Cupertino High School Era (2019–2022)

Category: History Period: High school years, approximately 2019–2022 Last updated: 2026-04-06

Overview

Cupertino High School is where Jack grew up — intellectually, socially, and in terms of ambition. Located in Cupertino, California (the Silicon Valley city where Apple is headquartered), CHS sits in one of the highest-performing public school environments in the United States. Jack’s years there left a deep imprint visible across the entire writing archive.

Cupertino in Jack’s Archive

Cupertino appears more than any other place in Jack’s writing, always with a specific quality: the people were exceptional, and Jack didn’t fully appreciate it while he was there.

From his 2025 nostalgia entry: > “Cupertino High School — it’s not like everyone is hustling. There’s still some level of variety.”

And: > “I didn’t really take advantage of [Cupertino people] because I didn’t know back then (too spoiled). Perhaps there is even the same idea for Georgia Tech Era people, so I want to not do that again.”

The core regret: surrounded by high-signal peers and didn’t extract the full value because he didn’t recognize what he had.

The Academics

Jack’s Notion archive contains evidence of his Cupertino academic life: - AP Spanish — studied seriously, with vocabulary sheets and conversation practice logged in Notion - UC Application essays — the November 2021 log documents the final week of UC application writing: multiple days of “9 hours on UC essays,” activity lists, additional information essays, academic history essays - Academic planning — A January 2022 Notion page titled “2022 Course Plan: General Academic Outline & Strategy” shows Jack planning his post-high-school trajectory carefully

The College Application Sprint (Nov 22–30, 2021)

Jack’s Notion contains one of his most vivid historical logs: the final week of his UC application (November 22–30, 2021), titled “Final UC Application Week.”

Daily structure: - HG Morning (habit goal) - HG Night - Shower - Planning - Reflection - UC Essay (4–9 hour blocks) - Homework (AP Spanish and others)

The final day, November 30, is labeled “Final Day.” December 1 continues — submission was likely midnight November 30. The penultimate day, November 29, is logged as “(1 day left).”

This level of documentation — even for a routine high school deadline — is characteristic. Jack’s Notion was already his operating system.

Applications submitted to: UC schools. He ultimately transferred to Georgia Tech.

The SAT

Jack logged his SAT test experience in a September 2021 reflection titled “SAT Test Experience & Performance Reflection.” The details are not available in the block content, but the fact that it merited a dedicated Notion page with a 1-star rating (meaning it was significant enough to document and revisit) suggests it was a meaningful moment — either a good result worth capturing, a difficult experience worth processing, or both.

Social World

The names from Jack’s early Notion and dream archive reveal his Cupertino social world: - Jolie — appears in a March 2022 dream; someone with problems that Austin was asking Jack about - Austin — appears in the same dream; likely a close Cupertino friend - GodZhang — the “GodZhang Garage” named in running logs; a friend whose garage was a training venue during the summer 2021 running project - Luis — appears in the UC application week log (“Return paper to Luis”)

The running project reveals Jack’s Cupertino geography: Lawson Middle School, Cupertino High School, Wilson Park, Creekside Park, Great America (the nearby amusement park), and the private garages of friends. This is the texture of a Bay Area suburban childhood — parks, schools, strip malls, and the lawns of people who mattered.

The Nostalgia Problem

Five years after leaving, Jack still measures environments against Cupertino. Georgia Tech is evaluated against Cupertino. Boston is evaluated against Cupertino. MIT is desired partly because Cupertino was the best environment Jack had experienced, and MIT feels like the institutional equivalent.

The insight Jack reaches by 2025: “I didn’t appreciate it because I was too spoiled.” The corrective: don’t repeat that mistake at Georgia Tech or MIT. Recognize the exceptional people in front of you.

But the insight and the behavior are different things. The writing archive shows Jack still longing for Cupertino people even after articulating this lesson.

Related

• Nostalgia Burnout Georgia Tech
• Social Reflection 2022
• Mit Operation Frosh
• Running Project 2021
• Jack Luo