If I could go back in time to high school, I’m not sure I could resist the urge to grab my teenage self by the shoulders and shake her. (Not that I’m so wise now but... ) Like pretty much anyone else, I made some questionable decisions in high school — and not just in the fashion arena. Actually, those super-loud floral Converse? I’d totally still wear them if they hadn’t died a tragic death by bleach. But, anyway, your typical high-schooler, I toed the line between utter confidence at how my future would turn out (yup, ignorance is bliss) and a too-shaky self-esteem that hung on the opinions of others.

My personal kryptonite? Likeability. It’s a hot topic nowadays, but back when I was in school, it felt like it was — unquestionably — my obligation to be nice and polite, mild and accommodating. As a natural people pleaser, the hat fit just right. But the time I spent trying to fulfill others’ expectations clouded my sense of who I was and what I wanted. It wasn’t until later (than I care to admit) that I realized happiness is kind of more about having the confidence to rock the boat and knowing you can deal with the things that have fallen overboard.

This is only one thing I wish I’d learned in high school. I also wish I’d smiled less (when I didn’t want to), yelled more (when the situation merited it), and slept in every. single. Saturday. But frankly it would probably be more productive to hand my high school self a stack of the following books than to attempt some sort of (pretend) adult lecture.

Bad Feminist by Roxane Gay

Looking back, I really do think I’d cringe less at my choices if I’d read a little bit more about feminism — not feminism in theory, but contextualized into an author's life experiences. Gay’s take on feminism is awesome and important because it’s not dogmatic, but rather reflective and personal.

Click here to buy.

Yes Please by Amy Poehler

Frank, funny, and fierce, Amy Poehler is the perfect role model at any age. Her catchphrase (well, one of many) “Good for her, not for me” perfectly encapsulates a lesson it takes many of us a lifetime to grasp. The time we spend comparing ourselves to others is time wasted, wiled away. And who has time for that?

Click here to buy.

North and South by Elizabeth Gaskell

Elizabeth Gaskell is the 19th century’s most underrated author. She gets overshadowed far too often by Jane Austen, but Gaskell was not only a trailblazer in the world of the serialized novel, she also wrote one of the sassiest, most compelling heroines of the time. While I’ve heard people brush North and South aside as Pride and Prejudice’s lesser plot-cousin, plot outline aside, these novels are very different — and Margaret Hale is just as worthy an opponent as Elizabeth Bennet. In North and South, Gaskell explores human relationships in tandem with the social and economic changes of the industrial era, tackling subjects of especial relevance today: economic inequality, social class, access to opportunities.

Click here to buy.

Middlemarch by George Eliot

Bear with me. I know Middlemarch is a veritable brick of a novel but it is as wise as it is heavy. If there has been one novel that has shaped the way I see the world and the person I want to be, it is Eliot’s magnum opus. Her claim that all of us have an “equivalent center of self” is an oft-repeated mantra in my day-to-day life. None of us is the center of the universe. (Not even Ted Cruz). It is only when we realize how laughably unimportant we are — how sometimes we’re the hero, sometimes the bad guy, and sometimes we’re just a detail, a footnote in someone else’s story — that we can begin to focus on the truly important stuff outside us, like how to make sure we leave behind a world that’s slightly better than the one we arrived to.

Click here to buy.

The Brief Wondrous Life of Oscar Wao by Junot Díaz

Here’s hoping this one makes it onto many a high school required reading list! Díaz’s debut novel features Oscar de Leon, nerdy Dominican kid with big literary aspirations and an even bigger heart. Told primarily through the eyes of Yunior (a complex, whip-smart character who resurfaces throughout Díaz’s works) this roller coaster of a novel tackles the subject of identity in its many iterations: personal, social, cultural. I won’t say the story of Oscar’s life is particularly cheery or inspirational, yet Díaz’s ability to touch on chords of tragedy and comedy simultaneously is refreshing and real.

Click here to buy.

The God of Small Things by Arundhati Roy

This haunting family saga took home the 1997 Man Booker. A thoughtful and incisive exploration of love, pain, and trauma breaking through class lines, this novel probes at the humanity in all of us, even those who, like dark-skinned carpenter Velutha, an “untouchable,” seem deemed by society to be inhuman. Primarily the story of twins Estha and Rahel, The God of Small Things is a lyrical page-turner.

Click here to buy.

