
I first noticed Caleb Rainey—a Spoken Word poet based in Iowa City—on social media. One video, and I was hooked. I had to get him to Okoboji. Never mind that not a single participant on the pre-retreat survey expressed interest in Spoken Word.
This is something an entrepreneur can do: gather customer data... and then completely ignore it.
I didn’t tell Caleb that no one wanted what he was offering.
The night before the retreat kicked off, our speakers gathered at the Oakwood Inn—a finely appointed, bed-and-breakfast with fine china, lush gardens, and innkeepers who truly care. Bridget Johnson, the proprietor, insisted on hosting a wine and cheese welcome party.
I had a sound system set up in the living room. After a short welcome, some odd instinct kicked in, and without warning, I handed the mic to Caleb and asked him to perform something he’d written.
He owned the room like we’d rehearsed it for hours.
Within minutes, a room full of hardened journalists, acclaimed authors, editors, a couple of local leaders, and a playwright or two stopped their small talk and stared at this self-described “negro artist.”
Tears welled up in transfixed eyes.
We fell in love—with Caleb, and with his performance art.
The next morning, I handed him the mic again in front of the full group. Same reaction.
Within seconds of launching the second retreat, the tone was set: Expect the unexpected. Be deeply moved.
By the end of the day, his workshops were well attended.
Caleb returned the following year—of course. He wouldn’t miss an Okoboji Writers’ and Songwriters’ Retreat now.
At the next wine and cheese night, he told the story of how he ended up in northwest Iowa, at my insistence.
“Who is this old white lady who won’t stop calling me about going to a small town I’ve never heard of?” he said, laughing. “And now I’m hooked.”
Later that night, he lost the key to his room at the Crescent Beach Resort. It was off-season, no staff in sight. Nik Heftman and Doug Burns—friends and fellow speakers—invited him to crash on their couch, next door.
Nik was so moved by Caleb’s work that he decided this was the story he had to tell. He had already earned an Emmy while working for CBS Mornings—producing and directing stories in New York and Los Angeles as part of the show's award-winning team.
One year later, we packed the 300-seat Lakes Art Center Theater for the premiere of The Negro Artist, Nik’s first full-length documentary.
I slipped in the back just as the lights dimmed. Caleb paced near the control booth, while I stood about 15 feet away. Neither of us had seen the film.
Scene after scene unfolded—ethereal, powerful, intimate. Nik’s lens pulled us into Caleb’s world with skill.
When the lights came up, the audience erupted in cheers.
Caleb and I stood in near disbelief, the magnitude of what we had sparked together beginning to settle in. Something bigger than all of us had taken root, and continues to live on in the multiple showings still being booked today.
Nik, characteristically quiet and composed, had a dazed look. I asked him what the night had taught him.
“I can do anything now,” he said.
Believe it.
Phoebe Wall Howard (another standout retreat presenter) arranged multiple showings in Detroit. Our audience members carried the film back to their own towns across the state and country.
Doug Burns helped book screenings nationwide. Standing ovations are now routine.
So are hoots, hollers—and tears.
Why this is on my mind…
Today I texted with a woman who saw The Negro Artist at the Sebastopol Documentary Film Festival in California. She met Nik and Doug there. When she heard about the Okoboji retreat—mentioned in the film—she knew she had to come. She's now enrolled and wants to bring four or five more people with her.
We shall see.
Her father’s family has deep ties to Arnolds Park. And just reading between the lines of our text exchange this morning... there’s a memoir to come.
One full of drama.






Stories
There are all kinds of stories about connections made, and inspiration planted. Come and create yours.
For a current list of speakers:
Look Who's Coming to the Okoboji Writers' and Songwriters' Retreat
Click on the topics listed to go directly to the speakers by category:
I’ll be posting updates about the retreat on this platform. If you do not have an interest in these posts, simply unsubscribe.
If you like what we’re doing, tell a friend or two.
You are a force for good, Jules. And we all win. xox
A place where dreams can come true, or watch them and people blossom into where and what’s possible. This sense of adventure and belonging, like magic is what’s drawing me to this place, where seeing and listening can change lives. Exactly, the place where journeys begin. Or memories begin. Can hardly imagine the feeling of being surrounded with such hope and joy. September can’t come too soon.