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1996-1997
- Moved to the San Jose Campus of The Bolles School to begin high school
- Continued on the rowing team
- Read the Robert Fagles translations of The Iliad and The Odyssey, fell in love with the classics
- Stereotypical "student with promise who doesn't apply himself"
- Achieved the rank of Eagle Scout, however, so must have been doing something right
- Hiked ~75 miles at Philmont Scout Ranch
1997-1998
- Had a fire lit under ass by biology and English teachers, became dedicated student
- Performed as Napthali in Joseph and the Amazing Technicolor Dreamcoat; performed again several months later at the Florida State Thespian Festival — every theatre person has "that show" that they will never forget, and Joseph was it for me
- Spoke at the University of Florida Junior Symposium on Engineering, Humanities, and Sciences
- First participated in the Junior Engineering Technical Society's TEAM+S competition; team placed first statewide, 10th nationally
- First read Henry David Thoreau's Walden, become an adherent to Thoreau's philosophy (minus transcendentalism)
1998-1999
- Directed first show, Disturbed, which won Golden Mitton(sic) Awards for Best Director and Best Actress
- Designed lights for A Midsummer Night's Dream; again traveled to the state festival only to watch the antiquated building equipment erase my light board and cause me to swear more than I ever have in my life
- Discovered Adobe Illustrator, began learning graphic design
- Captain for JV squad fielded at TEAM+S competition
1999-2000
- Quit rowing team to focus on theatre
- Performed as Lazar Wolfe in Fiddler on the Roof
- Designed lights for mainstage production of Rhinoceros
- Captain of Varsity squad for TEAM+S competition, placed second in state only to Bolles's other varsity squad
- Received Headmaster's Award for distinguished service to The Bolles School, Cothurnus Award for Distinguished Senior Drama Students, membership in National Honor Society and Japanese Honor Society
- Graduated, matriculated to University of Virginia