Reflect, Connect, and Take Care: Advice for Leaders | Facing History & Ourselves
Facing History CEO Desmond Blackburn speaking at the 2023 South Bay Fundraiser

Reflect, Connect, and Take Care: Advice for Leaders

Facing History CEO and President Desmond K. Blackburn shares advice for school and district leaders.

Across the US, schools are beaming with life again. Since I was a kid, the back-to-school season has always been one of my favorite times of year. Even when I started teaching and then as a principal and superintendent, it always held the exciting promise of new beginnings – new students walking the halls, new parents to meet, and new teachers to welcome into the community. I have come to recognize just how important it is to approach these first days of school intentionally, to make time to renew relationships with students, staff, and families, which sets a strong foundation for successfully navigating the inevitable twists and turns each school year brings. As an educator I have come to embrace three priorities during the back-to-school season: internal reflection, authentic connections, and self-care.

Internal Reflection

As education leaders, it is paramount for us to be aware of our beliefs, values, biases, and emotional responses.  All of these inform the ways in which we are able to show up for our schools and districts.

Education is the key to economic and social mobility, and to meaningful civic participation, and every child has the right to all three. As a first-generation American and a first-generation college graduate, my family’s experience has shown me the pitfalls of poor schooling and the potential of great education. My grandmother, born and raised in Jamaica, stopped her formal education after only the third grade after being repeatedly scolded in front of her peers by classroom teachers for her academic errors. My grandfather left school after completing eighth grade because he didn’t find the classroom challenging or engaging. Their limited formal education had implications for their economic opportunities, which in turn impacted my mother’s upbringing and my own. 

I know intimately the potential of a school environment to change the trajectory of a student’s life – all students, whether school fails to engage them, like my grandfather, or fails to create a safe learning environment for them, like my grandmother. My family’s immigration experience from Jamaica to the US and our generational advances in educational attainment – from my parents completing high school to me participating in higher education and earning a terminal degree – fuels the “why” behind my career choices. It’s the reason I have stayed the course in education. Reminding myself of this each year ensures that I start the year with renewed enthusiasm and purpose, and that I am thoughtful about my decisions and interactions. Only with a full cup can I pour into others.

Authentic Connections

Looking back, it’s clear that any success I had as a leader was directly tied to my ability to be present with my community. To effectively support staff and students and partner with families and community, we must be in touch with their needs and concerns. This is only possible through the creation and maintenance of authentic relationships. As leaders, we must take every opportunity to remind the members of our school community that we care about them, and we must provide opportunities for open communication in all directions.

During my tenure as a principal, I had an encounter with a parent who used an offensive racial term while describing his concerns about another student's interactions with his daughter. We were on the phone and had never met in person. He didn’t realize that when he spoke of a student’s race in a derogatory way, he was also speaking of my racial background. At that moment, I chose to operate with grace. Instead of reacting with hurt, anger, or defensiveness, I opted to look for common ground upon which we might be able to connect. I invited the parent to meet with me in my office for a face-to-face conversation, during which we were able to share our mutual concern as parents for our children’s safety. The connection I built with him that day resulted in him becoming an active contributing parent at the school.  

As a leader, people will often share parts of themselves with you – not all of them pretty – and you must listen with grace and be willing to share a part of yourself in return to build a connection. Not only do these relationships foster an environment of care in your school, they will also translate to trust and support later as you have to make tough decisions throughout the year.


In high school, I ran track under the guidance of the school’s coach, Melvin Harris. Coach Harris used to tell us that lack of conditioning would make cowards out of us. “In every race,” he said, “there will come a time when you want to assert yourself, and the decision to assert or not assert will be based on the confidence you have in your body and the training that you've taken part in.” I've taken that lesson and applied it to my career.

School leadership is ever-rewarding work. It also requires nonstop high-stakes decision-making that can be taxing mentally and emotionally. While I always felt supercharged at the start of a school year, it wouldn’t be long before the demands of the job started to weigh on me. It was in these moments that I would revisit Coach Harris’ lesson, which served as a reminder to build my capacity by maintaining my conditioning. As important as it was to recharge my staff for the year, it was equally important for me to spend time renewing my own energy. In 2020, I took up biking for my physical and mental health. Every few days, I get up with the sun and ride about twenty miles to clear my head and gain perspective on the day to come. If you follow me on social media, you already know that sometimes I turn these thoughts into what I like to call my Bike-to-Life Lessons. Dedicating time in my calendar to do this on a regular basis allows me to remain intellectually and emotionally available to the folks who need me the most.

When I joined Facing History, I found the values I held as a principal and superintendent reflected in Facing History’s classroom, school and district programs. Our programs help leaders build an educational culture that is safe, inclusive and reflects the principles of democracy. 

I’d love to stay in touch. Sign up here if you would like to receive a monthly email with reflections and resources for leaders in your inbox. Until then, remember to reflect, connect, and take care.