Hello my friends,
It feels so good to be back home in Mexico after an unforgettable two months abroad. I had the joy of leading three incredible retreats in Italy, (one with my wonderful family), and exploring the Greek islands on a scouting trip for next year’s adventures. I made new friends, picked up a few Greek words, and (as always) came home with some fresh life lessons. There were a lot of “firsts” on this trip — some exhilarating, some downright uncomfortable. Let’s just say international travel will stretch you in all the ways.
And it got me thinking… about expectations — the ones we pack without realizing it, and how they shape our experiences.
Let’s be real — we all carry expectations.
They get packed quietly next to our swimsuits, sunscreen, and journals… and they come with us everywhere. Into conversations. Into relationships. Even into sacred spaces like retreats and women’s circles.
We expect the trip to be smooth.
We expect to get along with everyone.
We expect to feel transformed by Day 3.
We expect the magic to show up on our timeline.
And when it doesn’t?
We question ourselves.
We question others.
We question the entire experience.
After leading dozens of retreats, here’s what I’ve learned:
Expectations live in the future cuddled up next to anxiety.
They dwell in “shoulds” and "perfectly planned scenarios.”
They come from a need for control — a way to feel safe in the unknown.
But retreats — and real growth — ask us to do the opposite.
They ask us to be here.
To trust what’s unfolding.
To surrender to the magic in the missteps.
To find beauty in the breakdown.
I’ve seen this play out over and over again…
The woman who cried for two days thinking she was failing — then had her breakthrough on Day 4.
The one who came for peace but found chaos — and met her truest self in the mess.
The woman who longed for connection, but didn’t expect the fear of being truly seen.
Sometimes the thing we’re resisting the most… is exactly what we came for.
And when we step into sisterhood, it can feel even trickier.
We expect to be accepted instantly.
We want effortless connection.
We hope there’s no awkwardness, no hard conversations, no emotional landmines.
But real sisterhood is a practice.
It asks us to:
-Communicate with care
-Own our triggers
-Take up space and make space for others
-Stay open when it would be easier to shut down
-Consider the whole, not just our part
And when we travel? Well… definitely expect the unexpected.
The ferry leaves early.
The luggage doesn’t show up.
The weather shifts.
A casual wine tasting cracks your heart wide open.
When you release the plan, you find your presence.
You become more adaptable, more grounded, more you.
You learn resilience & resourcefulness.
You move from control to inner leadership. “I can do hard things”
So this month, I’m inviting you into something deeper:
-What invisible expectations are you carrying into your next adventure?
-What assumptions show up in your relationships or group dynamics?
-What if the real magic is hiding in the awkward, the slow, the not-what-you-planned?
This is the work we’re doing this month inside The Sisterhood Rising — and it’s the heartbeat of every retreat I create.
We’re not here to perfect the experience.
We’re here to live it — fully.
With curiosity.
With grace.
And with a willingness to let go.
With much love,
Cheryl
PS. Tulum and Greece retreats 2026 will be opening for registrations soon! You will be able to get all the details here: http://www.cheryldavenport.com
