In 2013, I moved to Madison, Wisconsin, to work as a State Education Consultant for the Wisconsin Department of Public Instruction. I came with a heart full of hope and purpose, unaware of the stark challenges Black students faced in Madison’s education system. I soon learned that Madison, at the time, had the worst education outcomes for Black students in the country. I was alarmed and deeply moved—it felt as though God was calling me to use my talents and gifts to make a difference right here, in what had quickly become my new home.
This divine nudge led to the birth of CEOs of Tomorrow in 2016. Fueled by a commitment to rigorous, relevant education, the organization focuses on underrepresented students, equipping them with the tools to transform the world through social entrepreneurship. From the outset, our curriculum was aligned with academic standards and correlated with college-level business courses, which facilitated a quick partnership with Madison Metropolitan School District and Madison College. These collaborations enabled students to earn both high school and prior learning college credits for successfully completing our courses—a critical advantage for a population too often denied equitable access to such opportunities.
Amid this new and transformative journey, I met Milele Chikasa Anana. Or rather, Milele met me. I didn’t know her at first, but she made it her business to know me. Somehow, she learned about CEOs of Tomorrow in its earliest days and decided to take me under her wing. “You need to join the UpStart program,” she told me one day, her tone a mix of encouragement and insistence. UpStart, a WARF initiative, was life-changing—a program that provided me with the knowledge and resources I needed to strengthen my business and deepen its impact. It was a gift I wouldn’t have found on my own, and Milele made sure I didn’t miss it.
But Milele didn’t stop there. She spoke about CEOs of Tomorrow to others in the community, amplifying our mission and connecting me to allies I didn’t yet know I needed. She invited me to events she felt would enrich me personally and professionally. And in the unassuming, matriarchal way she had, she called to check in. Milele kept a loving pulse on my progress, her support steadfast and unwavering.
She always believed in me. Her presence was a constant reminder that I wasn’t walking this entrepreneurial path without support. Milele’s guidance, encouragement, and fierce advocacy became a cornerstone of my Madison journey. She made me feel seen and valued, a rare and priceless gift in those early days.
Milele’s influence extended beyond our professional relationship. She had an incredible ability to unite people and foster collaboration. At every event she invited me to, she would introduce me with such warmth and conviction that it felt like she had known me forever. Her words carried weight, and her endorsement opened doors I hadn’t even considered knocking on. She was a true matriarch, wielding her influence with both grace and determination, ensuring that others thrived under her guidance.
As I reflect on her impact, I am overcome with gratitude. Milele wasn’t just a mentor – she was a nurturer of dreams and a beacon of hope. Her life was a testament to the power of community, the importance of lifting as we climb, and the profound difference one person can make when they choose to care. Though she is no longer with us, her legacy lives on—in CEOs of Tomorrow, in the lives she touched, and in my heart. Milele Chikasa Anana was, and will always be, someone extraordinary.
Milele Chikasa Anana
January 31, 1934 –
May 6, 2020
