I hate seeing people struggle.
Before Topia, I spent years running my own retreats. And looking back, there are so many things I wish someone had just sat me down and told me. It would have saved me a lot of time, a lot of money, and honestly — a lot of heartache.
I get it. There’s real value in learning things the hard way. I wouldn’t be where I am without those lessons. But part of why I went through all of it is so I can pass it on. So if you’re in the thick of it right now and feeling the weight of running events, these are the exact things I had to learn on my own — and I’d rather you didn’t have to.
1. Your first sell-out is a gift. It’s also a trap.
My very first retreat sold out in a week. It was hard work to pull off, but I had a blast and I knew immediately I wanted to do more.
Because it filled so fast, I didn’t even stop to think about the fact that the next ones might not. I went home and scheduled three more retreats for the following year, fully convinced the momentum would just carry over.
It didn’t.
I ended up canceling one completely. The other two were way smaller than I’d planned, and I had to hustle hard to fill even those. The first time around, I hadn’t needed to think about marketing at all — and I’d convinced myself that meant I never would.
That was a rude awakening.
What I didn’t understand then is that your first retreat draws from a very specific well — your closest friends, your most loyal students, your family. People who show up because they love *you*. My parents came to that first retreat. My best friend came. They weren’t coming to the second one.
After that, you’re marketing to people whose main question isn’t “how do I support Chelle?” It’s “what am I going to get out of this?” Which is completely fair — but it requires actual marketing work. I thought all those blogs and newsletters about how to fill retreats didn’t apply to me.
Spoiler: they did.
2. Picking partners based on affection instead of alignment
That first retreat, I ran solo. Even with Kris supporting me behind the scenes, it was a lot. So when I scheduled those three upcoming retreats, I wanted collaborators.
I picked three teachers I genuinely liked and believed in. What I didn’t do was think through the division of labor — not the teaching part, but everything else. The buildup. The marketing. The behind-the-scenes logistics of actually running a business together.
One of those partners is still one of my favorite teachers to this day. Her studio classes were packed. I assumed that meant she could sell a retreat. It didn’t mean that at all. We didn’t sell it. We had to cancel.
I made a classic rookie mistake: I focused entirely on the content and the connection, and completely overlooked the operational side of the partnership. Loving someone’s teaching is not the same thing as being aligned in business.
3. Cannibalizing your own bookings by offering too many choices
When I launched those three retreats, I put all of them on sale at the same time. I thought I was being efficient. I thought I was giving people options.
What I was actually doing was splitting my own audience three ways and creating decision paralysis.
When people have too many choices, they end up choosing nothing. Instead of building real momentum around one retreat, filling it, and then rolling that energy into the next launch — I scattered everything. Three dates, three themes, three times the marketing work, a fraction of the results.
If I could go back, I would have focused on one retreat at a time. Build the container. Fill it. Create urgency around that specific date. Then — and only then — introduce the next one.
4. Working with a venue that doesn’t over-communicate
On one of my early retreats, I worked with a center where getting basic information felt like pulling teeth. They were never upfront about anything. I had to beg for photos. I had zero tools to help me understand the space, so I ended up selling the rooms incorrectly. Every time I reached out for clarity, I was made to feel like a nuisance.
The financials were even worse. I thought I understood the pricing — until I didn’t. The structure was so vague that I didn’t realize what I was missing until it was too late. I walked away making significantly less money than I expected, literally in tears trying to get the details I needed just to understand my own bottom line.
I later found out that this kind of opacity is practically standard in this industry. Which is infuriating.
That experience is a big part of why I built Topia. Not just because I wanted to own a retreat center — but because leaders deserve real support and total transparency, and I couldn’t find a venue that was actually providing it. We give leaders every detail upfront so they can protect their margins, set accurate expectations, and show up to lead without the background stress.
My honest advice: if you don’t feel completely informed and supported from the very first conversation with a venue, trust that feeling and move on.
5. Relying on handshakes instead of requiring trip insurance
This one still stings.
On one of my early retreats, I had no contract and no refund policy. Everyone paid via Venmo. Nobody signed anything. It was all handshakes — total rookie stuff, and I knew better.
Then one of my guests was diagnosed with breast cancer. She asked for her money back. I told her I couldn’t. She told me she really needed it.
How do you say no to that?
I refunded her on the spot. And because it was last-minute, I couldn’t fill her spot. The bills I owed the venue didn’t go away. The financial commitment didn’t shrink. One cancellation, and a massive chunk of my profit was just gone — straight out of my own pocket.
Here’s the reality of this business: people don’t cancel because they changed their mind. They cancel because life falls apart. A diagnosis. A death. A divorce. You’re not going to look someone in the eye during the worst moment of their life and read them your no-refund policy. You’re just not.
Which is exactly why trip insurance needs to be non-negotiable from day one. It takes *you* out of that impossible position. Your guest is protected by professionals. You’re protected financially. And you don’t have to choose between being a decent human being and keeping your business alive.
It’s the only solution that’s actually fair to everyone.
