Ryan Hennessey. Photo: Jamie Sukow
A former teacher launches retreats and coaching sessions to help clients find fulfillment.
When Ryan Hennessey walked away from teaching in the middle of the 2024–25 school year, it wasn’t an impulsive decision—it was a carefully orchestrated “escape plan” that set an example for his beloved students: “It’s okay to walk away from something you once loved,” Hennessey says. After a decade of teaching science in Maple Grove schools, Hennessey had found himself at a kind of crossroads. The birth of his daughter, Stella, in April 2024 sparked one realization. “All of a sudden … my time became precious,” he says. He’d also attended a retreat for entrepreneurs in Los Angeles, where he says he had a “line in the sand” moment. “It really solidified for me that I wasn’t able to get what I needed anymore from my career in teaching,” he says. “I have these gifts to share with the world.”
Hennessey has always been something of a polymath; he’s renovated camper vans, received his pilot’s license and explored science experiments in and out of the classroom. His new chapter, he says, will focus on helping others achieve the same kind of personal growth and fulfillment he’s experienced over the past few years. He’s launched a three-pronged business model: individual coaching services, tutoring and wellness retreats. “I’m creating a space that’s what I needed when I was going through those darker times,” Hennessey says.
His first (Re)Align Retreat, held in Canada’s Banff National Park this August, was designed for men and focused on personal growth, skill-building and self-discovery. “I love traveling and hiking,” Hennessey says. “In times when I felt stuck or was navigating grief, going on hikes and challenging myself let me figure out what I was capable of.” The retreat featured hikes above Lake Louise, fishing lessons with local guides, mindfulness practices and other activities. Hennessey orchestrated every detail, letting participants simply show up with an open mind.
In the coming months, Hennessey will lead a second retreat—this time to the Island of Hawai’i (the “Big Island”)—that’s open to anyone. “Hawai’i has this way of making you feel the magic,” Hennessey says. “You’ll be watching rocks form as lava cools, swimming in a volcano and seeing the Milky Way galaxy—it’s one of the most magical places I’ve ever been.”
His new coaching services complement the retreats, offering one-on-one support for individuals who are navigating challenging life transitions or questions. Drawing from his personal experiences, including a difficult divorce, Hennessey helps clients set goals and build more fulfilling lives. “Those painful moments can be the best thing that ever happened to you if you approach them with a growth mindset,” Hennessey says. “It’s getting really clear on your goals. What do you want to bring into your life? Where are you feeling stuck? What areas are drawing or sucking your energy?”
Through all of his new ventures, the fingerprint of Hennessey’s background as a teacher is still visible. Fittingly, the third branch of his new business model is tutoring high school students. “It’s my way to continue teaching and to engage with math and science,” Hennessey says. He works with students one-on-one or in small groups as they work through challenging concepts or prepare for tests.
“Stepping away from teaching was aligned with my integrity,” Hennessey says. “I want to be able to make an impact and lead people to positive outcomes—and to continue to set that example for my students.”
Ryan Hennessey
Instagram: @iamryanhennessey
