An open letter to Milton Academy

William Yu
11 min readJun 7, 2017

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Dear Milton Academy,

The moment is so clear in my mind. Spring 2009. A sunny afternoon. Wigglesworth Hall. Mr. H's African-American Studies course. My fellow classmates and I sat around the Harkness table. Some leaned back in their chairs, knees up high. High school was almost over, we were seniors. Obama was president. We were discussing the current political climate. Media outlets and pundits were claiming that racism was officially in our rear view mirror. It was a new day.

I don’t think I realized what I was saying when I said it. I thought it was a throwaway statement. Looking back, I realize that they were words that carried a weight and reflected an identity still lost.

“I don’t think I will ever see an Asian-American president in my lifetime.”

I had considered the math. I was 17. Let’s say I pass at 85. 68 years for this event to happen. 16 presidents at most. 8 presidents at least. I’d have almost 70 years to see a commander-in-chief that looked like me. 70 years to go to a check a box for someone with a last name like “Yu” or “Lee” or “Kim”. And I couldn’t imagine it. Not even close.

Me at Milton Academy graduation

What scares me now when I think of that moment isn’t the pessimism I felt at that age. It isn’t that I was sharing these thoughts in such an open forum. Or that my hopes haven’t really changed since that day.

What scares me when I think of that moment is that not a single student batted an eye. Amongst a diverse classroom with white, black, brown, and yellow students, only nods and silence followed. At a school where diversity — of thought as much as race — is prided, I had never felt so dismissed, so alone.

The Boston Globe’s headline for the recent acts of on-campus racism that included depictions of blackface and yellow face.

When it comes to facilitating the conversations of race and identity, this wondrous institution that I adore consistently falls flat. And in light of the recent racist acts of blackface and yellowface that have been shared on campus, Milton Academy continues to come up short when managing these discussions throughout the school year. Three moments during my Milton experience stand clear in my mind in which my beloved high school did not adequately equip my fellow students and me. I hope that highlighting these gaps and identifying some opportunities can provide some learning for this institution that I hold so dear.

The Transition Program

In theory, the concept of Milton Academy’s Transition Program makes sense. For one week, incoming students of color — mostly freshman, a mix of international and local students — would take simulated classes, get used the culture of a New England prep school, and discuss their differences within a safe community. However, in practice, this program is flawed in its ability to prepare its students — both those that attended and those that were not included — to facilitate and manage discussions about their race and identity.

This inability would inevitably scar the first few weeks of each school year. The same detractions and questions would arise. Reverse racism. Exclusion. Why can’t white kids have their own Transition program? And each year, the conversation would spike, subside, and be swept under the rug. The division in the community would eventually heal. The school year would carry on.

As a freshman, I expected Transition to be an inclusive experience that would empower my fellow minorities and me. Instead, I felt that the social waters of how we fit into the Milton community were muddied and unclear. During evening discussions before the academic year started, I felt an uncomfortable sense of “us” and “them” begin to form. This sense was never discussed. I certainly didn’t feel comfortable enough to bring it up. Once the rest of the students arrived on campus, I remember being just as confused as my white counterparts regarding their attitudes towards the program. I had signed on for a program that I thought would bring me closer to other students, not feel ostracized from them. Why was no one talking about why the Transition Program existed? What was its purpose? Questions abounded, but no real answers or understanding ever surfaced.

As a counselor, I gained a more personal mission of why I cared about an initiative like Transition Program. As much as I appreciated the camp-like environment of the program, I wanted to provide a connection and bond to new students. A bond that I had never had. It was about mentorship and setting an example. While there were many Asian and Asian-American students at Milton, there were few who reached back to lower classes. But as someone who had been a student government representative, a Chamber Orchestra lead, a varsity athlete, an Asian Society board member, I felt that maybe I could have some perspective to offer to these new students.

