How do local teenagers think about their identities?
Poignantly, powerfully, painfully.
And very, very honestly.
TEAM Westport’s 12th annual Teen Diversity Essay Contest may have provided the most personal prompt ever.
It certainly drew some of the strongest, rawest responses in the dozen years the contest has asked young Westporters to reflect on their lives, and the world around them.
The prompt said:
In our community, each person’s unique identity — shaped by their race, religion, ethnicity, sexual orientation, and other aspects of who they are — contributes to the character of Westport. In 1,000 words or less, we invite you to reflect on how your own identity shapes your perspective and the experiences you have in Westport. Please address the following considerations in your response:
- Which aspects of your identity feel most central to how you wish to be understood and accepted?
- How do aspects of your identity shape your daily school and community experiences, including both challenges and opportunities in expressing these parts of yourself?
- What specific changes could our community make to decrease identity-based bias, bullying and hate?
Plans called for 3 prizes. The judges added a fourth, because of the impressive breadth and depth of the nearly 2 dozen submissions.
(And those judges are no slouches. Retired professor Dr. Judith Hamer headed a 6-person panel that included Shonda Rhimes.)
The 4 winning writers — announced last night at the Westport Library — addressed the subject differently. Two are Black; one is Indian, the other Chinese. All attend Staples High School.
Senior Annam Olasewere took first place, and won $1,000 for her essay “Understood. Connected. Valued.”
Sophomore Aanya Gandhi was second, earning $750 for “White Paint and Other Lies.” Junior Souleye Kebe took third place, worth $500, for “S-L-M,” while freshman Sienna Tzou was named honorable mention ($250) for “The Value of Identity From the Start.”
All 4 students express gratitude for their Westport experiences. None, however, has had an easy time.
From left: Annam Olasewere, Aanya Gandh, Sienna Tzou, Souleye Kebe.
The winning essays are below.
As you read them, reflect on their writers — and on all the other Westporters, of every age, they interact with every day.
Then remember those essays, and the young men and women behind them.
Not just the day after the diversity contest. But every day you are a Westporter.
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1st Place — ANNAM OLASEWERE: Understood, Connected. Valued.
Growing up in Westport, I quickly learned what it meant to stand out. In a school of hundreds, I can count on one hand the number of students who looked like me. More often than not, it was just me – in classes, walking the halls, or sitting at lunch as the only girl of color in the room. Those moments made me more aware of the gap between how I saw myself and how I was seen by others.
Westport prides itself on being a welcoming community, but belonging is not just about physically being in a space with others — it’s about being understood. It’s about being connected to your community. It’s about being valued. While I’ve never been directly told, “You don’t belong here,” here,” I’ve felt it in a thousand quiet ways — the double takes when I say Westport is my hometown, the disbelief when I step into leadership roles or excel in AP courses, or the doubt people show when I pursue activities outside the norm for “someone like me.: It’s not outright hate; it’s something more subtle yet just as isolating-a quiet bias that makes me feel like I must constantly prove my worth.
Annam Olasewere
And nowhere have I felt this more than in my sport. Fairfield County’s athletic teams are known for their excellence — but not necessarily for their diversity. As a competitive swimmer, I step onto the pool deck knowing that, more often than not, I am the only brown-skinned girl in the water. Even when I succeed, the reaction isn’t admiration but disbelief — comments like, “How can you possibly balance everything? The academics, the athletics, the extracurriculars?” No one asks others who succeed in mulciple areas these questions. It’s as if my accomplishments are unexpected, as though they were not supposed to be possible for someone like me.
Yet, despite these challenges, my identity has also been my greatest source of strength. Being different has given me a deeper sense of determination and resilience. I don’t settle for less. I see the signs of bias now, and I don’t lee them define me. But here’s the thing — belonging isn’t just an internal issue. It’s also shaped by our structures and systems.
Westport wants to be a place where every student feels like they belong, but how can we when there are almost no role models and peers who look like us? Walking the halls, sitting in classes, and joining school activities, I rarely see faces that reflect my own. It’s not just a feeling — it’s a reality. African American students make up only 1.8% of the school district’s population, meaning that in a graduating class of 400-500, there are maybe seven of us. Seven.
Not in one classroom, not on one team — but in an entire grade. We aren’t just underrepresemed; we are scattered, spread so thin that it’s easy co feel invisible. And it’s not just among students. In a building with about 200 educators, I can count on one hand the number of teachers of color. Five — maybe fewer. In all my years of school, I’ve never had a teacher who shares my background, who understands — without explanation — what it’s like to walk into a room and immediately feel like an outsider. To be the only brown-skinned girl in a classroom, in an AP course, or on a team. To always feel like I have to prove that I belong.
