A CONVERSATION WITH RECENTLY RETIRED PRINCIPAL TONYA TOLBERT On Leadership, Legacy, and the Transitions That Shape Us
After years of service in Chicago Public Schools and two elected terms as CPAA’s Vice President of Elementary School Principals, Principal Tonya Tolbert has transitioned into retirement. As many CPS principals and assistant principals stand at similar crossroads, weighing the personal and professional implications of such a step, her reflections come at just the right time. Transitions like this one are complex. Retirement isn’t a single decision. It’s a shift in identity, a change in pace, and in many ways, a leap of faith. And for school leaders, the stakes feel even higher. We don’t just carry our own responsibilities; we hold communities, students in crisis, shifting mandates, and our own dreams for what schools could be. That load is heavy. It’s no wonder that the line between personal readiness and professional burnout can sometimes blur. What we hope for every school leader is a moment when the decision to step away comes from clarity, not exhaustion; from reflection, not resignation. In this spirit of transition, we sat down with Principal Tonya Tolbert to talk through the why, the when, and the what now. We asked what helped her find her moment, how she’s adjusting to the shift, and what advice she might offer others navigating this unique kind of life change. And because our union, too, is in a moment of leadership transition, we asked for her thoughts on what’s next for CPAA… and how we carry legacies forward. Knowing When It’s Time For Tolbert, retirement wasn’t a sudden leap, it was a plan years in the making. “My plan had been to do four contracts and retire,” she said. “I then signed a fifth contract and retired in the second year of that contract. I really felt obligated to leave the school in a good place.”
But even the best-laid plans can meet resistance, especially when your heart is still wrapped around the work. “Many people said, ‘Why do you care who comes after? You did your time.’ But it was extremely important to me,” she reflected. “It felt like putting your baby up for adoption—and hoping, praying—that the next parent would love your baby just as deeply. Maybe even in ways you couldn’t. That doesn’t make it any easier to let go. But when you know it’s what’s best for the future, you do it anyway. You trust that love can look different and still be whole.” There’s always more work to do—especially when you love the job, the staff, the students, the community. But there comes a point when the role takes more from you than it gives back, and you have to be honest about that. Change can be painful, but it can also be necessary. She came to realize that leaving didn’t mean the end of her impact—just the evolution of it. “I didn’t leave because of one big thing,” she explained. “It was the slow buildup of weariness. I started the 2024- 2025 school year under duress. I kept pushing back my decision—I wanted to set up the school year, finalize the budget, get the staffing right... but I eventually realized: nothing was going to be perfect. The next principal would have to make it their own. And that’s OK. I can still make my mark—it just looks different now.” And in the end, there’s power in sticking to a decision made with your eyes wide open. When she submitted her retirement form in September, it came with a strange sense of peace. “I could no longer change my mind,” she said. “And that brought clarity. There was nothing left to wrestle with. It was done. And I could begin to look forward.”
38 • CPAA QUARTERLY MAG | Q3 AND Q4 2025
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