I’m the Problem

Josh Olson asks, “How do you stay the course with task management?”

As part of the new gig, I’m continuing with [Workflowy] as my personal to-do system. It’s a bookmark called “Brain” and it’s roughly a page-long outline, but it’s still early in the gig. I’m bracing for the inevitable flood of tasks when I leave the honeymoon phase.

When this flood does occur, I’ll likely do what I’ve done in the past. When the work associated with task management become onerous, when it’s 1am and I’m dragging and dropping tasks hither and fro, I’ll think, There has got to be a better way.

There is. And it has nothing to do with well-designed productivity software.

I eagerly evaluate every single shiny new productivity system because my sincere hope is that they’ve solved for… me. They need to solve for the fact that I excite easily, but I have a short attention span. They need to solve for the fact that I eagerly embrace the disruptive new, I’m not beholden to the past, and will adapt to whatever new craziness they’ve designed. But they also need to account for the fact that new craziness has an incredibly short half-life.

It’s an impossible design specification and my advice for productivity software vendors is to ignore it.

We spend a lot of time asking too much of our tools when, in fact, what we really need is just good practices. I’m certain I could keep track of my individual tasks on a torn coffee-stained napkin reliably as long as the practice around the maintenance of that napkin list was reasonable and, more importantly, maintained consistently.

I eagerly evaluate every new productivity solution that shows up because I truly want them to be “the one,” but after doing this for over a decade, I’m certain the tool isn’t the problem. I am. Where the innovation needs to occur is not within Asana, Things, or Workflowy, it’s with how I choose to spend my time. It’s developing a well defined protocol for myself regarding maintaining my to-do list, and then religiously following this protocol and consistently investing my time.

Fact: to-do list management is boring. It’s like writing unit tests for your life. It’s maintenance work and we engineers both understand the value of maintenance work and excel at finding brilliant excuses to not do it. A simply delicious way of avoiding this boredom is to keep it interesting by changing the rules, finding a new application, and talking about your productivity workflow rather than maintaining that workflow.

Which is what I’m doing right now. See, I’m the problem.

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