I’m a finisher. Perhaps overly oriented to checking things off the list. Steeped in classical American values, reliability is my primary character self-test, even with regard to tasks that don’t really need to happen. Even I get fed up with myself when my life seems to be a list. I occasionally do a list-fast. The problem is that most if not all tasks are fractals. Once you get into them, they get more complicated than you anticipated. I often feel bad about myself when I can’t quickly dispatch a task.

My weekly planner is designed partly to keep my arbitrary ambitions in check. The bottom third of the page is devoted to three columns: “urgent”, “process”, and “next”. The tasks listed vary dramatically in size, but this half page tidily captures all the work and admin. Every Monday morning I copy last week’s pending items to the new week.

The top part of the page is devoted to daily planning. Each day’s column begins with appointments and is followed by three priority tasks. Often I do more than this, but these are the things that really need to be done TODAY. Setting the day’s priorities is something I do during my imperative morning coffee and blank paper session.

The last rows of the daily columns allow me to track exercise, diet, cash expenditures, and billable hours with super low friction. This data can wait there until I have time to enter into spreadsheets.

This system has been in place and functioning for more than five years.

Recently I took on a new project that is more fractalous and more challenging than many I’ve done before: Managing an estate.

My planning process has always involved known tasks whose subtasks and length I could estimate. Now I face a list of tasks that I have actually no idea of the scope, materials, tools, and skills required. I’ve developed a new approach to task management: circuits.

At the start of one of these tasks I no longer presume to imagine a timeline. I just start making regular visits and forays, initially 15-20 minutes long. [1] Go look at it. Then go have a cup of coffee and make some drawings.  [2] Examine some relevant materials in a store. [3] Go look at it again, try out some tools. See how resistant it is to manipulation. [4] Walk around the whole property looking for unused materials that might help. [5] Do some internet research, get some ideas, knowledge, options, models. [6] Go look at it again. [7] Manipulate a small part of it toward the objective. Get a lot of new information about how hard it is. Take a nap. [8] See who I know who might help me strategize and talk to them. [9] Invest in tools and materials and give it a go. (Just a little one.) [10] Now I have a sense of scope and strategy and can plan completion.

Most of the visits do not involve any visible progress on the task, but each one reveals a lot of new information. Every pause between visits involves reflection, passive and active research, and design strategy. My old system involved devoting myself to the task without interruption and often without the proper tools in order to finish in one day or one weekend. Often I restricted myself to just one trip to the hardware store, making do with whatever I was able to organize. Stretching the task across more calendar time results in a more efficient resolution, usually less hours of labor, more repurposed materials, and a better design, which has been refined nine times instead of once.

Originally posted on Syntax of Power