Courtney Bailey, middle school principal at CAC: Each week, My Morning Routine looks at how a successful member of the community starts their day — and then throws in a couple of random business questions just for fun. Speaking to us this week is the middle school principal at Cairo American College (CAC), Courtney Bailey (LinkedIn). Edited excerpts from our conversation:

My name is Courtney Bailey, and I am the middle school principal at Cairo American College (CAC). I am a third-culture teacher, having lived overseas for 32 years. Egypt is the country I’ve lived in the longest, for around 13 years.

Before Cairo, I taught in Beijing, Cambodia, Tanzania, Abu Dhabi, Dubai, the Ivory Coast, and Zaire (now the Democratic Republic of Congo), where I started my international teaching career. My time in Zaire was cut short after three months due to an evacuation, but the experience cemented my desire to teach internationally.

I began my teaching career in Toronto, teaching in the Toronto public school district for two years. Initially, I wanted to be an athlete but I soon realized my passion was working with kids. Born in Jamaica and raised in Toronto from 12, I’ve always been drawn to education.

I transitioned from classroom teaching to leadership in Cambodia, beginning as an athletic director. I loved organizing activities and creating opportunities for kids to have fun. Encouraged by mentors, I sought an assistant principal role, leading me to Cairo.

I’ve always wanted to lead, and I found my passion in middle school. Middle school students are at a critical developmental stage, an inflection point where we can profoundly shape their values, routines, and character. That’s why I love what I do.

I wake up at 5am during the week. I allow myself an extra hour of sleep on weekends because I’m off to play golf. My morning begins with mindfulness meditation, whether yoga or mobility exercises, followed by warm water and a bit of salt water to kick-start my day. I'm at the office by 6:30am or 6:45am, using the quiet time before everyone arrives to settle in, check my calendar, and prepare for the day ahead by checking that the building is clean and everything is ready to go. By 7:30am, I’m outside, welcoming students as they arrive.

My day is structured into chunks. I meet with my counselor and assistant on Sunday for about 45 minutes to review what’s coming up during the week. Mondays, for example, begin with a leadership meeting. I meet with the team leaders at 6:45 on Wednesday morning. Then, I spend time around the students, being present and accessible to kids and staff.

Strategic, long-term projects often happen after hours. School ends at 3:05pm, but I typically respond to emails, meet with teachers, and handle immediate tasks until 4:45pm or 5pm. Afterward, I head to the gym for a 45-minute workout before going home.

In the evenings, I reflect on strategic priorities, like upcoming presentations or long-term planning, often jotting down notes to follow up on the next day. I avoid communicating with my faculty outside work hours to respect their time.

The one constant in my day is the students. The students always know where to find me. I’m at the gate at 7:30am to greet them, and from 11:05am to 11:40am, I’m supervising them on the field or in the gym.

I rely on a network of trusted colleagues for decision-making. I bounce ideas off like-minded individuals, not necessarily administrators because diverse perspectives help refine my approach.

The beauty of this school is that there is so much diversity around me. When hiring, I prioritize diversity, aiming for a team that reflects our student body and shares our values. I need to ensure that the kids can see their reflection in the person I’m putting in front of them. This is why I try to get to know the person himself or herself rather than just what’s on paper.

Instilling values is integral to my leadership. Goals are essential, but values provide the foundation for why we do what we do. It goes back to being an athlete. One of the things that you’re taught is that you need to set a goal for yourself, but I realized that you can't get where you want to go just by setting goals. You have to have values. Values guide behavior and decisions for students, and I always return to these principles when addressing or guiding challenges.

I use a planner to structure my day, the same one the students use. This helps me stay aligned with the students’ schedules and follow their pace and structure, so I feel like I’m in it with them. I focus by listening to ambient music or chanting.

Mindfulness is a daily practice for me. Whether through focused breathing or staying present in the moment, it helps counteract the thousands of thoughts we process daily. I often remind students to “just breathe” to center themselves.

My next professional goal is to complete my doctorate. I’m nearing the dissertation phase, as I’ve already finished three chapters, so it’s just a matter of submitting it and beginning my research. While considering becoming a head of school, I’ve realized that my passion lies in being with the students. Being around them energizes me, and I find liberation in knowing I’ve reached the desired success level.

I play golf on the weekends and recently helped create a golf simulator at school. I’ve recently been drawn to podcasts focusing on AI for entertainment. I like listening to Thomas Frey as I find his insights into AI fascinating. Currently, I’m reading Golf Beneath the Surface by Raymond Prior, which explores the psychology of golf, and Ego Is the Enemy by Ryan Holiday, a powerful book on stoicism recommended by a friend who is a professional athlete.

The best advice I’ve ever received is to enjoy whatever you’re doing so it doesn’t feel like work. That’s the mindset I bring to my role every day, and it’s what I try to teach my students.

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