The Real Reason You’re Not Finishing Your To-Do List

If you’re like most workers, your daily to-do list looks more like a wishlist. In a 2012 LinkedIn survey, only 11% of professionals reported having finished everything on their to-do list. At times, it can feel torturous—a way to remind you of all the things you haven’t done and never will. Even though a lot of people find to-do lists are ineffective and painful, around 63% of us keep them.

That’s a pretty big gap. But since a lot of us start to-do lists without finishing them, it’s clear we think there’s some utility there. And we’re right—to-do lists themselves aren’t the problem. In fact, they can be really helpful in getting your work done in an efficient and motivating manner.


The real problem is that most people who keep to-do lists are structuring them all wrong. They find themselves at the whim of a to-do list that’s created by their email inbox, their colleagues, or their families. Instead of controlling their task list, their task list controls them.

But with a little bit of to-do list reorganization, you can turn that around.

Get Your To-Do List Out of Your Inbox

Email is a great tool for communicating. No matter how much bickering there is in the online community about what next app is going to replace email, it’s clear that email is here to stay as a communication tool. But if you’re using it for task management, you’re doing it all wrong.

Email-as-task-management is all too common these days—you might not even realize you’re doing it. But if you use email as a tool to keep projects or tasks on your radar, you’re setting yourself up for failure. As the Harvard Business Review writes, it’s an easy trap to fall into:

The reason so many of us fall into the trap of conflating email and task management is that email is inextricable from much of what we do in work and in life: many of our tasks arrive in the form of email messages, and many other tasks require reading or sending emails as part of getting that work done.

Using email for task-management detracts from its utility as a communication tool. The Palo Alto Research Center conducted a longitudinal study measuring how knowledge workers were utilizing their email and found that it wasn’t just a communication tool—it was being used for practically everything.

Communicating, reminders, storing information, sending documents—it all happened within the inbox. Researchers concluded that email was being “overloaded.” And that had nothing to do with the staggering amount of emails we get every day, it was entirely about the quality of tasks, or “complexity of email management,” as the researchers put it.

Your to-do list is about maintaining control over your schedule, and if your to-do list is your inbox, you relinquish that control. You need to remember that email is built as a communication tool, it’s not built for getting work done.


As customer success experts at Glide Consulting write, this is especially problematic for anyone involved in service, or customer success, since it means that they’re always firefighting. You wind up constantly at the beck-and-call of each email in your inbox, which doesn’t give you time to take care of the stuff at the bottom of your list. That to-do list just keeps growing.

Their advice is to “Heisman” your inbox—check it twice a day, and then “give it the stiff arm.” This means combing through your inbox twice a day to delete spam, archive closed threads, and move tasks from your inbox to an external list. There’s so much conversational noise in email that it’s impossible to gain focus. If you can extract your important tasks out of your email twice a day and then rapidly re-adjust your prioritized task list as required, you can have the best of both worlds.



Sort Your Tasks

In their book, Willpower, science writer John Tierney and research psychologist Roy F. Baumeister write that a typical American has about 150 items on her to-do list, which amounts to way more than can be accomplished in a single workday. This effect only increases for executives, whose to-do list for a single day might realistically take a couple of weeks.

The researchers posited that the solution, hard as it might be, is to eliminate some of those tasks. It’s the same technique Tim Ferriss uses in his “4 Hour Workweek” method. Eliminating tasks (or at least prioritizing them) gives you the clarity you need to actually focus on necessary tasks, instead of being bogged down by the impossible or long-term ones.

If your to-do list isn’t sorted into things that need to be done today, need to be done this week, and need to be done in the future, you don’t get the perspective you need to actually complete tasks. If a list reads “Wish Jeremy a happy birthday” and then “Learn Russian,” you’re just weighing down a task list with things you’re not going to accomplish.

Once your tasks are out of your inbox, it’s important to take a look at the things you want to get done, and do an assessment. Which tasks on your lists are absolutely necessary? Which ones need to be done by tomorrow?


