Scaling a Productivity System

I’m somewhat of a list ninja. I can create specific lists for any corner of my life and I have systems in place to execute on those lists properly. I’m always learning, but I’ve also been learning for over a decade.

Someone on a subreddit asked about how to start with todo lists. It made me think back to my start with to do lists. Back in 2006, when I realized I just wasn’t organized enough naturally, I turned to the Getting Things Done book to try and get myself together.

My first to do list was a piece of paper. I had about 8 tasks. This was before I knew about capture, or the art of noticing the opportunity for new tasks. It’s likely why I was so unproductive. I was conducting my life based on how I felt on the moment, not with any true intention.

Once I got better at capturing tasks, the number of items I had to deal with suddenly ballooned. I gathered a bunch of multicolored index cards and a space pen that I lost and repurchased many times. I put a binder clip on the cards and put them in my pocket. There was a list for business ideas, songs, blog posts, and general todo items.

My life at the time, though it didn’t seem like it, was pretty simple. I had coursework and a job, and eventually the task of getting a post college job. That was about it.

When I got my real job I had so many todos that my index cards weren’t really holding up. I had more tasks than ever, more categories of tasks than ever, so the system scaled: I started putting stickies on the perimeter of my cubicle, like how a cook takes orders.

And as life got more intense, so did my system. In 2014, I discovered OmniFocus which allowed me to do things like hide tasks until a certain date, or only show one step of a project at a time, so I wouldn’t get overwhelmed and could break complex projects down. I was a teacher at the time, and became super reliable using OmniFocus. I was using OmniFocus by creating lists of location based contexts: I had a list for morning tasks at school, which was reserved for more cognitively demanding stuff like lesson planning. The afternoon list had more physical labor, like copying.

And then as I started to get into the phase of my life involving property and children, my tasks yet again ballooned, and so did my system. I started using the perspective feature in OmniFocus, slicing up my tasks multidimensionally, by project and by context. One filter or perspective I use shows me tasks related to any project that isn’t considered creative, and is due within 4 days and/or flagged as high priority. Another one shows me all creative ideas yet to be executed on. It’s another layer on top of context and project, a modular way of bringing up only tasks that can be executed on quickly and immediately.

At this point, a decade in, I like to think that I could handle any project that was thrown at me. Running a marathon, writing a book, stating a business, whatever. I went from 8 tasks on paper to hundreds of tasks with distillers and filters.

But it will occasionally require me to scale my system. Which means my systems must remain scalable. And it’s important to pick the right moment to scale. Too late and you’re drowning, too soon and your productivity vehicle is about as good as a boat in a bathtub.