Another Year, Another Todo App Crisis

Last week, Alireza Bashiri published a piece called “I Tried Every Todo App and Ended Up With a .txt File”.

The narrative is a familiar one:

  1. Author tries every productivity app under the Sun
  2. Author buries himself in complexity
  3. Author does not get things done
  4. Author returns to simplicity
  5. Author gets things done

Pieces like this emerge every 6 months, and I always find them fascinating. They provide sharp insight into what’s essential.

(Another recent candidate is Oliver Burkeman’s probing into whether Read-it-later apps are helping us to read, or fulfilling some other desire.)

I also lean towards low-fi systems for getting things done, but I’m not here to convert you to my system.

Instead, I think these articles should leave one message ringing in your ears: if there’s even a chance that a radically simple system can work better, then our assumptions about the complexity required to get things done are off by an order of magnitude.

Said again: if we’re constantly investing time and money into complex software that can be matched by a .txt file or a pen and paper, then we’re buying into a false narrative about what we need to get by.

And as engineers and nerds with a love of new tools and tech, we’re even more likely to fall prey to this temptation.

But how can we know that we’re being led astray?

Here’s a question to cut to the heart of it:

Am I trying to get more done, or am I trying to escape some discomfort?

My personal experience is that investing in complex systems is often a way of avoiding the discomfort of acting imperfectly today. Not always. But often.

GTD tools are built to be enjoyable to use. They offer many features and encourage you to make use of all of them. You can organise projects, create subtasks, assign tags, and re-arrange priorities through an aesthetically pleasing interface. It all feels good and important. But the discomfort of action is held at arm’s length.

There’s nothing inherently wrong with removing friction, but it’s not the same as getting things done.

And so these tools remove discomfort in the short-term, but create much more in the medium term, as your organisational fetish sucks up all of the energy you needed to deliver the goods. By the time someone is writing the annual “Do I need all this?” blog post, they’ve realised the Faustian bargain is not going to pay off.

Manual and analogue systems also require frequent review. Apps try to remove this, along with any other friction. We want an app to take away the pain, to tell us what belongs where and what to do first. We want the app to cut a clean, digital path through our existential unknowing.

But it turns out this friction is essential to keep things relevant. Our lives and goals are dynamic and complex. No amount of digital organisation or AI is going to remove the need for you to look with fresh eyes, attuned to the ring of your values in that moment.

In the end, productivity isn’t a contest between apps and notepads. It’s a contest between doing the work and dodging the discomfort of doing it. Friction feels like the enemy, but it keeps our systems alive and real.

The temptation of complex tools is to soothe us with polish and features, but the real test is whether we can sit with the rough edges, and act in spite of them.

p.s. If any of this hits home, working 1:1 with a skilled coach can help uproot the beliefs that keep you spinning in Todo App shaped circles. I have 2 spaces left for clients in September. You can book in a free chat here.