Anant Jain

A Reading Map for Your 20s

Book List

This is a meta-directory of books I was lucky to read in my 20s, organized as tracks that an ambitious new grad can work through. Each track builds a different muscle. The year in parentheses is when I read the book.

Part 1: Understanding How Humans Think

Track 1: Psychology & Decision-Making

  • Thinking, Fast and Slow. Daniel Kahneman. (2017) (Review)
  • Predictably Irrational. Dan Ariely. (2016) (Review)
  • Influence. Robert Cialdini. (2017) (Review)
  • Pre-Suasion. Robert Cialdini. (2019)
  • Blink. Malcolm Gladwell. (2018) (Review)
  • The Tipping Point. Malcolm Gladwell. (2016) (Review)
  • Stumbling on Happiness. Daniel Gilbert. (2017) (Review)
  • Incognito: The Secret Lives of the Brain. David Eagleman. (2015)
  • Algorithms to Live By. Brian Christian and Tom Griffiths. (2018) (Review)
  • Nudge. Richard Thaler and Cass Sunstein. (2020)
  • Misbehaving. Richard Thaler. (2020)
  • The Charisma Myth. Olivia Fox Cabane. (2019)
  • I Am a Strange Loop. Douglas Hofstadter. (2019)

Track 2: Behavior, Habits & Persuasion

  • The Power of Habit. Charles Duhigg. (2017) (Review)
  • Atomic Habits. James Clear. (2019)
  • Mindset. Carol Dweck. (2016)
  • Made to Stick. Chip Heath and Dan Heath. (2016) (Review)
  • Contagious. Jonah Berger. (2016) (Review)
  • The Power of Moments. Chip Heath and Dan Heath. (2017) (Review)
  • Switch. Chip Heath and Dan Heath. (2022)
  • Decisive. Chip Heath and Dan Heath. (2020) (Review)
  • Hooked. Nir Eyal. (2014)
  • Indistractable. Nir Eyal. (2019)

Part 2: Worldviews & Wisdom

Track 3: Nassim Taleb's Incerto

  • Fooled by Randomness. (2016)
  • The Black Swan. (2016)
  • The Bed of Procrustes. (2018) (Review)
  • Antifragile. (2018) (Review)
  • Skin in the Game. (2018) (Review)

Track 4: Philosophy & Mindfulness

  • Zen Mind, Beginner's Mind. Shunryu Suzuki. (2014)
  • Siddhartha. Hermann Hesse. (2017)
  • Old Path White Clouds. Thich Nhat Hanh. (2016)
  • Tao Te Ching. Lao Tzu. (2020)
  • The Tao of Leadership. John Heider. (2016)
  • Meditations. Marcus Aurelius. (2020)
  • Man's Search for Meaning. Viktor Frankl. (2016)
  • 10% Happier. Dan Harris. (2018) (Review)
  • The Power of Now. Eckhart Tolle. (2021)
  • The Obstacle is the Way. Ryan Holiday. (2019)
  • Ego Is the Enemy. Ryan Holiday. (2021)
  • The Subtle Art of Not Giving a F*ck. Mark Manson. (2017) (Review)
  • The War of Art. Steven Pressfield. (2020) (Review)
  • The Courage to Be Disliked. Fumitake Koga and Ichiro Kishimi. (2023)
  • Zen and the Art of Motorcycle Maintenance. Robert Pirsig. (2024)

Track 5: Big History & Human Progress

  • Sapiens. Yuval Noah Harari. (2018) (Review)
  • Homo Deus. Yuval Noah Harari. (2018) (Review)
  • 21 Lessons for the 21st Century. Yuval Noah Harari. (2019)
  • Guns, Germs and Steel. Jared Diamond. (2020)
  • The Selfish Gene. Richard Dawkins. (2017) (Review)
  • Factfulness. Hans Rosling. (2019)
  • Enlightenment Now. Steven Pinker. (2024)
  • Superintelligence. Nick Bostrom. (2016)
  • The Master Switch. Tim Wu. (2014)

Part 3: History of the Tech Industry

Track 6: Apple

  • Steve Jobs. Walter Isaacson. (2013)
  • Becoming Steve Jobs. Brent Schlender and Rick Tetzeli. (2015)
  • Revolution in the Valley. Andy Hertzfeld. (2013)
  • Return to the Little Kingdom. Michael Moritz. (2014)
  • iWoz. Steve Wozniak. (2014)
  • Jony Ive. Leander Kahney. (2014)
  • Insanely Great. Steven Levy. (2019)

