Hi All,

I'm Ryan Hennessey—an educator, coach, and adventurer dedicated to embracing courageous vulnerability. I've spent my life breaking conventional molds, learning through every detour, and passionately building a life defined by purpose, connection, and authentic adventure.

My mission is simple: to craft the most vibrant, aligned, and fulfilling life possible—and to inspire and guide others in doing the same. I believe true transformation comes from stepping boldly into the unknown, trusting yourself, and daring to be fully seen.

Life isn't about discovering who you are—it's about intentionally creating who you choose to become.

Ready to redefine your story? 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.

In the spotlight

Check out this featured article that dives into my approach to education—blending heart-led teaching, authentic connection, and creative thinking to inspire lasting impact. It’s a reflection on the power of relationships, the magic of the classroom, and what it truly means to show up for students in a way that matters. Read more HERE.

Join me as I chat with Gabby Ianniello on the Corporate Quitter Podcast, diving deep into my journey from passionate educator to bold entrepreneur. We explore courageous vulnerability, breaking free from societal expectations, and how courageously embracing authenticity can lead to the life you're meant to live.

Tune in as I share my story on the Teacher in Transition Podcast—reflecting on the emotional journey of stepping away from the classroom to follow a deeper calling. We talk about identity shifts, redefining success, and how choosing alignment over certainty can open the door to a more fulfilling, purpose-driven life.

explore My Latest WritinG