Chosen, Not Chasing: Dr. Markay Winston’s Leadership Journey

In this deeply inspiring episode of Breakthrough Conversations with Rhoda & Co., Rhoda sits down with Dr. Markay Winston, whose rise to the superintendency is less a story of pursuit and more a story of preparation, sponsorship, self-belief, and courageous acceptance.Dr. Winston’s journey spans more than three decades in K–12 education, from school psychologist to district leadership, shaped by equity-driven purpose, resilience, and powerful sponsors who saw her potential before she fully saw it herself.Rather than chasing titles, Dr. Winston focused on excellence, service, and impact, trusting that the right doors would open at the right time. When they did, she had to confront her own doubts, lean into belief, and step fully into her calling.This episode is a masterclass in: The power of sponsorship over self-promotion Leading with humility, authenticity, and courage Navigating imposter syndrome and stepping into big leadership roles Building trust through deep listening and community connectionIf you’ve ever questioned your readiness, struggled with self-doubt, or waited for permission tolead, this conversation will speak directly to your heart.Dr. Winston’s Leadership Journey Highlights 30+ years in public education Former School Psychologist Chief of Diverse Learners — Chicago Public Schools Assistant Superintendent → Deputy Superintendent → Superintendent (MCCSC) Architect of community-centered leadership strategies Champion for equity, access, and inclusive educationWhy This Episode MattersDr. Winston’s story reframes leadership success. Instead of asking, "How do I get there faster?"she teaches us to ask:"Who am I becoming while I prepare?"Her journey reminds us that: Sponsorship matters Self-belief is learned And leadership is something we step into, not chaseThis episode will resonate deeply with: Women navigating executive leadership paths Educators and administrators Professionals wrestling with imposter syndrome Anyone standing at the edge of their next breakthroughFavorite Quote from the Episode“I didn’t chase the role — I had to accept that I was ready for it.”Host Message This episode is a reminder that your breakthrough doesn’t always come from pushing harder, sometimes it comes from believing deeper.— Rhoda Banks Breakthrough Conversations with Rhoda & Co.