Why To-Do Lists Do Not Work For Me


Joshua Mitchell / September 02, 2020

9 min read

dark to do list

Photo by Priscilla Du Preez on Unsplash

I was meditating the other day, thinking about my dissatisfaction with my productivity levels. Then, I had an itch on my back.

I scratched it, and got back to thinking.

Suddenly, I had a thought. What is the difference between the stuff I have to do and the itch on my back?

I didn’t even have to think about scratching my back. It would have taken more effort to not do so. On the other hand, getting myself to do stuff I have to do is like herding cats.

What factors are at play here? Let's start with external (i.e. the environment) and internal (i.e. the mind) factors.

External Factors#

I see a lot on the internet about negating external factors. This includes tried-and-true techniques like planning (i.e. creating S.M.A.R.T. goals), outsourcing the hard parts, creating tight feedback loops, removing ambiguity, etc.

Internal Factors#

On the other hand, I don’t see negating internal (i.e. psychological, emotional, and cognitive) factors covered frequently. At least, not with granularity.

There is a lot of one-size-fits-all content. A few examples:

  • Why waking up at 5am makes you more productive
  • Why you should wear a suit doing everyday tasks
  • Why you should make your bed to be more productive

Of course, it’s also hard to have tailored but general content in this domain. It’s unlikely that a high school student, a lawyer, an executive, a bartender, and a surfer all resonate with the same vocabulary, stories, and metaphors.

The Psychology#

Nonetheless, I think the psychology of the To-Do list is applicable to lots of people reading this, so I want to use that as a chance to be specific, yet widely applicable.

Time to make some assumptions. Who reads stuff about productivity? People who aren’t as productive as they’d like, of course! That probably means you.

You’ve also probably made a To-Do list at some point in your life. How’d that work out?

Now’s the part where I share my experience, expecting it to be relatable to yours.

Making a To-Do list is therapeutic for me. It mostly serves to enhance my sense of control and alleviate anxiety about forgetting things.

Ultimately, however, it doesn’t make me do the things on the list. The productivity barriers still exist. Why?

I’ll give you a few thoughts I’ve had staring at my To-Do list, trying to get myself to start. Call the most important thing to do that day task A.

  • They all seem relatively equally important. They all “have to get done” anyway. What should I choose?
  • Ok, well, A is the most important task. But I have no idea where to start.
  • This list is stale - most of this stuff is either done, irrelevant as of now, or uninteresting.
  • There’s so much stuff on there that I just don’t feel like doing any of it.
  • So much of this stuff I’ve tried to start for several days now, so what's another day? I’ll just blow it off again.
  • Why am I trying to be superman and get all this done again? It’s okay to be a regular Joe, I’m just going to blow it off.
  • These are all part of a bigger project. I know myself: I don't finish big projects. I’ll just abandon the project anyway. Why bother starting? Let’s blow it off.
  • Honestly, not doing any of this sounds so much better than doing it. Let’s blow it off.
  • I spent too much time messing around already today, and the day’s almost over. Let’s just start tomorrow.
  • I just don't effin' feel like any of this is my vibe right now.

Here are some themes:

  • Purpose (What’s the point? Why bother doing this?)
  • Faith (I won’t see this through, why start? I’m not like Elon..)
  • Motivation (I really don’t feel like it because..)
  • Ambiguity (What should I be doing right now? What’s step 1?)

Let's simplify all of productivity and project management into starting problems and finishing problems. We'll focus on starting problems.

Starting Problems#

Starting problems come from lack of purpose, faith, and/or motivation. Finishing problems come from ambiguity and/or lack of intermittent dopamine hits (i.e. not being able to build momentum).

Let’s focus on starting problems (the biggest source of my, and probably your, lack of productivity).

Starting problems come from the overhead of making the decision to start. Before you’ve mentally accepted that you will “do the thing,” there are several factors that can contribute to analysis paralysis. You might feel fear, anxiety, or anger. You might debate exactly how you’ll do the task. You might decide that you need to weigh other options first.

Most commonly, you might feel a tinge of unpleasantness when you think about having to do the task, and your brain is holding out for an excuse to do something else.

