Diana Agostini shared their story and experiences with us recently and you can find our conversation below.
Diana, we’re thrilled to have you with us today. Before we jump into your intro and the heart of the interview, let’s start with a bit of an ice breaker: What is something outside of work that is bringing you joy lately?
In Italian we have a saying: “you’ll never forget your first love.” For me, that first love was Muay Thai. I began training at 16 in my hometown of Varese with my sister, and it quickly became a lifelong passion leading me to compete nationally and even train in Thailand. After moving to San Diego, I continued competing until the loss of my beloved coach made me step away from the sport. For the past eight years I thought I was done, focusing instead on yoga, ultrarunning (and also became a mom!). But this summer, living walking distance from a Muay Thai gym, I decided to return. Training again at Easton Centennial, surrounded by knowledgeable coaches and a caring community, has been a true joy, like coming home to a part of myself I thought I’d lost.
Throughout my life, people have often been surprised to hear I practice Muay Thai, since I’m known as being nurturing, gentle, and kind. But that contrast is part of the joy too: it reminds me that we can carry unexpected strengths, and that discipline and compassion can absolutely coexist. After all, my favorite quote is: “there is nothing as strong as gentleness, and nothing as gentle as true strength.”
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Diana Agostini, and I currently serve as the Director of Admissions and Financial Aid at Aspen Academy, a Preschool through 8th grade independent school in Greenwood Village, Colorado. Aspen is a truly unique place, our mission is simple yet powerful: Be Kind, Do Good, Work Hard, Make the World Better. That ethos is woven into everything we do, from our nationally recognized LiFE program (Leadership, Finance, and Entrepreneurship) to our daily focus on cultivating kindness, curiosity, and confidence in children.
My own story is shaped by both international roots and a deep love for education. I grew up in Italy, worked for international organizations in Europe and Africa, until I moved to the United States in my late twenties. After having spent more than a decade in education leadership I can confidently say that what is unique about Aspen is that it’s not just a school: it’s a community where students are encouraged to dream big and families feel they are part of something larger. Right now, I’m especially energized about our West Campus expansion, home to our Nature Center and Outdoor Lab and of our Early Learning Division which will open up even more opportunities for young learners to thrive and learn as we develop an outdoor learning curriculum.
Outside of work, I’m a mom to a spirited four-year-old, a lifelong lover of literature and movies (I ran the San Diego Italian Film Festival during my time in California), and, perhaps surprisingly, a Muay Thai enthusiast. All of these roles – educator, parent, athlete, immigrant – shape the perspective I bring to my work: that education at its best should inspire courage, curiosity, understanding, and compassion in equal measure.
Okay, so here’s a deep one: Who saw you clearly before you could see yourself?
When I think about people who saw me clearly before I could see myself, two mentors immediately come to mind: Isabella Medici and Victor Laruccia.
Isabella, my boss at Helvetas Swiss Intercooperation, was the first woman leader I worked closely with, and she remains one of my greatest inspirations. She taught me grit and determination while also showing me that true leadership is rooted in grace and humanity. She believed in me enough to entrust me with projects that stretched me beyond what I thought possible. In a short time, she shaped me in ways I’m not even sure she realizes, and I will always treasure the learning, laughter and conversations we shared.
Victor, the founder of the San Diego Italian Film Festival, changed my life in a different but equally profound way. I met him when I was at one of my lowest points fresh from a transatlantic move, a divorce, and trying to rebuild my own professional and personal identity. He saw in me a connector, a leader, and someone capable of drawing people in with creativity and heart. He believed in me so deeply that he entrusted me with leading the organization he founded as Executive Director. Victor not only allowed me to grow professionally in areas new to me like operations, event planning, and program design, but also gave me the gift of feeling seen, supported, and loved like a father. Losing him in 2022 felt like losing a piece of my heart, and not a day goes by without me thinking of him.
Both Isabella and Victor saw strengths in me I couldn’t yet see in myself. Their belief gave me the courage to step into leadership, to embrace both grit and grace, and to carry forward the same gift they gave me: helping others recognize their own potential.
If you could say one kind thing to your younger self, what would it be?
If I could say one kind thing to my younger self it would be: “You are special, even if you don’t have one single talent that defines you.”
When I was younger, I struggled with the feeling that I wasn’t extraordinary at anything. My friends seemed to have clear passions or talents: they were incredible athletes, musicians, or had that one specialty they knew was their calling, while I was good across many subjects and sports, but felt I was lacking that One defining gift. For a long time, I believed that meant I wasn’t truly special or worthy.
What I didn’t realize then is that the very things I took for granted like empathy, connectedness, the ability to see the bigger picture, were rare and powerful strengths. These “skills” became the foundation of my life and career. They allowed me to lead with compassion, to build authentic relationships, and to bring people together around a shared vision. Looking back, I see that those quiet strengths were never something to dismiss, they were exactly what would make me successful in many ways.
Sure, so let’s go deeper into your values and how you think. What do you believe is true but cannot prove?
I believe education saves lives. When I worked in Mozambique, I helped running educational programs that not only kept children away from drugs and prostitution, but also helped teachers heal their own unaddressed grief so they could show up fully for their students and find healing. On a personal level, education has always been a refuge and a safe environment even when home wasn’t. And in any context, the more we educate people, the more they understand how deeply interconnected we all are. Education is both protection and possibility.
Okay, so before we go, let’s tackle one more area. What will you regret not doing?
Not taking the leap to create something of my own. I’ve been fortunate to lead within incredible organizations, but there’s a voice inside me that challenges me toward building something that reflects my own vision (maybe an Italian Film Festival in Denver!). I would also regret not carving out time to travel the world with my family, expose my son to different cultures and ways of living, and learning through his curious eyes. Both building and exploring are about legacy to me: creating something lasting, and also filling life with experiences that shape who we are.
Contact Info:
- Website: https://www.aspenacademy.org/
- Instagram: https://www.instagram.com/aspen_academy/
- Linkedin: https://www.linkedin.com/in/diana-agostini-69a7362b/
