Cheryl Collins
I met Cheryl through the incredible organization that is Chicago Women in Philanthropy, and have since been continuously in awe of her calm wisdom and deep commitment to the work she does. I was delighted when she agreed to be interviewed for the series.
Looking at her varied career, from classroom educator to Principal and CEO, it is easy to assume a linear path in education from day one. But as Cheryl candidly shares, her journey began somewhere entirely different.
When I ask her about her origin story, she reflects on growing up in Chicago in a hardworking household, and watching her parents model perseverance and hard work every day. While her teachers recognized early on that she was smart, capable, and destined for great things, Cheryl recalls being a serious teenager, constantly wondering what her true calling would be.
Initially, that calling seemed to be medicine. During her junior and senior years of high school, she participated in a unique practical nursing program through Chicago Public Schools, splitting her days between classes and the hospital floor caring for patients. She graduated as a Licensed Practical Nurse (LPN), using her nursing work at Northwestern to put herself through college.
But during her freshman year at Loyola University, she came to the realization that medicine was not the right fit for her. She knew she was meant to help people grow, but hospitals weren’t the environment where her spirit thrived. Remembering how much joy she found as a student helping others learn, helped her decide on a pivot into education.
In 1984, she joined Westside Preparatory School, the historic institution founded by renowned educator Marva Collins. Teaching in mixed-grade classrooms spanning ages junior kindergarten through eighth grade, she practiced “looping” with students for up to two years at a time. From there, she transitioned into administrative leadership, spending a decade directing K-8 programs at Providence St. Mel School, while simultaneously earning her Master’s in Educational Leadership from DePaul University. In 2004, she stepped into the role of Principal at Holy Family in Chicago, an institution she would nurture for 14 years before ultimately becoming Chief Executive Officer of Holy Family Ministries in 2017 (for which she was asked several times before accepting).
When I ask her about any career missteps or learnings, she shares that she regrets not pursuing her Master’s degree earlier in her career, noting that doing so might have paved the way for a doctorate or a superintendency.
She also opens up about the insidious role self-doubt and fear can play in our choices. When she was initially approached to become CEO at Holy Family, she turned down the offer three times before seeing the organization's need and finally stepping into the role. Stepping past that hesitation taught her a lesson about trusting her own capabilities and saying yes to leadership even when the insidious voice of imposter syndrome tells us otherwise.
What keeps her going professionally has always been a profound belief that high-quality, early-intervention education is one of the single most transformative solutions for systemic inequities in our communities.
As an “introverted extrovert,” she refuels personally through intentional quiet and enjoys reading, journaling, and beginning her days with prayer and meditation. Nature, in particular, has become a restorative outlet for her and she speaks fondly of peaceful, grounding walks around the Lily Pond in Lincoln Park to clear her head and reconnect.
Looking toward the future, she is entering an exciting new chapter after formally ‘retiring’. Through her executive coaching and consulting practice, she is expanding her public speaking, writing and publishing a book, and coaching leaders and organizations. Personally, she looks forward to more travel and soaking in time with her family, especially her granddaughter.
When I ask her about formative influences, she immediately speaks of her mother, Edna, who modeled lifelong learning by earning her bachelor’s and later completing her Master’s degree in her late 70s. She also credits her eighth-grade teacher, Harvey Harvell, who challenged her with demanding literature and instilled in her an appreciation for vocabulary as a window into the world, as well as trusted mentors and coaches like Jackie Davidoff and her husband John who helped her navigate executive hurdles as well as her most current coach Sarah Emerson who helped her make the transition from CEO to entrepreneur.
Toward the end of our conversation, she reflected on a pressing challenge she sees for the next generation: the encroaching influence of AI and social media on children’s social development, the rise of cyberbullying, and the loss of authentic, human connections. Much like our broader struggles to enact sensible policy for safety, she worries about what the absence of healthy boundaries means for kids today, reaffirming her lifelong commitment to protecting and nurturing the well-being of young people. To learn more about her work contact Cheryl through her website or email her at cherylwcollinscoaching@gmail.com