17 Reasons I Hate My To-Do List

Let me preface this by sharing the dumb way I use to-do lists. As I go through the week, I update a list of all the things I need to do. Five to ten times a week I'll schedule the big things in my calendar, and I'll complete the smaller things as I have time. I typically don't finish my weekly to-do lists. In 2015 I've introduced three to-do lists (low, medium, and high priority), which helps a bit, but I'm still generally annoyed with my process. Here's what I hate about it:

  1. Stress. I can really only hold three things in my head at a time - any more than that, and I can easily become overwhelmed. The things I have to do creep into my subconscious and make me weary before I even get started. In fact, if you want to feel overwhelmed,  I recommend making a big, gross to-do list and stare at it for a while.
  2. Variable Task Types. Maybe I'm just using to-do lists wrong, but I always end up with a huge variability across task types (e.g. Laundry, Taxes, Coding Project, Go for a Run).  Placing these items on the same list makes them appear homogenous, when in reality they should not even be compared. Should I work on this coding project, or read about how to make my business more effective? Deciding between very different tasks each time I look at my to-do list is taxing. 
  3. Binary Outcomes. According to my to-do list, a task has either been completed or not. This really sucks for tasks with dependencies, multiple steps/stages, or where I'm waiting on someone else.
  4. Variable Task Lengths. Some things I can knock out in five min, some five hours, some could take all week if I allowed them to. Putting these on the same list and picking between them imposes a false dichotomy and is unnecessarily taxing.
  5. Priority. To-do lists do not reflect the relative priorities of tasks. This is especially true for longer time horizons (the long-term things that will matter a lot in a year to two often appear less important when compared to things that need to get done this week).
  6. Timing. Some tasks need to be done at certain times, to-do lists have no way of handling this.
  7. Scheduling. My to-do lists lives separately from my calendar, which is fine for some tasks, but not optimal for bigger things
  8. Deadlines. To-do lists don't take deadlines into account.
  9. No Connection to Long Term Goals. How do the things on my to-do list fit in with where I want to be personally and professionally in 1, 5, or 10 years? Further, once tasks are on a list, it's easy to forget the purpose - why I'm even doing something - how is this pushing me forward?
  10. Don't Take Switching Penalties Into Account. I incur a high switching penalty when moving between complex tasks. My brain really needs at least a few hours on one task to do good work. When I switch between complex tasks, my brain is too often stuck on the last task. I can't give the new task enough attention, and fractured focus tires me out quickly.
  11. Overly Ambitious. My lists are often too ambitious and not-realistic, resulting in more stress.
  12. Uncomfortable Things Get Avoided. To-do lists make it easy to avoid uncomfortable (which typically means important) tasks and kick them down the road from week to week.
  13. Reactive, Not Proactive. With to-do lists, it's very easy to adopt a reactive mindset - "these are the things I have to do this week".
  14. Unbalanced. Some tasks are creatively restorative, while some are taxing. Writing code and running are very well balance activities for me. After programming for 3-5 hours or until I become stuck, going for a run allows me the space for my whole mind to internalize a problem. It's very rare that I go for a run and don't come back with new insight into my work. Putting "Write Code", and "Run" on my to-do list doesn't really capture this.
  15. No Sense of Time. No daily, weekly, monthly demarcations.
  16. Created and Executed in Different States - beginning of the week I'm too ambitious, by the end I’m just trying to get shit done.
  17. No Room for Multiple Approaches. Often, the first way I try to achieve a result doesn't work. Only though trial and error, and changing my strategy do I get where I want to go. To-do lists, by definition, contains tasks and not outcomes. Focusing on a single tasks means I may miss the big picture, and other, more effective ways to get where I want to be.

I currently don't have much insight into how to fix these issues, and many of them probably don’t have a "solution". I do have some observations. First, to-do lists are poor guides for execution.  I think the to-do list is really the input of a planning system. The output of our system is how we actually spend our time, and using a to-do list as the only guide as we go throughout the day is not a good idea.

What a to-do list is really doing is compressing, or reducing the dimension of the process of allocating your time and focus throughout the week. Allocating your time and energy is a complex process, plagued with dependencies and biases. The to-do lists' advantage, simplicity, artificially reduces the complexity of the very important decision of how you spend your time. At the end of the day, the way you spend your time is your life, and a to-do list is a poor, low dimensional abstraction of the trade-offs and considerations that should go into planning and executing on the future you're trying to create.

Obviously, there is no fix-all solution here. Deciding how to allocate your time is a never-ending process, and that's ok. It should be. However, I've grown tired the way I use my to-do list as part of my decision making, and am ready to change something. I don't know what to change yet, but I do have some questions I'm going to think about:

  1. Across what dimensions does my to-do list reduce the complexity of my life, and is this a good trade-off? Where could/should I reintroduce dimensions (task priority/time frames/deadlines/balance…)?
  2. Are there ways I can reduce the stress of a big pseudo-homogenous list of tasks hanging over me each week?
  3. Is it possible to create a system where a to-do list is just the input, and tasks are somehow sorted to reduce my complaints above, without being artificially complex or bulky?