Field Notes #003

There is an old saying that shows up everywhere in personal improvement advice: That you ought to “Plan your work, and then work your plan.”

The idea is appealing, but it is challenging advice to follow. This is in part because it’s just tough to stay disciplined, but also because the idea of “responding to change and staying on the lookout for emergent opportunities” matters a ton.

Sometimes those two factors even bleed into one another: it’s easy for me make an excuse to “change up my plan” in favor of chasing down a new idea or opportunity to collaborate when in fact I’m just avoiding some more difficult or tedious work that I don’t want to do at that particular moment.

When changing plans last minute results in a good outcome, I pat myself on the back for being flexible. When they result in a bad outcome, I chastise myself for a lack of discipline. This isn’t a healthy way to look at things, and it’s a habit I’m trying to get myself out of.

One technique I’m using to rewire my approach towards planning is to pay just as much attention to what I’m actually trying to accomplish in life as I do to what I’m trying to get done week by week and day by day. This is not something I do just once in a while as reflective exercise, but on a continuous basis.

The approach I use is simple enough: I use a tool to send myself a handful of questions each day, which I can answer via email in just a few seconds. The tool collects my responses over time, and I can review them whenever I’m doing deeper planning or just need a reminder of what’s been going on inside my head lately.

Here are the current questions I send myself and their schedules:

  • What is my mission in life? (Every Sunday)
  • What am I doing too much of? (Every Sunday)
  • How can I be of service? (Every Monday, Wednesday, and Friday)
  • How can I live well? (Every Tuesday, Thursday, and Saturday)
  • What am I doing too little of? (Every Wednesday)
  • What is ONE THING I want to focus on today? (Every day)

And here’s a quick example of what typical response to these questions look like for me:

Screen Shot 2018-03-20 at 9.04.59 AM

I find these questions to be quite like a continuous integration system for my daily life. I can tell when my plans and my work are “breaking the build” by the answers to these questions observed over a few days or weeks.

This process gets me thinking about this whole “Plan your work, and then work your plan” idea in a different light. It adds a step zero which is “Align your plans with your purpose.”

Little by little, I feel like this process of continuous reflection is helping me live and work better. If you want to try it out, I strongly recommend it! There are a few things to keep in mind, though:

  • It’s better to have too few questions in your list than too many, don’t overdo it.
  • It’s important that you can answer your questions in no more than a few seconds.
  • If a question stops being helpful, remove it or reword it.
  • Make sure to schedule time at least once per week to review your answers.

If you try this out, let me know how it goes by tweeting @practicingdev or emailing

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