creating my most beautiful life imaginable.

empowering others to do the same.

Man wearing a plaid shirt and a brown vest, smiling indoors, with hands in pockets.

Hi All,

I’m Ryan Hennessey—an educator, adventurer, and lifelong learner passionate about doing things differently. I’m on a mission to build the most beautiful life imaginable for myself and walk beside and encourage as many others to do the same as possible.

“Life isn’t about finding yourself, it’s about creating yourself.” - George Bernard Shaw

I’ve redefined myself countless times, embracing each transformation as an opportunity to grow, and I’m committed to continuing this journey of exploration and reinvention. Let’s rise together!

Work With me

Two men posing on a rock near turquoise water, with the iconic Torres del Paine rock formations in the background, under a blue sky.

Personalized Coaching

Personalized coaching for those ready to align their lives with their deepest purpose. We’ll explore what sets your soul on fire, envision your most beautiful life imaginable, and set to work building it.

A scenic view of Emerald Lake in Banff surrounded by mountains and pine forest, with a person paddleboarding on the calm water reflecting the blue sky and landscape.

(Re)align retreats

(Re)Align Retreats offer transformative experiences in breathtaking locations that build community, provide clarity and direction, and set the foundation for meaningful change in your life.

Two people collaborating at a desk with laptops and notes

Collaborative tutoring

Collaborative tutoring provides both small-group tutoring and individualized 1:1 sessions, tailored to help students navigate academic challenges, build study skills, and achieve their educational goals with confidence.

Connect with me on Instagram

View fullsize ADVENTURE ALERT: Enrollment is about to open for the ultimate adventure-based men’s retreat this August—set in the breathtaking beauty of Banff National Park, Alberta. This isn’t your average trip. It’s for the guys craving s
View fullsize Feeling that call of the mountains again. The call to take on something that’ll break me down to build me up. Wrote about it in my latest piece. Give it a read and subscribe! 🔗Link in Bio.
View fullsize Life has a way of unraveling the identities we cling to most tightly. Whether through divorce, career changes, or other major transitions, these moments of rupture can feel devastating—but they also offer us the chance to rebuild something str
View fullsize The most common question I’ve been asked since leaving teaching has been, “So what exactly ARE you doing now?” The short answer is - I took the most wonderful aspects of teaching and combined them with my love of travel and advent
View fullsize I was overwhelmed by the love and support I received after sharing my reflections on teaching and why I needed to step away. This next piece feels just as important—my letter to my students, and what I truly hope they carry with them beyond the
View fullsize After ten years in the classroom, I’ve made the difficult decision to step away from teaching. As I enter my final week, I want to share a piece of writing that means a lot to me. Writing has been my way of untangling and making sense of some
View fullsize
View fullsize Hennessey Whenever we’re asked who our favorite teacher would be, it’s always you, Mr. Hennessey. Your beard is luscious, your beard is long. We love you Mr. Hennessey, that’s why we wrote this song. You’re good at science an

Explore My Latest WritinG