These are the books that defined my 20s. Read them to become a better writer—or a more interesting person.
Each of these books will teach you new ways of thinking about things you’ll face — or are now facing — in your twenties.
If you’ve already read some of them back in high school, read them again now that you’re older and wiser. They will tell you new things.
As you approach the end of your twenties in particular, these books are signposts that will point your way through the woods.
Oh yeah, you know the woods I’m talking about. You’re right in the thick of it.
All right, enough intro. Let’s talk about great books. These are in no particular order, because ranking your favorite books is stupid.
1. Ray Bradbury – Zen in the Art of Writing
Remember the stories you wrote when you were a little kid? You’d have unicorns and dinosaurs exploring magic islands with Disney characters, and you weren’t thinking about plot or prose style or writer’s block because all you wanted was to discover what happened next. You wrote, in other words, for the sheer joy of writing — because you yourself had no idea how the story would turn out, and your characters were taking you on a wild ride.
This book will show you how to rediscover that feeling. It’ll teach you how to bring that energy and honesty back to your writing. It’ll do more than just end your writer’s block — it’ll unleash a flood of ideas that you may not be able to turn off. And it’ll give you back the fun of writing, which alone is worth the price of admission.
2. Ernest Hemingway – The Sun Also Rises
I didn’t start traveling the world until I was 30 years old. That was a mistake. This book will introduce you to a band of rowdy writers and aristocrats who careen across Europe, flirting, fighting, lusting, wisecracking and drinking copiously at every stop. You will start to feel like one of the gang. You may find that you want to try this lifestyle for yourself — or at least meet the people who live it.
If nothing else, you will start to feel a hankering for far-off places with beautiful foreign names. Along the way, you will discover that great writing can convey a universe of meaning through simple declarative sentences of one-syllable words. You will learn what restrained writing is, and how it can make you sound much smarter and more insightful than a writer who uses a slew of thousand-dollar vocabulary. You may not pick up on all this on the first read. If not, wait five years and read it again.
3. Tim Ferriss – The 4-Hour Work Week
If I was a real douchebag, I could tell you about how I always believed that “live your dreams” crap was for other people but not for me, until I read this book and followed its steps and ended up traveling the world as a freelance journalist. Forget about all that. This book will still teach you how to value your time more highly, plan your day more rationally, and increase the time you spend doing things that actually interest you.
It explains all these changes in clear, down-to-earth steps that I hesitate to say are foolproof, but are still pretty hard to screw up if you take them one at a time. The end results might sound unbelievable— and in a way they are — but the steps themselves are very doable, and will lead to practical changes you’ll start to see right away. Use as directed.
4. Herman Melville – Moby-Dick
The first few chapters will make you want to throw this book in the trash. The narrator walks around a town, attends a church service, then has some weird quasi-erotic scenes with a South Pacific islander who he describes in very racist terms. Do not give up. Persevere until you’re on the boat. There you’ll meet a sharp-tongued captain and a man-eating whale who’ve sworn lifelong vows of vengeance against each other.
But that’s not even the best part. As one critic said, “this book is a classic because it defies classification” — in other words, it is balls-out insane. One chapter is a scientific treatise on every known whale. There’s a multi-page digression about clam chowder. There’s a ship called the Bachelor that’s described as being “full of sperm oil.” No book like it has ever been written, or is likely to be written. It stands alone, an alien artifact in the history of literature.
5. Sun-Tzu – The Art of War
Yep, it’s the cliché to end all chichés. Yep, every neckbeard pick-up artist cites it. Are ya done? This book is quietly brilliant in ways that are very hard to catch on a quick read. I keep coming back to it thoughout my life, and I get something new and useful out of it every time. One of its most beautiful ideas is that while anyone can win a battle, it takes a genius to win elegantly.
