Best Philosophy Books: 14-Day Challenge to Think Deeper & Live Better

Looking for deeper meaning and clarity in life? This 14-day challenge explores the best philosophy books, distilling timeless lessons on decision-making, resilience, and personal growth.

Day 1

Meditations by Marcus Aurelius is a classic of Stoic philosophy and shows us how to become more self-disciplined, stop caring what people think, and control our emotions.

The author was a powerful Roman Emperor about 2,000 years ago and wrote down these ideas in a private journal to himself.

"Choose not to be harmed—and you won't feel harmed. Don't feel harmed—and you haven't been." —Marcus Aurelius
Day 2

Man's Search for Meaning was written after Viktor Frankl survived the concentration camps of WW2.

He noticed that his fellow prisoners who could find purpose and meaning in their suffering found the strength to survive, while others perished.

This book is also a guide to finding meaning in your life.

"Everything can be taken from a man but one thing: the last of the human freedoms—to choose one's attitude in any given set of circumstances, to choose one's way." —Viktor Frankl
Day 3

The Alchemist by Paulo Coelho is a simple yet profound story about a shepherd boy named Santiago who follows his dreams, going on a journey to find treasure in Egypt.

Along the way, he finds love, danger, and wisdom.

The book inspires readers to listen to their hearts, risk adventure, and seek life's meaning.

"There is only one thing that makes a dream impossible to achieve: the fear of failure." —Paulo Coelho
Day 4

Ikigai is about finding our life purpose and living longer, according to wisdom from Japan where people do live longer than average.

The key ideas include: doing activities that make us feel 'flow', nurturing enjoyable relationships, keeping busy after retirement, and daily light eating and exercise.

"Concentrating on one thing at a time may be the single most important factor in achieving flow." —Hector Garcia

Why read it?

This book sends you on a heroic quest to uncover your life's secret mission—minus the tights and cape.

Your ultimate purpose is *spoiler alert* probably not binge-watching the latest series, but finding that sweet spot where your passion, mission, and other people's needs intersect.

Sounds intimidating?

You don't need to cure cancer.

It's just about finding a reason to jump out of bed in the morning, even if it's about feeling joy in the little things with a community you belong to. 🕺

Day 5

Letters from a Stoic is about how to stop feeling unsatisfied in life or worried what people think.

Seneca says we must first reduce our desire for pleasure, wealth and social approval.

Then we can become less fearful and hesitant with techniques like remembering that we're all gonna die.

"If you really want to escape the things that harass you, what you're needing is not to be in a different place but to be a different person." —Seneca
Day 6

12 Rules for Life is about putting your life in order and taking responsibility for what happens.

Jordan Peterson begins each chapter with a simple Rule like "Stand up straight" then he launches into thought provoking lessons from science, religion, history and psychology.

"In the West, we have been withdrawing from our tradition-, religion- and even nation-centred cultures, partly to decrease the danger of group conflict. But we are increasingly falling prey to the desperation of meaninglessness, and that is no improvement at all." —Jordan B Peterson
Day 7

Sapiens is about how we went from being simple primates 2.5 million years ago... to walking on the moon.

Yuval Noah Harari explores the Cognitive, Agricultural and Scientific Revolutions, which made us who we are today.

He says common myths like money, laws and nations hold human societies together.

"Just 6 million years ago, a single female ape had two daughters. One became the ancestor of all chimpanzees, the other is our own grandmother." —Yuval Noah Harari
Day 8

The Black Swan is about understanding unpredictable extreme events like the 9/11 attacks, rise of the internet, and stock market crashes.

Nassim Taleb says we are unprepared for the next big event like this because we rely too much on incomplete theories, limited models and flimsy historical narratives.

"Years ago, I noticed one thing about economics, and that is that economists didn't get anything right." —Nassim Taleb
Day 9

Discourses of Epictetus is a compilation of lectures on Stoic philosophy from almost 2,000 years ago.

The book delivers timeless wisdom that continues to be intensely practical, guiding us on how to stabilize our emotions, become more self-disciplined, and live a good virtuous life.

