Monday Cup of Love

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From the archive

November 2026

Why should I buy this pumpkin pie? Conversations of an overthinker.

Monday Cup of Love, November 2026

Hello, friend,

Is this the first Monday Cup of Love to land in your inbox, or the first you have heard from me in a while? Welcome.

You may know me as a coach, a friend, a connection, or maybe not at all because you are new to this community.

Two things can be true: I am so happy to have landed here, and if this is not for you right now, please simply unsubscribe, which you can find at the bottom of this email. No hard feelings at all.

The First Thanksgiving

Last week I sat in the hot seat as a featured guest for The Authority Alliance, and I was asked to describe how my work actually helps people. The first picture that came to mind was Thanksgiving, and more specifically, the very first Thanksgiving you ever hosted in your own home.

Maybe you remember it, or maybe it’s coming up this year.

The groceries are sitting on the counter, the turkey is thawing in the sink (hopefully), and you have no idea how anyone gets every dish onto the table at the same time and at the right temperature. Meanwhile all the role models in your life can whip up a perfect Thanksgiving without breaking a sweat, and you’re quietly worried about serving your family a turkey that is overcooked, undercooked, or somehow both.

That was me many years ago. These days I’m pretty good with timing, and it took a lot of grace for my mistakes to get here.

The Pie in Aisle Five

Years ago, I was standing in Publix with my grocery list, and it had pumpkin pie on it. I was already feeling ashamed for not baking it myself, because I was about to buy this pumpkin pie knowing my mom had made hers from scratch every year. She would labor for days for this meal.

Somewhere in my grocery store musings, I realized I don’t even like pumpkin pie, and even more importantly, nobody in my family ever eats it. We just end up throwing it out.

So why was I buying it? And why did I feel ashamed about even thinking about buying it?

Of course, I walked away from it, but I was still thinking about it, because it was a family tradition.

Should I get it anyway? What if somebody comes over and is expecting their favorite pumpkin pie? Or what about pecan pie? And then, absolutely not, nobody wants pecan pie. Maybe I should make an apple pie. I don’t know, do we even really need pie? I mean, who needs that much food anyway? Surely somebody else will bring the pie, and I don’t need to be doing this, right?

So I bought the groceries I wanted to prepare for Thanksgiving and left the pie, confident that somebody was going to walk through the door with a Publix pumpkin pie, which usually happens.

These are the conversations that happen in the brain of an overthinker. That’s me. Is it you too?

Your Table, Your Way

Thanksgiving for my family is simply a really nice dinner together. For other families it’s a very formal tradition, and both can be wonderful. Some families gather at a fancy table, and others eat their turkey around the football game with plates balanced on their laps, which is quite lovely too.

The trouble starts when we try to host someone else’s holiday with our own kitchen, our own people and our own energy.

We used to have a tribe of people around us to fill in the gaps for the things we weren’t so great at, and many of us are now doing it on our own, at home and in business.

So when you find yourself being today years old at something new, whether that’s a holiday menu, a new role or a business that is growing faster than you are, let yourself laugh a little.

“Being new at something is how every one of us got good at it.”

Quote card: Thanksgiving for my family is simply a really nice dinner together. For others it is a very formal tradition, and both can be wonderful. Leonne Sherr

A Tool for This Week: Notice, Decide, Move

This one is simple enough to use this afternoon with your holiday list, your calendar or the task list for your business.

Notice what’s on the list and which items are there out of habit, or because the lady next door would have them.

Decide what truly belongs to your family or your business this season, and give yourself permission to take the pumpkin pie off the list.

Move one step forward with something that suits you better, and at the end of the day, stand back and look at what you created with the tools you have.

Quote card: Your confidence isn't going to grow until you allow your courage to happen for yourself. Sherri Sladek on the WonderMama Coffee Chat

Affirmations for the month

  • I am allowed to set a table that fits my own family and my own energy.
  • I can notice the conversations in my head and choose which voice to follow.
  • I do not have to bring everything to the table, because the people who love me want to bring something too.
  • I am today years old at something new, and I am learning with grace.
  • My courage grows every time I allow myself to begin.
November at a glance: Happenings

The WonderMama Coffee Chat. Every Wednesday at noon Eastern, I sit down live with guests who are using their gifts and talents to bring good into the world, and afterward the conversation continues privately inside The WonderMama Community. In November you'll meet Hanna Curman, Ilze Krastina, Nicole LeMastre and Mo Cooper. You can watch live on Facebook or catch every episode on YouTube: @theWonderMamaCoffeeChat

Your next season roadmap, Thursday, Nov 5, 8pm Eastern. This is a free live working session on Zoom where we write a letter from the version of you who has already made it through the next six months, and then take apart what stands in the way. There is nothing to buy. Register at leonnesherr.com/webinar. If Nov 5 doesn't work for you, we gather again on Thursday, Dec 3, and registration for that session opens at the same link right after this week's class.

A group class for moms begins in January. The WonderMama Compass is coming back as a small group for moms who have poured themselves out for everyone else and are ready to come back to calm, clarity and self-trust. You're hearing about it here first, and if you'd like to be among the first to know the details, join us in The WonderMama Community or book a time to talk.

A new home for my books. My books and tools now live together in one place, including The Calm Before the Monday planner, my journals and the anthologies I'm honored to be part of. A friend recently gave two of my journals away as door prizes at her summit, each with a little note from me inside, and afterward a woman found her, holding the journal, and said, "I needed to feel seen today." That is why I write a note in every signed copy I send. Those anthologies hold some of the most powerful stories I've ever read, and in January I'm launching The Whole Chapter, a new podcast where coauthors share the whole story behind the chapter they wrote. If you're starting to think about holiday gifts, take a look at leonnesherr.com/books.

Wherever your table is this month and whoever is gathered around it, I hope there is room for grace at every seat.

With love,
Leonne

Leonne Sherr

Leonne Sherr | Founder, The WonderMama & Wayfinders

Find the corner of my world that fits you best.

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