What I still want out of time management tools

April 25, 2020 · 2 min read

I made my first todo list almost 25 years ago. Ever since, I’ve been evolving my tools and system for tracking tasks, managing time, and improving productivity.

A personal productivity toolbox is a very personal and contextual thing. I find that my own systems have to be revised every few years, as my life and work situation changes. What worked in college is not what I needed as an employee; what worked as an engineer is not what I needed as a manager.

Right now there are two things I need:

Focus, without rigid schedules or artificial time slices

I have tried Pomodoro-ish things, like Vitamin-R. I’ve also tried distraction-blockers like StayFocusd and Freedom. And I use social media time limits on iOS. They all sort of work, but I’ve never stuck with any.

I think the mechanism of time is too rigid. There isn’t an optimal amount of time to spend on social media, or optimal hours of the day, not exactly.

An alternate mechanism, which I find valuable but have never seen productized, is deliberate transitions (a concept I learned from Jean Moroney). So, if you want to take a break, you can do that—but as a conscious choice, rather than an absent-minded distraction. If you want to browse Twitter, you can do that, but as a conscious choice, not out of habit.

I think this could work better, especially if combined with some desired allocation of time to different buckets, and something that nudged you towards whichever bucket was relatively farthest from todays’ goal.

I kind of want something that takes over my browser new-tab experience, so that every time I open a tab it reminds me of what I decided to do, and prompts me to either stick to that, or make a deliberate transition.

A way to triage tasks, articles, and emails

All todo-list apps help you track what to do. I haven’t seen one that helps you decide what not to do.

Tracking is easy—I can do that in any text file or notes app. My problem is that things linger on the list forever. Same problem with reading lists (like Instapaper). I save more stuff than I can ever realistically read.

Rather than fight this, I want to embrace it. I’m always going to write down more tasks, and save more articles, than I’m ever actually going to get around to. That’s natural and even healthy. What’s needed is good triage.

I have this idea for a todo list where items fade away the longer they’ve been on the list, and eventually disappear. If you want to rescue them, you have to mark them important—at which point they get more red-hot and insistent as time goes on. Call it “To-Don’t”.

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I’m really tempted to build one or both of these. Please save me by telling me that someone has already built exactly what I want.