Opened Ground by Seamus Heaney

Heaney is a poetic master and Opened Ground, a thoughtful, well-curated collection, is a great place to start with his writing. Among many other things, Heaney is concerned with Irish politics and the limitations imposed on us by spending time in the classroom instead of the fields. In his famous poem Digging, Heaney writes: “But I’ve no spade to follow men like them” in reference to his farmer dad and grandfather. But he finds that his own writing, his academic prowess, is his own weapon, his tool: “Between my finger and my thumb, the squat pen rests. I’ll dig with it.” Whether or not you’re entering a higher education portion of your life, it’s important, I think, to worry about the way books can distance you from life or help you engage more deeply with it.

Click here to buy.

Ella Enchanted by Gail Carson Levine

I know this book is meant for a younger audience, but, come on, Ella Enchanted is timeless. Ella is a fascinating heroine to boot: intelligent, kind, witty, tough-as-nails… though she’s been under a vow of obedience since she was a baby, Ella still manages to be as outspoken and rebellious as she can. She can teach us a lesson or two about resilience and about true selflessness in love.

Click here to buy.

Looking for Alaska by John Green

When Miles Halter decides to leave home during his junior year to attend boarding school, he tells himself: “I go to seek a Great Perhaps,” the last words of poet Francois Rabelais. Miles has a strange obsession with famous peoples’ last words, believing that the final sentences someone utters say a lot about how that person lived. When he meets Alaska Young at school, he is blown away by her wisdom, beauty, and intensity: “if people were rain, I was drizzle and she was hurricane.” But tragic events unfold that leave Miles reeling and questioning his decision to live an examined life.

Click here to buy.

The Little Prince by Antoine de Saint-Exupéry

I refuse to tell you just how many times I’ve watched the trailer for the upcoming Little Prince film, but I will say this is one of the wisest, sweetest books ever written.

Click here to buy.

The Glass Castle by Jeannette Walls

Jeannette Walls’s harrowing memoir about her unconventional, nomadic childhood will break then mend then break your heart. In The Glass Castle , Walls recounts the adventures of her childhood, examining the ways that she and her siblings first embraced and then tore themselves away from the life their parents—Rex, the impulsive dreamer, and Rose Mary, the irresponsible, irrepressible artist—created for them. A wise and lyrical tale of grit and survival.

Click here to buy.

The Orange Girl by Jostein Gaarder

Gaarder is best known for Sophie’s World, his very relatable history of philosophy. However, this short sweet novel asks some of the same questions that have plagued philosophers for centuries. Georg Røed’s dad died when he was four. At 16, George comes across a letter and story that his dad left behind for him in the lining of his red stroller. What is our place in the universe? What if we had never existed? How many loves do we get in our lifetime? Simple and beautifully told, this book is much deeper and more complex than its title suggests.

Click here to buy.

A Little Princess by Frances Hodgson Burnett

I know A Little Princess is also meant for a younger audience, but Hodgson Burnett’s novel makes more statements for equality and humanism than most books aimed toward older audiences. The illustrious Sara Crewe has grown up as the much-indulged daughter of a rich ex-pat in India but she is intelligent enough to as the same question that opens Michael Sandel’s philosophical treatise Justice: Why do we have what we have? Do we deserve it? Or is it purely accidental that we’re living this life instead of another?

Click here to buy.

Things Fall Apart by Chinua Achebe

Achebe needed to be on this list, if only because everyone should read the Nigerian wordsmith at some point in their lives. I didn’t read Achebe until my second year of college, yet Things Fall Apart shifted my approach toward literature and history, and helped me think about the ways in which social and political contexts have shaped my own reading choices.

Click here to buy.

Who Can Throw the First Stone? by Mario Benedetti

I will admit that when I read this book in high school, I completely missed the point. It was, after all, a school assignment, so I probably rush-read it during a quick break between tennis and dinner. But when I picked up the Uruguayan writer’s short novel about a year ago, I realized I should have paid much closer attention. This book is, essentially, about perspective. Alicia, Lucas, and Miguel form a complicated love triangle and they are never on the same page; the book lends insight into how each of them experienced their joint romantic history. “Who can throw the first stone?” Benedetti asks, when every single one of us has at some point failed to live up to the best versions of ourselves.

Click here to buy.

What We Talk About When We Talk About Anne Frank by Nathan Englander

A bold, fearless short story collection. Englander writes with skill and wit about subjects other authors might choose to shy away from. Equal parts hilariously grating and sensitive, Englander has one of the most unique voices in contemporary literature.

Click here to buy.