Kanonical

Unusual Books For Teenagers

April 17, 2021

I’m in the middle of re-reading Doyle Brunson’s classic poker book: Super System. It popped into my mind again recently because of some Twitter conversation or other, and I realized my copy was torn in two and borrowed out from my library to someone and won’t ever be seen again. So I bought another copy and have been shredding through it.

It’s still the canonical book on poker, but it’s also much, much more. Reading it again, I realize that it’s at least as much about perspective on life, understanding psychology (yours and others), and knowing when and how to take reasonable risks. These are high quality Life Skills, and at some point I realized that this is exactly the kind of book I want my teenager to read. And I’ve been trying to figure out exactly why that is.

We have a tendency to focus on the fiction reading habits of our children, mostly because the most important part of reading early on is enjoyment, and if they like the story they’ll keep on going. But at some point as they get older, they grow able to ingest deeper and more comprehensive text. Non-fiction is different from fiction. It can still be a story in some way - the best non-fiction usually is - but it doesn’t contain the same beat, rhythm and regular dopamine rush of the situational fiction that kids start with.

Schools often introduce our kids to more “adult” fiction books in the worst way imaginable. We combine the transition away from the always-exciting children’s fiction with a trend away from engagement. Joseph Conrad’s Heart of Darkness, or any other assigned fiction in high school, is usually a slog to a 21st century kid. In fact, the only “classics” I can think of that aren’t a slog are Twain and Swiss Family Robinson. That’s because they’re still fun adventures. I remember thinking every time I had a reading assignment in high school, “God why are all these books so depressing? Is this what adulting is like?”

Non-fiction is worse. The closest most kids get to non-fiction seems to be the stultifying textbooks or essays assigned in high school and college. But as I’ve gotten older, I’ve gravitated more and more towards non-fiction. It ends up being more interesting and exciting than fiction. My conclusion is that we’re feeding our kids the wrong books. Kids want to learn about really cool topics from people that are out there in the world doing it.

Super System fits this mold perfectly. Poker is super cool and still considered slightly subversive. Doyle Brunson is one of the O.G.s of professional poker and he’s had an amazing life full of intrigue, success, and failure.. and he shares it with his readers. And most importantly, you get way more out of reading Super System than just poker skills. Doyle and his guest writers teach you how to think about mathematical odds and how to apply those odds in different situations depending on the type of person you’re playing. They make you think about how much capital is required to make more money and not just how to play the games but which games you should pick to maximize your odds.

You learn statistics and probability - the most woefully undertaught mathematics in school - psychology, and games. You could learn a lot of this by reading something like Annie Duke’s Thinking in Bets too, another great book that starts with poker. But where Duke’s book is more of a narrative about poker, Brunson’s book is deep in poker itself, focused on the difference between how to bet split-pair vs concealed-pair hands in Limit 7 Card Stud. Especially for kids, the narrative version isn’t as exciting.

A quick note about subject matter. My wife and I have had a long running conversation with some of our friends about when and how to introduce more adult topics to our kids. We humans go from believing in ghosts and monsters to being ready to go to college in about ten years, and the answers will rightly vary based on the kids and the parents. In general though, I am of the opinion that we shelter our children from the world of ideas too much, and shelter them from the artificial worlds that teenagers make for themselves too little: how much worse is social media than Lord of the Flies?. And in the world of ideas, books are the perfect first medium to share different, exciting, or disturbing perspectives; better than TV or movies. The sensationalism and provocation of movies is too powerful. To this day, I’ve watched Schindler’s List only once; the girl in red still haunts me. And how much more sensational has media gotten in the 21st century?

To think our kids will never be exposed to sensational, depraved or highly complex topics is wrong. Better to equip them properly to understand and reflect. Better to discuss directly with them or to show them your perspective by what you read. Books provide a perfect way to approach topics like risk, death and destruction, sex, addiction, deceit, politics, or power. Movies or TV can do this too, but books are more “pure”, for lack of a better term. To use a fictional example, I’d rather my 16 year old read Game of Thrones than watch HBO’s ratings-veneered version.

