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There’s a reason it’s called a “challenge.”

Every year, TEAM Westport — our town’s multicultural commission — challenges high school students to think hard about an important topic. They’re then challenged to write about it.

The 2020 Teen Diversity Essay Contest prompt said:

In 1,000 words or fewer, describe your experiences witnessing, delivering, and/or being subjected to stereotypes focused on race, ethnicity, religion, sexual orientation, and/or gender identity, and describe the impact that such experiences are likely to have upon recipients. Consider steps that organizations, schools, and/or individuals could take to counteract stereotypes—whether as initiator, recipient or witness.

As always, they responded. The winners include a Sikh American woman, a gay teen, and a blonde girl.

Their writing is honest, powerful, raw. And it is very, very important.

Sahiba Dhindsa — a Staples High School graduated headed to Cornell University — won the $1,000 first prize for her essay “Stereotypes, Stories, and the Worlds We Create.”

Second place — and $750 — went to recent Staples grad Zachary Terrillion for his story, “Stereotypes: Crippling Standards.” He’ll attend Oberlin College.

Third place, worth $500, went to rising Staples junior Tori Holoubek-Sebok. She wrote “Bombshell.”

The awards were presented virtually Thursday night, at the Westport Library. Click here to see the ceremony (beginning at the 6:50 mark). Better yet, scroll down, and read them below.

1st place: Sahiba Dhindsa, “Stereotypes, Stories, and the Worlds We Create”

Stereotypes are reductions. In a culture of compression, stereotypes reduce long, rich stories into a few descriptive words. By the time we realize what stereotypes are and the damage they do, we have already started internalizing the very ideas from which we seek to break free.

From a young age, I faced many stereotypes. It was easiest for me to assume that others’ actions against me were based on stereotypes rooted in my skin color. I failed to see that it was so much more than my skin color. As a young Sikh American woman, religion and race based stereotypes have driven the microaggressions I have faced in my school and town.

In elementary school, I understood that the lack of knowledge on Sikhism led people to assume I was part of a strange tribal religion that forced me to not
cut my hair. I didn’t tell my peers I was Sikh for 11 years to avoid assumptions about my personal life.

In eighth grade, I had a classmate tell me that I should be his slave because my skin was brown. My gut response was to be defensive. I lashed out and told him that he needed to find a better set of jokes.

Sahiba Dhindsa

I was astounded that someone would say that to me. Through self-reflection years later, I still find it difficult to understand the origin of my classmate’s comment. Because I felt so hurt by these words, and I felt so small––that my whole identity lay in my skin color––I started subconsciously internalizing these
ideas. When I described myself, I was the brown Indian girl who was Sikh and that was it. When I saw others, I immediately differentiated them from myself before they had a chance to differentiate me.

I othered myself to protect myself. Every person who was not on my “side” was the “threat”. I started stereotyping my white peers out of my own frustration.

Angry and frustrated that I was required to defend myself, I started seeing them as ignorant, difficult, and uninterested in making social change.

Freshman year, I had a disagreement with a boy sitting a few seats away from me. I don’t remember what the disagreement was about, but I do remember what he said to me: “Trump’s gonna send you back to wherever you came from.”

It was his final statement––a way to shut me up and make me insecure about my skin color and my ethnicity. While I brushed it off in the moment, it pained me to hear such a hateful comment. I had worked so hard to create a place for myself in this community––to feel as  though I was no different than anyone else despite having a different skin color and religious background.

In that moment, I felt that the confidence I had built for all these years was crumbling. Being brown, being Indian, being Sikh didn’t make me any more immune to hate speech. The stereotype that because

I’m brown, I’m not American, and I don’t belong here, has dominated much of the narrative that others had written for me.

Two years ago, for my U.S History final, my group and I did a presentation on the history of Sikh discrimination in America. At the end of our presentation, my teacher asked me about the correct pronunciation of Sikh and the significance of turbans. To others it may have been a normal expression of curiosity, but to me it was more. It was an individual approaching me from a position of inquiry rather than a position of seeking to reduce me for the sake of simplification.

I now realize that this was a turning point in realizing that I did not have to define myself with a few words simply because some of my peers had done so to me. I could take those words and re-write my story and then share it back with others. I could remove those phrases and instead define myself through the rich story I know I have.

Through this, I learned the true power of storytelling. Storytelling is so much more than simply sharing anecdotes and life experiences. Storytelling is fighting against the desire to define someone or something in a few words. Instead, it is a way to allow one to look at people with a nuance that does justice to their spirit, who they are, what they represent, and what they aspire to be.

We live in a world where everything is compressed and simplified. We’ve shortened our words from long phone conversations to texts to comments on social media. We communicate less and less with each other and by virtue of that compression, compassion becomes harder to come by. I knew if I had
gone through this journey of confronting stereotypes and reimagining myself, my other peers must have gone through it as well.

