1. Tiny Beautiful Things, by Cheryl Strayed
If you love reading or getting advice, then you need Tiny Beautiful Things right now. This collection of letters compiled by Cheryl Strayed — aka Dear Sugar at The Rumpus — is packed with wisdom, and enough tough love to remind us that we make our own choices.
2. Hyperbole and a Half, by Allie Brosh
Brosh is really funny, for starters. So, while she writes letters to her younger self, and talks about how exhausting it is to be an adult, you’ll be laughing until you cry.
3. The Defining Decade: Why Your Twenties Matter — and How to Make the Most of Them Now, by Meg Jay
When you’re in your twenties, 30 can seem like it’s a long way off. So having to grow up gets put on hold. But Jay reinforces the idea that by the time you hit 30, your identity is pretty well formed. In other words: What you’re doing now actually does matter. She even uses examples from case studies to prove it, and also to help you apply the life lessons she’s learned to your own work, body, brain, and personal life.
4. Love Is a Mix Tape, by Rob Sheffield
This book kind of has it all: humor, music, and heartbreak. (What else do you need, really?) It’s about great love and great loss, and it will leave you longing for a great love of your own.
5. I Was Told There’d Be Cake, by Sloane Crosley
Crosley’s essays about being a young woman in New York and experiencing things like her first job will remind you that WE ARE ALL IN THIS TOGETHER. Plus, it’s really all quite funny.
6. Of Human Bondage, by W. Somerset Maugham
This book, written in 1915, is loosely based on Maugham’s life. As you read, you get to be inside the narrator’s head, and watch him grow into a man, where his decisions come with consequences.
7. Lost in the Cosmos, by Walker Percy
If you’re feeling like your life is offtrack, then you should read this book. Lost in the Cosmos will shape the way you communicate with the world, and answer a lot of questions about why we behave the way we do.
8. Treasure Island!!!, by Sara Levine
So, the main character of this book reads Treasure Island, becomes obsessed with it, and redesigns her life to live more like the book. It’s basically the best book about a meltdown ever.
9. I Totally Meant to Do That, by Jane Borden
Need a laugh? Pick up Borden’s hilarious essays about graduating college, moving to New York, and continuing to live like she’s in a frat house.
10. The Monsters of Templeton, by Lauren Groff
This is one of my all-time favorite books. Not just because it’s about a grad school dropout who returns home to figure out her life — and everyone loves a good breakdown. But this book is also insanely well written, and deals with themes of abandonment, growing up, and dealing with the consequences of your actions. (Oh, and there’s a lake monster. I should mention that as well.)
11. Dreams from Bunker Hill, by John Fante
This very easy and very funny read is about a young man coming of age in Los Angeles circa 1930. You get to see some Hollywood characters (think a name-dropping screenwriter), and the book is optimistic, even if there isn’t a happy ending.
12. The Mysteries of Pittsburgh, Michael Chabon
Most people know Chabon for The Amazing Adventures of Kavalier & Clay, but it’s his first novel, The Mysteries of Pittsburgh, that really needs a read. Chabon wrote this novel when he was just 21 years old, and a student, and it’s about a young man who watches his world collapse and emerge all at once.
13. Let’s Pretend This Never Happened, by Jenny Lawson
Everyone has something they have to work through, and for Lawson it’s depression. But the way she chooses to deal with it is what really makes her unique and inspiring. Did I mention the way she deals is through laughter? You’ll definitely be laughing.
14. At The Bottom of Everything, by Ben Dolnick
Are you in a place where you didn’t think you’d be? Meet 26-year-old Adam Sanecki, he can relate. He lives in Washington, D.C., just went through a breakup, and is trying to give his life some meaning by tutoring middle school kids.
15. The Marriage Plot, by Jeffrey Eugenides
Admittedly, it can take a little while to get to the meat of this novel, which is all about the challenges we face after college. If you were a lit major of any kind, you’ll appreciate a lot of the references. If you weren’t a lit major, then read it for the funny love triangle.
