Collaborative Life Syllabus

This page is the result of a project undertaken to gather the collective wisdom of many of my friends. Commenced in 2007, the project interviewed many friends, asking for their five all-time favorite books. I wanted the books that had changed their lives; the ones that continue to influence them years later; the ones that they are compelled to re-read every few years. In early 2008, I also decided to include specific books recommended by authors and thinkers I respect, if they recommended them as similarly influential to their lives or craft. The results of this project, organized very loosely by subject, and reviewed in contributors’ own words, are listed below. I would love your contributions to this list as well — if you are interested in participating, please just email me your favorite five books and I’ll add them here. Without further ado:

Finance, Economics, & Investing



  • A Random Walk Down Wall Street, Burton Malkiel. This is the book I recommend to all my friends who want to learn more about investing. Written by a prominent academic, it remains readable by someone who doesn’t have formal finance training. This book will pay for itself many times over.
  • The Intelligent Investor, by Benjamin Graham. I do not profess to be an investing savant, but this is the granddaddy of value investing advice, heavily promoted by the Oracle of Omaha himself. My investing strategy has yet to indicate its success relative to other theories and techniques, but enough people seemed to have made enough money by following the advice in this book that I’m convinced.
  • “Finance & Accounting for Non-Financial Managers”. Reading this is critical if you care about money in any way. Accounting is the language in which money flows are described in business. If you get a paycheck, then someone above you is in charge of understanding the accounting for how and why you get paid. You can never transcend your position in the economic order if you don’t understand it as well as the people above you.
  • “Margin of Safety,” by Seth Klarman. The best investing book I have ever read, and critical to shaping my orientation as a value investor. (The book is long out of print and used copies go for thousands of dollars, but you can print your own hereMore Klarman writings.)
  • “Reminiscences of a Stock Operator,” by Edwin Lefevre. See also the annotated version. Jeffrey Gundlach calls this the best investing book of all time.

Also of note: 

Strategy, Decisionmaking, & Math

Productivity, Practical Skills, & The Workplace

  • Getting Things Done, David Allen. (2 votes) I discovered a couple years ago that getting organized can change your life, reduce your stress level, and make you a happier person. This book offers a prescription for how to organize yourself at work and at home.
  • Winning through Intimidation by Robert Ringer. Learnings: Unfortunately, many people we deal with in business and the workplace often use intimidation to exploit us, if for no other reason than to promote their own interests. This book taught me–as a naïve, twenty-something fresh off the Iowa farm–how to recognize and “type” these intimidators and how to proactively protect myself from their evil ways. This knowledge served me very well, as I met these intimidators time and again during my 28+ years in the workplace. Must reading for anyone in the business world. Don’t be turned off by the title.
  • Your Money or Your Life by Joe Dominguez and Vicki Robin. I am forever grateful to my friend Joan Piper who gifted me with this life-changing book at the tender age of 38. It helped me question assumptions that I’d unconsciously adopted about money, position, and success during my early adult life. More importantly, it helped me develop a road map which enabled me to achieve financial independence before the age of 50. What a gift! While I do not agree with the investment advice provided at the end of the book (100% of capital invested in US Treasury bonds to provide life-time income), I endorse everything else about this book. Quote: “There’s a big difference between making a living and making a life.”
  • The 48 Laws of Power — Robert Greene.
  • TranceFormations — Richard Bandler and John Grinder. (Note: this book is out of print but this updated version is not: Richard Bandler’s Guide to Trance-formation.
  • “How to Win Friends and Influence People” by Dale Carnegie. I read it when I was 14-15 years old and it had a profound impact on me and taught me how to interact with people better. I actually stopped arguing and disagreeing with my parents and used some of the techniques in the book to get what I wanted 🙂 This books teaches you how to connect with people right away and how to best communicate with everybody around you. It taught me how to resolve problems and find compromises.
  • Surviving Success by Jeffrey Hansen – This book has helped in my career to determine what type of person my boss was and how I could better understand or relate to them and how I might better fit into a firm or job function. It also helped me understand how to think critically about improving the places I work.
  • “Getting to Yes.” This is a crucial piece. People argue their asses off without understanding how and why negotiations work. If you ever negotiate (which is to say, if you are ever a free actor communicating with other actors about something you want to exchange) you must read this.
  • Influence: The Psychology of Persuasian (Cialdini).

