The Problem of Tools

Digital tools are great. They keep lists, remind you of deadlines, can re-order lists dynamically, and — crucially — move with you, synchronizing between phones, laptops, desktops, etc.

But it seems that these tools often fall into at least one of several traps:

• They’re simple and easy to use, but can’t quite do enough (I have this problem with Wunderlist)
• They’re super-flexible, but you spend an incredible amount of time changing settings and writing custom code (hi, Org-Mode)
• They have a particular model for doing things, and you have to fight to work in a slightly different model

Taskpaper is among the better ones I have tried; its light structure and nearly-free-form editing make for a good combination. The fact that everything is text makes it really easy to write little scripts that do useful things.

But at the end of the day, I still felt like I spent more energy wrangling TODO entries than getting things done. I suspect that part of the problem is feeling like the tool should be able to do more for me, so I try to get it there.

Many tools and methodologies also steer us towards a mindset that the tool should take care of the tracking and management and just tell us what to do next; this is especially true with features like Taskwarrior’s automatic prioritization. We do our weekly reviews to maintain our projects and lists, and then we just keep checking off next actions.

Thinking

For me, this automated task-queueing view of work does not provide sufficient reflection for me to make meaningful progress. I’ve become convinced that the best work management system for me is one that doesn’t let me offload everything.

One of the most productive things that I do is take time to think, each day and each week, about what I need and want to get done. I find analog rituals to be powerful; they provide the necessary space to think about what I am trying to do and what might not get done.

So if I have one piece of general productivity advice, at least for academics, it would be this: take regular time to think about what you are going to do.

Planning Desired Outcomes

Thinking about desired outcomes for each day, week, or term has helped me a lot. Jennifer got me started down this road: when I was struggling with productivity and organization in grad school, and had failed to make Getting Things Done work for me, she suggested making a list each day of 3 things I wanted to get done. That changed the game, and has evolved into the system I use today.

These are like next actions in GTD-style methodologies, but have a higher-level conceptual focus. A next action focuses on what I am going to do; a desired outcome focuses on what I want to have, with the action as a means to that end. They often center around the same thing: ‘prepare assignment 4’ is an action (prepare the assignment), while ‘Assignment 4’ is an outcome (the assignment is prepared and ready to give to students). But I find the desired outcome framing helpful in maintaining a focus on why I am doing the things that I am doing. If I do this work, what is different about the world around me?

Dave Lee’s week chart is a very useful starting point for building this kind of thinking into a week’s work structure. My own strategy is a little different now — that is the topic for the next post — but embodies many of the same ideas, and I recommend the chart wholeheartedly.