MSS Speakeasy

Inside Our First MSS Speakeasy

September 30, 2026•5 min read

The Door Is Open

By Jill Pakledinaz & Cheryl Garcia · Co-Founders, Midlife Secret Society


Sometimes you don't realize you needed something until you leave it.

There was a moment after our very first MSS Speakeasy when we got a message that stopped us in our tracks:

“I really needed yesterday and didn't realize it until after I left.”

Honestly? That might be the best review we could have gotten.

Because the Speakeasy was never really about the fall bucket list.

Well… technically, it was.

We talked about little things. Big things. Why-not things. We shared ideas for things to do around Charlotte, things we've been meaning to try, places we'd like to go, and things that have somehow landed on that mysterious “someday” list.

There were laughs. There were introductions. There were a few “Wait, YOU want to do that too?” moments.

And there was a lot of fall.

But underneath all of that was something a little harder to put on an itinerary.

Space.

Space to step away from the usual Saturday. Space to talk to women you didn't already know.

Space to think about what sounds fun to you. Space to say something out loud that you've been thinking about quietly.

And maybe, just maybe, space to remember that you're allowed to have things you want to do simply because you want to do them.

So… What Exactly Is a Speakeasy?

The MSS Speakeasy is our new monthly gathering for Keyholders.

Each month will have a different theme, a different experience, and a different excuse to get out of the house and into a room with other women.

Sometimes we'll make something. Sometimes we'll try something.

Sometimes we'll explore something. Sometimes we'll have a little adventure.

And sometimes we may have absolutely no idea what we're doing until we get there.

That's kind of the point.

The Speakeasy isn't meant to be another workshop where someone stands at the front of the room and tells you how to improve your life. (Although Cheryl absolutely did this-even after she said “Don’t let me stand up there and "teach"!)

Cheryl here: I absolutely did! And I blocked the door! It was like I wasn’t letting anyone escape early…🤦 Jill and I had a laugh about that later. I promise not to do it again….well how about not always! lol

We're interested in something a little different.

We want to create experiences for the things women actually want to do.

Want to try something you've never tried?

Let's find a way.

Want to learn something random?

Let's learn it.

Want to go somewhere?

Let's go.

Want to finally do the thing you've been saying you'd do someday?

Well…

Why not?


Because Midlife Can Be a Strange Little Chapter

One of the things we've learned through MSS is that midlife isn't necessarily about figuring everything out.

Sometimes it's about realizing that the version of life you've been living doesn't have to be the only version available to you.

The kids are growing up — or already grown. Careers change. Relationships change.

Friendships change. Our bodies change whether we invited them to or not.

The things we used to care about sometimes don't matter as much anymore.

And the things we've pushed aside for years can suddenly start tapping us on the shoulder.

Hey. Remember me?

You always wanted to try that.

You said you'd go there someday.

You used to love doing that.

It can be exciting. It can be confusing. It can be freeing.

It can also be really nice to sit in a room with other women who don't need a lengthy explanation for any of it.

That's one of the reasons we believe creating space for connection matters.

Not networking. Not finding your tribe according to some carefully curated personality quiz.

Not sitting around talking about how to become the best possible version of yourself.

Just…

Being with people who get it.

Jill here: This is really why I wanted to build MSS in the first place. I kept thinking about how many women get to this stage of life and realize they want more connection, more fun, and honestly, just more reasons to get out and DO things again. Making new friends in midlife isn’t always easy, and neither is finding someone who wants to say “yes” to the same things you do. I wanted MSS to be a place where we could make that part a little easier. Where you can walk in not knowing anyone and leave thinking, “Okay…these might be my people.” And after our first Speakeasy, I feel like I got to see a little glimpse of exactly what Cheryl and I hoped this could become.

Women who are somewhere in this wonderfully messy middle of figuring out what comes next.


The First One Was Fall

Our inaugural Speakeasy was all about The Fall Bucket List: Little Things. Big Things. Why-Not Things.

We filled our Field Guides with ideas.

We tossed anonymous “Why-Not” ideas into the Fun suitcase.

We shared local places and experiences.

We talked about things we wanted to do this fall — from tiny seasonal pleasures to bigger adventures.

And somewhere along the way, a group of women who didn't all know each other when they walked through the door were laughing together like they'd been doing this for a while.

That's the part we hoped would happen.

We just didn't know exactly what it would look like.

Now we do.


This Is How the Society Grows

The Speakeasy isn't a predetermined calendar of activities that we created and expect everyone to follow.

It's meant to grow from the women inside MSS.

What are you curious about?

What have you always wanted to try?

What sounds like fun?

What would you do if you had someone to do it with?

What have you been putting off because you keep waiting for the right time, the right person, or some imaginary permission slip?

Those ideas matter.

They might become a conversation.

They might become a Field Guide prompt.

They might become a Coffee & Conspiracies mystery.

They might become a BTC Studio experience.

Or they might become the next Speakeasy.

Because that's what we're hoping to build with MSS:

Not a place where someone tells you what your next chapter should look like.

A place where you get to explore it.

Together.


And Then We Got That Message

“I really needed yesterday and didn't realize it until after I left.”

We keep coming back to that sentence.

Because sometimes the thing you need isn't another goal.

It isn't another podcast. It isn't another five-step plan.

Sometimes you need two hours where nobody needs anything from you.

You need to laugh. You need to meet someone new. You need to remember something you enjoy. You need to talk about something that has nothing to do with your to-do list. You need to be around women who are asking some of the same questions you are. You need a little room to wonder:

What if?

What else?

Why not?

That's what we're hoping the MSS Speakeasy becomes. A monthly excuse to open the door.

Come inside. Try something. Meet someone. Laugh a little. And maybe leave with something you didn't even know you needed.

The next Speakeasy is coming.

The theme will change.

The experience will change.

But the invitation stays the same:

Come see what's behind the door.



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