⇐ Blog
Managing Tasks is a Hard Problem
What do you do when you don't know what to do?
May 07, 2026
To-do lists are often touted as the solution to task management. It makes sense on the surface—what better way to keep track of what needs to be done than by writing everything down in a list? This mode of task management has sprouted into a massive productivity industry selling notebooks, bullet journals, and an untold number of apps all of which promise to help the user finally get their life in order.
Despite their ubiquity however, to-do lists are rife with serious problems.
In a to-do list, completed tasks and pending tasks comingle; A to-do list will list tasks you’ve finished alongside tasks you’ve not finished and tasks you’ve not even started. This leads to to-do lists being very visually noisy, as well as leading tasks to being scattered all over especially long lists that span multiple pages.
As to-do lists grow in size, they grow in complexity. All outstanding to-do items will be visible regardless of priority. Breaking down complex items into smaller subitems only exacerbates this problem as task breakdown causes exponential growth of tasks. Paper lists cannot handle this mode of task organization.
For those whose brains house dysfunctional reward mechanisms, the mere act of organizing a to-do list can often be just as if not more satisfying than actually doing tasks—even those which one is highly motivated to perform.
Software applications built on providing to-do lists often worsen these problems by integrating into other services, adding timed reminders, deadlines and such. This might be useful in certain contexts, but not in others.
To-do lists supposedly require habitual use to work correctly, but these flaws often make it difficult or even impossible for some to properly engage with a list. All systems work with persistence, but hostile systems make it effectively impossible to persist.
I released a new app in early March of this year. In its aftermath, I was unsure what to do—I knew I had work to be done but nothing gripped me. Without tools to organize myself, I tend to work with capricious whimsy. There’s nothing necessarily wrong with this approach (it has after all led me to starting and finishing many projects) but it left me without the context of what I was up to before my last big project.
Really, what I wanted was not necessary a way to keep me on task, but to be able to bring me back to what I was doing before a digression, no matter how long. While searching for something very different, I ended up stumbling into exactly what I wanted: the project stack.
The idea of a project stack is quite simple: write down what you’re doing. When you want to break a task down, write down the first smaller piece you can think of and do that. If you’re distracted, track the distraction too. Want to do a different project instead? Put it on top of the stack. Have a message or a new work item that’s been reported? Push it, do it. Once you’re done a task—either by completing it or because you no longer want to do it—you simply remove it from the stack and throw it away.
The structure of a stack allows you to track digressions exactly as they come up. Old tasks are hidden by new ones, and with only one task visible at a time there’s never a question as to what your priority should be. It solves all of the problems of a to-do list while also specifically embracing distraction because some distractions happen for a good reason.
The project stack was so incredible to learn about that I had to immediately put one in place for myself. I understood immediately that it would have helped me return to whatever I was doing prior to finishing my last app, and I wanted to make sure that I’d have that trail in place for my next project. However, I wanted to avoid needing to buy a large amount of sticky notes for my own project stack. Unfortunately, there were no good apps for stack-based task tracking at the time.