Hacking Reflection

The idea of hacking reflection seems counterproductive. Reflection, after all, is supposed to be a slow and thoughtful and even meandering process. Hacking implies something else entirely.

But I have found that, due to its very nature, reflection often takes a backseat to activity. You can race through your entire workday until the last moment — when you often have to hustle to a personal responsibility (picking up children, meeting someone for dinner, cooking dinner, etc.). Thinking about thinking (or systems, patterns, habits) feels like a distant luxury — costly and out of reach.

I hack reflection, therefore, because it is both important and impractical. I know it could probably help my future self find new meaning and purpose (and pathways), but my present self finds it difficult to schedule.

Without a hack.

Here’s mine: I don’t schedule reflection, but I do schedule small activities that require or drive it.

For example, writing a near-daily blog post is (a) easy to schedule, (b) fun to cross off a list, and (c) requires reflection. Since blogging is the sole writing activity in my life for which I refuse to take notes in advance, the activity is usually entirely backward looking. I sort through my memory to see what stuck with me — what made an impact or impression — from the day that has passed. Then I write about it until I’ve captured it clearly, publish it, and return to it later for further polishing if I have time. Regardless of the quality of the final product, the memory crawl is a form of reflection.

“Tidy up (physical world)” and “Tidy up (digital world)” are (a) easy to schedule, (b) fun to cross off a list, and (c) require reflection. You can’t organize your things without thinking about them, moving them, turning them over (i.e., reflecting on them); you can’t file documents without matching them to a category (i.e., reflecting on them).

“Read folder names” or “Read file names” is (a) easy to schedule, (b) fun to cross off a list, and (c) drives reflection. Even just a glance at certain documents reminds you that they exist, which reminds you to reach for them at the right moment, which helps you to make use of them when they can have an impact on a project or decision.

“Read your notes from _____” is (a) easy to schedule, (b) fun to cross off a list, and (c) requires reflection. Many leaders with whom I speak are very good at writing things down during meetings; actually looking at what they’ve written down, actually making sense of it by reading it, actually converting scribbles into fuel into motion, is something that frequently gets lost.

I’m a big fan of making sure that the important things aren’t lost. Tactically, this means assuring that they do not become insurmountable or rare. In fact, I try to make them easy and regular, falling in line with the conventional wisdom about fitness — if the best exercise is the one that you will actually do frequently, the same holds true for reflection.

Frequently, then: Adding reflection-rich action items to lists ensures that reflection will take place in your daily workflow. Crossing things off lists adds to a sense of momentum and wellbeing. And the reflection that can happen, even upon the completion of simple tasks, will feed your future plans and actions. That’s why you should hack an activity that, on its surface, defies hacking.

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