"You Only Regret What You Don't Do": John Reid on Failure, Risk & Growth

In today's episode, we sit down with John Reid, the Head of School at The Rosedale Day School, whose career is a testament to the power of embracing unexpected opportunities.

John's journey began with a plan to pursue medicine, but a "gap year" teaching job in the remote northern community of Moosonee changed everything. It was there he discovered that education wasn't just a job, but a lifestyle, a profound realization that would shape his entire career. This path led him across Canada and to California, where he led a school dedicated to neurodiverse learners, proving that "not all great minds think alike."

This is a raw, honest, and deeply inspiring conversation. John opens up about the mentors who shaped him, the challenges of leadership, and the simple truth that the most important work happens through relationships. He shares why he believes the biggest misconception about teaching is underestimating the sheer effort it requires, and offers powerful advice to his younger self: "You're only gonna regret the things that you don't do."

Whether you're an educator, a leader, or simply someone charting your own course, John's wisdom and authenticity will leave you inspired.

TIME STAMPS:

0:00 - Intro
1:50 - The Fork in the Road: Medicine or Education?
3:00 - "I Stayed for Four Years": The Life-Changing Decision to Teach in Moosonee
5:59 - The Mentor Who Taught Him to Stand at the Door Every Morning
8:11 - Unlocking the Potential of Neurodiverse Students in California
11:49 - Beyond Tests: How Do You Assess Students Who Think Differently?
17:13 - Why Being a Head of School is a "Lifestyle, Not a Job"
25:48 - The Biggest Misconception About Teachers: "Wear Your Running Shoes"
28:13 - Advice to His Younger Self: "You Only Regret the Things You Don't Do"
31:33 - The One Thing Every Leader Needs to Stop Doing
32:13 - The Final Question