1. The War of Art by Steven Pressfield Via amazon.com Why: This book is all about overcoming the inevitable obstacles that stand in the way of creative success — but it can also apply to everything, not just artistic endeavors. Definitely a useful companion for when you start questioning your college major and feel overwhelmed by finals. 2. A Field Guide to Getting Lost by Rebecca Solnit Via amazon.com Why: The collection of essays is centered around self-discovery and explores the idea of enjoying being lost. Because, yes, life outside high school is no doubt confusing, but there's also a lot of beauty in not knowing what lies in store. 3. The Alchemist by Paulo Coelho Why: It's a famously beloved, magical story about a boy who follows his dreams and discovers more about himself along the way. Graduating high school is a huge and exciting accomplishment, so why not celebrate by reading a beautiful, feel-good fable that will get you excited about the unknown ahead? 4. Daring Greatly by Dr. Brené Brown Via amazon.com Why: If high school was all about trying to fit in, the rest of adult life should be about taking risks and shedding that crippling fear of failure we all had when we were 16 and weren't sure if we should join drama club or not. If there's any book that proves making mistakes is the only road to success, it's this one. 5. Fangirl by Rainbow Rowell Via amazon.com Why: It's a lighthearted story of a girl who harbors an obsession for a fictional equivalent of the Harry Potter franchise, and is given a rude awakening when she heads off to college and starts to feel pressure to let go of her passion. Whether you belong to a fandom or not, the novel smartly approaches the topic of moving on from the things we've always loved, which is no doubt a huge part of every newly graduated high schooler's life. 6. The Secret History by Donna Tartt Via amazon.com Why: Chances are, your upcoming college experience won't turn into a psychological thriller involving on-campus murders and a clique of extreme social misfits (though who knows, really?). But reading Tartt's lengthy novel will do more than simply entertain — the main characters deal with adjusting to life in a small college and try to figure themselves out, making it relatable to any incoming freshman. 7. The Rules of Attraction by Bret Easton Ellis Via amazon.com Why: Yet another book set in an posh liberal arts college, this one deals with three emotionally confused students who find themselves drawn into a romantic triangle that further magnifies their anxieties about their futures. The tone is both biting and comical, commenting on the mess of feelings and fears many college students try to wade through. 8. Letters to a Young Poet by Rainer Maria Rilke Via amazon.com Why: Like the title suggests, this book is comprised of letters addressed to a young aspiring poet that give advice ranging from how to unlock creativity to how to open up and embrace love. Poet or not, there are lessons in here for every young person facing a new world. 9. The Unbearable Lightness of Being by Milan Kundera Via amazon.com Why: This lauded novel reads almost like a collection of sketches rather than in-depth analyses of the characters, offering a philosophical look into the power dynamics of relationships. It's a stunning meditation on life, and it'll make you wonder why it was never on your high school reading list to begin with. 10. Wise Blood by Flannery O'Connor Via amazon.com Why: Although the protagonist is older than the average high school graduate — and, oh yeah, is also a prophet — his struggles and meditations on self-discovery and redemption make this a worthwhile and rich novel to read while being introduced to a new chapter of life. 11. On Writing by Stephen King Via amazon.com Why: It doesn't matter if you're an aspiring writer or not because A) it's an entertaining and enlightening read regardless and B) chances are, it'll still provide you with a few good tips on how to nail the inevitable college essay. 12. The Moviegoer by Walker Percy Via amazon.com Why: It's a tale of an emotionally detached stockbroker who tries to find meaning and beauty in an increasingly shallow world by going to movies alone and trying to come to terms with his existential crisis. Definitely a good read before entering post-high school life and trying to figure out your career/goals/ultimate dreams. 13. The Autobiography of Malcolm X by Malcolm X and Alex Haley Via amazon.com Why: The Spike Lee quote in the cover image says it all, really. 14. Lucky Jim by Kingsley Amis Via amazon.com Why: Told from the perspective of a professor rather than a student, this novel navigates through a stuffy campus and provides a clever, intensely satirical take on postwar British university life that proves to be applicable to everyone who's ever dealt with pretentious classmates. 15. The Mysteries of Pittsburgh by Michael Chabon Via amazon.com Why: It's the ultimate coming-of-age story, often compared to high school reading list favorites The Great Gatsby and The Catcher in the Rye, and walks through the life of a boy who's sorting through complex relationships with his father, his friends, and, most importantly, himself. 16. The Savage Detectives: A Novel by Roberto Bolaño Via amazon.com Why: Besides being a must-read for anyone studying Spanish, this layered book poignantly addresses the many madnesses one faces in life, playing around with style and structure in ways that deviate from the books read in high school. 17. Siddhartha by Hermann Hesse Via amazon.com Why: Because it's beautiful and highly enlightening. And you'll sound like the smartest freshman on campus.