures intended to assess how their personality traits align with what psychologists call the big five: conscientiousness, agreeableness, neuroticism, openness, and extraversion.

About half of the students in that study made some kind of to-do list, says Pychyl. And those who wrote their to-do lists down ahead of time tended to procrastinate less compared to those who made mental notes, or ad-hoc to-do lists.

“Your to-do list ... it's influenced by your emotions, your expertise.”

The study found that those who were conscientious to start with tended to make to-do lists and stick to them. The to-do list is helpful, but the motivation to stay organized was likely there the whole time. Making a list just focuses that trait, allowing it to shine through.

“It seems to me that part of the unfortunate truth is that the rich get richer, says Pychyl. “Highly conscientious people use to-do lists and they procrastinate less. In a way, that’s one of their mechanisms for being dutiful, organized, and planful.”

If that doesn’t sound like you, it doesn’t mean you can’t become more organized or conscientious, says Pychyl. It just means that you may have to “act out of character.” But you may have to be more patient with yourself and form the habit from scratch.

We’ve discussed turning goals into habits before in earlier newsletters, but I particularly like the way that Pychyl talks about making a to-do list a habitual practice. He references the idea of a keystone habit, in other words, a habit that tends to lead to other healthy habits. (For reference, the idea of a keystone habit comes from journalist Charles Duhigg’s book The Power of Habit, which discusses the science behind habit formation.)

Pychyl says that making a to-do list is certainly a keystone habit – a particularly “powerful” one. For what it’s worth, one 2018 study on 57 adults found that those who wrote down specific to-do lists for the next day fell asleep about 10 minutes faster than those who wrote down lists of what they completed that day.

To help form that habit, you might consider using an implementation intention, says Pychyl. That boils down to the simple formula: “In situation X, I’m going to do behavior Y,” he explains. For example, when you are having your morning coffee, you will open up a calendar and make your to-do list.

“For those of us who have to act out of character, an implementation intention is a key strategy to establishing a new habit, he says.

Get too specific with your to-do list and you run the risk of feeling overwhelmed.

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Don’t forget the why

One thing I often struggle with when it comes to to-do lists is how to pick tasks that make the list. Exactly how granular should a task be? Get too specific with your to-dos, and you run the risk of a list that’s intimidatingly long. But keep things too broad and you’ll find that very little ever gets crossed off.

Specificity has advantages, says Pychyl.

“Specificity lends itself to knowing exactly what you need to do. You can take those next little steps,” he says. “The paradox is that if you make it too specific, it can be overwhelming.”

So rather than focus on the size of the tasks at hand, he suggests we look at things differently.

Look at your projects in terms of how questions: those are those little steps you need to get things done (think: send an email, fill out a Google sheet, make a phone call).

But then think about the why behind those hows. In fact, he suggests you add a second column to your list in which you write down that why reason (think: I am sending this email so I can teach Strategy readers about to-do lists).

“You’ve got meaning and manageability,'' he says. “You have to find that sweet spot behind the why and the how. If you go too far into the how, it can be overwhelming, but if you don’t go into the how, you wonder, Why do this at all?

That tradeoff between manageability and meaning is constantly changing. On days when you feel yourself lacking motivation, lean into the why. On days when you are struggling to begin and need a clear roadmap, don’t run away from the how, but don’t let it get too granular, either.

If you’ve ever struggled with a to-do list, perhaps it’s because you’ve never given it the gravitas it deserves. It’s more than just a collection of bullets. It’s a psychological document. Construct it so it reminds you why you set out to do these things in the first place.

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