Health & Travel

Architecture, Construction, & Urban Planning

Pop Culture & America



  • “The Fountainhead” – Ayn Rand (3 votes). This book represents the closest thing to religion that I have found in my 31 years of life. I read it every couple of years to stay on track. It is about the power of human will. Learnings: Think independently, maintain your individuality, dream big and stick to your vision–despite the consequences. Eventually, lesser mortals may come to appreciate you and your work, as you’re probably just ahead of your time. / Probably one of the few books that can have profound impact on the way you live your life, as it is a framework of ethics you will never get anywhere else. I would recommend all of her books, once you read the fountainhead you won’t be able to resist the rest. / This book changed the way I understand the world and the philosophy behind the social decisions that are impacted by economics. I read all the Ann Rand books and couldn’t get enough. This one is her masterpiece. It strikes a good balance between her capitalistic/libertarian philosphy and classic literature with an underdog hero we can all aspire to. There might be a flash of romance in it as well.
  • 1984 – George Orwell (2 votes; also, according to a reader poll at England’s The Guardian newspaper, the definitive book of the 20th century.)
  • A Prayer for Owen Meany, John Irving (2 votes).
  • Howard’s End, E. M. Forster (2 votes).
  • The Prophet — Kahlil Gibran (2 votes).
  • “High Fidelity,” by Nick Hornby (2 votes). Better than the movie, which to me is really saying something. It’s one of the only books I’ve read that’s honest about masculine emotion, and it’s also one of the sharpest books on pop culture around. / Along with “Of Human Bondage,” the sharpest book I’ve read about romantic relationships from the guy’s perspective.
  • The Secret Life of Bees – Sue Monk Kidd (2 votes).
  • Ender’s Game, by Orson Scott Card (2 votes). Maybe not the most life changing, but a great story and fascinating read. Once you start, very difficult to put down. This one is just for pleasure, but it’s one of those “keep coming back to it kind of books.” It’s about a boy genius who must save the planet from aliens. A little far fetched, but I think curiously interesting to anyone who strives to overachieve at a young age (a category most readers of your list probably fall into). This book was also the subject of one of my U.Va. admissions essays, and seeing as how I ended up there, the book must have played some part.
  • Of Human Bondage, W. Somerset Maugham. If Jane Eyre were written for men, it would be this book.
  • Starship Troopers by Robert Heinlein. The classic Sci-fi book about ethics, morality, duty, honor and responsibility. Shows that liberty and freedom must be paid for and that democracies ended when they failed to realize this.
  • The Blue Knight by Joseph Wambaugh. One of his best early works about the last 3 days of an old LAPD beat cop. A little out dated as far as police procedures but a great one for really understanding the cop psyche. Also recommended, The New Centurians and The Choirboys.
  • Gates of Fire by Pressfield. Outstanding historical fiction about the battle of Thermopylae which saved Western civilization. About heroism and discipline and loyalty between men and to a state.
  • Flashman by George McDonald Frasier. A politically incorrect book for lovers of historical fiction in the Victorian era as seen through the “lost diaries” of the hero Harry Flashman, likable coward, cad, scoundrel who always comes out smelling like a rose. This and the many successor books will leave you considerably more educated about the important events of the 19th century. One of the few books that I laugh out loud when reading.
  • Walden; or Life in the Woods by Henry David Thoreau. This classic chronicles Thoreau’s experiment in simple living. From 1845-47, Thoreau went into the woods to “live deliberately” and contemplate Western culture, consumerism and the destruction of nature. Helped me critically evaluate (fortunately at an early age) what is truly essential to a life worth living and what is not. Quote: “A man is rich in proportion to the number of things he can afford to let alone.”
