Embracing the Entrepreneurial Mindset
When I first stepped into school leadership after years of running my own businesses, I realized that many of the principles I used as an entrepreneur applied directly to managing a school. In both arenas, there are obstacles—limited resources, shifting expectations, and high stakes—that demand creative thinking. As an entrepreneur, I learned to view every challenge not as a setback but as a chance to innovate. In my time as a principal and superintendent, I’ve applied that mindset to turn budget constraints, staffing shortages, and academic accountability pressures into strategic opportunities that benefit our students, teachers, and broader community.
Identifying Challenges as Opportunities
In the business world, I owned and operated J3 Timing and Wine Run 5K with my brother. Every year, organizing a large-scale event taught me to expect the unexpected—bad weather, equipment failures, or volunteer no-shows. Rather than panic, my team and I used those setbacks to build redundancy, improve communication, and develop backup plans. In education, similar unexpected challenges arise: a teacher resigns midyear, a curriculum pilot falls short, or test scores dip unexpectedly. Instead of treating these issues as failures, I encourage my staff to ask, “What can we learn from this? How can we leverage this obstacle to strengthen our school?”
For example, when our school faced a sudden decline in math proficiency scores, we didn’t simply increase homework or add test prep sessions. Instead, we convened a cross-disciplinary team of math teachers, instructional coaches, and data analysts. Together, we examined student work, identified specific skill gaps, and redesigned our intervention model. What began as a crisis in performance became an opportunity to develop a more targeted, personalized approach to student learning. In doing so, we transformed a challenging data point into a comprehensive improvement plan.
Building Strategic Partnerships
Entrepreneurs know that growth often stems from collaboration. When I organized the Stockton 3-on-3 Basketball Tournament for 15 years—raising over $50,000 for local causes—I relied on partnerships with local businesses, media outlets, and community volunteers. Those same skills translate seamlessly into school leadership.
Schools often face constrained budgets that limit programming. Instead of viewing this as an insurmountable obstacle, principals can reach out to local businesses, nonprofit organizations, and higher education institutions for support. In my experience, building relationships with community partners not only brings in financial and material resources but also enriches learning experiences. For instance, when our vocational program needed updated equipment, we partnered with a local manufacturing company that donated supplies. In return, our students completed internships and gained hands-on experience. This partnership converted a funding challenge into a mutually beneficial opportunity for workforce development.
Leveraging Grants and Alternative Funding
Securing grants has been a vital strategy throughout my administrative career. As a former entrepreneur, I understood how to craft compelling proposals that highlight a clear need, propose an innovative solution, and demonstrate measurable impact. In 2022, our school was awarded a High-Impact Tutoring Grant through Illinois State University, and in 2024, we received a Stronger Connections Grant from the Illinois State Board of Education. Rather than treating grants as one-off boosts, we designed programs with sustainability in mind—building partnerships with community organizations and integrating new initiatives into our school’s strategic plan.
When a staffing shortage threatened our literacy program, we used grant funding to hire trained tutors and purchase digital resources. Simultaneously, we collaborated with local college students studying education to serve as volunteer mentors. By combining grant dollars with community involvement, we didn’t just fill immediate staffing gaps; we created a scalable model for ongoing academic support. This approach transformed a staffing crisis into a long-term tutoring network that continues to benefit students each year.
Fostering Innovation and Smart Risk-Taking
Entrepreneurship thrives on trial and error. As a principal, I encourage teachers and staff to pilot new instructional methods, even if there is a possibility of initial failure. For example, when we introduced blended learning in our middle school, some teachers worried about integrating technology into busy lesson plans. Instead of mandating a top-down rollout, we identified a small cohort of tech-savvy teachers as “innovation leaders” and provided them with additional training. These educators tested new learning platforms, collected student feedback, and shared their insights during weekly professional learning community meetings.
Although the pilot had its share of hiccups—connectivity issues and uneven student engagement—the honest feedback allowed us to refine our approach. We improved Wi-Fi bandwidth, adjusted our professional development schedule, and created user guides for students. Ultimately, what began as a risky experiment evolved into a fully integrated blended learning model that increased student engagement and personalized instruction. Viewing risk not as a threat but as an opportunity to refine processes is central to the entrepreneurial principal’s mindset.
Cultivating a Growth-Oriented School Culture
An entrepreneurial culture celebrates curiosity, perseverance, and collaboration. As a school leader, I’ve worked to cultivate that same environment among teachers, staff, and students. Early in my tenure as principal, I organized “Idea Exchange” sessions—informal meetings where staff members presented problems they faced and brainstormed solutions as a group. Whether it was reducing absenteeism or improving school climate, these sessions encouraged open dialogue and collective problem-solving.
By soliciting input from all staff members—veteran teachers, new hires, and support personnel—we built a culture of shared ownership. When a challenged teacher saw that peers genuinely wanted to help, they felt empowered rather than isolated. In-turn, this collaborative spirit extended to students: they learned that their voices mattered, and they became more invested in school initiatives. Cultivating a school-wide growth mindset transformed an environment driven by individual concerns into a community focused on collective success.
Turning Setbacks into Forward Momentum
One memorable challenge occurred when our district faced significant budget cuts that threatened extracurricular programs. Many viewed this as a final blow to student engagement initiatives. Instead of accepting program reductions, I convened a committee of students, parents, and staff to explore cost-neutral or revenue-generating alternatives. Together, we redesigned our after-school clubs to include community service components—students could raise funds through local fundraising events, and volunteers from local nonprofits provided supervision. Our football and drama clubs became self-sustaining, with students hosting community showcases and ticketed performances.
By transforming a budget shortfall into an opportunity for student-led entrepreneurship and community collaboration, we preserved critical programs and taught students valuable skills in organization, fundraising, and leadership. This experience underscored a core principle: the entrepreneurial principal does not accept limitations as permanent roadblocks but sees them as catalysts for creative solutions.
Leading with an Entrepreneurial Spirit
Throughout my journey from business owner to school leader, I’ve carried the conviction that challenges can be reframed as opportunities for growth and innovation. Whether addressing academic performance dips, financial constraints, or staffing shortages, applying an entrepreneurial lens allows principals to move from reactive problem-solving to proactive strategic planning. By identifying opportunities in obstacles, forging strategic partnerships, leveraging grants, fostering innovation, and cultivating a growth-oriented culture, school leaders can turn setbacks into springboards for success.
As principals, we have the privilege and responsibility to shape the future of our schools. By thinking like entrepreneurs—boldly embracing risk, valuing collaboration, and constantly seeking new solutions—we can guide our schools to achieve outcomes that once seemed out of reach.