True story:
Anna Rita Pergolizzi-Wentworth went to college planning to become a spy.
She studied Russian at Middlebury. Spent time in Siberia. Had the whole international espionage thing mapped out.
Then she taught English to Russian business professionals and everything changed.
Fast forward a few years and she's in the jungles of Costa Rica with her boyfriend (now husband), helping five families build a school from scratch.
They started with 30 students.
By the time she left, they had 120.
Today? Nearly 400 students.
Here's what this teaches us: The best educational leaders don't necessarily follow predictable paths.
They observe. They adapt. They take risks on unproven ideas because they see what others miss.
Anna Rita could've played it safe — stayed in traditional schools with their 50-100 year legacies and governance structures that resist change.
Instead, she built something new.
And here's why this matters to you: Right now, every school around you is preparing kids for a world that no longer exists.
They're teaching like it's 1985 while AI reshapes everything.
They're banning technology instead of teaching students how to use it as a tool.
They're choosing compliance over curiosity.
Meanwhile, leaders like Anna Rita are building "future fluent" learning environments at places like Pine Street School in Manhattan where students:
Spend entire days creating AI-powered companies.
Learn Mandarin starting in kindergarten.
Develop cultural intelligence that actually prepares them for an interconnected world.
Use tech as producers, not just consumers.
The gap between traditional methods and what students actually need is widening at light speed.
So here's what I want you to do:
She breaks down how Pine Street stays deliberately small (and why that matters), her approach to teacher happiness as a retention strategy, and how she balances cutting-edge innovation with timeless human development.
Plus, you'll hear about her "Guardians of Nature" program that started in Costa Rica and now operates at district and national levels.
This isn't theory.
It's a school leader who's actually doing it.
Keep Making a Ruckus,
Danny
PS … Anna Rita's marquee message for every school in the world?
"Raise thinkers, embrace humanity, teach for tomorrow."
If that resonates, you need to hear this episode.
TODAY’S RUCKUSCAST IN PARTNERSHIP WITH
IXL — Over 1 million teachers rely on IXL because it is empowering, it helps them make better decisions with reliable data, and it adapts instruction based on student performance. Learn more here.
ODP Business Solutions® — Looking to create the kind of campus experience students never forget? ODP Business Solutions® transforms ordinary spaces into extraordinary learning environments. Learn more here.
PlayPiper — Too often, kids who love gaming don’t see themselves as scientists or engineers - but what if play could open that door? Get students excited for STEM with hands-on kits and engaging curriculum. Learn more here.
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