As an experiment, I tried to think of some other books that I’d want my older teenagers to read, especially non-fiction that they might find engaging and that teaches them about the complex world we live in. Here’s a starting list I came up with, probably wrong and definitely incomplete. It occurs to me looking at this list that the primary similarities are that the authors are honest (sometime brutally so) and earnest about whatever it is they’re writing about. There’s a commentary to be had on how we can be more honest about the world with our kids.

  • Super System - This book is about poker, but in the process Doyle discusses his optimism battling cancer while his wife was pregnant, how to manage risk, how to think about money, probability and psychology.
  • Letters to a Young Contrarian - Christopher Hitchens is brilliant, contrarian and heretical. He makes you think about how and when to question authority, what it means to think independently, and his command on language will make you want to improve both your writing and your speaking.
  • Leisure, The Basis of Culture - Most teenagers think you grow up and then you start working and that’s what adults focus on. But Pieper points out that work isn’t really the point. Culture and leisure and understanding life is the point. And out of this far better and more interesting construct (especially for a teenager), comes religion and an appreciation of beauty.
  • Displine Equals Freedom - For the kid that thinks discipline is stupid, frank language that demonstrates the opposite.
  • Starting Strength - Rippetoe’s classic is THE starting point for any teenager ready to hit some weights.
  • Conspiracy - A deepdive into a modern topic (Peter Thiel’s secret takedown of Gawker) that discusses the power and danger of media, free speech, and subtly asks the question: are some secrets and conspiracies in the world a good thing?
  • On Writing - King brilliantly explains why and how writing is such a powerful medium.
  • A Mathematician’s Apology - Not for everyone, but too many teenagers think math is boring.
  • How To Win An Election - as kids get interested in government and what’s going on in the world, this one will give perspective on exactly what’s going on and what playbook politician’s use on the public. In two thousand years, it hasn’t really changed much.
  • On Success - Charlie Munger is Warren Buffet’s long-time fabled business partner and his wisdom runs deep.
  • Hackers and Painters - Essays about computers and thinking and education.
  • The Personal MBA - if a teenager reads this, they will rightly avoid business school. They’ll already know everything they need to know and have a leg up on everyone their age.
  • How To Get Rich - They’d probably rather read this than the Personal MBA if they’re interested in business and entrepreneurship. And frankly, this one is better. This one looks like a joke but ends up being a jewel. Felix does, in fact, teach you how to get rich, but he also teaches you why you probably don’t want to as well.
  • The Mom Test - Another entrepreneurial book, this one teaches you when and how to trust opinions and how to properly ask questions to get truthful answers.
  • On The Shortness of Life - More people need to read the Stoics in general, and this one reminds you of how to use the valuable time you have.
  • The Subtle Art of Not Giving A F*ck - The cursing and more cool version of the stoics with more relatable language than Seneca. If you give this to a 17 year old to read, chances are they will, and the lessons are profound.
  • Zen and the Art of Motorcycle Maintenance - This one is a novel, strictly speaking, but it’s a great way to learn some of the romantic ideals of the Greek philosophers. And it’s full of great quips. (“You want to paint perfectly? It’s easy, just make yourself perfect and then paint naturally.“)
  • Fragments of Sappho - Some fo the most beautiful love poetry ever written.
  • Microcosmographica Academica - A not-so-subtle reminder that maybe at the tender age of under 20 you don’t actually know everything. Great satire and recognition that politics is everywhere, even in pure academics.
  • Socialism Sucks - The errors of the 20th century shouldn’t be forgotten in the 21st. This one gives funny insight into one of the biggest.
  • Hitler’s Table Talk - It looks like this one is hard to get now, and it’s not the kind of thing you read thoroughly. But there’s no better way to learn one of the other major blights of the 20th century than straight from the depraved and fascist mouthpiece of the Nazi party.
  • The Book of Satoshi - An anonymous person invents a whole new currency (bitcoin), becomes a multi-billionaire, and remains a mystery to this day? How is this story not more famous, and how could this not be exciting to a teenager? You can read what he wrote, understand what Bitcoin is and why it’s important in the 21st century, and get into his head.

Greg Olsen
Hi I'm Greg. Occasionally, I do things.