In other words, success itself — in any domain — can be achieved crudely, or it can be a piece of art as lovely as a brushstroke or a backflip. This principle can be applied in business, in art, in negotiation, and a thousand other areas — and it’s just one principle among hundreds, most of which I’m probably still not picking up on. Part of me wants to say take this book slowly, but even that may give you a lot of nuggets without the underlying veins of gold. I’ll say this: read it carefully, take from it what you can, and come back to it every few years for new gold.
6. Frank Herbert – Dune
Do not take writing lessons from Frank Herbert. His dialogue is wooden and his scenery is vague. No; come to Dune to learn how to lead, how to read people and spot traps within traps, how to inhabit the mythos of your time, and how to keep sight of yourself in that whirlwind. Yes, this is a sci-fi book — but it’s actually about oil wars in the Middle East.
It’s also about Eastern philosophy and capitalism and desert ecology and tribal sociology and shamanism and the subtle dances of international politics and war. It plays out on a timescale of tens of thousands of years, across a galaxy of interconnected planets — but mostly in the minds of a few characters whose thoughts and plots are described with scalpel precision. It also has giant sandworms that produce psychedelic drugs in their guts, which is pretty cool.
7. Bhante Henepola Gunaratana – Mindfulness in Plain English
Your first thought on seeing that title is probably that this is one hell of a far-out book. Nothing could be further from the truth. This book is the most concrete, no-B.S. manual on meditation that you will ever read. If you’re feeling stressed, angry, and unsure of what to do, you need to learn how to meditate, now. I don’t care if you’re atheist, theist, pantheist or Satanist, a little mindfulness will do you a world of good.
If you’ve tried meditation and haven’t gotten much out of it, read this book. It’s free — you can download it in PDF right now. It’s like 50 pages long. Meditation is supposed to be fun. It’s supposed to be interesting. It’s supposed to be easy to understand, and fairly easy to do, with a little practice. It’s also a topic about which a mind-boggling universe of unnecessary crap has sprung up over the centuries. Forget the dogma and the stigma and the expectations. Just learn the basic technique. What you do with it beyond that is up to you.
8. Herman Hesse – Steppenwolf
Some people read this book in high school. I didn’t read it until much later, and I wish I’d read it much sooner — preferably before I’d read Catcher in the Rye and labeled myself an edgy outsider. This book demolishes the binary between the edgy and the ordinary. It’s the story of a man who’s always thought of himself as a “wolf of the steppes,” a wild untameable beast who’s actually just terrified of authentic human interaction.
Hesse paints an utterly relatable picture of the Steppenwolf’s bleak pride in his lonely existence — then takes that wolf on a whirlwind journey through all the things his edgy nature fears most: playful conversation, loud nightclubs, dancing to pop music, ambiguous sexuality, group identity, and, ultimately, the soft beating heart of his hidden childhood self. We outsiders pride ourselves on staring into the heart of darkness — but sometimes the light is much scarier to confront.
9. Neil Gaiman – The Sandman
It’s not a book, exactly; it’s a graphic novel. A series of them, actually. A long series. It is so completely worth it. The first couple chapters are pretty cartoony, and I almost gave up. I am so glad I didn’t. I would’ve missed out on one of the great epics of modern literature.
Here’s how it starts: the Dream King returns to his kingdom after a very long absence, to find that the whole universe is going mad. Lucifer is quitting his job as the Devil. The old gods are vying for his spot. Fictional worlds are bleeding into reality. The Dream King retreats to his library, which holds every book that was ever imagined but never written, and calls his estranged family together to try to talk things out.
If you have any love for literature at all, this story will get inside your soul. Shakespeare is here. Shelley and Byron. Thor and Loki and Orpheus and Calliope and all the angels and demons. It sounds like a sprawl, I know, but it all weaves together in ways that will leave you breathless about the art of storytelling.
I probably left your favorite book out, I know.
Call me out in the comments if you like, but this is my list and I’m stickin’ to it; unless you know me well and there’s an obvious one I forgot, in which case I will add it and pretend it was there all the time. If, on the other hand, you love one of the books on this list, leave a note and tell me why. Let’s geek out together.