Representation is not just a statistic. It’s about walking into a space and seeing proof that you can thrive there — that your ambitions are not anomalies, and that you don’t have to be the first or the only one to be excellent. When we don’t see ourselves reflected in leadership, in education, in success
stories, we are left to wonder — do we truly belong here?
This isn’t just an oversight; it’s a missed opportunity. Representation matters –not just in the classroom, but in the way students see their futures. When teachers of color stand at the front of a classroom, they aren’t just educators; they are proof that we belong in those spaces and that we can be scholars, leaders, and intellectuals.
Westport needs to hire more diverse staff — not just to tick a box, but to show that they truly value all students and their experiences. While representation is important, the attitudes of educators also help unlock the potential students see in themselves.
In my psychology class, I learned about implicit bias: how even well-intentioned people can unknowingly hold prejudices that affect their actions. Studies show that people can often — without realizing it — have lower expectations for students of color, are more likely to discipline them harshly or assume they need extra help. This is not because they are bad people, but because bias is deeply ingrained in all of us.
This is why all teachers need to take implicit bias tests, not as an accusation, but as a tool for self-awareness. They need to recognize their biases, educate themselves, and actively work to do better. It’s not enough to say, “I don’t see color.” Because the truth is, the world does. Pretending otherwise doesn’t erase the experiences of students like me-it erases the chance to change them.
For me, Westport has always been home and I will always love my home. But home should be a place where you don’t have to fight to fit in. It should be a place where no student ever questions whether they are out of place because of their identity. Where our differences are not just seen, but celebrated. Where the next girl of color walking into a classroom or diving into a pool doesn’t have to wonder if she’s the only one — because she won’t be.
Westport is not a place of hate. But it is a place of gaps — of blind spots, of unintentional marginalization, of well-meaning people who don’t truly understand ochers’ realities. By sharing my story, I hope we can stare closing chose gaps and creating a community where true belonging means being understood, valued, and connected to those around you.
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2nd Place — AANYA GANDHI: White Paint and Other Lies
I used to believe that identity was something you could package neatly, something that could be shaped to fit whatever mold was required of you. After all, I had done it myself — layering coats of white paint over a canvas splotched in black, covering the parts that didn’t seem to belong. A fresh coat each time the paint started to peel. A fresh performance each time the mask began to slip.
Moving to Westport was like stepping into a world that had already written its script. Individuality was celebrated, but only in its most polished form — never raw, never messy. There was a right way to be unique, a right way to be different.
I learned early on that there were two versions of myself: the one that fit and the one that didn’t. The one that could blend seamlessly into the rhythm of this town, and the one that pulsed just slightly offbeat.
Being a “hyphenated American” means existing in the space between the lines. It means translating parts of yourself depending on the audience, slipping between languages, between customs, between ways of thinking. It means carrying the weight of two histories at once, even when the world only asks for one.
Aanya Gandhi
In Westport, I have felt this duality in ways I never had before. My roots extend far beyond the pristine lawns and quiet affluence of this town, but here, those roots are invisible. The fast-paced, electrified streets of India live in my memories, the rhythmic clatter of rickshaws and the rich aroma of spice stalls feeling like echoes of another life.
But in Westport, there is no space for those echoes. Here, I am expected to exist in a singular dimension. To be American in a way that is digestible. Acceptable.
The challenge is not just being different — it’s being different in a way that others don’t quite understand. It’s the subtle mispronunciations of my name, the casual dismissal of my traditions as “exotic,” the assumption that my heritage is an accessory rather than an integral part of who I am. It’s the way my culture is celebrated when it’s convenien — Diwali as an aesthetic, Bollywood as a novelty – -but dismissed when it challenges the narrative of what “American” should look like.
I have spent years walking the tightrope between belonging and erasure. I have become fluent in the language of masking — of saying “I’m fine” when I’m not, of laughing off moments that sting, of folding myself into smaller and smaller shapes to fit the space allotted to me. But even paint has its limits. Even masks begin to crack.
There was a moment when I realized that the burden of translation should not fall on me alone. That my identity is not something that needs to be repackaged or rebranded to be understood. That my presence — unfiltered, unpolished — is enough. The true challenge of identity is not just existing within it, but demanding that others see it for what it is, in all its complexity.
Westport has the privilege of being a town that welcomes diversity in theory, but struggles with it in practice. The change we need is not just more cultural festivals or acknowledgments in school assemblies. It’s deeper than that. It’s in the way we teach history — not as a singular narrative, but as a melting pot of perspectives. It’s in the way we talk about identity — not as a check box, but as an evolving story. It’s in the willingness to listen, not just to respond, but to understand.
