October 19, 2026
Kimberly’s Wanderings & Wonderings: October 2026
Falling Leaves. Fewer Bricks. Fourth Quarter.
Picture this: You look down at your phone, and the “remember these” photos pop up. There you are, looking at your kids as little munchkins around the kitchen island, carving pumpkins. What a memory (a messy one, but precious).
As the kids got older, we stopped carving. I do not even buy my pumpkins until about two weeks before Halloween because I get annoyed at the squirrels who pick away at the beautiful pumpkins.
There is nothing better than fall. As much as I am a summer girl, fall is always special. Football. Apple pie. Leaves changing to every shade of amber and gold. This fall has been stunning, and I have been soaking up every minute of it.
But it is more than the beauty. The change in seasons stirs me. Every single year. It is as if the world hands me permission to notice what is shifting, outside and in.
Here is something I cannot stop thinking about. Trees do not lose their leaves. They let them go. As the days shorten, a tree grows a thin layer of cells at the base of each leaf and seals it off, on purpose, so it can hold on to what it needs to make it through winter and grow again in spring.
The most beautiful season of the year is, at its heart, a season of release.
And here we are. The fourth quarter. The mad dash to the end of the year. The calendar fills (and mine is getting uncomfortably full), the list grows, and the clock keeps running.
The Wider Lens
We tend to do the opposite. As the year winds down, we pile on. One more project before year-end. One more commitment, because saying no feels harder than saying yes. One more expectation we never stopped to question. We treat the fourth quarter like a sprint to the finish line, when it is really a threshold: the space between a chapter that is ending and one that has not quite started yet.
Earlier this year, I wrote about a moment at SoulCycle when an instructor stopped mid-climb and said something that hit me square in the chest:
“If you keep carrying the same bricks, you will build the same house.”
At the time, I thought I was writing about spring. I was not. I was writing about transition. Spring cleaning, the fourth quarter, any threshold where the old chapter is visibly ending and the next one has not begun. That is when the bricks get heavy enough to notice.
Why did I think this was a good idea?
So, earlier this year, when the opportunity came to speak at TEDxStriversRow, I said yes before “Chester,” my inner critic (and yes, I named it), could talk me out of it. I have always aspired to give a TED talk, but now, only weeks away, I think it was a bad idea!
My talk is still very much in progress, in the in-between, which feels like exactly the right place to be writing from. And exactly the wrong place. I should be pencils down and learning to memorize and work on the “performance.” I am in the messy middle.
Back in January, I joined a women’s mastermind program to sharpen my research, my business strategy, and my writing. If you know me at all, you know that signing up for a structured program with five other women would not have been high on my list. Retreats, weekly morning Zoom calls, monthly deep dives, and a lot of preparation. One of the many things I am doing to help get me to this talk.
Preparing for this has required me to shift priorities in ways I did not see coming.
A true TEDx talk is in service of others. In order to do that, I have had to discover exactly which bricks I am still carrying that are getting in the way. For me, it is two: The need for perfection. And, the need to not disappoint.
I have been desperately trying to set them down, one draft and one rehearsal at a time. And I am wondering: did I ever choose either of them? Or were they handed to me, and I simply kept carrying?
Neither was wrong. They just are not mine to carry into this season. Like the trees outside my window, I am learning that letting go is not loss. It is preparation.
Football and Family Time
I have watched more football this season than in years past. My youngest, Ash, is totally into it. Thursday night. All day Sunday. Monday night. It is a lot. But I am treasuring the family time. Ash is going to move out again and start their next chapter. So I am embracing this time as a gift.
Between the Q4 craziness, the energy around my TEDx talk, and kicking off year two of Keep Wondering Why, I am trying to carry a little less into this season and hold on a little tighter to what matters. What will you carry a little less of? What will you hold a little tighter? I would love to know.
Drop me a note or find me on LinkedIn. I read every response. I mean that.
In case you missed it, here are some other recent posts and a podcast you might enjoy.
Pick a pumpkin and carve it. Be nostalgic. Have fun. The wondering continues.
With love and curiosity,
