We’re excited to introduce you to the always interesting and insightful Mary Ostrowski. We hope you’ll enjoy our conversation with Mary below.

Mary, looking forward to hearing all of your stories today. Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.

Not too long ago, I realized that risk-taking is a theme that runs through my life. I even have a name for the big ones: my “Sure. Why not?” moments. These are the decisions that didn’t always make logical sense, but something intuitively called me. Answering the call required doing some homework on the opportunity, developing an entrance (and exit) plan, and most importantly – trusting myself. Here are a few notable examples.

After graduating with a degree in Accounting and a minor in Rhetoric + Writing, I landed a job at a mutual fund firm in Baltimore. I liked city life. Then, seemingly out of nowhere, a college friend suggested I volunteer as a high school teacher in Belize. I had zero teaching experience — especially at the high school level. “You can teach math,” he said. It made no sense… and yet, I couldn’t shake the idea. My parents were horrified: “You want to do what?!” But at 23, I packed my bags and moved to Benque Viejo del Carmen, a small town about a mile from the Guatemalan border. Because – sure. Why not? I taught Algebra, Literature, and Journalism. Two years later, I came home, earned my master’s in educational leadership — and launched a 20+ year career in education.

About six years into teaching elementary school, an administrative role opened up at my school. I hadn’t considered leadership before, but something nudged me. I applied, interviewed over Skype while on vacation, and got the job. Sure. Why not?

Fast forward 15 years, I was Head of School at a PK3–12th grade international-style school in Panama City, Panama. I’d been there seven years in total — first as curriculum coordinator and Assistant Director, then as Head. But something was shifting. I wanted to work with families differently. I wanted to be my own boss. With no fully mapped plan, I gave notice and finished out the school year. Can I build a business from scratch? Sure. Why not?

The following fall, I “accidentally” bought a preschool. Financially and logistically, it made no sense — the school was in Annapolis, MD and I was still living in Panama with no plans to leave. I’d managed schools but never owned one, and early childhood education wasn’t my comfort zone. And yet… that familiar feeling returned. So I bought it. Sure. Why not? It’s been one of the best decisions of my life. Owning a preschool gave me the space to grow as a leader and entrepreneur — in a setting that was both new and familiar. And it’s what ultimately led me to create The Drizzle Effect, the educational services company I’d been envisioning for years.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’ve spent more than two decades in education — teaching, leading, building, and constantly learning. Over the years, I’ve worked across every level: from high school math classrooms in Belize to teaching all subject areas in upper elementary school to serving as Head of School for an international-style PK3–12 program in Panama. I’ve trained teachers, built curricula, and now own a joyful little preschool in Annapolis, Maryland [Weems Creek Nursery School]. I also run two education-centered ventures: The Drizzle Effect and AI consulting through maryostrowski.com.

The longer I’m in education, the more I feel we’re prioritizing the wrong things:
Structure over play.
Readiness over curiosity.
Product over process.

And kids feel it.

I’ve seen bright, curious learners lose their spark — caught in cycles of perfectionism or checked out entirely. I’ve watched the adults around them wonder how to help, where to focus, and what success even means anymore. And slowly, I started to notice something: parents are pausing. They’re asking bigger questions. *Is this really what learning is supposed to look like?*

That question became the spark for The Drizzle Effect® — and later, The PATH from EI to AI™. These aren’t just programs. They’re an invitation to reimagine learning from the inside out.

At Weems Creek, our preschool is rooted in joy, curiosity, and connection — a space where play is the foundation of real learning. Through The Drizzle Effect, my team helps families build the life skills kids need most: self-awareness, resilience, time management, and critical thinking. Our flagship curriculum, DROPLETS™, supports elementary and middle school kids using creative, story-driven learning to nurture emotional intelligence and executive function.

