A Ritual of Retrospectives

New Year’s Resolutions are forward-looking—commitments we make (and likely don’t keep) with ourselves to create a future we’d like to inhabit. But if we don’t consider the past, we might set our sights on the wrong destination.

Retrospectives are a means to reflect on past performance and garner lessons to apply in the future. One-off retrospectives are good, but regular retrospectives are best. Here’s how to create a retrospective ritual:

  1. Pick a cadence. Reflecting on a whole year is too daunting, but reflecting on a single day is too much overhead. Weekly or monthly retrospectives fall in that goldilocks zone—enough to make it worth it without being overwhelming. I do it weekly.
  2. Follow a format. Start simple and evolve. Crack out a journal and list bullet points under a few headings. I find that three things (surprised?) are sufficient:
    1. Highlights. What worked well?
    2. Lowlights. Where did you fall short?
    3. Learnings. What did you learn?

A simplistic example for my Turtle’s Pace newsletter in December 2021: