The Magic of One: How My 'Failed' Retreat Became an Unexpected Success Story

In 2023, I got really excited about holding my first serious, business-focused, in-person retreat. I had been doing solo retreats for quite a while and found them to be supremely useful in my own life and business. 

Despite many unsolicited bits of advice to the contrary, I had decided to hold it between Christmas and New Years; certain that this was the perfect time for most business owners to head out to the coast and spend a few days resetting and realigning before the new year. It is after all, MY favorite time to do it. 

It turns out that this is not such a terribly ideal time for most people, and especially business owners; while the desire is there, energetically it can still be a truly manic time with the after-effects of holiday chaos and end of year business contracts and tasks. 

It thus came to pass that my first in-person retreat that was initially booked out with two facilitators plus myself and a nice little group of women started to...dwindle. One facilitator got covid (though, bless, she still offered to come teach basically wearing a biohazard suit shouting from outside a window). The attendees had various holiday-related issues come up, and the other facilitator, who also happened to be in charge of making all of the food, had a bit of a life crisis meltdown and bailed the day before, after I had purchased the entire grocery list for her to execute her nutrition vision. 

And then there was one. 

I was somewhat prepared for this possibility, it being basically a rite of passage for anyone doing small group in-person events, especially when you're new, and especially for events that might have a bit of a unique take. 

Thankfully, I had had a nice long chat with my new friend at the time - musician, writer and visual arts performer (yes, an annoying talent stack if it weren’t for the fact that he is a supremely nice and cool guy and also a huge advocate for women) - Nick Jaina. 

He holds events at the Sou’wester too, a venue he describes as ‘the place that you never knew you needed, but absolutely do’. Side Note - if you come across this fellow holding his Spektrum Tea Service anywhere within a few hundred miles of you - GO!

In relation to his many events at the Sou’wester and elsewhere, he chatted me up around the possibility of Just One attendee. He said: it’s really up to you to manage your energy around it. It could be awkward AF, or it could be really freaking special. Obviously you don’t have total control over this outcome, or the One Person who shows up, but if you do everything in your power to make it something really meaningful (and you can float the likely financial hit)...do it. 

I had also received the same advice from my coach, who, quite accustomed to my melodrama over all kinds of business executions at this point, encouraged me to just do the thing I had set out to do and see what magic could unfold when you take some freaking chances around here already. 

I had never met the woman who signed up for this retreat, Jessi. I had no idea where she came from, who referred her, or how she even heard about the event. I had emailed her and given her the lowdown - ahem, yes, I had promised a group retreat, and I could fully understand why she might want to cancel. (Sort of hoping she would cancel.) But alas she said she was down! Hurrah! Also… shit! 

In the very cozy lobby of the Sou’wester with the Christmas stockings still hanging and a fire in the hearth, at our now two-person total scheduled ‘Meet and Greet, I finally connected with Jessi, a very interesting, smart, and engaging woman about my age who runs a nonprofit on the Oregon Coast. She informed me that the night before she had gathered with some elders and told them about being the sole attendee of an upcoming retreat and they said ‘GREAT! You’ll get all the attention! You HAVE to go!”. (Cue silent gratitude prayer to the elders.) 

We chatted a bit and went over the agenda and I left our little meeting actually pretty excited rather than dreading the two looming days ahead. 

What transpired over the next 48 hours was indeed, so special. Jessi was an extremely willing and open retreat participant; curious and excited to learn. She also happened to be hilarious and just a really warm and wonderful person to spend a few days with, probably doing anything at all I imagine. We did some of the sessions and meals in my room (the, ahem, Bridal Suite since that had the biggest workshop-like space for a very small group), held some sessions in the tiny Q-tea trailer, milled around the property taking some b-roll and photos for her organization; took a sauna. We laughed a lot. 

Now, one could say that I got super lucky with such an ideal client avatar landing in my lap. Ok, I was, in part. It could also be argued that while my reach was still very small, I had properly positioned the branding and voice to appeal to just this kind of magical person, which was a pretty big victory in itself. 

After two full days of staring at each other, and sharing, and talking, and doing, one might assume we would heartily say farewell at the close of the retreat. But she very generously invited me into her trailer (the cutest wee Potato Bug) and gave me what ended up being the most fascinating and spot-on oracle reading I had ever experienced. We chatted about her life and laughed a lot and drank more tea, and it was just freaking wonderful. 

I will always love this agenda 👇

Fast forward a year and a bit, and Jessi and I met up on Zoom last week. She showed me one of the big posters from the retreat that still hangs in her office. She’s continuing to fearlessly lead her organization and grow and learn. And, she’ll be attending the upcoming Reset for Q2 retreat at the Sou’wester at the end of March. 

Want to join us there? Check out the upcoming Reset for Q2 Retreat at the Sou’wester, and until March 7, use the code JESSI for $100 off.