Calendars

I am a recovering productivity nerd with a keen sense of my own mortality that spends time with computer systems professionally. Because of this, I’ve accumulated opinions about dates and calendars.

  • Dates should be written in ISO 8601 format e.g. 2024-12-31.
    • The year-month-day order eliminates any ambiguity between month/day/year and day/month/year.
    • year-month-day strings are sorted the same both alphabetically and chronologically; n.b. prefixing filenames with dates is a great way to help organize data.
  • Weeks are the most useful unit of time.1 Months are too long to go without a recap. Days are too short to identify any trends. The week number helps anchor it in context; I track two:
    • The current year e.g. 2024 WK 45
      • This can be displayed in calendaring software:
        • MacOS Calendar: Settings > Advanced > Show week numbers
        • Google Calendar: Gear Menu > Settings > General > Language and region > View options > Show week numbers
        • Outlook (Mac): Outlook Settings > Other: Calendar > Calendar Options: Show week numbers
        • Fantastical (iOS): Settings > Calendar Views > Calendar Weeks
    • The week of my life e.g. 2167 (of about 4000). I was born on a Friday so I increment my “death clock” week number at the end of the workweek.
  • Weeks start on Monday.
    • This best reflects the rhythms of school, 9–5 office work, and similar job schedules.
    • It keeps the days of the weekend together on the right hand side of a 7-day calendar view making it easier to plan your weekend as a contiguous chunk of time. This reduces context switching when toggling between 5-day (work) and 7-day (personal) week views.
    • There is wide support for starting the week on Monday in modern computer and phone operating systems.
      • MacOS: System Settings > Language & Region > First day of the week
      • iOS: Settings > General > Language & Region > First day of the week
      • Google Calendar: Gear Menu > Settings > General > Language and region > View options > Start week on
      • Outlook (Mac): Outlook Settings > Other: Calendar > Work Schedule: First day of week
      • Fantastical (iOS): Settings > Calendar Views > Start Week On
    • You can configure the Periodic Notes plugin for Obsidian to support creating notes like this by setting the Format for Weekly Notes to YYYY/MM/YYYY [WK]ww.
  • Months are not long enough for long-term planning. If you need to execute a strategy or manage a long-running project, use a one-page year-long compact calendar.
    • There is an Excel template that does the heavy lifting. I customize mine to include both types my week numbers and work-specific times e.g. quarters or program increments.
  • Calendaring, like note-taking, benefits from being physically tangible. You don’t have to draw your calendars from scratch (although that can be satisfying); printing out a compact calendar and annotating it by hand works well.

I’ll leave thoughts on time and task management for another day.


  1. For time management anyway; the most useful unit of time for doing is 20 minutes↩︎