As the Independent School Moonshot Podcast approaches episode 100, here are the conversations I keep coming back to.

I didn't expect to feel anything when I noticed the episode count. But when I looked at the number recently and realized we're approaching 100 episodes of the Independent School Moonshot Podcast, I paused for a minute.

Nearly 100 conversations with heads of school, strategists, practitioners, researchers, and operators. A lot of ground covered over the past couple of years.

Summer feels like the right time to step back and revisit some of it. And when I did, one thing stood out clearly: the same few questions keep surfacing across very different conversations. How do we build a more sustainable financial model? How do we hold onto good people? How do we make smart decisions when the path forward feels uncertain?

Those aren't new questions. But the conversations below address them in ways that stuck with me. Any one of them is worth an hour of your time before fall planning season starts.

On Revenue: Treating Non-Tuition Income as a Strategic Asset

Breakthrough Revenue Strategies: How Auxiliary Programs Revitalized Breakwater School

David Sullivan served as Head of School at Breakwater before becoming a Senior Advisor at SPARC, and that background shows up in every part of this conversation. He's not describing what auxiliary revenue could look like in theory. He's describing what he actually built, the decisions he made, the resistance he navigated, and what changed as a result.

What the team built at Breakwater wasn't a side project. It became a genuine strategic lever that changed what the school could do both financially and programmatically.

I reference this episode regularly in my work with schools because the question it raises is deceptively simple: what would it look like to treat non-tuition revenue as core to the model rather than an add-on? The answer is more actionable than most schools expect, and David gives you a real example to work from.

If your school is still thinking about auxiliary programs as nice-to-have supplemental income, this conversation will challenge that framing in a useful way.

On Culture and People: Rethinking the Generational Narrative

Why Generational Conflict Is the Wrong Diagnosis

When I talk to school leaders about retention and hiring, the generational narrative comes up constantly. Younger staff want this. Older staff expect that. The assumption is that the gap between generations is the problem.

Megan Gerhardt, professor of management and leadership at Miami University, reframes the whole conversation. The tension most leaders are experiencing isn't really about generational differences. It's about mismatched expectations and assumptions that nobody has made explicit.

Her thinking shifts the question from "how do we manage younger staff?" to "what are we actually communicating, and to whom?" That's a more productive place to start. And it puts responsibility back where it belongs, with leadership, not with whoever happened to be born in a different decade.

This one is particularly useful if you're heading into a fall with any open positions to fill or faculty dynamics that feel stuck.

On Risk and Strategy: What Safety Actually Costs You

The Hidden Risks of Playing It Safe in Independent Schools

This is the episode I think about the most.

Amol Tripathi, a strategic business coach with Focal Point, introduced me to the concept of antifragility, and it reframed how I think about school strategy. The instinct to hold steady and avoid risk is understandable, especially right now. But the argument Amol makes, and I find it hard to push back on, is that the places that feel safest are often exactly where the real fragility hides.

Schools that consistently defer hard decisions, avoid bold moves, and optimize for stability over adaptability don't usually collapse suddenly. They erode quietly until the options narrow. That's a harder problem to fix than the one they were trying to avoid.

This one is worth your time before you head into fall planning, particularly if "stay the course" is the default posture in your leadership discussions.

A Note as We Approach Episode 100

If you haven't listened to the podcast yet, any of these three would be a good starting point. They reflect the kinds of conversations I find most useful to have with school leaders: specific, honest, and grounded in real experience rather than best-practice generalities.

And if you've been listening for a while and have an episode that stuck with you, I'd genuinely like to know which one. Reply to this post or send me a message directly.

More to come as we close in on episode 100.

The Independent School Moonshot Podcast publishes every Monday. You can find the full archive at moonshotos.com/podcast.

Interested in going deeper on revenue, strategy, or school leadership? The Business Competency Self-Assessment is a good place to start.