Leading with Love

Head of School Todd Bland departs Milton with gratitude for a community full of generosity and caring.

“Let’s go football! Go field hockey! Go soccer! Go cross country!” The pep rally leaders were a cyclone of energy, hyping up their peers to support the athletes about to compete that weekend. Then, without skipping a beat: “Let’s hear it for the robotics team! Give it up for speech and debate!”

If the shift from athletics to stem and performance teams registered with anyone in the audience, they didn’t show it. Each group received raucous applause. For Milton students, recognizing athletic prowess in the same breath as other skills was seamless and natural. For me, it was one moment—out of thousands of similar moments—to witness something our students do with astonishing regularity and enthusiasm: celebrate each other.

Every year since I became head of school at Milton, I have guest-taught in classes at all 13 grade levels. It’s not only a window into the transformative work of our faculty, it’s an opportunity to see our students in their truest form, as empathetic and compassionate young people who are as caring as they are smart, as generous as they are ambitious. As my time in this role nears its end, and I reflect on the lessons I take from this place, I know that the love students show one another has left an indelible mark. Their celebration in good times and their determination in hard times has made me a better leader and Milton a better school. Whether they’re packing theaters for performances or asking thoughtful questions around the Harkness table, Milton kids show up for one another.

Milton has built an environment where students feel comfortable sharing their whole selves: their talents and interests, their cultural and family traditions, and their forays into new experiences. Students who enter the school planning to play three seasons of sports end up on stage in musical productions; kids with exceptional math and science skills find ways to express themselves in art. What feels remarkable about our school—and what fills me with hope for our future—is how ready and generous they are with praise for one another. They honor opportunities to learn from peers with differing life stories. Yes, they are competitive, as high-achieving students tend to be, but not at the expense of their classmates. They push themselves and root for others.

Students were the deciding factor in my coming to Milton. I had opportunities during my hiring process to meet the kids, to talk with them about the school and their interests. Their diversity, not just in their identities but in their passions and talents, was a critical hook for me. Even then, Milton had long been committed to enrolling a range of students from all walks of life— something we’ve continued to expand each year, and each one has something to teach all of us.

“Dare to be true” is more than a motto when it comes to this community. Milton students are honest and tenacious in the face of challenges and injustice. They come to our ongoing discussions about what diversity, equity, and inclusion mean at Milton with open hearts and open minds. Without the frank perspective of students of color, particularly Black and Latinx students, the significant progress we have made would have taken much longer or stalled completely. Similarly, transgender and nonbinary students have shared critical perspectives that have informed new policies and programs for students of all genders. The thoughtfulness, care, and commitment of all our students continually moves us toward a more inclusive environment. It’s not lost on me that for many of these students and the alumni who echo their stories, sharing experiences of not be- longing or feeling unseen has been painful. I have tremendous gratitude for them and for the allies who have lifted their voices. One thing I have noted while listening to these stories is that almost every single one of them is rooted in love: love for diverse cultures, love for one another, love for future generations of students, and love for Milton, even when it’s hard.

I often urge our students to love one another. Sometimes they cringe. Maybe it’s a little corny, and maybe it prompts some eye-rolls—especially from the teenagers—but there is no doubt in my mind that Milton students do love each other, whether they use the word or not.

In the ways that they encourage, fight for, and laugh with their peers, Milton kids fill this campus with love every day. Whether it’s our youngest students greeting others with hugs or our older students championing their friends’ unique identities and talents, I have been lucky to witness expressions and acts of love at Milton for 14 years. Even when they’re angry with each other or frustrated with the institution, they choose love. It’s a lesson I hope we can all take from these students: Keep loving one another. Keep loving Milton. I know I always will.