16. Moby-Dick, by Herman Melville
Hey, Moby Dick is a classic for a reason, right? This book is a lot about the limitations of ambition, yearning, understanding, and so much more, especially in the Ishmael musings. It’s great in more of a “there is nothing better in this world than art” kind of way.
17. Tales of the City, by Armistead Maupin
Set in San Francisco, this reads like a loveable soap opera about a group of post-college friends. There’s sass, gay culture, death, romance, and drag queens.
18. The Line of Beauty, by Alan Hollinghurst
This is a more contemporary — and darker — take on being gay in your twenties than Tales of the City.
19. The Namesake, by Jhumpa Lahiri
Your parents want you to be one thing, but you’re just trying to figure out what the hell you want. Such is the fate of Gogol Ganguli, who isn’t particularly fond of his name, or the life his traditional parents expect him to lead. This book will make you weep, and it’s really beautifully written.
20. The Magicians, by Lev Grossman
If you feel too old to read the Harry Potter books, (though, no one is too old for that, let’s be honest), then you’ll feel OK about reading The Magicians. It’s Harry Potter for adults, basically, because it’s a bit darker and more serious. Same old reliable socially awkward boy wizard, though.
21. The Journey Is The Destination, by Dan Eldon
Dan Eldon was only 22 when he was killed, but he’d lived a lot of life. He was a journalist whose work appeared in Time and Newsweek, and this collection of pages from his journals (ages 14 through 22) captures just how insightful he was. This book will remind you of what’s really important, and encourage you to live fearlessly.
22. Letters To A Young Poet, by Rainer Maria Rilke
This book really does contain the best and most real advice on how to be an artist and a person. It’s 10 letters written by Rilke to a young German soldier who is trying to decide what his career should be.
23. In a Strange Room, by Damon Galgut
This is a stunning and heartbreaking novel (but reads like a memoir, and very well might be a memoir) about backpacking across eastern Africa, Europe, and India. The narrator struggles, unsure of what he’s looking for. (Can’t we all relate a bit to that?)
24. Sputnik Sweetheart, by Haruki Murakami
This book might make you a bit of a mess, emotionally, as it is gut-wrenching and deals with the perils of unrequited love. But reading this book will remind you that loving fully is a way to tap into your raw emotions, and perhaps make you a little less closed off.
25. The War of Art, by Stephen Pressfield
If you feel like you’re hitting a block creatively, then The War of Art can help. It’s about overcoming obstacles to reach your full potential.
26. Gone Girl, by Gillian Flynn
Gone Girl is a fun read more than anything else. It’s about Amy Dunne, a woman who has to reinvent herself after some rather unfortunate events occur to her husband. I won’t spoil the book, but definitely read this if you’re thinking about becoming an entirely new person. (It might just make you change your mind.)
27. The Joy Luck Club, by Amy Tan
Being in your mid-twenties means that you’ll likely feel misunderstood by your parents at some point. They don’t know why you can’t just stay at one job for more than a few months, and you don’t know why they can’t accept the fact that you have dreams, damnit. Enter The Joy Luck Club, which is a great book for any daughter who is currently annoyed by the fact that their mother doesn’t get them.
28. The Unbearable Lightness of Being, by Milan Kundera
A lot of this book has to do with sex, but it’s not just sex for the sake of it. (Not that there’s anything wrong with that, mind you.) But Kundera poses a lot of questions about indifference, freedom, truth, and the idea of polar opposites in this book. All of which will leave you to form thoughtful questions (and hopefully answers) as to what you want out of life.
29. The Stories of Breece D’J Pancake, by Breece D’J Pancake
There’s something about Pancake’s personal struggles — he took his own life at the age of 26 — that will speak to you on a “get through this” level. A bunch of the stories have to do with being a young man, dealing with family, feeling lost, and not knowing what to do with your life. Also, (on a non-quarter-life crisis note), it has one of the creepiest stories regarding a mild mannered serial killer that I’ve ever read.