Track 7: Google

  • In the Plex. Steven Levy. (2015)
  • The Google Story. David Vise. (2014)
  • How Google Works. Eric Schmidt and Jonathan Rosenberg. (2015)

Track 8: Amazon

  • The Everything Store. Brad Stone. (2014)
  • Amazon Unbound. Brad Stone. (2021)
  • Working Backwards. Bill Carr and Colin Bryar. (2022)

Track 9: Social Networks & Sharing Economy

  • The Facebook Effect. David Kirkpatrick. (2014)
  • Facebook: The Inside Story. Steven Levy. (2021)
  • Hatching Twitter. Nick Bilton. (2014)
  • Things a Little Bird Told Me. Biz Stone. (2017)
  • Without Their Permission. Alexis Ohanian. (2016)
  • The Upstarts. Brad Stone. (2017)
  • Super Pumped. Mike Isaac. (2019)

Track 10: Computing & Software History

  • Hard Drive. James Wallace and Jim Erickson. (2014)
  • The Innovators. Walter Isaacson. (2015)
  • Masters of Doom. David Kushner. (2020) (Review)
  • Hackers: Heroes of the Computer Revolution. Steven Levy. (2017)
  • The Dream Machine. M. Mitchell Waldrop. (2024)
  • Creativity Inc. Ed Catmull. (2015)
  • The Pixar Touch. David A. Price. (2019)
  • The Idea Factory. Jon Gertner. (2016)

Track 11: Founder Stories & Company Biographies

  • Elon Musk. Ashlee Vance. (2015)
  • Elon Musk. Walter Isaacson. (2024)
  • Liftoff. Eric Berger. (2021)
  • Shoe Dog. Phil Knight. (2018) (Review)
  • Delivering Happiness. Tony Hsieh. (2018) (Review)
  • The Ride of a Lifetime. Bob Iger. (2022)
  • Build. Tony Fadell. (2022)
  • Onward. Howard Schultz. (2017)
  • No Rules Rules. Reed Hastings and Erin Meyer. (2020)
  • Bad Blood. John Carreyrou. (2018) (Review)
  • Billion Dollar Loser. Reeves Wiedeman. (2024)
  • The Nvidia Way. Tae Kim. (2025)

Track 12: Silicon Valley & Startups Meta

  • Founders at Work. Jessica Livingston. (2013)
  • Launch Pad. Randall Stross. (2014)
  • Once You're Lucky, Twice You're Good. Sarah Lacy. (2014)
  • Lost and Founder. Rand Fishkin. (2019)
  • The San Francisco Fallacy. Jonathan Siegel. (2019)

Part 4: Investing & Wealth

Track 13: Investing

  • The Intelligent Investor. Benjamin Graham. (2016)
  • Common Stocks and Uncommon Profits. Philip Fisher. (2017)
  • Poor Charlie's Almanack. Peter Kaufman. (2020)
  • Charlie Munger: The Complete Investor. Tren Griffin. (2016)
  • The Snowball. Alice Schroeder. (2016)
  • Tap Dancing to Work. Carol Loomis. (2025)
  • The Psychology of Money. Morgan Housel. (2021)
  • Fortune's Formula. William Poundstone. (2020) (Review)
  • Business Adventures. John Brooks. (2014)
  • The Richest Man in Babylon. George Clason. (2020)
  • I Will Teach You to Be Rich. Ramit Sethi. (2019)
  • Rich Dad, Poor Dad. Robert Kiyosaki. (2025)
  • Economics in One Lesson. Henry Hazlitt. (2025)
  • The Lessons of History. Will & Ariel Durant. (2022)

Part 5: Creating & Communicating

Track 14: Design

  • Creative Confidence. David and Tom Kelley. (2015)
  • The Art of Innovation. Tom Kelley. (2015)
  • Change by Design. Tim Brown. (2021)
  • The Design of Everyday Things. Don Norman. (2017) (Review)
  • Don't Make Me Think. Steve Krug. (2017) (Review)
  • Rocket Surgery Made Easy. Steve Krug. (2017) (Review)
  • Envisioning Information. Edward Tufte. (2016)
  • The Visual Display of Quantitative Information. Edward Tufte. (2015)
  • Refactoring UI. Adam Wathan and Steve Schoger. (2018)
  • The Vignelli Canon. Massimo Vignelli. (2022)
  • How to Make Sense of Any Mess. Abby Covert. (2017)
  • The Pocket Universal Principles of Design. William Lidwell. (2017)
  • Just Enough Research. Erika Hall. (2022)
  • Steal Like an Artist. Austin Kleon. (2018) (Review)
  • Show Your Work. Austin Kleon. (2018) (Review)
  • Design Is a Job. Mike Monteiro. (2018)