  • What I Loved- Siri Hustvedt. This was an enjoyable psychological read about relationships that struck me as notable because it didn’t feel too cliche, in spite of how cheesy it sounded from the summary.
  • The God of Small Things- Arundhati Roy. This one was written in a way that I thought was really touching and beautiful.
  • The Curious Incident of the Dog in the Night Time- Mark Haddon. The author works with autistic kids and does a great job of narrating from the perspective of a 9 year-old boy– a quick, fun read.
  • The Unbearable Lightness of Being- Milan Kundera
  • Four Quartets — TS Eliot
  • “The Portrait of a Lady,” by Henry James. It’s long, it’s relentlessly psychological, and it aspires to the absolute pinnacle of artistry, with none of these qualities making the novel an especially entertaining read. But I know of no other book that leaves its readers so certain that they’ve known its characters intimately. The plot follows Isabel Archer, a young American who, thanks to an unexpected and vast inheritance, has nearly limitlessness freedom. We see her successes and failures, and by the novel’s conclusion feel them as intensely as if they had happened to ourselves.
  • The Counterlife, by Philip Roth. One of the most imaginative of our living novelists, Roth offers us a story that continually backtracks on itself, runs in differing and contradictory directions, and leaves the reader wondering whether we really do live in an infinitely dimensional universe in which every contingent possibility of existence is being played out somewhere, somehow. Utterly mindbending and yet full of hilarious stories and interesting characters, “The Counterlife” leaves us with a sense for the vast and barely scratched possibilities of literature.
  • The Phantom Tollbooth, by Norton Juster. An allegory of the lifelong pursuit of knowledge, and written for children. But it’s the kind of story that can make even an adult excited about reading again.
  • The Time of Our Singing, Richard Powers. Powers is a great, unfairly intelligent writer. The novel traces the lives of two multiracial boys in mid-century America, with their black mother and Jewish immigrant father attempting to raise their children “beyond race” and through musical training. The novel is hugely incisive on matters of music, ethnicity, and personal identity, but it’s the emphasis on theoretical physics — the father is a scientist who fled Nazi Germany — that lifts “Singing” to an almost ludicrous level of showmanship. How any one writer can know so much and weave so many fields of knowledge is beyond me, but it’s exhilarating to experience.
  • Notes from the Underground by Fyodor Dostoevsky – I struggled with my single favorite Russian novel and I chose this one because it was part of the reason I became interested to learn Russian language and history. I also chose it because it is short. It is a good foray into Russian literature without needing much background. It requires deeper thought about human nature, but can also be entertaining as a superficial read. For a shorter, more Byronic read check out Hero of Our Time by Lermontov.
  • Beloved – Toni Morrison
  • The Kite Runner – Khaled Hosseini
  • A Fine Balance – Rohinton Mistry
  • Middlesex – Jeffrey Euginides
  • Love in the Time of Cholera — Gabriel Garcia Marquez. This was the first time in my life that I read a “love story” and actually understood the power and passion behind being in love. It could have been because I was in my late teens and reaching a critical point of maturity, but it changed my life in that it truly made me excited to find that one person who I was meant to be with and to (more importantly) not f*&k it up. It also helped me realize the depth of heartache. However, I do have to say that this is so much more than a love story. Also, Marquez’s capacity of language is incredible; his ability to describe situations and place you “in the moment” is unmatched by any other author I have read.
  • Atlas Shrugged — Ayn Rand. This book made me rethink whether our society is best served as a “social” democracy and welfare state, as opposed to following the straight code of capitalism. I found myself in constant struggle; my heart and my mind did not agree. If you are a Republican, capitalist and/or Homo Economicus, then you need to read this book as it will invigorate you and you will love the philosophy. If you are a socialist, you will hate the book but will still be captivated by it.