I no longer wish to be understood in fragments. I refuse to be seen in halves. I am not just the parts of myself that are easy to digest, easy to praise, easy to fit into a pre-approved template. My identity is not something to be painted over, polished, or rebranded. It is vibrant, uncontainable, and wholly mine.
And for the first time, I am learning to stand in that truth — without apology, without translation, without another coat of paint.
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3rd Place: SOULEYE KEBE: S-L-M
Whenever a person asks you who you are, the natural response is to give your name. What else would suffice as a distinguisher? From birth, it is the go-to summary of a person’s identity. My name is Souleye, and for most of my life, I had no clue what my name meant. Turns out it’s derived from Sulayman, which is translated into English as Solomon. Since my family is West African, we use many variations of Abrahamic names like Solomon, names that would be considered “exotic” or “peculiar” in the United States. I always took pride in my clearly African name, however, seeing it as a stronger distinguisher than the numerous Johns or James here. I always knew that I was Souleye Kebe, an African.
Being born an African, I had to come to terms early on that people who look like me haven’t had a historically positive relationship with the United States. What made it easier was that I didn’t have to accept that by myself, because I lived in New York City where everybody came from diverse backgrounds, many of them having similarly complex relationships with the country we were born in.
Souleye Kebe
Coming to Westport was admittedly a culture shock, since I had never seen so many people with such relative conformity. The students here had the same clothes, same style of speaking, and same style of general being. They also shared the same statements: requests like “Can I touch your hair?” remarks such as “I don’t see color,” and “boasts” like “I had a Black friend in elementaiy school.” I thought that these words were nothing more than stories, and so I was astonished to hear people say them to my face. Through that, I remained Souleye Kebe, an African from New York City.
Despite me going to school here for three years, I still wouldn’t rush to ever call myself a Westporter. I value my outsider perspective too much to seemingly diminish it with that title. I’ve found many outlets here to express that perspective, such as with my position on the Board of Education allowing me to filter the opinions of students and to discern which pieces of feedback best represent us as a school. These outlets, however, are more representative of my identity as it relates to attending Staples High School, and not of my identity as a “Westporter.” These outlets make me Souleye Kebe, an African from New York City attending Staples High School.
When TEAM Westport asks students like me to propose specific changes to combat hatred and bias, I wonder why this burden of fixing systemic exclusion falls upon those already navigating its harms. The unabated truth is that it’s not my responsibility, nor the responsibility of any other kid, to act as Westport’s savior, driving it towards diversity and away from hatred. While I can and will support the town in any way I can towards that goal, it is incumbent upon the residents of Westport to seek that change for themselves.
Every person must look inward and examine their own potential predispositions and immediate judgements, determining for themselves whether they want to put the effort towards a more kind and tolerant Westport. We can mold students towards that mindset by implementing diverse thought processes in all parts of their education, showing them that the world they live in is a mere slice of true reality, and is not reflective of how diverse the world truly is. However, we can’t force them to make a positive step, it’s entirely on them.
Living here, I see my identity spread between the two continents of America and Africa. The distance between these two places has made me realize that I am in trnth a child of the world, as all people are. We often forget how we are all inhabitants of the same planet, being too caught up in the immediate to notice. We think and say disgusting things to others outside of our close proximity because the distance protects us. This is not a proper way to live.
I doubt that I would subscribe so fully to this realization had my identity not been spread as far as it has, had I not been afforded this perspective uncommon to the people of Westport. While I think this perspective is a strong impetus towards global thinking and away from prejudices and bias, it is incumbent upon the Westport community to carry that energy forward.
I will not tell this community the minutiae of every step they need to take to make Westport a more welcoming place, the town must first see for themselves the peace that can be made and that can exist by celebrating diversity and opposing hatred. ‘
Look at the names of the people of the world. My name as well as its many variations are all derived from the triliteral root S-L-M. We hear it in Salam and in Shalom and in Solomon and in Shlomo and in Sulayman and in Souleye. This root means peace, which is something we can all strive for. My name is Souleye Kebe, an African from New York City attending Staples High School, who is working to be an advocate of peace.
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4th Place: SIENNA TZOU: The Value of Identity From the Start
By the first hour of my first day of kindergarten, I had heard “Say ‘hi,’ Sienna” from my mom about a hundred times.
I stood behind my teacher when she introduced me to the class. I ducked my head, stared at my shining, coruscant ballet flats, and whispered as feebly as possible, “Hello.”
That was the only word I knew in English.