Track 15: Writing

  • On Writing Well. William Zinsser. (2016) (Review)
  • On Writing: A Memoir of the Craft. Stephen King. (2018) (Review)
  • Writing to Learn. William Zinsser. (2018) (Review)
  • The Elements of Style. William Strunk Jr. (2020)
  • Draft No. 4. John McPhee. (2020)

Part 6: Building Startups

Track 16: Startup Fundamentals

  • Zero to One. Peter Thiel. (2014)
  • The Lean Startup. Eric Ries. (2014)
  • The Hard Thing About Hard Things. Ben Horowitz. (2014) (Review)
  • The Great CEO Within. Matt Mochary. (2019) (Review)
  • Good to Great. Jim Collins. (2019)
  • Only the Paranoid Survive. Andy Grove. (2014)
  • The Innovator's Dilemma. Clayton Christensen. (2021)
  • The Innovator's Solution. Clayton Christensen. (2022)
  • Loonshots. Safi Bahcall. (2025)

Track 17: Customers, Growth & Product

  • The Mom Test. Rob Fitzpatrick. (2020) (Review)
  • Talking to Humans. Giff Constable. (2015)
  • Traction. Gabriel Weinberg and Justin Mares. (2014)
  • Crossing the Chasm. Geoffrey Moore. (2022)
  • The Cold Start Problem. Andrew Chen. (2022)
  • Nail It Then Scale It. Nathan Furr. (2017)
  • Disciplined Entrepreneurship. Bill Aulet. (2019)
  • Escaping the Build Trap. Melissa Perri. (2023)

Track 18: Process, Metrics & Execution

  • Measure What Matters. John Doerr. (2018) (Review)
  • Sprint. Jake Knapp. (2016) (Review)
  • High Growth Handbook. Elad Gil. (2022)
  • Good Strategy Bad Strategy. Richard Rumelt. (2021)
  • The Crux. Richard Rumelt. (2024)
  • Playing to Win. A.G. Lafley and Roger Martin. (2024)
  • 7 Powers. Hamilton Helmer. (2025)

Track 19: Basecamp Philosophy

  • Getting Real. Jason Fried and DHH. (2013)
  • Rework. Jason Fried and DHH. (2015)
  • Remote. Jason Fried and DHH. (2013)
  • It Doesn't Have to Be Crazy at Work. Jason Fried and DHH. (2018) (Review)
  • Company of One. Paul Jarvis. (2019)

Track 20: Fundraising & Boards

  • Venture Deals. Brad Feld and Jason Mendelson. (2016)
  • Startup Boards. Brad Feld. (2016)
  • Angel. Jason Calacanis. (2017)
  • A Dozen Lessons for Entrepreneurs. Tren Griffin. (2025)

Part 7: Career & Craft

Track 21: Productivity & Focus

  • Getting Things Done. David Allen. (2020) (Review)
  • The 7 Habits of Highly Effective People. Stephen Covey. (2018) (Review)
  • Deep Work. Cal Newport. (2016) (Review)
  • So Good They Can't Ignore You. Cal Newport. (2016) (Review)
  • Digital Minimalism. Cal Newport. (2019)
  • Slow Productivity. Cal Newport. (2024)
  • Make Time. Jake Knapp and John Zeratsky. (2018) (Review)
  • Essentialism. Greg McKeown. (2022)
  • Four Thousand Weeks. Oliver Burkeman. (2023)
  • Smarter Faster Better. Charles Duhigg. (2018) (Review)
  • Eat That Frog. Brian Tracy. (2025)
  • Ultralearning. Scott Young. (2019)
  • The Inner Game of Tennis. Timothy Gallwey. (2020)