  • Lolita (Vladimir Nabokov): The ultimate American road trip novel. There are two kinds of people in the world–those who love Lolita, and those who find it insincere or offensive. If you’re in the first group, the story will make you laugh and cry in the most non-cliche way possible. (Editor’s note: also check out The Annotated Lolita — Nabokov uses so many little linguistic tricks that they would be easy to miss. This version catches them in footnotes. I’m personally blown away by how great Nabokov’s prose is given that he wrote this book in English, his second language.)
  • Time and Again, by Jack Finney. A warm and whimsical historical novel (though technically classed as science fiction).
  • Bleak House, Charles Dickens. Bleak House is a tough book– it takes a real commitment from the reader and isn’t easy to read. That said, it is my favorite of all Dickens novels, and I am a Dickens lover (having named my dog after Sydney Carton in A Tale of Two Cities). It deals with a generations-old lawsuit and the notoriously horrible chancery legal system in England. Among the many themes explored are love, lust, money, class, and honor, just to cite a few. There are some great Dickensian villans, as well one of the most complex and interesting female characters in all of Dickens, Lady Dedlock. The recent BBC miniseries of this is quite good as well. Worth reading for the character names alone.
  • Remains of the Day, Kazuo Ishiguro. Not legal in nature, but probably my favorite book ever. Read it for the most gorgeously restrained writing. The tone is pitch-perfect, and the author brilliantly uses the butler as the first person narrator, yet evokes certain truths for the reader that the narrator himself is not aware of. I really, really love this book. Any of Ishiguro’s other work is just a pale shadow of this. Also a good movie. The book is beautiful, sad, pathetic, and just heartbreaking.
  • Watership Down. I don’t see this as a children’s book, although I did first read it as a child, maybe 5th grade? Then I loved the complexity of the rabbit language and the idea that bunnies could have a society! Now, I find the book to be a great meditation on leadership, character, and the dangers of power.
  • The Master and Margarita by Mikhail Bulgakov. The story behind its creation, release and social impact in the Soviet Union is as good as the novel. Penguin Classics translation.
  • The Electric Kool-Aid Acid Test (Tom Wolfe). Just a kick-ass fuckin’ book about hippies, and the best part is it’s all true (more or less).
  • The Plague, Albert Camus.
  • Babbitt (Sinclair Lewis). Required. No one ever talks about the 1920s anymore — this is an engrossing world created at the time, satirizing the times and upon its publication influencing the times. Read it and appreciate your grandfathers’ Elks memberships more.
  • Wicked: The Life and Times of the Wicked Witch of the West, Gregory Maguire.
  • What Matters Most is How Well You Walk Through the Fire, Charles Bukowski.
  • American Psycho, Bret Easton Ellis.
  • Catch-22, Joseph Heller. So bizarre and hilarious, and it does a great job of making war look like a circus.
  • The Catcher in the Rye, J.D. Salinger.
  • “The Count of Monte Cristo” by Alexandre Dumas. What would you do if you were falsely imprisoned for a capital crime, then found unlimited resources to pursue your revenge?
  • “The Short Happy Life of Francis Macomber” by Ernest Hemingway. A very fast read, and a hell of a story.
  • “Gone With the Wind” by Margaret Mitchell. I was afraid it would be an overblown romance novel, but it turned out to be an epic story of independence and survival.
  • City of Thieves, David Benioff. Great story about two boys fending for themselves during the Nazi siege of Leningrad. Funny, page-turning story of coming of age and the absurdities of war.
  • Street of No Return (David Goodis).
  • Old Filth (Jane Gardem).
  • The Shadow of the Wind (Carlos Ruiz Zafon).
  • Any Human Heart (William Boyd).
  • Never Let Me go (Kazuo Ishiguro).
  • The Glass Bead Game (Hesse).
  • Crime and Punishment (Fyodor Dostoyevsky). Make sure to get the Pevear Volokhonsky translation.