"There is only one way to happiness and that is to cease worrying about things which are beyond the power of our will." —Epictetus
Day 10

Homo Deus offers a thought-provoking look into humanity's future; It talks about how advances in technologies like artificial intelligence and genetic engineering could radically transform us.

Yuval Noah Harari proposes the uncomfortable notion that we may try to become like gods to avoid death and unhappiness.

"This is the best reason to learn history: not in order to predict the future, but to free yourself of the past and imagine alternative destinies." —Yuval Noah Harari
Day 11

The Power of Myth explores how stories shape our perception of the world, and why myths continue to be relevant in providing direction to our lives in modern times.

Joseph Campbell explains universal lessons from myths, like discovering our personal "Hero's Journey" and following our bliss.

"Follow your bliss, and the universe will open doors where there were only walls." —Joseph Campbell
Day 12

Civilization and Its Discontents was written by Sigmund Freud, possibly THE most influential psychologist of all time.

He said people are unhappy in modern society because they are forced to suppress many of their instincts for sex and aggression.

"Beauty, cleanliness and order plainly have a special place among the requirements of civilization." —Sigmund Freud
Day 13

The Way of Zen is a comprehensive introduction to Zen Buddhism, including the history and practices.

Alan Watts explains how the ancient Chinese philosophy of Taoism combined with Indian Buddhism to form Zen.

He also shares many practices of Zen such as meditation, koans, and arts.

"..." —Alan Watts
Day 14

The Subtle Art of Not Giving a F*** is like your smart but impolite friend explaining some great lessons from philosophy.

Mark Manson shows how to live by your values so you can act with less hesitation, do what's most important to you, and stop worrying what people think.

"Who you are is defined by what you’re willing to struggle for." —Mark Manson
📚 Bonus Books: These are extra recommendations to go beyond your challenge!
Day 15

1984 is a novel about a terrifying future where everyone is controlled by a totalitarian political "Party" led by "Big Brother." George Orwell predicted many real-life methods of government overreach including: strict censorship, mass surveillance, "Thought Police," manipulation of language, and rewriting history.

"Who controls the past controls the future. Who controls the present controls the past." —George Orwell
Day 16

The 48 Laws of Power by Robert Greene is a self-help book that explains how powerful people have gained and maintained their control over the centuries.

While controversial for its manipulative tactics, this book also shares eye-opening insights into history, strategy, and human nature.

"Powerful people impress and intimidate by saying less. The more you say, the more likely you are to say something foolish." —Robert Greene
Day 17

As a Man Thinketh says our thoughts set the course our life, not our circumstances.

James Allen says thoughts are seeds for actions, so our mind is a garden where we must cultivate the right seeds.

This short, inspiring book still influences many modern self-help teachers.

"Men do not attract that which they want, but that which they are." —James Allen
Day 18

Thinking, Fast and Slow explains how people make decisions using two mental systems: "fast" thinking is instinctive and emotional, while "slow" thinking is deliberate and logical.

Daniel Kahneman helps us understand our when our mind fall into common biases and irrational shortcuts, so we can make better decisions in the future.

"A reliable way to make people believe in falsehoods is frequent repetition, because familiarity is not easily distinguished from truth." —Daniel Kahneman
Day 19

Maps of Meaning says that myths have a tremendous unseen value.

They laid the foundation for large, stable and successful civilizations that lasted thousands of years.

Myths also provide time-tested wisdom to help us eradicate evil in the social world, and move past unpredictable catastrophes in our personal lives.

"I don't think that you have any insight whatsoever into your capacity for good until you have some well-developed insight into your capacity for evil." —Jordan B Peterson
Day 20

The True Believer shows how the same human frustrations drive all mass movements—whether social, political or religious.

People join mass movements to escape their ineffectual and helpless individual self.

Eric Hoffer wrote this book 70 years ago, but it's still frighteningly relevant today.

"Faith in a holy cause is to a considerable extent a substitute for the lost faith in ourselves." —Eric Hoffer