Reflecting On A Failed To-Do List

I’m constantly trying out new to-do list systems. I feel like I’m always in a state of organizing and revising my thoughts and wishes and obligations, imagining one day I’ll eventually learn how to be a machine of perpetual productivity.

I imagine a calm and gentle machine, where I give it inputs of desires, obligations, and available time, and it outputs only a minimal list of tasks in order of priority. It’s not that I need to get everything done, it’s that I want to know what are the right things to get done in order to be secure and confident and excited about the future.

Last week, I had a hypothesis that maybe what was going wrong with my current implementation of my productivity machine/to-do list system is that I had too many goals at the same time and I needed to prioritize completing fewer goals before moving onto the next one. So I created several lists to represent the different priorities. I imagined a workflow where as soon as something on the highest priority list gets completed, I go back to the backlog and move something into scope. And then, whenever I have a fleeting thought about something I’d love to do one day (“Write a musical!”), I can add it to the lowest priority backlog list with some confidence that I’d eventually get to it.

A week later, I haven’t looked at my lists.

At all.

Yep, I literally just checked my Quip history and I haven’t made a change to the documents since exactly seven days ago.

Great! Yay for the scientific method, yay for invalidating my hypothesis, yay for learning something new about myself! But what went awry?

  • If I didn’t check the intended list of tasks, how did I end up deciding what to do?
  • Why did I default to that system?
  • Is the problem that I didn’t remember to use my new system or that the new system was ineffective for my problem and so I never created a successful feedback loop?

But then, as I go over my past week, I realize despite not using my revolutionary to-do list system, I’m still getting things done. I wrote at least one poem a day. I made progress with the current book I’m reading. I went to poetry readings and theatre workshops and other scary events that pushed me outside my comfort zone and helped me meet new people. I thought that I wasn’t prioritizing things enough to make progress in any direction, but looking back on my week the data shows I did prioritize things that felt good to me.

Maybe what went wrong was that my hypothesis was formulated on an inaccurate premise to begin with. It’s interesting because initially when I was reflecting on how I ended up not executing my life-changing productivity machine, I was feeling disappointed in myself. My brain had immediately jumped to the narrative of “I’m never any good at follow-through or execution”.

Makes me wonder how often I blame myself for lack of discipline and execution of solutions for problems that was never there to begin with.