Also of note: NPR’s “You Must Read This,” where good authors recommend their one favorite book. Most of these are fiction.

History, Politics, & Biography

  • Man’s Search for Meaning, by Victor Frankl. Learnings: Everything can be taken away from you (think divorce, job loss, or the death of a loved one) as it was for this survivor of Auschwitz. The only thing we truly “own” is our attitude and our ability to choose how we react to the many curves life throws us. Quote: “When we are no longer able to change a situation…we are challenged to change ourselves.”
  • She’s Not There: A Life in Two Genders, by Jennifer Finney Boylan.
  • The Things they Carried, by Tim O’Brien
  • Ultramarathon Man: Confessions of an All-Night Runner — Dean Karnazes. Ultra-marathoner Dean Karnazes shares his infectious love for running in this memoir painting a picture of an insanely dedicated endurance athlete.
  • The Writings of John Muir. Haven’t tackled one of his own books yet, but The Wilderness Writings of John Muir is a good start — particularly excerpts from “Youth and Childhood” and the window into the world of the man who prompted the creation of the world’s first national park.
  • Let Us Now Praise Famous Men. A contemporary look at the impact of and personalities captured by The Great Depression. Honest.
  • Looking Backward (Edward Bellamy). Socialist utopian tale from the late 19th century. Aristocrat sleeps for 100+ years, awaking to find himself in the year 2000 (?) in Boston – a masterpiece of social engineering. Predicts invention of credit cards (concept), radio (pipes w/live performances only, no recordings), shopping malls. Required reading for anyone who wants to understand the American industrial revolution.
  • All the President’s Men (Woodward and Bernstein). Once, there were journalists.
  • American Theocracy – Kevin Phillips. One of the most frightening tales I have ever read, namely, because it is about the current trajectory of this experiment called America. This book chronicles the downfall of the Roman, Dutch, and British Empires and correlates their falls to a simple formula that we happen to be following to the letter.
  • Neorealism and its Critics edited by Robert Keohane – This book is a survey of international relations theory of sorts in that it invites those who disagree with neorealism to criticize it. Some do so from within the context of their own theories (outside the context of neorealism) others critique from within. It isn’t that I ascribe to any one author or theory found here, but it provides a decent cross section of political thinkers. I spent a year in undergrad studying international relations/political economy and if it wasn’t for that time spent I think I would be a much weaker critical thinker. It has been useful in interpreting world conflicts beyond the partisan wrangling of 24hr soundbyte media.
  • The Social Transformation of American Medicine, by Paul Starr. Although published in 1982, this continues to be the definitive work on why the United States is stuck with its current healthcare system. It won the Pulitzer Prize, and no author has yet to top it. Pretty much required reading for any person serious about succeeding in the healthcare industry, this book delves into the motivations and machinations of our scary system. Although dense at times, it is the singly most important book in my field.
  • The Closing of the American Mind, Allan Bloom. Recommended by Ross Douthat re: politics.
  • Manhunt: the 12-Day Chase for Lincoln’s Killer, by James Swanson. Incredible, historically-accurate tale that reads like a Tom Clancy novel. Couldn’t put it down.
  • “Wind, Sand, and Stars” by Antoine de Saint-Exupery, the same guy who wrote “The Little Prince.” This is an autobiographical and philosophical account of establishing the early airmail routes in northern Africa and South America.

Religion & Spirituality

  • Tao Te Ching — Lao Tzu
  • Siddhartha. Story of a man’s search for purpose, in which he experiences almost every philosophy, and his resulting conclusions. Rough parallels to the Buddha’s story.
  • Zen and the art of Motorcycle Maintenance, Robert Pirsig. Kind of a difficult read, I get something new from it every time I go through it. I like it because of the author’s relentless battle to logically tackle some of the key contradictions in life, which eventually causes the protagonist in the story to have a mental breakdown. The story is written after this has happened and he keeps getting occasional glimpses into what happened before and why.
  • Book of Mormon: Another Testament of Jesus Christ – You said mind-changing, and that is what it did for me at about age 24 when I was looking for the purpose of life. I aspire to read it once a year. It is an ancient history of a few groups of people who left Jerusalem and fled to the Americas. It chronicles their rise and fall as individuals and as nation-tribes. It sounds like a strange historical text, but the spiritual lessons are the reason to read it. One simple example and a common theme throughout the text (other than testifying of redemption through Christ) is that pride (or hubris) is a stumbling block to spiritual and temporal prosperity.
  • Prometheus Rising — Robert Anton Wilson


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