The Four Reasons Why To-Do Lists Fail

There are four factors that normally impact our ability to incorporate a to-do list into our life:

  1. They become unmanageable (complexity)
  2. We forget we have them (habit)
  3. It takes too much time to use (time)
  4. The list is overly ambitious (achievable)

Your to-do list is in jeopardy if any one of these factors fails, but hit the mark with all four and you’ll be in good shape. Next, let’s take a look at these issues and what can be done to address them.


For many, a to-do list is a repository of thought. Work tasks, shopping lists, and recommendations all find their way onto our lists. Eventually, you have so much stuff that the list becomes unmanageable. To-do lists are about getting things done, and it’s a problem if you’re spending more time searching your list than taking action. Before you know it, your to-do list has become a ‘junk drawer’ of ideas.

You start avoiding your list when this happens. How do you fix this? The trick is to stop using one to-do list for everything. A simple solution to try first is to have two lists. Keep one for immediate work tasks and another for aspirational tasks (like restaurants you want to try). You’ll keep your lists less cluttered and more usable this way.


Building the habit of using a to-do list can be challenging, but it has to happen to ensure success. In Switch, the bestselling book by Chip and Dan Heath, the authors examine what it takes to fall into a new habit. They point to three different requirements: direction, motivation, and shaping the situation. When we start a new to-do list we almost always have the direction and motivation down. The key requirement to focus on is how we shape our situation.

The two most applicable aspects of this for to-do lists are tweaking the environment and setting action triggers. Tweaking the environment is about making sure you’re putting yourself in a position to succeed. Identify instances you forgot to use your list and figure out what would help prevent that next time (then make the changes needed). Action triggers require associating a particular event with an activity. You could commit to reviewing your to-do list every time you get on the train in the morning. Slowly this turns the train into a reminder of your list and helps you remember to use it. You can get really creative with both solutions, but they are vital for establishing good habits.


To-do lists are about saving time. They’re useless if it takes too long to add an idea or get information from them. When deciding to use a to-do list, find a solution that you work well with. If it’s an app, look for features that support the reason you’re using the list in a way that saves you time. Be mindful that too many features can result in added time-consuming complexity.


Sometimes we get too ambitious with our to-do list tasks. It might make sense to put ‘get oil change’ as a to-do item, but ‘get oil change’ isn’t really one task. David Allen mentions this in his classic book Getting Things Done. He asserts that much of the time we fail to take action because the tasks we set for ourselves are too big or nebulous. We put down ‘get oil change’ but what we mean is find an oil change place, call and get a quote, make an appointment, and go in for an oil change. Subconsciously we know all of this, but when we read ‘get oil change’ it calls to mind the related tasks which bounce around in our head and keep us from taking action as we try to pin down where to start.

When you set tasks in your to-do list make them straightforward and actionable. Breaking tasks down into smaller achievable pieces allows you to check stuff off more often. Accomplishing smaller tasks often will reinforce regular usage of your list.

Get Ready to Do More

Now that we understand the pitfalls of to-do lists we can avoid those problems in the future. Start building the habit today with to-do lists that are simple, quick to manage, and straightforward.

You may even want to start another list for all the great things you can do with the time your to-do lists will save you.

Good luck!

What do you think? Have you already found success with your current to-do list? What works for you? Let us know in the comments below.

[Want more? Visit for updates Monday through Thursday or see what we’re working on at]

Like what you read? Give Gojurn a round of applause.

From a quick cheer to a standing ovation, clap to show how much you enjoyed this story.