When Creativity Meets Leadership

Charleigh Wright’s journey through entrepreneurship education started earlier than most—back in middle school, when she helped run a small coffee cart we called The Mini Cup. What started as a club with a scaled-down menu and a handful of customers became her first experience with leadership and ownership.

She was in eighth grade when she sent me an email asking if she could be part of the high school coffee bar the following year. That might not sound like a big moment, but it told me something about Charleigh—she was ready to step into something real. She wanted more responsibility, not less. And she wasn't afraid to speak up and ask for the opportunity.

By her senior year, she was the Chief Operating Officer of the Leaning Eagle—our student-run coffee bar at Cincinnati Hills Christian Academy. She built a leadership team that played to the strengths of others, delegated in ways that showed emotional intelligence, and made improvements that still exist on campus today. She ran events, set goals, analyzed sales, managed a team of students, and all the while found ways to grow as a communicator and problem-solver.

But what stands out most to me about Charleigh’s story isn’t what she accomplished in high school—it’s how naturally she now connects those experiences to her current work as a student at Ringling College of Art and Design. She’s majoring in illustration, minoring in the business of art and design, and building a bridge between two worlds that are too often seen as separate: creativity and entrepreneurship.

In our conversation, she talks about learning how to take critique, how feedback in the art world mirrors what she experienced running a student business, and why visual thinkers can—and should—bring their full creative selves into spaces that require leadership and decision-making.

She also reflects on something I think every educator needs to hear: that stepping into leadership, collaborating with a team, and setting and reaching real goals—all of that began behind the coffee bar. That was the lab. That was the classroom. That was where the mindset started to take root.

Listen for These Highlights:

• Why she believes creativity is essential in business

• How she handled critique in her art classes by applying what she learned in entrepreneurship

• The surprising shift in how students communicate when they’re working on something that matters

• How she’s still using what she learned in middle and high school to navigate group projects, self-doubt, and big dreams in college

We often talk about how the entrepreneurial mindset can lead to transformation in schools. Charleigh reminds us that it can also lead to transformation in a student’s life. When students get the chance to lead something real—to make decisions, solve problems, collaborate with a team—they begin to see themselves differently. And that sense of agency doesn’t disappear after graduation. It travels with them.

Charleigh’s story is a reminder of why we do this. Not to create entrepreneurs, but to help students step into who they’re becoming—with resilience, creativity, and purpose.