David Allen, creator of the Getting Things Done Method, instructs people to contextualize their tasks. When you contextualize a task, it tells you where or when it needs to get done. For example, if you need to call your mom and ask about holiday travel plans, you might tag something as #home. Likewise, if you need to talk to people from Product and Accounting about a board presentation you’re giving, you might tag those tasks with #boardpresentation.

ScribblePost lets you use hashtags to tag and track everything you need to get done, according to context, priority, and due date. So if you’re about to go to that board presentation, you can contextualize all the tasks you’ve been working on in preparation for it, you can easily go to that hashtag and find all the information you need.

Contextualizing tasks allows you to do a better job of prioritizing. Try grouping similar tasks together, like emails or phone calls. Label how much time you think each one will take, and when it’s due. This also helps you avoid the switching cost involved in switching tasks, which means you’re using mental energy (and time) in the process.

It’s all about finding a system that works for you, whether that’s color-coding, inserting an @ symbol or #, or just writing in different columns. In any case, finding a way to separate out tasks will make prioritizing easier and less of a burden.

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Make a Timeline

In an MIT study, undergraduates predicted how long it would take them to complete their senior thesis. Less than a third were even close to accurate. Most of them predicted around 32 days, if everything went perfectly well. In the end, it took them an average of 55 days, holed up in the library working all hours of the night.



A lot of this, researchers concluded, was because they had other things on their plates while they were writing their theses. In a study of users, remote standup tool iDoneThis found that only 15% of overall completed tasks started as “to-do’s.” We don’t anticipate a lot of the things we do throughout the day—they just come out of the blue.

As the MIT researchers concluded, it was because undergraduates typically chose to attack these smaller tasks first, since they felt more pressing, even though they mattered less in the long run. The students had such a wide variety of tasks to complete, that they put the ones with a far-away deadline (like their thesis) at the bottom of their to-do list.

This happens in the workplace all the time. Let’s say your boss told you to draft some emails to send to a client. You weren’t expecting this task for the day, and you suddenly push your to-do list aside. Not only do you not get the satisfaction of crossing an item off your list, but also when you’re done with drafting the emails, you turn back to your to-do list and you have to reprioritize.

A well-structured to do list helps you keep a big-picture view of the big deadlines that need to be taken care of.


Deadlines help—a lot. The researchers found that their subjects’ predictions were pretty weakly associated with completion times, but their deadlines were strongly associated with completion times. This is because deadlines—including deadlines along the way, helped externalize the sense of when it needed to be completed.

It was also incredibly encouraging to make meaningful progress along the way. Completing a chapter of their thesis not only chipped away at the students’ workload, but it encouraged them to keep going. That’s because the power of small wins also increases your confidence, which the same researchers found helps you get tasks done.

Above All, Demand Satisfaction

The worst part about to-do lists is that they can be really demoralizing. You finish a long day’s work, you take a look at the lofty goals you set for yourself that morning, and you let out a sigh. Nothing got done, you think.

But that’s not quite true. You may not have accomplished things on your to-do list, but that doesn’t mean you didn’t have  a productive day. Marc Andreesen, co-founder of Netscape and the venture capital firm Andreesen-Horowitz, has a solution to this—the ultimate way to show your to-do list who’s boss. As the VC writes,

“Each time you do something, you get to write it down and you get that little rush of endorphins that the mouse gets every time he presses the button in his cage and gets a food pellet. And then at the end of the day, before you prepare tomorrow’s 3×5 card, take a look at today’s card and its Anti-Todo list and marvel at all the things you actually got done that day.”

That’s right: marvel. You’re probably more productive than you’re giving yourself credit for. Whip your to-do list into shape by organizing, prioritizing, and getting your tasks out of your inbox once and for all. The to-do list, when done right, can be motivational and invigorating—you’ll get those things done and feel better in the process.