I’m a digital strategist. Naturally, I spent years trying to build the perfect digital system for managing my work.
It did not go particularly well.
I’ve built systems in Trello, Akiflow, TeamGantt and plenty of other tools. Usually the process started the same way: I’d spend considerable time designing an elegant structure for projects, tasks and priorities.
For a little while, it felt great.
Then work got busy.
Within a month, the system I’d carefully designed was usually gone. What remained was essentially a very sophisticated place to keep an extremely long to-do list.
More organization didn’t create more clarity
I can trace this problem back much further.
About ten years ago, while working with ColorJar, I remember getting feedback about flooding our system with SEO tasks.
The criticism was fair.
I could identify a hundred things that could be done. And digital systems were excellent at capturing all hundred of them.
They were much less helpful at answering a simpler question:
What should I actually do next?
For years, my response was to keep designing better systems.
Eventually I started questioning that assumption.
Back to a pocket notebook
Early in my career, I worked as Donna LaPietra’s assistant around the Chicago Public Library Foundation gala. I almost always carried a little notebook in my pocket.
It was also a period when I was consistently praised for my ability to produce, follow up and keep things moving.
Years later, after spending much of my professional life working digitally—and after learning more about how my own attention works—I started wondering whether I had been trying to solve the wrong problem.
Maybe I didn’t need to make increasingly complicated systems work for me.
Maybe I needed a system that was almost impossible to complicate.
No login. No internet. No notifications. No elaborate taxonomy. No deciding which project, label or status something belongs to.
Just a small piece of paper containing what matters right now.
When I started carrying small notebooks again, the difference was immediate. I felt more grounded in the work and much more capable of seeing what was actually in front of me.
I haven’t stopped using digital tools. They’re my profession, and they’re extraordinarily useful.
I’ve just stopped expecting them to do everything.
Increasingly, I think my best work happens somewhere between the two: digital infrastructure with an analog surface for thinking.