The Penguin Strategy: Why Now Is the Time for Retreat Leaders to Huddle Up
Your Empty Rooms Aren’t a Personal Failure—They’re a Sign of the Times
Right now, something strange is happening in the retreat world and no one's really talking about it publicly. Let me say it out loud: retreats aren’t selling like they used to. Not for most people.
I just got off a Zoom with Erin Fish from WanderWell—a company I admire for its ethics, collaboration-first mindset, and above-and-beyond customer service. (I’ve been recommending them to my customers for travel insurance and we all could not be happier.) Erin and I were talking about the state of the American travel industry, and one thing became glaringly clear: people are struggling to fill retreats. Period.
Which, for me, is weird. Mine usually sell out in hours. Maybe a couple of days, tops. But now? I’ve got empty rooms.
And that’s when Erin said something that sparked a wildfire in my brain:
“What if collaboration isn’t just a value we preach—but a literal survival strategy?”
What If We Co-Retreated?
Here’s the idea: instead of one retreat leader trying to fill a 12-person retreat on their own, what if three or four of us teamed up and shared the same retreat space at the same time?
Same venue. Same dates. Different programming.
Say I’m doing a men’s clothing-optional retreat. I already know folks doing clothing-optional yoga and someone else doing a men’s cuddling retreat. What if we pooled our resources and said, “Let’s all head to the Imaloa Institute in Costa Rica the same week”?
Each of us runs our own retreat, tailored to our audience. But we share meals. We meet up for sunset cocktails or cacao ceremonies. We cross-pollinate.
So maybe one of my naked guys gets curious and joins a yoga session. Maybe a yoga guest dips into a cuddle workshop. And suddenly, we’re not just running retreats—we’re creating a community.
Why It Works Now
This kind of model works especially well during economic slowdowns. Why? Because:
Everyone only needs to sell 4–6 spots instead of 10–12.
It reduces financial risk for each retreat leader.
You get built-in cross-promotion from the other leaders.
Your guests get bonus experiences without extra costs.
It's not permanent. It’s a smart pivot. Like penguins huddling for warmth in a blizzard. As Erin put it, “We survive the storm together.”
When Travel Bounces Back…
…we can go back to running solo, high-margin, deeply immersive retreats. But right now, while interest is shaky, wallets are tighter, and group energy is still healing, this could be the bridge we need.
If you’ve been staring down an empty roster and wondering if it’s just you—it’s not. The travel winds have shifted. But we can adapt, share the load, and keep our magic alive.
So maybe the question isn’t how do I sell my retreat anymore.
Maybe the question is:
Who do I want to retreat with?