October 2026
Your monthly roundup from Midlife Secret Society 🗝️
A little news, a few things to look forward to, and your monthly reminder that midlife is allowed to be fun.
🍂 From Inside the Society
Welcome, October. 🍁
Fall is officially here, and Jill and Cheryl are very happy about it-both unapologetically fall people. Cooler weather, changing leaves, football, cozy coffee dates, sweaters, and—perhaps most importantly—lots of good reasons to get together.
September was a busy one behind the scenes at MSS. Jill and Cheryl spent much of the month planning the rest of the year, and there's something about this time of year that makes planning especially fun. There are so many possibilities for getting together, trying something new, and making a little room for the things we actually want to do.
And then there was our very first MSS Speakeasy, built around one of our favorite ideas:
Little Things. Big Things. Why-Not Things.
Because not everything on your list has to be a life-changing adventure. Sometimes it's coffee with a friend. Sometimes it's finally taking that trip. And sometimes it's simply saying, “Why not?”
We're looking forward to a very full fall at the Society. 🗝️
Last month: The Midnight Library
We met on September 3 to talk about The Midnight Library, and while we all agreed it was a great book, we also agreed that it was a heavy one.
One of our favorite parts of the month was actually the conversation that happened before our meeting. Cheryl loved receiving messages from members about what they were thinking and feeling as they made their way through the book.
That's the magic of Between the Chapters. Sometimes the conversation starts long before we ever get on Zoom.
Now we're trading heavy for magical.
Septembers Book: Magical Midlife Madness
We're ready for a much lighter read!
Magical Midlife Madness brings us magic, midlife, and yes… a little madness. And our main character is in her 40s, so we're already feeling pretty well represented. 😉
📅 Thursday, October 1
⏰ 7:00 PM ET
We'll gather on Zoom to talk about the book, compare notes, and see where the conversation takes us.
Haven't finished the book? Come anyway. There are no book-club police. 🕵️♀️
Not part of Between the Chapters yet? Join Here
This One's for Jill — And Every Woman Who Never Got Her Girls Trip
She spent 20 years keeping the skies safe.
The girls trips never happened.
This one is for every woman who kept putting her getaway off until someday.
Read the latest Society Pages post →
Last month at Coffee & Conspiracies…
In September, we visited Bill and Bob's Coffee Bar in Stallings, NC—and what an absolute beautiful space it is.
The space was once a bar and was converted into a dual-purpose community space: coffee by day, and a place for AA and Al-Anon meetings in the evenings.
We found it beautiful, welcoming, and comfortable—and, of course, the coffee was great. ☕
We're always looking for interesting places to gather, so we're excited to keep exploring.
There's quite a bit happening inside the Society this month.
📚 October 1 — Between the Chapters
Magical Midlife Madness
🕵️ October 10 — MSS Speakeasy
A new theme. A new excuse to get together. Same secret-society energy. Our October Speakeasy has a brand-new theme and another excuse to step away from the ordinary and do something a little different with other women. Just a secret-ish gathering, a fun experience, and the kind of Saturday you might be very glad you said yes to.
Peek inside the October Speakeasy →
🧭 October 13 — BTC Studio: The Midlife Expedition launches
What if 2027 wasn't about becoming a “better” version of yourself—but about getting curious about the life you actually want to live?
The Midlife Expedition is our newest BTC Studio experience, inspired by The Happiness Project. Think of it as a bookish spin-off with a little more adventure, a little less self-help, and plenty of room to figure out what sounds exciting to you.
We're launching October 13. 🗺️
Learn more about The Midlife Expedition →
☕ October 24 & October 30 — Coffee & Conspiracies
As always, members can find the full details—including times and locations—inside the Clubhouse.
A Note from Jill & Cheryl
Here come the “Ber” months.
October becomes November, November becomes December, and suddenly we're wondering how Christmas got here so quickly.
Before we get swept up in holiday plans, family obligations, shopping lists, traditions, and everything else that comes with this time of year, we want to remind you of something:
Don't let the busy season take up every inch of your calendar.
Make room for the things you actually want this season to hold.
Maybe that's a holiday tradition.
Maybe it's a weekend away.
Maybe it's a girls' night.
Maybe it's an afternoon with a book and absolutely nobody asking you for anything.
Maybe it's doing something completely impractical just because you want to.
You are allowed to make space for you as you are now.
Not who you were when the kids were little.
Not who everyone else needs you to be.
Not who you thought you'd be by this age.
You. Now.
Because making space for yourself isn't something you have to earn after everyone else is taken care of.
It's part of the plan.
So as the calendar fills up, make sure you leave yourself a little room on it, too. 🗝️
October's little reminder:
You don't need a reason.
You don't need a milestone. You don't need to be celebrating something. You don't need to wait until everyone else is available. You don't even need to be particularly good at the thing. Want to take the class? Take the class. Want to wear the ridiculous outfit? Wear it. Want to plan the trip? Start planning. Want to go somewhere just because you've never been there? Go. Want to learn something completely useless? Excellent. Midlife is a pretty good time to stop waiting for “someday” to become a valid reason. Sometimes “because I want to” is enough. Consider this your official permission slip.
🗝️ The Society has spoken.
