Don't use to-do lists to drive your work

TLDR;

To-do lists are a simple, efficient tool for tracking open tasks. However, (mis-)using them as the sole driver of daily work can lead to several problems, which can be mitigated by using an additional time-management technique like timeboxing.

The problem with to-do lists

To-do lists are everywhere - and with good reason; they are a very simple and effective way of keep keeping track of things. Yet, they are often used as the primary way to drive work - which is something entirely different!

If your only strategy to get work done is opening up your to-do list, staring at it and then trying to complete the items one-by-one, you may find yourself struggling with the following problems:

  • Everything needs to be a task
  • Struggling with tasks of varying size
  • Procrastination
  • Anxiety & Stress
  • Staying motivated

Let's look at each of these problems in detail and explore their origins.

Everything needs to be a task

Let's start with the obvious one: If you're only working from your to-do list, you are kind of required to create a task for what you are working on. But there are different kinds of work that don't fit well with this approach.

For example, open-ended tasks that lack specific completion criteria fall outside the traditional to-do list framework. Activities such as brainstorming, research, optimization, marketing, editing and design or styling improvements are examples of tasks where the more effort you invest, the more you can achieve.

When dealing with this kind of work, it becomes challenging to determine when to consider it complete and move on.

Another example is tasks which require some amount of research before you can begin. Let's say your task is to obtain X. First you have to figure out where you can find X and its cost. Alternatively, you may discover that X requires Y and you need to obtain Y first. Maybe it would be more cost-effective to built X yourself?

It may require an investigation task, such as "Find out how to get X", that is put first and it's output are the follow-up tasks. But it could also turn out that getting X is straightforward and could be completed during the investigation itself. In either case, a to-do list is not necessarily the best fit for managing these types of tasks.

Struggling with Tasks of varying size

Other problematic categories are lots of small tasks. Creating a task for each chat or e-Mail message might seem overkill - until you have to answer that 20 question e-Mail that requires careful thought.

Do you create eight tasks for each message where seven are trivial and creating the to-do item takes more time than answering them directly, while the last one turns out to be a biggie? Or do you create one task "reply to e-mails" and then get stuck on the last e-Mail making it impossible to complete the task at all? Alternatively, do you go back and dynamically split them up then in someway?

It's not that there a no viable solutions to these kinds of problems, it's just that those solutions are only geared towards pleasing the to-do list process. Unfortunately they don't bring any benefit on their own and you end up multitasking between the task at hand and updating the to-do list.

Procrastination

Some tasks are more fun than others, but some are a real bother. Maybe because the task is unclear or it's really difficult and it's chance of success is very low. It could be that the task is gargantuan and even looking at it seems daunting. The exact reason doesn't really matter.

If you are driving your work solely with a todo list, there will be tasks on that list that produce more internal friction and require more effort to even get started. If the effort required to start a task exceeds the available energy, the task will be procrastinated on.

Anxiety & Stress

To-do lists have a tendency to grow fast, as adding an item is far quicker than completing one. Working off a to-do list for hours on end and see it only grow can induce stress or feel overwhelming.

Continuously looking at the to-do list and thinking about future tasks while working on the current one can lead to unproductive task switching and further increases anxiety.

Staying motivated

Staying motivated (or managing your dopamine levels) is very important to continuously produce good work without a crash in motivation. Motivation is highest right before receiving a reward and lowest if the next reward is far in the future.

With a to-do list, the reward is often crossing out the item, marking it done, dragging it into the "completed" column. An additional reward could be a small break, like getting a cup of coffee or tea or a quick walk.

The issue here is, that the reward is handed out by the completion of a task. This makes the size of the task, which is to a certain degree arbitrary, really important. Too small of a task and we get to many rewards and breaks, which may also lessen the impact of them and make them feel unimportant.

But a task that takes too long to complete is also a problem. Because the reward is far in the future, motivation is low and we without rewards, missing the breaks needed to prevent exhaustion and maintain performance. One could grind a full day or more before marking completing a single task.

Using Timeboxing to Tame the To-Do list

One effective way of addressing the shortcomings of the to-do list based workflow is to switch to a timeboxing approach. Instead of committing to solving specific tasks, we dedicate pre-allocated periods of time to work on them. This results in a shift from focusing on outputs to efforts.

A focus on efforts - not outputs - has some major benefits, the biggest being that our effort is fully under our control, while completion of a task is not. That's why focusing on efforts is the core skill needed for a growth mindset.

Additionally it comes with a couple of benefits that help alleviate the to-do list based problems mentioned earlier, because it:

  • Provides the freedom to ignore the to-do list when it's not a good fit.
  • Sets time limits on open-ended tasks.
  • Remains indifferent to tasks of varying sizes, eliminating the need to micro-managing the to-do list.
  • Reduces procrastination by committing only to a reasonable effort, regardless of the difficulty of a specific task.
  • Alleviates anxiety and stress by prioritizing effort and incorporating breaks at regular intervals.
  • Keeps motivation high by rewarding you for your effort rather than random task sizes.

Summary

By using a to-do list as a daily driver of work, we are putting it in charge of our anxiety and stress, our feelings of achievement and our motivation.

If we do that, we are forced to obsess over the number and size of each task, carefully adjusting it to keep it's effect on our psyche in check.

A better approach is to use the to-do list for what it was meant to be - a simple way to track open tasks and use a different technique to drive our daily work - like timeboxing - which does a much better job at that.

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