10 Books That Will Make You Rethink Your Life


There are books we read to lull us to sleep, and then there are the books we read to jolt us awake. You know the difference. Certain page-turners are fun reads, while others enrapture us in a spell — making us revisit our beliefs, goals, and what we’re doing with our one and only life. These books are timeless, transcending trends and pushing us to look at the world deeply, reminding us what we truly want, how we fall, and how we lose track of it all in our struggles and short-sightedness. 

Popular self-help books have their place and can be life-changing in their own right, but these books take “life-changing” to the next level, and will inevitably become a part of you. Mostly comprised of stories (with one exception) — this short list will challenge you as much as it will change you.

The Frontiersmen: A Narrative by Allan W. Eckert

Fair warning: once you start reading this book, you’ll be upset this wasn’t required reading in high school history class. Despite the old western movies, the West was “won” in what’s now the Midwest — in places like Ohio and Kentucky. Although this reads as historical fiction, it’s completely immersive and entertaining, and shockingly entirely true. Eckert, a seven-time Pulitzer Prize nominee, did not embellish as he artfully weaves together a tale of the lives of Native Americans and the rough frontiersmen of the 18th century. You’ll find yourself consumed by the complicated world of the pre-settled wilderness, where good men and evil men are working on the same land. Mainly focusing on the lives of opposing, yet inspiring heroes — Tecumseh and Simon Kenton — you’ll cry, you’ll cheer, and you’ll think: This was when men were men!

Honestly, this is an HBO mini-series waiting to happen. 

Black Like Me by John Howard Griffin

Let’s just say “woke” is an understated way to describe this book. Before the Civil Rights movement took root in 1959, a white-born investigative journalist, John Howard Griffin, wanted to expose the atrocities of racism. Sponsored by the black magazine Sepia, he went undercover as a black man with the help of a dermatologist, UV light, and good ol’ fashion makeup. He began his journey in New Orleans, barely recognizing himself, and eventually moved into the deep South in Mississippi and Alabama, where his new status as a black man put him in real danger. If you struggle with the phrase “white privilege,” reading this piece of shameful history will open your eyes. 

Why I Write by George Orwell

Are you an independent thinker, or do your opinions merely mimic others? This might be an extremely short read — but it’s a profound one. You don’t necessarily need to read Orwell’s more famous works — like Animal Farm or 1984 — to understand how these essays still ring extraordinarily true for contemporary civilization, but you’ll want to after this read. Many of his insights continue to stand the test of time, and will challenge your perspectives on media, politics, and humanity’s messy interpretation of truth. Plus, he can be rather funny — in that cutting, British sort of way.  

Wise Blood by Flannery O’Connor

O’Connor’s first novel might be her most haunting. Filled with wit, satire, shock, this Southern gothic writer gives Game of Thrones a run for its money when it comes to surprise twists. You’ll want to read this a dozen times — it just doesn’t get old. False prophets, stubborn blindness, self-destruction, and wisdom — O’Connor puts us in a front-row seat describing unhinged personalities set in the poor, post-war America of the rural South. It is not for the faint of heart as you witness its 22-year-old protagonist (or antagonist, perhaps?) Hazel Motes struggle with the big questions of life. As one Amazon reviewer states, O’Connor “will slap you in the face with your own prejudices before you can even say ouch.”

A Gentleman in Moscow by Amor Towles

It’s not entirely fair to categorize this book as historical fiction. It’s a love story, it’s a thriller, it’s a modern classic that explores our existential questions and our very human drive for real purpose and meaning. It’s 1922, and the aristocratic Count Alexander Rostov is sentenced to house arrest across the street from Moscow’s Kremlin Palace. Decades pass and Rostov is essentially forced to live a life of contemplation in an attic during one of the most chaotic times in Russia. He is brilliant, witty, and elegant — which is quite the respite in today’s brash culture. If I can’t convince you to read this, consider these words from Bill Gates: “Fun, clever, and surprisingly upbeat . . . A Gentleman in Moscow is an amazing story because it manages to be a little bit of everything. There’s fantastical romance, politics, espionage, parenthood, and poetry.” 

