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10 Books to Help You Explore Life's Deepest Questions
Matt Karamazov
October 13, 2025 • Estimated Reading Time: 39 minutes
YOUTUBE đź“š CREATOR LAUNCH ACADEMY đź“š PATREON
When I finished reading my 100th book, I thought I was getting to be pretty smart.
Five hundred books into my reading journey, however, I started to realize that the store of human knowledge and wisdom went a lot deeper than I had initially imagined.
Sure enough, when I finished reading Book #1,000 (this one), I was convinced that I was never, ever, ever going to get to a point where I could consider myself “well-read.”
Now, even after reading more than 1,400+ books since 2014, I have more questions than ever before - and certainly more questions than answers. I have precious few of those.
I do have this boundless, insatiable curiosity though, which draws me to deep, fascinating, thought-provoking books like the ten that I have for you tonight!
Before we get into those, I want to pass along an important book that just came out called The Formula for Better Health: How to Save Millions of Lives - Including Your Own.
Written by one of the most influential public health leaders in the US, the book takes on some of the world’s deadliest diseases and shows how we might start turning the tide against them.
Like I said, it just came out, and I haven’t had a chance to read it all the way through yet, but it looks really good! I have a few health books on my TBR, and this is now one of them.
I did finish reading 10 great books last month though, and my full review is up now on YouTube. Like, comment, subscribe - all that “influencer” stuff. You know what to do :)
Now, before our coffees get cold, let’s hit the books!
Tonight, Inside The Reading Life, We’ve Got:
“If thou wouldst right the world, and banish all its evils and its woes, make its wild places bloom, and its drear deserts blossom as the rose - then right thyself.
If thou wouldst turn the world from its long, lone captivity in sin, restore all broken hearts, slay grief, and let sweet consolation in - turn thou thyself.
If thou wouldst cure the world of its long sickness, end its grief and pain, bring in all-healing joy, and give to the afflicted rest again - then cure thyself.
If thou wouldst wake the world out of its dream of death and dark’ning strife, bring it to Love and Peace, and Light and brightness of immortal Life - Wake thou thyself.”
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This month’s book is How To: $10M, by William Brown, a great business book that contains everything you need to know about scaling a coaching and/or e-learning business to more than $10,000,000 in revenue.
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After achieving my (somewhat meaningless) goal of reading 1,000 books before I turned 30, I set a new (also meaningless but cool) goal of reading 10,000 books. As of today, I’ve read exactly 1,422 books, including 68 books so far this year, and if you’re interested, here’s my full Reading List.
“The pathless path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It's a call to adventure in a world that tells us to conform. For me, it's also a gentle reminder to laugh when things feel out of control and trust that an uncertain future is not a problem to be solved."
The chances of a perfect life path being successfully scripted for you by someone else are precisely zero. We exist in a community of others, but individually, we are completely alone and our lives are up to us.
More than that, we have the opportunity - the ability - to curate our own reality every moment, and by definition, no one can do this for us. We think that the meaning of life is "out there" and that we have to find out what it is. When in reality, it is Life that asks us the questions, and how we live is our answer.
In the same way, Paul Millerd doesn't have any answers. There are no hacks or step-by-step formulas in this book, no mandatory reading lists, and no milestones you have to hit in order to live a meaningful life.
Instead, The Pathless Path is about the invisible scripts that shepherd us into prescribed modes of living and being in the world; it's about freedom and creativity; it's about money, meaning, and work; and it's about being fearlessly, unapologetically yourself, in a world that shouts back, "You can't do that!"
It's also about going somewhere, but not following anything. Getting lost, and finding yourself. Leaving, but never arriving.
The default path - doing what everyone is doing, living the same day, week, month, and year that everyone else is living over and over again - used to work for most people. But this future that we're building together is not a default future.
We have so many more options and opportunities - possibilities for our lives that we can explore and take to their logical conclusions. The default path is dying away, and we have to come to terms with our own freedom and what we want to do with it.
I mean, here you are, the universe's most spectacular creation, and you're just kinda getting by. Living a "good enough" life, surviving day to day, coasting through a default world you never made.
