Colin Darling

The Eisenhower Matrix has a way of revealing uncomfortable truths. As I sorted my work into urgent versus important quadrants, a pattern emerged that I suspect many of us recognize: my urgent work rarely appears in my actual job description, while my most important work—the legacy-building, culture-shifting work—gets swept under the rug.

But here’s what surprised me most: the work that keeps calling to me isn’t just professional development. It’s personal completion.

The Gap That Demands Attention

At HTS, there’s a disconnect that’s been nagging at me. On one side, we have families and alumni who have “seen the light”—they understand the transformative power of an HTS education while they’re experiencing it. On the other side, we have those who never fully grasp the blessing they’ve received, or worse, never come to understand it at all.

The result? Families paying tuition without understanding where their investment goes. People who love HTS deeply but don’t know how to channel that love into lasting legacy.

What’s missing is education—not just about our status as a registered charity, but about the profound impact their contributions make. We’re missing the stories that make the invisible visible.

My Thread: Digital Storytelling for Cultural Transformation

Among all the interconnected pieces of this challenge, one thread pulls at me most strongly: creating digital storytelling that educates, empowers, and motivates donors to see themselves as change makers in the HTS community.

I envision a series of video testimonials—relatable, candid, and raw—that live both on our school’s social media and on the new donor wall we’re installing in the new year. These won’t be polished marketing pieces, but authentic conversations with current parents and alumni who can speak their unfiltered minds about why they give and how it helps our school grow.

Picture this: someone walking past our donor wall and suddenly hearing a real person’s authentic story about their journey from loving HTS to understanding how to channel that love into action. That moment of connection between digital story and physical space—that’s where transformation happens.

My Declaration of Intent

This work feels like the legacy I want to leave at HTS as an alum who acknowledges how much this school did for me. I want HTS to be a place where people don’t just think about the future of educational environments—they do something about it.

My commitment for this year is clear: I will build our capacity for digital storytelling that transforms culture. This month, I’ve started by identifying current parents that are alumni who volunteer and donate—those who are living the story right now, watching their own children benefit while actively contributing to that future.

This isn’t just about donor education. This is about completing my own circle of gratitude by helping others discover theirs. It’s about becoming the bridge between people’s love for HTS and their understanding of how to channel that love into lasting impact.

The urgent work will always be there, demanding attention. But the important work—the work that builds legacy and transforms culture—that’s where I’m choosing to focus my creative energy this year.

Because when someone watches one of these stories and thinks, “I want to be part of this legacy,” that moment of connection will honour everything HTS gave me by helping others discover everything they can give back.

That’s my thread. That’s my commitment. That’s how I’m choosing to make change this year.

UPDATE:

Heading into our second Cohort Session, the power that this kind of curated, visual content holds has never been more apparent to me. Recently, I stood up in front of our grade 12s and talked to them about legacy, something I’ve done every year when asking them to consider what kind of HTS alum they hope to be.

And in that presentation, we layered in a video from a graduate of last year’s class who was a recipient of financial aid. He was the type of kind, put together, model student who everyone gravitated towards and he agreed to speak candidly about not only what financial aid gave him at HTS, but also what he might have lost without it.

Now this video wasn’t edited, no name key graphic, no music. Nothing but a selfie video of a community member who was more than keen to, in his words, “do anything [we] need[ed]” of him to give back to the community he grew up in.

This doesn’t change my declaration of intent or the kind of output I hope to produce, but it might change some of the language around my “how might we” question. I think now it needs to acknowledge that everyone has a story, a connection, a thread to contribute to the cause. All you have to do is ask those that have a pulse on the community, those that have trust.

Because trust is everything in independent schools. Trust that we care and see each and every student for who they are and who they’re becoming. Trust that we are caretakers of all those that came before us (students, staff, parents) and the history they wrote. And most importantly in my case, trust that the time, treasure and talent our community decides to pour back into our community will be stewarded and invested back into the school in ways that maximize value for all involved.