Some things, like blinking, have next to zero overhead - hence, if blinking were on your to-do list, it wouldn’t take any of that other stuff (purpose, faith, etc). You’d just do it. Bam. Done.

But then again, blinking doesn’t come with psychological or emotional baggage. Filing taxes, for example, brings a whirlwind of negative associations to most peoples’ minds. You need motivation to make yourself consciously commit to doing it and, hence, starting it.

To further illustrate this point, imagine bringing a martian into your home, sitting him/her/it down on your office chair, and pulling up TurboTax. Though you might not be particularly motivated, the martian might be fascinated - or, at the very least, not filled with an inevitable sense of dread.

So, why does this baggage prevent us from starting again? Here’s why.

At the time of writing this, I had just woken up Sunday, August 30th, 2020. I sat down at my desk, opened my MacBook, and a draft of this post was on the screen in a Google Doc. I put it there the night before to remove as much friction between myself and starting as possible - hoping my future self would just start it without thinking about it.

“Ah yes! I remember this. Yeah, let’s do it. Let’s make today really productive. Let’s get started riiiight away.”

Then, a surge of anxiety. What if I get stuck? What if it sucks because I rushed it? What if I can’t finish it today? It’ll just be more proof that I’m an unproductive loser.

That’s my inner monologue. They don't seem super logical, but that's only because you're viewing them from the outside looking in. All of those questions are easy to disprove and dismiss on paper with neutral eyes.

But, they become quite powerful when they’re able to roam freely in the gray area between my conscious and unconscious, not subject to the scrutiny of my frontal lobe and prefrontal cortex.

Think of the strategy of Coke commercials: they know you’re probably not going to see them and think, “Oh wow, gee whiz, I need a coke now!” - that’s not their goal. Their goal is to build the positive association slowly and subtly, without the arbitration of logic. They take advantage of the fact that nobody asks, “What does sugar water have to do with polar bears?”

Eventually, 6 months down the road, you see a 12 pack of coke while at the grocery store and it makes you feel pleasant. You don’t really know why, but for some reason, Coke sounds really good. Hence, it ends up in the basket and soon it's in the back of your car in a grocery bag.

So How Does One Become More Productive?#

We tend to seek pleasure and avoid pain. Coke tries desperately to be associated with good feelings. Starting things on the To-Do list tends to be associated with bad feelings.

Hence, my answer to, "How to be more productive?" is to remove as much baggage as possible from the thought of starting.

The best way I’ve found to do that is to literally stop in your tracks anytime you feel a twinge of negative emotion (particularly when you think about starting), and put those feelings under a microscope.

Take this seriously:

Close your eyes, turn off the music, television, and other sources of stimulation.

Listen and feel.


Ask yourself questions, pose scenarios, and replay the moment in your mind over and over.

Be annoyingly introspective.

Don’t be discouraged if it doesn’t work well the first time. I’ve found that this might take a few tries.

Eventually, through these exercises, you’ll have a solid understanding of your fears and anxieties. Then, you can dispel them.

For me, I found that a lot of my anxieties came from feelings of inadequacy. I felt like I wasn’t worthy if I wasn’t smart, if I wasn’t productive, etc.

As a result, I approached pretty much everything with a project management, "What's the ROI?" kind of lens.

Hobbies. Side projects. Catching up with friends.

What am I getting out of this? What’s the goal?

I literally forgot how to have fun. My life became a To-Do list and I was just a tool to complete it - inadvertently smothering most of my intrinsic motivation.

Now, at least for non-work stuff, I deliberately practice having zero expectations.

If I blow it off, totally rad, dude. If it sucks, hey, hakuna matata. If a draft sits in the cloud collecting dust for months, that’s okay!

I’ve started asking myself, “What can I do to make this something I want to do?” instead of, “What do I have to do?” - if I can’t make it something I’m intrinsically driven to do and it’s not “required” (e.g. work, taxes), then I just don’t do it.

It's a tough habit to break. Meditating helps. Good luck!

Thank you to the Compound Writing member who reviewed this post: Tom White.

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