More Than A Retreat

The other night I had a dream that we were hosting Waypoint Retreat.

I honestly don't know where it was. Some random house somewhere. Dreams are weird.

There were people everywhere, all looking at me waiting for instructions. What's next? Where are we supposed to go? What's the plan?

And in my dream, I knew I hadn't planned for anything. I wasn't ready for people to arrive yet. I still needed more time to prepare.

I remember feeling completely panicked with all of those people looking to me.

I woke up literally sweating and my heart was racing.

I know this sounds dramatic... it's not like I was being chased and my legs didn't work (those dreams are awful), but this was a literal nightmare for me.

Once I was fully awake, I couldn't shake the dream. I care about this. Probably too much.

The first time we hosted Waypoint in September 2025, I had absolutely no idea what I was doing. I'd never even been to a retreat. I'd always thought of them as a little too "kumbaya," full of circles and feelings, which has never really been my thing.

But I loved the idea of bringing great people together and having them leave feeling different than when they arrived.

In 2023, while Greg and I were planning our wedding, my now sister-in-law sent me a link to a place called Whispering Springs. Safari tents tucked into the trees. Campfires. A beautiful open-air barn. It was exactly the kind of wedding we would have wanted.

For a number of reasons, we got married in our backyard instead, and I wouldn't change a thing. But I never forgot that place.

So when I finally talked Greg into this whole retreat idea in early 2025, Whispering Springs was the first place I called.

We drove three hours from Waterloo to Grafton to see it. Except everything was closed for the season and covered in snow. The safari tents were packed away, and the beautiful dining barn was filled with winter storage. We walked through the snowy property with Nina, the venue coordinator, trying to picture what it would look like in September.

Then we took a deep breath and booked the entire property anyway, based on our connection with Nina and the photos we'd seen online (which were mostly of weddings). We committed to a full property buyout, which meant that if nobody signed up, we'd still be paying for the whole thing.

The work began, and we were PUMPED, dreaming up ideas and promoting it every chance we got.

Then came the "no's." More than 200 of them. Yes… we had a spreadsheet and tracked every conversation we had.

"I can't make it." "Maybe next year." "It's just not the right time."

Every no chipped away at us. We joked that if nobody came, we'd just invite friends and family and throw ourselves an expensive second wedding.

But every time we questioned whether we were crazy for doing this, we kept coming back to the same feeling: this mattered. We were doing it, even if only a handful of people showed up.

And in the end, twenty people took a chance on us.

What happened over those three days exceeded anything I imagined. And looking back, it wasn't the agenda, or the workbooks, or even the property. It was that we'd built a space where people felt safe enough to simply... be.

Greg poured himself into the content, the frameworks, the conversations that helped people make progress. I obsessed over the experience: the welcome gifts, the playlists, the room setup, the meals. The small things ARE the big things. I've believed that my whole career, and I watched it prove itself again and again.

When people feel cared for, they show up differently. They stay a little longer at the fire. They ask better questions. They have conversations they wouldn't have had anywhere else.

One of those conversations became something none of us could have predicted.

During a property walk, Nancy Corcoran, one of the founders of Whispering Springs, told us about her granddaughter Ayla, who lives with quadriplegic cerebral palsy after a birth injury. Listening that day was Ellyn Winters-Robinson, who after her own breast cancer diagnosis had partnered with an AI company called Gambit to build AskEllyn, a companion app for people navigating breast cancer.

That conversation planted a seed, and today, Nancy's family has partnered with the same team at Gambit to build AskAyla, an AI companion for families raising children with disabilities.

We can't take credit for it. Nancy's family created it. Gambit built it. Ellyn inspired it.

We just created a place where the right people happened to meet.

People ask what actually happens at Waypoint. The easy answer is that you get three days at Whispering Springs, workshops, a guest speaker, chef-prepared meals, campfires, yoga, and time and space to think.

When we were naming our retreat, I came across the definition of "waypoint," which is a stopping place on a journey. A pause before continuing on. That was it exactly, a place for entrepreneurs and builders and dreamers where the right conversations happen because there's finally room for them to.

Ever since that dream, I've thought a lot about what it really meant.

In the dream, I was unprepared for a room full of people waiting to see what I'd built. And that's what building anything feels like. You're never as ready as you want to be.

But you do it anyway, because the not-knowing doesn't go away. You just get better at building next to it.

Twenty people took a chance on us last year. I have no idea how many will this year.

But we’re doing it anyway and I can't wait for it!

And I sure as hell will be prepared. :)

The story doesn't end here.

The place that inspired Waypoint has an incredible story of its own. We recently sat down with Nancy Corcoran, co-founder of Whispering Springs, to hear how she and her husband, John, built it from the ground up, and how one unexpected chapter of their lives led to helping thousands of other families.