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Belonging Before the Bell: Leading with Purpose episode artwork

Aug 27, 2026 5 min

Belonging Before the Bell: Leading with Purpose

from On The Way To School Hosted by Christopher S. Dennis

When did you first feel like you belonged? That question changed the conversation for me. In today’s episode of On The Way To School, I’m reflecting on a question that came up during my recent Lonely Graduation book conversation on Martha’s Vineyard: When did you first realize you were special? For me, the answer came much later than I expected. It wasn’t until my 30s that I fully recognized my unique gifts and understood that I had a responsibility to steward them well. But then my fellow panelist Connie asked a different question: When did you first feel like you belonged? And that question opened up an entirely different conversation. Because knowing you’re special is personal. Belonging is relational. You can know your gifts, understand your purpose, and still find yourself in a community where you don’t feel seen, valued, or connected. So as we begin another school year, I’m asking educators and leaders to consider: Do you feel like you belong in your current role—not just on the org chart, but in the community? If the answer is no, don't ignore it. Belonging can be the difference between showing up from obligation and showing up with purpose. It can help us sustain ourselves when the work gets difficult and the cup starts to feel empty. And sometimes, finding belonging starts with one honest question. 🎙️ On The Way To School 🎧 Listen to the latest episode wherever you get your podcasts. #OnTheWayToSchool #LonelyGraduation #Belonging #SchoolLeadership #EducationLeadership #IndependentSchools #WorkplaceCulture #Leadership #Educators #Purpose #Community

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Belonging Before the Bell: Leading with Purpose

0:00 5:50

Chapters

  1. 0:03 Opening Reflections
  2. 1:47 Lessons From the Vineyard
  3. 3:44 The Power of Belonging
  4. 5:06 Finding Your Place

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This episode was published on August 27, 2026.

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