I never saw myself as a head of school. It took me many years to acknowledge that it was even a possibility. I had no model of an Asian American woman as a head of school, but others saw the potential in me before I did.
When I look back, I marvel that the choices I made were, in many ways, brave, maybe with a tinge of naïveté. I am the product of immigrant Korean parents who didn’t stop me from following my passions, and of the independent school experiences they provided for me at Kingswood-Oxford School (CT) for middle school, then Loomis Chaffee School (CT) for high school. These places, and most importantly, the teachers and administrators shaped, challenged, and equipped me—they believed in me so that I could eventually believe in myself.
What I appreciate most about my independent school experiences is that I was encouraged to try new things, and the opportunities were abundant—especially the athletics teams I joined, which taught me that even the things I thought were too hard could be overcome as a team, by taking things one step at a time, and finding fun in the challenge.
In many ways, headship reminds me of a race: the moment that comes after countless hours of training, trust, and practice. When I got to college, I found myself trying out for the crew team. I was in Boston, and it seemed like the romantic thing to do. No one told me how grueling it would be, but I was into it. Even though it felt like my heart might explode in the middle of every race, I knew my teammates and I had trained for this, and together we’d reach the finish line, one stroke at a time.
I didn't know it at the time, but joining that crew team was the first in a series of yeses that would eventually lead me to headship. Some of the yeses were more passive than I wish they had been, but I kept putting one foot in front of the other, following the paths that eventually led me here.
Big Yes Number One: The Goldenrod Flyer
I thought I was destined for sports medicine and physical therapy, but I struggled as a science major. During a very long and protracted moment of frustration with physics and calculus, I opened my college mailbox to find a goldenrod-colored flyer telling me to apply to the graduate school of education. A fifth year to get a master’s degree? Was I ready to abandon my dream of driving a golf cart on a giant sports field? I took some education classes, fell in love, attended the Lynch School of Education at Boston College, and became an English teacher.
When I reached the classroom, I tried to emulate my incredible English teachers. Like the one who asked me to read my reflection on the Vietnam War Memorial out loud in sixth grade. Or my eighth grade teacher who, after I gifted him a silkscreen print I had made, framed it on the wall of his office. Or my 12th grade Shakespeare teacher who threw chalk at the board one day as he got into character reading one of Hamlet’s soliloquies, the chalk dust exploding everywhere. I wanted my students to love all of it as I had: literature, words, writing, syntax, grammar, especially grammar. I claimed I would never leave the classroom.
Leadership lesson: Look for signals and follow the signs.
Big Yes Number Two: The Bright Side
I admit I called administrative positions “the dark side” in the early days of my career. I loved the people, but I thought I’d hate the work. My first toe dip into admin was chairing an English department; this seemed OK because it was closer to teaching than admin. I discovered I liked spreadsheeting, mentoring, scoping, and sequencing, but I didn’t think I would step any further into the admin waters.
But then the unexpected happened. I found myself saying yes to my head of school one August when he asked if I would be the inaugural dean of faculty, effective immediately. I followed my yes with the happy news that I was six weeks pregnant with my first child.
The position required me to teach and chair the English department for one year while building the new dean of faculty position. But I could do anything for a year, even full-time teaching, department chairing, dean-ing, and growing a human.
It was the only position I thought could lure me away from full-time teaching, and I am grateful every day for this pivotal moment in my professional life. I ended up loving the arrangement because I got to do it all. This was when I created the systems and efficiencies that are my saving grace in headship today.
Leadership lesson: Seize opportunities, even if it sounds like too much. It often sounds scarier than it is, and if it really is, you can always pivot.
Big Yes Number Three: The Fellowship
Even though I told myself I would never be a head of school, I again found myself saying yes to attending the NAIS Fellowship for Aspiring Heads. My head, the same one who lured me into senior admin, said I needed to go because I was going to be a head one day.
I paused at first, but I did eventually say yes. This was the first time I seriously considered headship. I figured that even if headship was not in the cards, it’d be a great experience for any senior administrator to see independent school governance from the board and heads’ perspectives. And I did walk away with a newfound appreciation for my head of school. Even though I left that week in Atlanta still unsure of whether I could, or even wanted, to do the job, the seed had been planted, and the relationships I forged that week were invaluable.
Leadership lesson: Keep learning and keep an open mind.
Big Yes Number Four: The What?
I admit my first response to an actual offer of headship was “What?” I was expecting the obligatory, “Thank you, we loved meeting you, and we know you’ll be a head someday.” I had heard that variation many times over the six years that I’d been essentially dabbling in head searches, being very selective in what I applied for. Nonetheless, I was exhausted.
I had given up for the hiring season when I saw a headship that had just opened up and seemed appealing. In the 11th hour, I decided to brush up my materials; I sent them in, then forgot about it. I eventually made it to the semifinalist round, as I had many times before. In a span of less than 24 hours, I traveled from DC to San Francisco; said “thank you” at the end of the interview as if that was goodbye forever; and flew back on a red eye.
I wonder if it happened for me this time because I was most myself. I really didn’t have any expectations and just told myself to do my best. I had done my research and put my best foot forward, but I was too tired to “play the game.” It all felt natural. Unforced.
I had kept saying yes to get to this point: to continue applying, picking myself up after each rejection, and learning to not take it personally. I had kept saying yes to being the best version of myself.
Leadership lesson: Don’t turn yourself into a pretzel for anyone.
Big Yes Number Five: Coach and Be Coached
I may not have always been aware that folks were coaching me or that I was consciously saying yes, but I have come full circle to appreciate my path and the many people who invested their time and energy to coach me for and through headship. Thank you for continuing to answer my texts and calls.
Accepting a headship is just the beginning. A successful leader will account for the skills they already have, stay humble to gain new ones, and continue to practice using them to know which ones are right for the moment. Most importantly, a successful head will accept help along the way. Headships have become more complicated with more dilemmas to wrestle than problems to solve, but it is possible to train for this. There are so many coaches and mentors, even in unexpected places. Just ask. People are more generous than you assume.
Leadership lesson: Always take a learner’s stance.
Encouraging the Next Yes
A friend recently asked if I’m still on a quest to convince others to consider headship. Absolutely! Amid the stories that say it’s “impossible,” there are also stories of joy, inspiration, and life-changing moments. Only a head of school can touch all areas of a school, so your impact is exponential. And the sweet hellos, hugs, and notes you get from students certainly help make the job worth it. I count it a success if just one more person considers headship. Might it be you?