Suggested Reading

I’ve found that re-reading keeps the spark alive, so I’d encourage you if you find something that speaks to you, to keep coming back to it.

Below, you’ll find books, essays, movies, and rabbit holes to get ideas, inspiration, and ultimately to define your own path.

In the introduction, I called this book your vade mecum. That means: don’t treat it like a one-time read. Come back when you start drifting, when the machine starts working on you again, when you need a reminder that there are more doors than the ones on the official map.

I. College

This section is about college as an experience, institution, opportunity, and trap.

It includes practical advice, critiques of elite education, alternative ways to learn, and reminders that college is more than classes, grades, internships, or majors

1. How to Actually Use College

For navigating classes, routines, professors, friends, projects, and time.

Books

• How to Win in College — Cal Newport
  • I read it almost every Saturday during college.
• Hacking College — Dean Kohrs

Essays

• College advice for people who are exactly like me — Ben Kuhn
• My Weekly Review Habit — Ben Kuhn
  • See my version
• Doing well in your courses — Andrej Karpathy
• The Hitchhiker's Guide to College — Sahas Ramesh
• How to make the most of college — Luke Clancy
• Undergraduation — Paul Graham
• More Advice for Undergrads — Paul Graham
• What advice do I give to my students? — Michael Levin

My Essays

• How to College: Advice, Mistakes, and Thoughts
• The College Manifesto
• What's My Major?
• Don’t Network. Make Friends.
• Say’s Law for Your Curiosity
• Quad Day 2023
• Quad Day 2022

2. College as Formation

For understanding what college does to you over four years: ambition, confusion, loneliness, experimentation, disillusionment, love, and growth.

Essays

• 17-20: a Retrospective on Four Years in College — Alexey Guzey
• College Q&A — Alexey Guzey
• Fury and Freedom: Four Years at Amherst College — Alex Liu
• What I Wish I Knew in College — Becoming Eden
• freshman — Ismail Hozain
• 2023. Reflections and Updates — Ismail Hozain
• The Grand Unveil — Ismail Hozain
  • Ismail raised over $15,000 after this post for his project.
• Although of course you end up becoming yourself — Chris Peterson
• The Parties I Chased and the Quiet I Needed — Geoffrey Challen

Movies

• Good Will Hunting (1997)
• Dead Poets Society (1989)
• Meet the Robinsons (2007)
• Almost Famous (2000)
• Rushmore (1998)

TV

• Joan of Arcadia (2003)

My Essays

• The Endless Reminiscence of Your College Days
• Giving Up Optionality: Updating 2020
• Patience & Faith: Updating 2021
• Curious & Obsessive Experimentation: Updating 2022
• What Is It Like Being a Crazy Motivated High School Kid?
• Belonging in the 21st Century: The Quest for Self-Esteem

3. College as a Machine

For understanding status, prestige, conformity, credentialism, institutional pressure, and the hollow parts of elite education.

Books

• The Fountainhead — Ayn Rand
  • I came into college excited to learn, to think deeply, and to engage with people who were just as energized by ideas and possibilities. Instead, I encountered a culture that felt hollow. People driven more by grades, status, and approval than by curiosity, meaning, beauty, or truth. I saw conformity replace genuine inquiry, apathy overshadow passion, and a subtle cynicism dampen enthusiasm.
  • The Fountainhead gave me a language to articulate this disconnect. It revealed the distinction between those who live solely for others' expectations and validation, and creators who pursue work for its inherent worth and beauty. The book clarified that my frustration stemmed from witnessing conformity quietly corrode both institutions and individuals. This book showed me how to protect the part of myself that still cared deeply, to build independently, and to live by the standard of my own vision.
  • Above all, The Fountainhead is a compass toward the extraordinary potential of what can be.
• Excellent Sheep — William Deresiewicz

Essays

• The Disadvantages of an Elite Education — William Deresiewicz
• The Organization Kid — David Brooks
• Elite Disillusionment — Saffron Huang
• Ivy League Exodus — Armin Rosen
• The Value of College — Sibylla Bostoniensis
• Why I Left Academia (Since You're Wondering) — William Deresiewicz
• “Yay, College!” Part 1: The Smiley-Face Super-Villainy of American Higher Education — Ben Hunt
• The Entrepreneurial Generation — William Deresiewicz
• Generation Sell — William Deresiewicz
• Dressing Up — Harvey C. Mansfield
• On the Life We Come Here to Find: A Convocation Address — Mark Van Doren
• How have you spent your tuition dollars? — Ian Brown
• Relations Between Student Groups and the University Suck — Ian Brown
• How the UIUC Department of Aerospace Engineering has Failed Its Students, and What it Can Do About It — Ian Brown
• The Best Way to Not Get Tenure — Geoffrey Challen

Movies

• Accepted (2006)
• 3 Idiots (2009)
• Udaan (2010)
• Super 30 (2019)

My Essays

• A professor tells me to switch majors out of fury
• A professor tells me to drop out
• A professor tells me to do something else and does not allow me to come to class

4. College Beyond the Official Curriculum

For designing your own education instead of simply accepting the default path.

