Our five-year-old made an interesting observation the other day:

“Daddy,” he said, “I think November and February are the boringest months.”

“Oh yeah?” I replied. “Why is that?”

“Well,” came his thoughtful answer, “they’re just kind of in the middle of things. Like, fall is September, October, and November, right? But September is back to school, and October is Halloween…then there’s nothing fun in November except it gets cold.”

“Huh…” I said. “I suppose that’s true.”

“And winter is December, January, and February, right? But January is New Year’s and March has March Break, but February has nothing fun except it’s cold and there’s no decorations.”

I laughed, “well…there’s Valentine’s Day.”

“Yuck,” he said. “Do you know all of the Sobble evolutions?”

Usually we know that when the conversation has moved on from his deep philosophical insights to Pokémon it’s time to let the stream of consciousness flow.

But this has had me thinking non-stop, as often his observations will: what do we do with these “boringest” months?

He’s right, of course. The way he thinks of seasons is pretty accurate:

  • Winter is December, January, and February.
  • Spring is March, April, and May.
  • Summer is June, July, and August.
  • Fall is September, October, and November.


Kind of an accurate description, if you ask me. And when you break them down, from a kid’s perspective of celebration, it’s sort of like this:

  • Winter is Christmas, New Year’s, and…meh.
  • Spring is March Break, Easter, and…meh.
  • Summer is End of School, Canada Day, and…meh.
  • Fall is Back to School, Thanksgiving/Halloween, and…meh.

In The Four Hour Work Week, Timothy Ferris points out that his goal is to execute two months of concentrated effort for one month of “mini-retirement,” doing whatever he wants — be that learning, relaxing, travelling, or whatever.

Do we take the same respite? Do we look at those two-month blocks of hustle and bustle as our “busy” times, and just trudge our way through the “boringest” months? Or, do we try something a little different?

Planning for Respite

If we have a down-month like August, we can use that to strategize how we’re going to approach the coming quarter. We know we have to get new clothes, new shoes, new supplies, etc. for school. We know we have to schedule our afterschool activities and plan our collective organization around them. But, what do we do with the down part of the down month? When do we strategize for those times?

Slower months with less festive activity are great times for calm and reflection. They’re also great times to play catch-up on routine tasks and to lay the foundation for the upcoming busyness of the next season.

So, here we are nearing the end of September. Back-to-school has wound down into something approaching a routine. Next month we have Thanksgiving and Halloween coming. One of my sayings is “you can’t start practicing the day of the concert,” which really means it’s a good idea to start thinking about the Christmas season in October so you’re not caught off guard. But, what to do with November (you know, the “boringest” month of fall)?

Here’s what I’m thinking:

During September and October, you can start planning for how you’re going to “do November.”

  • Don’t plan any major projects for November. Use it as a time to take things easy.
  • Clear out the autumn decorations. Revert to simplicity and blank canvasses. It’ll be easier to decorate for December when the other stuff is put away.
  • Clean and organize mindfully. Take meditation in your space and on your space as a ritual activity.
  • Take stock of your supplies. Get things ready for December, including refreshing baking supplies, checking those decorations, and getting the winter gear ready.
  • Make room for fun. There’s nothing pressing on the schedule in November, so plan those outings, road trips, photoshoots, or whatever your family likes to do.
  • Take a health and wellness check. See where your health and fitness goals are, resupply as needed, and set your next target date (that would be February 1st, if we’re carrying this idea forward).
  • Do some wrapping. Because you can, and you don’t want to get slammed right in the middle of all your other holiday activities.


Obviously this isn’t carved in stone. You can do whatever you like. But to my thinking, with November just over a month away it’s a good time now to start planning out how to use that down time as a period of calm, reflection, and preparation. Cycling it this way means we have an opportunity to spend two months celebrating and bustling and one month in reflection and “mini-retirement.”

…and all of that came out of a conversation with a five-year-old about the boringest months of the year.


Keep the conversation going…

aWhat do you like to do with the “boringest months?” Do you use the time for preparation, planning, and reflection, or is it another trudge to the next round of busyness and bustle? Let us know in the comments below!

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