Track 22: Management & Leadership

  • High Output Management. Andy Grove. (2015)
  • The Making of a Manager. Julie Zhuo. (2019) (Review)
  • The Manager's Path. Camille Fournier. (2020) (Review)
  • Radical Candor. Kim Scott. (2020)
  • Resilient Management. Lara Hogan. (2021) (Review)
  • Trillion Dollar Coach. Eric Schmidt. (2019)
  • The First 90 Days. Michael Watkins. (2020) (Review)
  • The New One Minute Manager. Ken Blanchard. (2020) (Review)
  • Managing Oneself. Peter Drucker. (2018) (Review)
  • The Effective Executive. Peter Drucker. (2025)
  • Scaling People. Claire Hughes Johnson. (2024) (Review)
  • The Five Dysfunctions of a Team. Patrick Lencioni. (2019)
  • The Five Temptations of a CEO. Patrick Lencioni. (2019)
  • The Three Signs of a Miserable Job. Patrick Lencioni. (2020) (Review)
  • Death by Meeting. Patrick Lencioni. (2022)
  • Powerful. Patty McCord. (2021)
  • Extreme Ownership. Jocko Willink. (2019)
  • The Dichotomy of Leadership. Jocko Willink. (2022)
  • Thanks for the Feedback. Douglas Stone and Sheila Heen. (2022)
  • Nonviolent Communication. Marshall Rosenberg. (2022)
  • Never Split the Difference. Chris Voss. (2018) (Review)
  • Getting to Yes. Roger Fisher and William Ury. (2022)
  • The Coaching Habit. Michael Bungay Stanier. (2024)
  • Quiet Leadership. David Rock. (2025)
  • The 15 Commitments of Conscious Leadership. Jim Dethmer. (2025)
  • First, Break All the Rules. Marcus Buckingham. (2024)
  • Start With Why. Simon Sinek. (2024)
  • Amp It Up. Frank Slootman. (2025)

Track 23: Software Engineering

  • The Pragmatic Programmer. Andy Hunt and Dave Thomas. (2019) (Review)
  • Coders at Work. Peter Seibel. (2020) (Review)
  • The Mythical Man-Month. Frederick Brooks. (2021)
  • Peopleware. Tom DeMarco and Timothy Lister. (2022)
  • Clean Coder. Robert Martin. (2025)
  • A Philosophy of Software Design. John Ousterhout. (2025)
  • Accelerate. Nicole Forsgren. (2021)
  • Extreme Programming Explained. Kent Beck. (2022)
  • Tidy First? Kent Beck. (2024)
  • Software Engineering at Google. Titus Winters. (2023)
  • Designing Data-Intensive Applications. Martin Kleppmann. (2021)
  • Team Topologies. Matthew Skelton. (2023)
  • The Passionate Programmer. Chad Fowler. (2020) (Review)
  • Slack. Tom DeMarco. (2020) (Review)
  • Staff Engineer. Will Larson. (2021)
  • The Staff Engineer's Path. Tanya Reilly. (2024)
  • An Elegant Puzzle. Will Larson. (2019)
  • The Engineering Executive's Primer. Will Larson. (2024)
  • Smart and Gets Things Done. Joel Spolsky. (2013)
  • Hackers and Painters. Paul Graham. (2016)

Part 8: Life & Purpose

Track 24: Meaning, Success & Character

  • How Will You Measure Your Life? Clayton Christensen. (2018) (Review)
  • When Breath Becomes Air. Paul Kalanithi. (2018) (Review)
  • Being Mortal. Atul Gawande. (2018) (Review)
  • This Is Water. David Foster Wallace. (2019)
  • Outliers. Malcolm Gladwell. (2015) (Review)
  • Give and Take. Adam Grant. (2017) (Review)
  • Originals. Adam Grant. (2018) (Review)
  • The Road to Character. David Brooks. (2016)
  • Lean In. Sheryl Sandberg. (2018) (Review)
  • Designing Your Life. Bill Burnett and Dave Evans. (2019)
  • The Startup of You. Reid Hoffman. (2019)
  • The Alliance. Reid Hoffman. (2015)
  • Range. David Epstein. (2024)
  • The Almanack of Naval Ravikant. Eric Jorgenson. (2021)
  • The Great Mental Models. Shane Parrish. (2019)
  • Thinking in Bets. Annie Duke. (2021)
  • Thinking in Systems. Donella Meadows. (2022)
  • Principles. Ray Dalio. (2018) (Review)
  • What I Talk About When I Talk About Running. Haruki Murakami. (2018) (Review)
  • Born Standing Up. Steve Martin. (2014)