Due to my desire to hear the stories of others and share my own, I created a club called Unity in Diversity with a friend. The club’s aim was to work on minimizing stereotypes through storytelling. Beyond advocacy, the club became a safe space for individuals from varying racial, religious, ethnic, and sexual orientation backgrounds to tell their stories.

I would like to summarize my experiences and ideas in a few ways. First, I hope my experiences serve as a reminder that racism and prejudice based in ignorance is not a thing of the past, even in a community as inclusive as our own.

Second, I want to express how the acknowledgement and support of an educator can make a monumental difference in the life of a student experiencing microaggressions on a regular basis.

Third, there are few things as therapeutic as being able to share your own experience and being heard by your peers and your teachers. We often underestimate the importance of telling your authentic story: a story that has been defined entirely by you. These are the collective stories that change
the world.

2nd Place: Zachary Terrillion, “Stereotypes: Crippling Standards”

Stereotypes are a fixture of human society. Groups always look towards other groups and create pictures of their surfaces before exploring their depths. They are snapshots that have molded entire perceptions. These snapshots in their narrow borders have been hard to escape.

They are often a burden, sometimes a blessing, but for me, they are an ideal to reach. I have always forced myself to fit these societal Polaroids. For better or worse, I have been defined by these delusional struggles.

To begin, what comes to mind when you think of a gay man? Flamboyant? Outgoing? Sassy? It is these depictions that make up most of the representation, whether it be in dated ’90s sitcoms or even recent gay produced works, such as Ru Paul’s Drag Race or Queer Eye, both of which I still adore.

I am not saying these contemporary, effeminate representations are insensitive or even inaccurate, but they are a single story that has come to dominant the gazes of the heterosexual mainstream. They encompass a vision of a “traditional” gay man. How he walks, talks, and acts. To be considered genuinely gay, I must be fabulous and extroverted, just like the ones on TV.

Before I held myself to standards of queerness however, I dealt with standards of
masculinity. I was never one for sports, which can be difficult as a little boy wanting to fit in with all the other little boys. When my parents thrust me into the world of peewee soccer, I rejected the ball and ran about the field, pretending to be a Jedi. My parents, to their credit, realized manly sports were not my forte, and my overactive imagination was put to practical use within the realm of theater, an environment in which many gay people thrive. It was here where
my queer and creative facets came to fruition, as a supportive space was provided for these elements to emerge without fear of derision by society.

Stereotypes and expectations were not a player in the fluidity of improv or amateur playwriting. Still, because of being exposed to such loving communities from such a young age, I never felt the need to speak up for myself. Thus,
my introversion grew, and my burgeoning queerness became withheld, as no reason was provided for it to arise and be defended.

It was a presence in my life but not readily embraced or expressed. It was a strange median between self-hatred and love. Self-tolerance is how I would
describe it.

I expected my queerness to finally manifest in all its rainbow-colored flamboyance in high school. But, like the soccer fields of yore, I was the odd one out. The gay culture present was the same confident, expressive vision glimpsed on TV. Gays who preferred reading in corners or sitting on their phones at the edges of dance floors proved a rare find.

I was not just clashing with standards of masculinity as most gay men do, but also gayness itself. I somehow fit into neither societal trope. I loved to “spill the tea,” I adopted the feminine gestures shows and films so love to emulate, but I also enjoyed videogames and superheroes, familiar tropes of generalized masculinity. I could not connect with others from either spectrum of sexuality, as I seemed to inhabit elements of both, but resided in neither.

Zachary Terrillion

Because of these stereotypical divides, my introversion would soon devolve into social anxiety and immense insecurity, dreading rehearsals and classes that were once highlights of my week. I figured the only way to achieve social success was to emphasize my queerness above all else. To play right into the tropes
society had established for me, even if it did not connect to my personality.

My anxiety peaked the summer before my sophomore year when I attended a sleepaway program for the first time. Here, my plan to play up the gay would take effect. I escalated my flamboyant mannerisms, exaggerated my tone of voice, and emphasized that I was, in fact, very gay.

My earnest attempts backfired spectacularly. My anxiety only worsened by the end of the program, with not a single friend gained and even more insecurity to top. I wondered whether I was genuinely gay or just some poser. Was I worthy of being in the company of Johnathan Van Ness or was I just some guy who liked other guys.

Through all these struggles however, one aspect of my identity that society could not pin down remained constant. That being the creativity that bloomed on the soccer field, theater, and, currently, my writing.

Through writing, I had a voice true to myself, finding a diverse community of people through which I could thrive and depend on. A community discovered not by playing up parts of myself to adhere to the rules of stereotypes, but instead through the expression of my multifaceted truth.

All my interests and traits, both masculine and feminine, could be put into highly dynamic works of prose and poetry. These were pieces that explored the nuances of queerness that the media could not.

