The Gray Area · The Gray Area

Episode 16: The Legacy of a "Try-Hard"

September 28, 2020·51 min·3 clips
Emily admits her biggest personal weakness is self-confidence — and traces it directly back to years of academic comparison and ranking.
Erica and Emily open by acknowledging the episode was recorded last-minute during their senior year, one of their busiest periods. They frame the topic — the legacy of being a 'try-hard' — as something both have experienced since elementary school. Erica describes switching schools multiple times and ultimately thriving in a non-advanced class where teachers challenged her individually without fostering constant competition. Emily attended two elementary schools where ability grouping was unofficial but obvious, with seven-year-olds openly discussing which teacher's class was for 'dumb kids.' Emily recounts a vivid first-grade memory of a teacher assigning different minimum page counts for a book project based on perceived writing ability, done openly in front of the class. Both hosts argue that making these distinctions visible and public at such young ages was more damaging than the grouping itself. They discuss how elementary tracking fed into a formal middle school advanced program that required application essays and teacher recommendations from twelve-year-olds. This program, they say, deepened social divisions and reinforced the belief that academic placement determined personal worth. Both admit they held superiority complexes at various points, which caused peers outside their program to perceive them as unapproachable and judgmental. They acknowledge that some of this behavior was taught and some was within their control to change, and note they have grown since then. The hosts observe that some students never outgrow middle-school-style academic posturing, citing a peer who publicly questioned how anyone could take fewer AP classes than them. Emily connects years of comparison and ranking to her own persistent lack of self-confidence, describing a habit of waiting for classmates to show answers before revealing her own. She notes a striking generational gap: juniors in her current classes display far more confidence than her senior cohort, which she attributes to their cohort's specific conditioning. The conversation turns to class rank, with Erica expressing discomfort sharing that number because of how it has historically been weaponized in her social circles. Both hosts identify mental blocks as a direct consequence of being told perfection was the only acceptable standard. They critique the modern college admissions landscape, where YouTube and TikTok advice demands students be excellent in every subject and every type of extracurricular simultaneously, leaving no room for focused passion. Emily introduces the concept of Ivy League admissions shifting preference from T-shaped to L-shaped applicants, meaning depth in one area is now valued over superficial breadth. They argue that reducing a student's entire life to a single cumulative GPA number ignores the subjective reality of personal hardship, illness, or family crisis. The hosts defend their podcast as a genuine creative and intellectual project, pushing back against a peer who dismissed it as college application filler. They close by advising listeners to drop clubs they hate and invest that time in finding something they truly love, arguing authentic engagement will matter more in the long run than padding a resume with activities that mean nothing to them.

As heard by us

A grounded look at overachieving, status, and being called a try-hard.

The episode treats being labeled a try-hard as something learned in school, not just a joke or a badge of honor. It moves from elementary school through senior year and keeps circling the pressure around AP classes, clubs, and the urge to sound smarter than everyone else.

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Why you'd press play

You want to hear two seniors unpack the try-hard label without pretending it is simple.

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