A few of the 2009 Transition Program Counselors (That’s me second to the left)

While I support the Transition Program and would recommend it to many students of color, it needs to be more than a check in the school’s diversity box and must consider the entire journey of not just those that will attend the program, but those who will not attend it as well. How does the Transition Program support its students — both participants and non-participants — pre-, during, and post- the session? Though the community the program fosters is so significant to the well-being of the participants, the administration misses a chance to share this empathy with the greater student body. Without this empathy, base emotion will override constructive thought, and teenagers will give in to what is easiest: stereotypes, anger, and fear. This discomfort is a responsibility that the program and its administrators must consider and meet head on.

I understand that concepts like race, racism, and the complexities of identity may be difficult topics for fourteen-year-old students to dive into. But I implore you to bring them up sooner rather than later, especially during times like the Transition Program. By not acknowledging the difficult conversations all your students will face, feelings of resentment will begin to crack the foundation of your student body.

The Walkout

As an institution that professes highly effective learning, Milton Academy has always had a special place in my heart because of the values the school represents: Courage, thoughtfulness, and honesty. Unfortunately, I am disheartened to see that in times when the school has had moments to make real, generational change, the opportunity is squandered.

While individuals strive to express their outrage and usher in new thinking, the institution that we look to for retribution hesitates to take measures. During my freshman year, a member of the junior class touted on a club email chain that African-Americans should be grateful for slavery since it brought them to America. Students then organized a walkout during a morning assembly in protest of the administration’s lack of action in response to this racist act. As Annie Jean Baptiste ’06 eloquently states in her Option B post, “I realized that I could let this break me, or I could be the change that I wanted to see.” As it was then, so it is today. To my admiration, current students have organized and staged walkouts and sit-ins to protest the recent acts on campus. Meanwhile, the administration issues boilerplate responses acknowledging opportunities for growth and “productive conversation”. To me, the success of these efforts lie not in quick fixes, but in re-evaluating the culture of the school and redefining the line of what is allowed and what is right.

What I would ask my fellow Mustangs to also consider is the emotional experience that will accompany the requests you make of the administration. Reviews and handbook changes are a great place to start, but do your classmates feel like a shift is taking place? Regular conversations that encourage honest feedback are hard to have as there may not be a definite or final answer. This culture must be a holistic one that is built together with the students and the administration. Student resources — your class reps, club board members, team captains, band leaders — can all provide the continued support and feedback that your administration will need to make the change you seek.

Asian Society

Though Milton Academy’s Asian Society triggers a lot of positive memories — the annual Lunar New Year celebration, “Asia Runs On Rice” t-shirt sales — for me, these memories mask many of the tensions that were left unexplored during my time on campus. We gathered every Monday afternoon to talk and catch up with students who looked like each other and faced similar problems. As I grew up in the club and became a board member, I relished the chance to be a mentor to others in the group.

Milton seniors after an Asian Society dinner (I’m in the top middle)

And yet, I can’t help but feel I was short-changed of discussions and learnings that I desperately needed. For better or worse, the weekly topics at Asian Society were safe and easy. While celebrating cultural holidays provides some insight into Asian culture, conversations that delved deeper into the identities of the community were not at yhe forefront of our programming. Exploring the nuances of what it means to be Asian vs. Asian-American would have been a welcome discussion for many young students who are trying to determine where they fit not only in the school hallways but also in the world. Recognizing and dispelling the model minority myth, understanding the bamboo ceiling, and weighing the consequences of misrepresentation within media are all concepts that could have been introduced during our weekly Asian Society meetings. In this current racial climate, students need to be able to embrace their culture while also understanding the complexities of being an international or hyphenated student.

#StarringJohnCho is a project I created that imagined what Hollywood blockbusters would look like if an Asian-American were cast in the role of the leading man. The project has been featured on The New York Times, CNN, BBC, among other notable publications. (www.starringjohncho.com)

I recently returned to Milton to speak about #StarringJohnCho on a panel about the lack of Asian/Asian-American representation in media. After the panel, a junior introduced himself to me and asked what Asian Society was like when I attended Milton. He asked if the club was vocal on campus, if it talked to other groups about their issues. I was conflicted. I would have loved to say that we reached out, connected with other groups, and advocated for their voices as much as ours. But the fact of the matter is that while we were always one of the biggest groups on campus, Asian Society’s conversations rarely went past Wigglesworth Hall. I don’t think any of us realized that we could say something. That we were allowed to get angry. That we were allowed to rally and yell and cry over our invisibility. That we could call out those who have been telling us who we are and what we’re worth. And that we could embrace those people with love and understanding of the systems in place that had led us to that point.