Overall, I have never taken stereotypes as villainizing in the conventional sense. I have not suffered through discrimination or oppression instigated by their hand. Instead, they worked to force me into a box, a servant following the will of a director in a performance society mandates.

However, through honing my traits, those too complex and niche to be generalized, these stereotypes no longer must apply. One can discover their truth through distinction in the face of generalization.

We must encourage our marginalized youth to explore the nuanced parts of themselves in order to evade standards and achieve authenticity. Only then, will the maligned snapshots of yore fade away, so more layered, accommodating portraits may come to the forefront.

3rd place, Tori Holoubek-Sebok, “Bombshell”

Blue eyed, blond haired, athletic, female. With just those words you already have a picture in your mind of who I am, or who you think I am. The “dumb blonde” persona is an excruciatingly common stereotype, but one that is often overlooked. Everyone knows of it, yet no one considers it to be a legitimate offense.

Compared to others, it appears to be trivial; merely a lighthearted joke. However the consistent repetition and application of this stereotype, on both personal and general levels, has transformed the label into something with much more substance and impact than many can see.

In an era of political correctness and common decency, it is important to acknowledge that this stereotype in no way is any comparison to those applied with strong racial, religious, or truly hateful undertones. I understand that I am privileged in numerous ways and want to make clear that I would never compare my experiences to the endless number of minorities who face racism and discrimination daily, any member of the LGBT+ community who experience violence or negativity for being who they are, or any other individual who has to live through the hardships of prejudice and hate.

Though all examples, including my own, are instances of assumption and judgement based on physicality, the stereotype that I am labeled with is at a
lower degree than the others, and that should be made clear.

Despite this, being classified as the common dumb blonde is a hurtful label that I have faced my entire life. People repeatedly making assumptions about who I am from the way I look impedes my mindset and the way I view myself.

However, it is not only the direct labeling I experience that makes an impact. The media presence of this stereotype is outstanding and has its own consequences.

Actresses like Marilyn Monroe have been characterized as naive and
materialistic, acting as merely symbols of attraction when they have significantly more substance. Monroe was classified as a “blonde bombshell” and was virtually only cast for parts which represented that. The color of her hair was enough to form her identity and her true self was hidden by the layering of the same character over and over. People began to perceive her as
the characters she played because of the constant repetition of the same persona.

No matter how far her personality strayed from that of a dumb blonde, it did not matter. People saw this stereotype, and transformed it into who Marilyn was.

The overwhelming presence of stereotypes in the media also has effects on its consumers; people can second guess themselves and be overly critical when they are constantly surrounded by these personas.

No matter the stereotype, seeing its representation can prompt insecurities and doubts within oneself. I have often been unsure of my intellect because of these reasons. I see the negativity inflicted on women as soon as I open Instagram; anonymous accounts criticizing models or people of influence, saying that their words should not be taken seriously because they are blonde and therefore incompetent.

Tori Holoubek-Sebok

Often times in my classes I can be confident in an answer, but hesitate sharing it aloud, too afraid of what my classmates or teacher will think of it. The dumb blonde stereotype has created paranoia in my brain, leaving me to wonder if I do embody the characteristics of this persona.

Whether it be in school, at home, or by myself, I am never free from the labels I am assigned. From the people all around me to even myself, my integrity and
intelligence are consistently in question.

In most cases, a family is made up of the people that know you the most, the people who will always support you. Never did I think that those same people would make such a bold assumption of my character. I have always been athletic and have played a variety of sports, but exercise has never been an interest of mine nor something I had thought about until one Christmas day when my grandparents gave my siblings identical coding kits and gave me
exercise equipment instead.

I had never given my grandparents any reason to think that I would want a core exercise ball and a set of weights over the coding sets my siblings received, and yet, that is what I got.

Blondes have been commonly classified as vain and shallow, notorious for only caring about the way they look. My blonde hair represented a stereotype, so I was assumed to be this stereotype and appearance was taken as my main priority.

Meanwhile, I would have much preferred experimenting with coding just like my siblings. This particular occasion prompted a spiral of increasing self awareness in the way that I look and the way others perceive me.

I have since found myself constantly needing to prove my integrity to those around me. In my experience, the application of the dumb blonde stereotype is rarely intentional. Though there are instances of real hostility communicated through stereotypes, I believe that labeling in this manner is most often a subconscious ordeal.

Because of this, reasoning is not the necessary method to eliminate the beliefs in stereotypes Raising awareness of the presence of the stereotypes is. Spreading consciousness is the best way to begin the decrease unfair judgments, because ensuring that people know that these stereotypes exist will prompt them to be conscious of the way they may regard others.

Change can seem like an ambitious request, but all we need is a few people. These people can initiate the process and share it amongst the people in their lives and from there it can take off; going from towns, to states, to countries, the recognition of stereotypes will spread like wildfire.

If globally, and as a community, we can expand our wealth of knowledge and share insights with our peers, everyone will gain a greater understanding of their impact on those who surround them.