Books

• The Whole Earth Catalog — Stewart Brand
• The Whole University Catalog
• Deschooling Society — Ivan Illich

Essays

• Things You’re Allowed to Do: University Edition — Saul Munn
• The combinatorial space of possible transcripts (i.e., take unusual classes) — Geoffrey Challen
• Mind Over Major: The case for using college to become more interesting — Dan Edelstein
• Escaping High School — Skunk Ledger
• Towers of knowledge have no foundations — Christopher Xu
• The gap semester never ends — Christopher Xu
• Buy a house on the campus of my old university and take classes there for the rest of my life — Librarian of Celaeno
• The New 95 — 1517 Fund
• What I would do if I was 18 now — Levels.io
• OUR ENGINEERING STUDENTS are technically brilliant. They’re going to be fantastically successful in what they do. But can they reflect? I’m afraid that we’re getting them to think too much and do too much, but feel too little, imagine too little, intuit too little — Leon Liebenberg

My Essays

• How To Think for Yourself in College
• A Step into the Future: A Visit to the Fuller Dome House and the Unfolding Legacy of Buckminster Fuller
• The UIUC Talkshow Purpose & Meeting Wolfram (and Taleb)
• Mission Impossible: Illinois

5. College as Launchpad

For ambition, startups, side projects, independent work, and creating what your heart desires.

Books

• Elon Musk — Walter Isaacson
  • Read college chapters only.
• A Man for All Markets — Ed Thorp
• The Autobiography of Benjamin Franklin — Benjamin Franklin
  • Read my notes.

Essays

• Advice for ambitious 19 year olds — Sam Altman
• Advice for ambitious teenagers — Laura Deming
• Advice for ambitious Stanford students
• Advice for ambitious Stanford students interested in startups
• Interviews with current and former ambitious Stanford students: “What you’ll wish you’d known”
• A Student’s Guide to Startups — Paul Graham
• What I Worked On — Paul Graham
• Training the Idea Muscle — Aadil Pickle
• Why Side Projects Matter More Than a Perfect GPA: The Magic of Working on Your Own Projects (And a Mark Zuckerberg Story) — Geoffrey Challen
• why i dropped out of college — Dylan Murphy
• How I premiered my short film at 22 — Dylan Murphy

My Essays

• What I Learned from Auditioning for an A Cappella Group
• What I Learned From My First Guitar Concert
• What I Learned From Running My First Marathon
• What I Learned From Doing Stand-up Comedy
• College Boba: How My Friends and I Made $74.35 in Profit Selling Boba on a $46 Budget
• Pico Masala: How I Built a Restaurant Empire—Then Gave It Away for Free

II. Philosophy

This section is about the larger questions underneath college: how to think, how to live, how to work, how to choose, and how to stay fully alive.

1. Independence and Nonconformity

For protecting your own judgment.

Essays

• The Inner Ring — C.S. Lewis
• Self-Reliance — Ralph Waldo Emerson
• The Allegory of the Cave — Plato
• The Lesson to Unlearn — Paul Graham
• Speech at Palo Alto High School — Steve Jobs
• The Hacker Manifesto
• Jailbreaking the Simulation — George Hotz
• The Cook and the Chef — Wait But Why
• Blasphemy — COLDXMAN
• Breaking Addiction Is Socially Unacceptable — Naval Ravikant

Books

• Atlas Shrugged — Ayn Rand
• Jonathan Livingston Seagull — Richard Bach (1973 Edition)

Movies

• The Truman Show (1998)
• The Matrix (1999)
• Rose Island (2020)

2. Work, Ambition, and Seriousness

For doing what you’re called to do with your life.

Essays

• You and Your Research — Richard Hamming
• How To Be Successful — Sam Altman
• Are you serious? — Visakan Veerasamy
• Surely you can be serious — Adam Mastroianni
• Advice — Patrick Collison
• Inventing on Principle — Bret Victor
• Do What Makes The Best Story — Amjad Masad
• No yes. Either HELL YEAH! or no — Derek Sivers
• Ten Lessons I Wish I Had Been Taught — Gian-Carlo Rota
• The Tinkerings of Robert Noyce — Tom Wolfe
• Ask — Steve Jobs
• No Smarter Than You — Steve Jobs

Books

• Steve Jobs — Walter Isaacson
• Leonardo da Vinci — Walter Isaacson
• Benjamin Franklin — Walter Isaacson
• The Man Who Knew Infinity — Robert Kanigel
• From Counterculture to Cyberculture — Fred Turner
• The Engines of Our Ingenuity — John Lienhard
• The Motern Method — Matt Farley

My Essays

• How to Become the Mayor of a City, a Governor, the U.S. President, or Another Major Politician
• How to Cure Cancer, Fix the Climate, Build a Billion-Dollar Company, and Win a Nobel Prize

3. Career, Optionality, and Direction

For figuring out what to do with your life without becoming trapped by prestige or fear.

