What to do about todos?

by Chester Snuphanuph, PhD

"Task Management" – it’s a sterile term, yet may take it as a centerpiece of their life’s work. Is it necessary? Sure, to some degree. But is it commonly overapplied or inflated beyond the bounds of reason? Most certainly.

For a time, I was such an inflationist. I believed that the best way to do more was to have more to dos, and then to will a oneself, or guilt oneself into doing them. There’s a kernel of truth here. But it lives in dangerous disorder. To navigate it, we must be conscious of two opposing tendencies of human (ir)rationality. The tension between them can highlight the goldilocks zone of sufficient but not overly prescriptive planning. It’s in this goldilocks zone that managing tasks reaps the maximal benefit to productivity without hindering creativity.

First, the truth: having things to do, and having committed to them via some conscious intention, is usually preferable to having nothing at all to do. Better to be busy working towards previously defined goals than skipping from whim to whim.

Let's capture this principle with an impressive-sounding name: "The Principal of Previous Intent.” Your present self, if anything like mine, is capricious, prone to whimsy, and tends to inflate the value of immediate experiences while undervaluing the future. To him, the valuation of time is like this:

Arguably, this curve is rational in high-stakes environments like those of our hunter gatherer ancestors. If long-term survival is uncertain, of course you should value the present more then next month, which you might not be around to experience. Especially if an activity, like eating, helps you survive, you should do it presently, without hesitation.

But in the modern world, in which we are lucky enough to have more guarantees of long-term survival, this instinctive over-valuation of the present leads to strange choices, like taking $100 today instead of $200 in a year.

When it comes to deciding how we spend our time, we actually have two instinctual biases conspiring against us. Not only do our instincts lead us to overvalue the present, they also present an inflated perception of what in the present merits our attention, with preference given to things which seem dangerous or promise novelty. These were, again, helpful instincts in the pliocene (pay attention to the charging rhino, then investigate those weird tracks you noticed around camp). But for the office worker, these instincts lead to procrastinating while checking the news and then spending what time remains putting out little fires that arose while you procrastinated.

Hence the Principal of Advance Intent. From a (temporal) distance, the distortions of the present and the importance of seemingly urgent tasks fade. We'd rather accept $200 in three years than $100 in two years. Rationality is required to supplant the tyranny of irrelevant instincts and this rationality works most clearly when done ahead of time, when one is clearheaded and free from temporal biases.

But beware the limits of human rationality! It's easy to extrapolate from the benefits of a rough schedule to the necessity of elaborate charts and lists with hundreds of tasks covering a project from start to finish. For example, a student working on her thesis might surmise “I have to write 60 pages in the next month, so every day, I'll write two pages." If only writing were as simple as this! What will actually happen? She'll stick with the regimen for a few days and then realize that her writing is disorganized, or needs more research, or that the idea she was pursuing is in some way flawed and the first ten pages have to be rewritten. An exhaustive plan might work well for things one does routinely, like applying for grant, doing chores around the house, etc; but for creative work, the terrain is by definition unexplored. You must be prepared to make the map for your journey as the journey progresses.

So this is the tension we must balance when budgeting our time. On one hand, we must employ of rational thinking in advance to escape the tyranny of instinct and impulse. But on the other hand, we have to account for the limits of our planning abilities. Neglect to plan, and you'll drift about putting out fires and spinning your wheels led, astray by mismatched instincts in a modern environment. But overplan, and you'll slowly drift away from the plan, becoming increasingly unmotivated by either its unrealistic demands or its irrelevance.

Bridging these two tendencies requires nimbleness and adaptation to the particulars of your projects, but there are general guidelines and practices which can help you find this sweet spot. I’ll be covering many of these in the coming weeks, including a knights errant themed approach to kanban-based task management, and some useful tools – and, for the aficionados, integrations with my favorite note-taking apps: Obsidian and Craft.