Chicago-born André Small learned early that education was something no one could ever take away. It was a lesson passed down by his mother, Diane, a single parent raising four boys while earning her own college degrees.
That unwavering belief became the foundation of André’s life, even during moments when his own educational path felt uncertain.
André began his schooling in Chicago Public Schools alongside his three younger brothers. When the family later moved to Calumet City, Illinois, he attended junior high and high school in the suburbs. While the transition offered new opportunities, André remembers feeling academically unprepared.
“I felt as if I was being pushed through school,” he recalled. “When I graduated, there were things I didn’t know that I should have known.”
For much of high school, André did not seriously consider attending college/university. That changed unexpectedly when he performed in a talent show at nearby Kennedy-King College. After the performance, someone asked the students where they planned to attend college and encouraged them to apply for scholarships and complete financial aid applications.
A foundation built on education
André followed the advice. He applied and was admitted to Western Illinois University on a music scholarship.
He started off strong during his first semester, energized by the opportunity. But his priorities got mixed up the second semester, and his GPA plummeted. He quickly realized his future was at stake.
Determined to turn things around, he refocused his efforts and joined Omega Psi Phi Fraternity, Inc. The fraternity provided structure, accountability and mentorship at a time when he needed it most.
“Seeing my fellow Brothers balance their activities and graduate with high GPAs was inspiring,” he said. “I wanted to be part of that successful track while helping to change the perspective that Black men were less likely to graduate.”
André committed himself to becoming a better student, especially in reading and writing. He vividly remembers receiving one of his first research papers back from a professor, heavily marked in red ink. Rather than discouraging him, the experience motivated him.
He began reading a wide variety of books and magazines, studying sentence structure, grammar and punctuation. He practiced deliberately, determined to master skills he felt he had missed earlier.
“I was committed to getting my degree and putting forth more effort,” he said.
That commitment paid off. In 1995, André earned a bachelor’s degree in industrial engineering with a minor in channel management logistics.
A career of continued learning
In the meantime, his mom and brothers had relocated to Madison, Wisconsin, a move André strongly supported.
“I talked my mom into moving my brothers out of Chicago and away from the negativity and street culture,” said André. “Moving to Madison changed the trajectory of their lives, and all three have gone on to successful careers.”
After graduation, André spent nearly two decades building a career in business management, working his way from entry-level roles to executive management positions. His career took him to Chicago, Madison, Atlanta, Los Angeles and then finally back to Madison in the fall of 2001.
In 2011, as his youngest child graduated from high school, André entered a new phase of life as an empty nester. Rather than slowing down, he chose to invest in himself once again. He enrolled at Cardinal Stritch University in Milwaukee, earning a Master of Science degree in management in 2015.
That same year, he enrolled in the university’s doctoral program. Treating his studies like a part-time job, André fast-tracked the program and graduated in three years with a PhD in Education and Leadership. His dissertation was titled, “Overcoming adversity: A phenomenological study of successful fatherless African American men who prospered based on their resiliency and the support of their mothers.”
André’s plan at the time was to use his educational and business experience to improve state service. While pursuing advanced degrees, André continued working for the State of Wisconsin, serving in the Departments of Health and Human Services, Workforce Development, Children and Families, Corrections, and Financial Institutions. Through this work, he gained insight into systemic challenges facing families and adults.
“I realized while working with different families, adults were missing a lot of basic skills and knowledge,” he said.
Answering the call to teach
In 2021, a conversation with Madison Metropolitan School District Superintendent Dr. Carlton Jenkins solidified André’s next calling. The district needed more classroom educators, and André felt compelled to act.
“I wanted to do something that felt more gratifying than my work in the business industry,” he said. “Helping students felt like a calling.”
He quickly obtained an Emergency Teaching License and was hired as a Career and Technical Education teacher at Madison East High School. Now in his fourth year, André teaches personal finance, entrepreneurship, computer science, marketing and sales, but his lessons go far beyond course content.
He emphasizes independence, accountability and preparation. He enforces strict deadlines, requires students to proofread their work and encourages them to ask questions—habits he knows will serve them well beyond high school.
“I love seeing the lightbulb turn on and the students shine,” André said. “And I love to see them excited and going through the planning phase as they prepare for life post high school.”
He pushes students to think intentionally about their futures, whether that includes college/university, trade programs, starting their own businesses or pursuing a career in the military. For those considering a gap year, he challenges them to think through the “what ifs,” reminding them that pursuing education is often easier before life’s responsibilities intervene.
André continues to model lifelong learning himself. He was one of 24 individuals sponsored by the school district, UW–Madison and the Wisconsin Department of Workforce Development to pursue a master’s degree in educational leadership and policy analysis, which he completed in August 2025.
Finding and sharing inspiration
At the heart of André’s journey is his mother, Diane, whom he credits as his greatest inspiration.
“My mom had a huge influence on me going to college,” he said. “She pushed me to get as much education as possible.”
Diane, who holds two higher education degrees, never gave up, even while raising four sons on her own.
“There is no giving up and no taking a break and no sabbatical,” she said.
She has attended every one of André’s graduations, from preschool through college, and remains immensely proud of his accomplishments.
André knows his degrees required sacrifice and perseverance, but he views education as an investment. When students leave his classroom, he wants them to believe that “life is what you make it, and no one will give you anything, you have to earn it, whatever that may be.”
He tells his students to pose humble inquiries.
“Not only should you learn something new each and every day, but you should ask questions and don’t act as if you know everything,” he said. “This will help you learn from other people and will also serve you well in the future.”
He also stresses financial literacy.
“Save, invest and create generational wealth,” he said. “You won’t regret it, and your future self and your family will thank you.”
Like his students, André’s future remains full of possibility. He may pursue educational administration, teach in higher education, focus on research or pursue other business opportunities. Whatever path he chooses, his four degrees, teaching license and lived experience position him to continue making a meaningful contribution—in the classroom and far beyond it.