The Screwtape Letters by C.S. Lewis

Imagine this: a pompous devil writing to his dear nephew on how to tempt a man to sin.  The premise might seem absolutely fantastical, but let me assure you, C.S. Lewis makes it feel all too real. Steeped in an astute articulation of human nature, every square inch of our psyche is analyzed in this satire through the rather humorous lens of the high-ranking demon Screwtape, who knows every trick in the book. His efforts remind us that modern-day evil isn’t always super obvious — it’s often cold, calculating, and can be very subtle. As Lewis himself describes: 

“I live in the Managerial Age, in a world of “Admin.” The greatest evil is not now done in those sordid “dens of crime” that Dickens loved to paint. It is not done even in concentration camps and labor camps. In those we see its final result. But it is conceived and ordered (moved, seconded, carried, and minuted) in clean, carpeted, warmed, and well-lighted offices, by quiet men with white collars and cut fingernails and smooth-shaven cheeks who do not need to raise their voice. Hence, naturally enough, my symbol for Hell is something like the bureaucracy of a police state or the offices of a thoroughly nasty business concern.

Crime and Punishment by Fyodor Dostoyevsky

If there’s one thing for certain, you won’t find this famous Russian classic boring. Complex and beautiful, it’s actually incredible how well the language translates into English. It starts with a murder plot, executed on the twisted logic of the psychologically tortured university student Rodion Raskolnikov. Surely, no one would miss a mean, ugly, old pawnbroker, right? That’s the rationale Raskolnikov ultimately acts on to gain a few coins. Taking place in mid-19th century Russia, this is a masterful tale of justice, love, guilt, innocence, beauty — and most profoundly, redemption. As the novel unravels, philosophical debates take life in brilliant character dynamics and genius storytelling as lives touch and truth is revealed. 

The Bell Jar by Sylvia Plath

You won’t think about mental illness in the same way after getting into the mind of Sylvia Plath’s main character. Esther Greenwood has everything — and everything ahead of her. Beautiful, brilliant, talented, highly-educated, privileged, and successful, she has the world at her fingertips — that is, until she starts sliding into a dark psychological breakdown, completely losing herself in insanity. This harrowing tale is made all the more real when you consider the author’s own short life. She tragically died by suicide at the age of 30. Inevitably, you can’t help but wonder if this is actually a secret memoir or a poignantly written cry for help. 

Brideshead Revisited by Evelyn Waugh

This book has everything: love, seduction, war, duty, alcoholism, marriage, divorce, money, power, and death all intertwine in this evocative classic. As an Oxford student in the early 1920s, Charles Ryder meets the charming partier Sebastian Flyte, who is very rich and very bored. Through their relationship, we’re introduced to the entire Flyte family of Brideshead, enigmatic people for their times because they were both Catholic, aristocratic, and divorced. Years later, grown-up and accomplished Charles falls deeply, madly in love with Sebastian’s debutante sister, Julia, and we’re taken on a glittering, spellbound journey filled with joy, frustration, pain, and ultimately redemption — all taking place during the glitzy 1920s and the war-torn 1940s.

Man’s Search for Meaning by Viktor Frankl

How can we not include Frankl’s brilliant take on purpose, life, death, and human existence? Long before he was sent off to a concentration camp in 1942, Frankl, an Austrian Jew, studied neurology and psychiatry, specializing in depression and suicide. 

This memoir, which depicts his time spent surviving three years starvation and oppression by the Nazi regime, is told in two parts. The first section illustrates both the horrors and humanity found in the concentration camp. The second is Frankl’s more psychological discoveries, mainly focusing on “logotherapy.” Frankl’s wisdom, perceptions, and thoughts will shake your worldview and remind you that meaning and purpose can endure in the face of suffering. 

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