Calendars and Planning for Rebels

Poster of Calendar

I pour over the calendar aisle in every store soaking in colors and bindings and smooth papers.

How does one choose something so important and personal?

When stressed, I obsess at planner porn and wonder how other people make them so pretty. How do they make their handwriting so neat? How do they know what pens and markers to use? How much flipping time do they spend writing out their schedules? Who has that much to write down? What do they do when they make a mistake? Why does anyone need a water log?

But alas, all this pretty is simply not useful or practical for me, because I’m a rebel.

One of the best things I learned from reading The Happiness Project was happiness begins by understanding our true nature, and not by pretending to be fantasy version of ourselves.

When I look at planner and journal porn, and the little voice in my head says, “maybe I do need a new planner,” what I’m really doing is imagining a fantasy Cherri, who is an upholder, and has a whole set of skills and habits that real-life rebel Cherri does not.

Gretchen Rubin’s first commandment of happiness is to “be Gretchen.” So for all personal organizational tasks, I must be Cherri.

Here is what I know about being Cherri when it comes to calendars and planners.


  • won’t write in a planner or journal if she paid too much for it. We could delve into the psychology of this, but this post is long enough.
  • doesn’t enjoy waste, nor does she like buying shit she doesn’t need, nor clearing out clutter fantasy Cherri purchased years ago. (She does, however, enjoy browsing, and often puts things in her cart while shopping and puts them back on the shelf again before leaving the store.)
  • prefers paper to digital systems. (Ideally I’d have a digital reminder system, but google calendar notifications stopped working on my account–and I’ve tried every trick to get them to work I can find–and so paper it is.)
  • prefers to use pencil in a calendar so it can be erased, but will use pen and whiteout tape when necessary.
  • likes to see a whole month at a time.
  • doesn’t write a to-do list in her calendar.
  • prefers low-contrast design with white paper and black/gray lettering.

I did not know these things about Cherri at ages 20, 25, 30. I mostly had them figured out by age 45, but still need to remind myself sometimes. I go into a panic every now and again about some aspect of my life, and for a brief moment, I think a new calendar or planner will fix it. Because, of course we should be able to organize the chaos of an uncertain universe with a few pieces of pretty paper. Of course.

Mostly, being Cherri means I know better.


Before you decide on a calendar/planner system—or before you revise the one that isn’t quite working–you might take an inventory of your actual habits when it comes to writing things down and keeping track of your must-dos. What you think is a gorgeous work of art and what works for your friend/spouse/parent might not be the right choice for getting your own shit done.

As far as my own calendar, as that is the theme for today’s challenge, I keep a simple monthly paper calendar where I write appointments, etc. If I have to be somewhere other than my normal work schedule, it goes on the calendar.

I don’t carry this calendar with me. I leave it at home on the desk. If I need to add something while out and about, I use my Penseive app to email myself then add it when I get home.

Originally published for #readwriteplan by Cherri Porter August 1, 2016.

Protip: Do not google “calendar porn” or “planner porn” without your safe search on. You can never unsee that!

Image Source: The Miriam and Ira D. Wallach Division of Art, Prints and Photographs: Art & Architecture Collection, The New York Public Library. “August” The New York Public Library Digital Collections. 1887 – 1922.

<©2018 Cherri Porter>