The Project Management Paradox

Why is it that I can manage large, complicated, technical projects at work, but be paralyzed with indecision when it comes to managing my own to-do list outside of work? What’s worse, I can’t even settle on a way to manage that to-do list.

I find myself thinking about this because I was revisiting an old favorite, Gina Trapani’s todo.txt system. Seven years ago, I wrote about my requirements for a to-do list app. There are five of them:

  1. The list be stored in an open format
  2. Priority is by list order
  3. One list to rule them all
  4. Easy archiving
  5. Accessible anywhere

I think these requirements still apply for the most part.

The paradox of all of this is that I am spending time trying to figure out how to manage my to-do list when I should be doing the things on that list. Over the years I have tried many task management systems and tools: David Allen’s Getting Things Done; Evernote; todotxt, todoist, bullet journals, and on and on. None of them have stuck permanently. The two best in terms of effectiveness and longevity were todoist and todotxt, and I think that is because they are relatively simple systems.

I am looking for a way out of this paradox. More and more it seems to me that to-do apps are a case study in great technology which can make us (well, make me at least) less efficient. I think about all of the time I have spent studying, testing, trying, and writing about to-do systems, and wonder how many practical items I could have slashed off my lists in that time.

Simplest is best. I find that I can too easily get bogged down in “features” and comparing and system to another, when I really need to be focusing on a system that is virtually invisible. I recently heard a podcast in which Jim Collins spoke about his own to-do list: he uses the Apple Notes program with a single note for his to-do items. What he does is lists the top three things to get done on a given day, and then separates the rest of his list by enough carriage returns so that when he looks at his phone, all he sees are those three things–but he can scroll down to see more. That is relatively simple, but not simple enough for me.

Last night, when I couldn’t sleep, I took to heart another piece of advice from Jim Collins: I applied the 20-minute rule. The rule states that if you can’t get back to sleep in 20 minutes, you should get up and do something. He says this is a great time for him to figure out what he needs to prepare for. I did that. I thought about how to tackle this problem once and for all. I’ve decided to go as simple as I possibly can.

First, I attempted to clear my head by dumping everything to a file in Obsidian. Call it my master list. This is everything. Well, almost everything. There are still things in my head that I haven’t gotten out yet, but I’m working on it.

Second, I picked three things I wanted to get done today. There is a stack of 200 index cards that have been sitting unused on my desk for months. I took one of those cards scribbled the date on the back, and then jotted down the three things I wanted to do in “next action” form. I included all of the information I needed to get those things done.

Third, I stuck the card in the back of my current Field Notes notebook. I always have the notebook with me so I always have the card with me.

Now I have a simple system for focusing on what I want to get done on a given day without it being difficult to maintain or overwhelming. On the back of the card I jotted an item from my master list that would be “nice to do” if I happen to have the time after getting the other items done.

At the end of the day, I remove the completed items from my master list, drop the old card in a box, and start a new card for the next day. Simple!

Someone is bound to ask why not just make the list in my Field Notes notebook. There are two reasons. First, I use my Field Notes to capture notes, observations, ideas, etc., but it is not meant to be for taking actions. I think of it more as a creative notebook, a creative record for my day. Second, I don’t want to begin associating mundane tasks with my notebook. I think it is better to have the card; the card represents the stuff I need to do. It’s the work. The notebook is the joy and fun.

I don’t know if this will work or not. Only time will tell. But it will be time I am not spending trying out this app and wondering if the features in that one aren’t better; or how I could automate my to-do list to show up in my Daily Notes in Obsidian each day; or any of a dozen other things that distract me from actually getting my tasks done. The index card also meets all of my to-do list app requirements.

I’ll let you know how it goes.


  1. I feel you!!!! David Allen talks about the relief that comes from writing down all your open loops, but I found just the opposite…when I made a gigantic list of everything I wanted to do, and would someday/maybe do, it essentially paralyzed me and robbed me of the joy of the things I actually did (instead of patting myself on the back for the 5 things I did do, I stressed over the 10,000 things still to do).

  2. I can so relate to this post. I feel I’ve tried just about every to-do app in the iOS App Store. At the end of the day, it’s probably more about choosing the right actions for each day with the right amount of information, rather than how it’s organized. BUT I love your solution. A place to dump everything, and a place to keep a physical list that’s simple and feels easy to tackle.

    1. Jesse, so far so good with this new routine. One small modification I’ve made: I draw a line below the three things I want to get done on the front of the card. Below that line I write out the 3 work-related things I want to get done. That way I can get that out of my head and have it all int he same place.

  3. Mentioned before the “Analog” card sytem to you, if I remember well, that shows similar solution, only the card is not stuck in the back of your notebook, but openly visible on your desk. Gives some more pressure to act, because your homemates can check your progress.

    1. Jaap, I do remember that. For now I am okay with keeping the list in my notebook because having it visible on my desk would be redundant. My wife and kids are already very good about checking my progress on things they would like me to do. 🙂


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