*In recently speaking with a former teacher, I was surprised to learn that while not all of conversations of identity were had, many topics like interracial dating and stereotypes had been discussed during my time at Milton. Whether they were during assemblies, meetings, or other forums, I must acknowledge that they did take place. To me, what I find intriguing is not that the topics were brought up, but that I have little to no recollection of these conversations. Why didn’t they stick? Was I not ready for such a conversation? Were there more effective forums that could have facilitated these discussions? Justified or not, this perceived gap exists in my mind and the minds of other alumni.

To my Asian and Asian-American brothers and sisters that are students at Milton Academy, it’s an exciting time to delve into the depths of your identity and start to ask the questions that you’ll face in the coming years. There has never been a time in recent memory when Asians in America have been as vocal as they are now. Find your idols — be they actress Constance Wu or actor Aziz Ansari, comedians Ali Wong or Hasan Minhaj, athletes Natalie Chou or Jeremy Lin, politicians Mazie Hirono or Chris Lu, writers Sarah Kuhn or Phil Yu — and celebrate them. Push for the hard conversations. Not just with those that look like you and understand your struggle, but also with those who don’t. You will be surprised at how much others don’t know about the things that you take for granted every day. But you’ll also be comforted by how much you have in common with them. Push your teachers and advisors to help facilitate these conversations. Ask for this help, you don’t have to do this alone. And lastly, resist the temptation to give in to those who would have you think that your conflicts and hurts are less worthy to discuss than others. Know that no one has the right to deprioritize your self-worth, your anger, your happiness, and your compassion. Milton cultivates a community of thoughtful thinkers. I know you’ve been told to keep your head down and carry on. But I call on you to reach out and connect. A rising tide raises all boats.

Milton Academy: I will never forget the four amazing years I had on your campus. The memories and friendships I made there still endure today. It pains me to hear that there are fundamental gaps that existed in my high school experience that still exist for many students today. But I am hopeful. Hopeful that you will learn from your mistakes and identify the spaces you have yet to explore. I am hopeful that you will provide ways to talk about difficult subjects and promote understanding for those who do not see the marginalized. I am hopeful that an Asian-American student will one day sit in Wigg and believe that a President can look like him or her. And I am hopeful that that student will feel empowered to take a stand for their identity, for others, and for the right to fulfill their ability to Dare To Be True.

With love,

William Yu

Class of 2009

Did this sound the Milton Academy you know? What has your experience been with discussing race and identity in your high school? Let me know with a comment below!

And if you care to discuss this more, follow me on Twitter at @its_willyu and we can chat further.

William Yu is currently is a Senior Strategic Planner at advertising agency TBWA\Chiat\Day NY. His project #StarringJohnCho, a viral social movement that literally shows you what it would look like if today’s Hollywood blockbusters cast an Asian-American actor — specifically, John Cho — as their leading man, has garnered over 1 billion impressions worldwide and continues the conversation regarding the lack of Asian-American representation in film. In addition to winning the 2016 Shorty Award for Best Use of Hashtag and the 2016 American Advertising Federation Mosaic Award for Multicultural Digital Campaign, Yu has worked on projects for brands like BNY Mellon, Accenture, Verizon, Mastercard, and many other notable companies. His work has been featured domestically and internationally from major media outlets such as The New York Times, BBC, CNN, NBC, CBS, The Huffington Post, Buzzfeed, and The Hollywood Reporter, and more.

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William Yu

Writer/Director. @Peacock TV Writer. @SundanceOrg Fellow. #BlackList2021 Select. @NBCULaunch Alum.