And through my consulting work, I support teens, parents, and educators in developing practical AI literacy. Because today’s kids won’t just grow up using AI — they’ll need to collaborate with it, question it, and lead alongside it. That’s what The PATH from EI to AI™ is all about: preparing this generation to confidently and creatively shape the future they’re stepping into.

Personally? I’m a stepmom, an aunt, and a mentor. I love to read, shop and travel. I’ve walked the fabled Camino de Santiago — and kept on walking to the Atlantic coastline (yes, all 555 miles). That journey taught me what all great learning does: to listen deeply, to move with purpose, and to trust the path even when it feels uncertain (unbearable?!).

If you’ve ever thought, “There has to be a better way,” I’m here to say, there is. Listen. Deep inside, you know all the answers.

How’d you build such a strong reputation within your market?

Honestly? Being good to people.

Everything comes back to the Golden Rule: treat others the way you want to be treated. Especially in education. Every child is a parent’s most precious treasure, and even the most level-headed adult can become emotional and even irrational when they feel their child is at risk. Is it hard to deal with sometimes? Sure. But I don’t consider it a flaw — it’s parenting! All children deserve to have an adult prepared to fiercely advocate for them.

I was reminded of this in spades not too long ago. We had a student — I’ll call her “Jane.” Her speech was still developing, and when others couldn’t understand her, she’d get so frustrated. She’d respond by pushing or grabbing; not out of malice, but from sheer inability to express herself. I’d heard through the grapevine that her parents hadn’t shared the full story about her prior school experiences. Our communication was strained, and it just didn’t seem like we were the right fit. Then I had a direct conversation with Jane’s dad. I had the opportunity to share that I knew they hadn’t been upfront with us and our trust was missing as a result. We couldn’t support Jane well without it. That cracked the shell. He told me everything: their struggle in previous schools, the heartache, and the fear of being rejected – again – because their child “wasn’t good enough.” It all made sense.

What they needed was grace — a safe space where their child would be met where she was, and accepted for who she was. Once that was in place, everything shifted. We became true partners, grounded in mutual respect and open, honest communication. And Jane? She’s grown so much!! I am grateful for this experience, and for the reminder that compassion and transparency can change everything.

Can you tell us about a time you’ve had to pivot?

One of the biggest pivots I’ve made recently was transforming DROPLETS™— the program I designed to help kids trust their ideas, take risks, and build resilience — from a hands-on, in-person experience into a fully online community.

Originally, DROPLETS™ was a creative, drop-off program for homeschooled children in grades K–5. We were multi-age, project-based, and rooted in real relationships — the kind of learning that lights kids up. But two things happened:

First, the financial reality began to settle in. Our revenue in year one just didn’t come close to the projections I had mapped out. As a single owner without investors, I couldn’t afford to take the same losses into year two. On top of that, I was running two brick-and-mortar businesses. The constant shuttling between locations — physically, mentally, and emotionally — was taking a toll. I realized that was an overall model that I simply didn’t enjoy.

So I pivoted.

I reimagined DROPLETS™ as a membership-based online community. Now, families can access resources anytime — the curriculum, hands-on activities, coaching — all designed to build a foundation in emotional intelligence through a literacy-rich lens. It’s not a rigid curriculum. It’s a flexible framework that adapts to real life.

Letting go of the tactile, in-person camaraderie wasn’t easy. The community we built was fairly magical and we all grew: the kids, the parents and me and my team too. But I trust this path. My body viscerally relaxed after announcing the decision, letting me know it was a good one. This new business model allows me to teach my philosophy to other adults, possibly impacting exponentially more children than the in-person model by working with parents and consulting with school groups too.

Contact Info:

• Website: maryostrowski.com and thedrizzleeffect.com
• Instagram: https://www.instagram.com/maryostrowski_official/
• Facebook: https://www.facebook.com/thedrizzleeffect
• Linkedin: https://www.linkedin.com/in/maryostrowskiofficial/

Image Credits

Lee Kriel Photography
Maureen Porto Studios