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How To Overcome Dread Tasks

There are things you want to do. There are things you need to do. Sometimes these are the same. This post is how to handle life when they aren’t.

The sensation of thinking of a task can be pleasant or painful. This is because your brain is always predicting how rewarding any future scenario will be. You experience joy when your mind is imagining a future fantasy where you’ll be engaged in flow (“when you get to that weekend side-project, things will be interesting, time will fly by”).

You experience pain when the prediction is monotony or failure. A dread task is an exceptionally bad case when the prediction is so painful, you can’t even properly contemplate what you need to do. For example: “I need to do my taxes… [ugh, hurts to think about that] when do I need them done by? [still in mental anguish]… can we think about anything else please?”

This is bad because starting a task and not completing it raises its future cost. Your brain models using past behavior. If you fail to execute the task, your brain will predict you’ll fail again. Which makes thinking about the issue emotionally draining. Which increases the odds of failure. A vicious cycle. Etc. Etc.

Thankfully, these predictions are frequently wrong. All you need to do is reverse engineer your thought patterns. Here are some strategies I find useful for tricking myself into doing what I need to do.

Make it stupidly small. You predict failure when you don’t understand what you need to do. Never, ever, ever have an ominous task on your list. Even “do my taxes” is too vague. How do you do that? Where do you get started? More importantly: what is the smallest step you can do today and make any progress towards that goal? Break down a big idea into small bits. Collect “stupidly small” tasks you can knock out with minimal anguish. We’re looking to build a good predictive model where you succeed at doing things, no matter how small.

Re-label. Don’t do the dread-thing. Just change the name of the dread-thing in your todo app. Don’t “do your taxes”. Just change the label to “gather finance documents”. This is the smallest increment of work. Surely you can commit to doing this right now. Doing that can “trick” you into unfolding the task into bite-sized chunks. And even if not, it resets my brains prediction model (and therefore anguish) when thinking of the task.

Visualization. Just fantasize. What will you do when you pay your taxes? Direct a movie in your mind. Some parts of it will provoke a neutral reaction. Some will be negative (“ugh, gotta assemble lots of documents… BORING!”). You’re feeding your brain positive training data to make the act of doing the task less daunting. You’re demystifying it. Athletes who visualize their sport find improved performance. Become an Olympian in productivity.

Talk to others. Talking to other people accomplishes three goals:

  1. They might have good ideas about it.
  2. It’ll make you more accountable, especially if you tell them you’ll get it done.
  3. It forces you to clarify your own thinking. Talking to others is a forcing function to think. And a more specific, detailed task is easier to accomplish.

Find another way. Sometimes I’ll have a dread task that I can either do manually or script. Doing it manually is faster. But if I find myself procrastinating, I’ll “treat” myself to scripting it, which feels nicer in my mind, because it’s a fresh framing of the problem.


I don’t think it’s sustainable to “boost” your willpower forever, but you can get a temporary jolt. You need to learn what things put you in a great mood and use those as tools.

Music. I have a particular playlist I use when I need energy. These are songs that I love and don’t listen to frequently. I find the potency of a song goes down if you play it endlessly.

Workout. I’ll often try to power through a dread task after working out. This works for two reasons. First, the endorphin rush just feels great. You’re more tolerant of pain. Second, since I have recently completed a “challenging activity”, my mind is more readily willing to predict that I’ll complete another. I make believe the task is just like an interval that I need to complete.

Coffee. The right amount of coffee puts me in a great mood. Too much and I get jittery. For me, the amount is small — 50mg or so. Experiment and find what works for you.

What are strategies that work for you to get anything done?