Essays

• How to Pick a Career (That Actually Fits You) — Wait But Why
• How To Do What You Love — Paul Graham
• What You’ll Wish You’d Known — Paul Graham
• The Trouble with Optionality — Mihir Desai
• The days are long but the decades are short — Sam Altman
• How to Spend Your Twenties — Charles Murray
• The Curmudgeon's Guide to Getting Ahead — Charles Murray
• Bluebooking for happiness — Zhengdong Wang
• Dear Graduates ... — Kevin G.
• Quit Your Job — Wolf Tivy
• There's a place for everyone — Adam Mastroianni

4. Character, Meaning, and the Inner Life

This section is about the deeper problem of college: not merely what to achieve, but what kind of person to become.

Books

• Man’s Search for Meaning — Viktor Frankl
• The Alchemist — Paulo Coelho
• Steppenwolf — Hermann Hesse
• Siddhartha — Hermann Hesse
• Narcissus and Goldmund — Hermann Hesse
• Demian — Hermann Hesse
• The Glass Bead Game — Hermann Hesse
• The Seven Storey Mountain — Thomas Merton
• The Culture of Narcissism — Christopher Lasch

Essays

• This is Water — David Foster Wallace
• Learning in War-Time — C.S. Lewis
• Everyone is numbing out — Catherine Shannon
• The Tail End — Wait But Why
• The New Illiteracy — Christopher Lasch
• Becoming a magician — Autotranslucence

Movies

• My Dinner with Andre (1981)
• Zindagi Na Milegi Dobara (2011)

My Essays

• Sonny Hayes as The Ultimate Jailbroken Character
• Curiosity is Love
• Eat The World Vs. Eaten by The World
• The Steppenwolf's Guide to Laughing at Life's Distortions
• We All Walk Past This Lady But She Has the Most Important Job at UIUC: PART 1
• We All Walk Past This Lady But She Has the Most Important Job at UIUC: PART 2

5. Inquiry, Questions, and Taste

For asking better questions and developing principles.

Essays

• How To Ask Questions The Smart Way — Eric Steven Raymond
• Theory of Change — Aaron Swartz
• 1,000 True Fans — Kevin Kelly
• 1,000 True Fans? Try 100 — Li Jin
• Charles Murray’s field guide to civil disobedience
• Commencement Address — Nassim Taleb
• 1999 Commencement Address at Agnes Scott College — Kurt Vonnegut
• Why? — Paul Schroeder
• All this is worth it right? FUCK NO YOU IDIOT — Str8OuttaLumbridge

III. UIUC

• The Whole University Catalog
  • My favorite UIUC discovery ever.
• An Illini Century: One Hundred Years of Campus Life — Roger Ebert
  • Available through the library, Internet Archive, Internet Archive interactive reader format
• An Illini Place: Building the University of Illinois Campus — Lex Tate and John Franch
  • If you’re on campus, just get it from the library.
  • If you do nothing else, read the supplemental materials to see a list of campus plans, an inventory of campus buildings, housing, demolished buildings, an explanation of Lincoln Hall's terra cotta panels, and so much more.
  • Did you know that there were 674 buildings by the time the book was published in 2017?
• Illini Years 1868-1950: A Picture History of the University of Illinois
• Some founding papers of the University of Illinois
• A Brief History of the University of Illinois
• [_Report of the Centennial Year of the University of Illinois February 28, 1967, to March 11, 1968]_
• No Boundaries: University of Illinois Vignettes — Lillian Hoddeson
• Voices from the 1960s: Reflections from UIUC Alumni of 1968–1972
• Radicals in the Heartland: The 1960s Student Protest Movement at the University of Illinois — Michael Metz
  • There is also this interesting playlist.
• The University of Illinois: Engine of Innovation — Frederick Hoxie
• The Friendly Orange Glow: The Untold Story of the PLATO System and the Dawn of Cyberculture — Brian Dear
• The Illio
  • Read all of them. Or as many as you can, from any year. You’ll realize we’re not so different from those who came before us. And you might even get a cool idea or two.
  • Some of them are available online, check them out.
• A Campus Ministry: Monsignor Edward J. Duncan and the Newman Foundation at the University of Illinois in the Twentieth Century — Patrick J. Daly, Jr.
• The History of the Carl R. Woese Institute for Genomic Biology — Harris Lewin

Movies

• Mission Impossible: Illinois (2023)
• golden hour x UIUC (college edition) (2023)

And...

The Jailbroken Guide to the University.

Follow the trailBuild your own syllabus.

It’s a practical, unconventional guide that helps students use college better: classes, professors, people, projects, resources, bureaucracy, and the hidden opportunities students usually discover too late.

Buy the book Open the map