I saw that some of my classmates snickered and very audibly attempted to imitate how I spoke. Others whispered and pointed their fingers at me, as if my Asian “exoticism” was a foreign contaminant that could somehow infect the class.
For the next two years, I made a silent resolve to avoid socializing altogether. I didn’t want kids mimicking how I spoke, and it gave me the excuse to not be obligated to answer the unfiltered questions I knew everyone wanted to ask me.
By the third grade, groups of girls were impersonating me by blabbering gibberish as my Mandarin, and pulling at the corners of their eyes behind my back. Thus, I forced a stoic, protective facade over my true identity, shrinking back into a silent reticence of social evasion.
This does still linger with me to the present day, for I do have a more indrawn nature and very often prefer solitude over intimacy.
This is not to say that I am solely a victim of prejudice and acts of hate. There was once a very apprehensive, timid Black girl in my second grade class. Many times, when our teacher was not paying attention, a group of White girls would pour scorn on her for trivial matters.
Sienna Tzou
Knowing that I was quiet and docile as well, they told me to do the same. I did feel inclined to, because it was one of the few opportunities I had for societal acceptance. Yet, I knew that there was a fundamental insecurity that the girls were projecting onto the timid girl. I was young and didn’t exactly know what it was, but I knew that demoralization was wrong.
She was exactly like me. She never spoke a word, but I knew we had so much in common. We were both afraid to speak out because we were different. We feared that saying something would get us further rejected and criticized.
So, I decided to befriend her. What would it hurt? I didn’t have any other friends and, if anything, we could come out of our shells together.
In the end it didn’t matter, and our friendship didn’t last, because she didn’t last very long. She and her family subsequently left the town or moved schools — I don’t know where life took her. I don’t think I ever will.
Already, as a young child, I knew that the community had an ingrained difficulty accepting people like me of a minority race. With white being the majority race, it was an inexorable curiosity that the youth would eventually weigh up: Was there room for kids who were “different”? Did we even belong here?
Young children may just be curious, but they are much more susceptible to bias or oppose those from various ethnic backgrounds, or those that are visibly difforent from everyone else. Neutrality is not always in their disposition.
Although, I will say, hate, bullying, and prejudice happen to be much less prevalent in the higher grades.
The reason for this might be higher stakes that have been implemented to breaking rules of conduct against discrimination of race, religion, sexuality, etc.
However, we must not forget that growing our youth properly is vital for the flourishing of the individuals and young adults that we will become. From the start when a child feels out of place, it molds their personality and their perspectives on their individual lives difterently. Almost invariably, being shunned at a young age by peers can have a lasting residue on one’s dignity and inherent qualities.
To prevent the silence of minority voices, we must raise them from the beginning. Children that enter kindergarten or new schools are often shy and unsure of themselves, which is a rational fear. Cliques start to be made after introductions — especially those who are inherently a bit more extroverted than others. Coming from someone who, as a child, just missed the train to be in any closely-knit clique, this is probably the most essential part about a kindergartener’s experience.
Bonding activities can be administered to implement more inclusivity. For instance, random pairing with a buddy, class matching activities for similarity, and writing notes to classmates that compliment their unique and likeable qualities can all build rapport over time.
Besides classroom engagement, primary schools can have guest speakers discuss the benefits of inclusivity and how to speak up from identity-based bullying or bias.
The community in general can also practice accepting unique qualities as special and welcome. This may contribute to more meaningful and sustainable connections, which is indispensable for our town’s youth.
Each person in this town deserves to get their voice heard. Those that have contrasting races, religions, or identity orientations are distinct, but not incompatible — we just need to be more accepting and see the different as people we can thrive and grow our youth with.
As I have grown into an adolescent, nevertheless, my morale has been augmented so that I can be the individual I am today. I take pride in the fact that I get to live with so many perspectives to ultimately mold me into an empathetic and discerning adult. I’m looking forward to the day where I can call myself that.
I am, of course, proud to be part of this community with exceptional education and boundless opportunities. I just do wish I could go back in time and adjust my younger self to be a more confident being.
I wish I could tell that girl with the shining, coruscant ballet flats and a dimpled, cheeky smile that everything you have to say is valued and the world is waiting for your worth to shine through.
From left: 1st Selectwoman Jen Tooker, Westport Library director Bill Harmer, Annam Olasewere, Aanya Gandhi, Sienna Tzou, Souleye Kebe, Staples High principal Stafford Thomas, TEAM Westport chair Harold Bailey. (All photos/Dan Woog)
He has received numerous departmental awards, including a Chief’s Commendation, an Honorable Service Award, a Lifesaving Award, and several Unit Citations.