The Pathless Path is Paul Millerd's answer to the question of what makes meaningful work and what we might aspire to in our lives. But you and I can never be Paul Millerd. His life is taken. You can only be yourself, and I can only be myself. The pathless path is narrow, wide enough for only one person. You.
Difficulty Rating: Easy
Deep Questions It Addresses: If you’re trapped on a life path (especially when it comes to your career) that some part of yourself knows isn’t right for you, this book will help you imagine a different path and play with different possibilities.
“Though there is a higher and wider significance to life, of what value is our education if we never discover it?”
I always describe Krishnamurti as someone standing between Friedrich Nietzsche and Jesus. Uncompromising in his stance against ideology, conformity, and antagonism between human beings, he always refused to set himself up as a teacher.
While he was alive, he used to insist that no one should blindly follow what he said as though he were some sort of authority.
You’ll notice, in fact, that most of the time Krishnamurti just keeps asking questions.
If you break down the transcripts of some of his public talks, it’s rare that he’ll make a concrete statement. He wants you to think for yourself. He wants you to question what you’ve come to believe is self-evident. He wants you to question the dominant culture of acquisitiveness, envy, ambition, and groupthink.
In this collection, the focus is on education, of course, and he says that there is no “method” that one can follow to become “educated,” if there’s ever an end to education at all. Intelligence is not separate from love.
True education is a movement of the mind away from fixed structures and prepackaged beliefs. It is the approach toward the essential, away from the superficial. Not in the past or in the future, but grounded in the present.
Difficulty Rating: Moderate
Deep Questions It Addresses: Krishnamurti forces you to question your longest-held values and beliefs, and helps you realize that there’s much more to discover about life than you’ll ever be taught in school.
“I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived.”
For some reason, I still remember that this was the 133rd book that I had ever read since I started counting. No idea why I remember that. Maybe it’s because Walden was one of the first books to hit me so hard and fast that it shook me alive as I was reading it and forever after.
Published in 1854, it's the nonfiction account of the time when American transcendentalist author Henry David Thoreau built his own cabin in the woods at Walden Pond and lived there by himself for two years.
It’s about the calming, reorienting power of solitude, about the transformative power of great books, and it’s about how to leave society once in a while so that you can be better prepared to return to it.
We often get caught up in our cares, concerns, and Twitter feeds, and all these demands on our attention tend to crowd out that inner voice we all need to listen to once in a while if we are ever to understand our own lives or what we want them to be about.
I doubt there are too many people in North America today who would be able to live by themselves in the woods for two years, but I’m sure that most of them would be much better off for doing it.
There are some truly profound and memorable observations scattered throughout these pages, and like I said, this book just completely took me over when I first read it in 2015.
You don’t have to move to the woods like Thoreau did in order to become a real person and reconnect with your authentic voice, but it sure as hell helps.
Difficulty Rating: Moderate
Deep Questions It Addresses: Sometimes you have to get away from everything for a while to get a really clear view of your life, and Thoreau might inspire you to take a hard look at many of the societal conventions we just blindly accept.
“Your worst sin is that you have destroyed and betrayed yourself for nothing.”
Crime and Punishment is a major Russian novel about Rodion Raskolnikov, a young, impoverished student in St. Petersburg. It’s the story of how he comes to murder and rob an old woman in what he convinces himself is an altruistic act, and of his subsequent complete psychological disintegration.
It’s one of Dostoevsky's most significant works, and a layered literary masterpiece that set the standard for psychological thrillers ever after.
The central moral question of the book, in my view, is whether a brutal act (in this case the murder of an old woman with an axe) can ever lead to good. You might not think that’s even a question! Of course that’s terrible and wrong and could never be justified…read the book.
You can also make a connection between the character of Raskolnikov and a kind of underdeveloped “Overman,” as described by Friedrich Nietzsche in Thus Spoke Zarathustra.
Raskolnikov believes that most people simply aren’t capable of taking drastic, courageous, aggressive action to change their lives or effect real change, and that only a relative few people throughout history have possessed the qualities necessary to radically alter their circumstances.
The book itself is an incredible read, just packed with suspense and populated with vividly realized characters you almost can’t believe wouldn’t be found in a real history book somewhere. None of these people existed, and yet, for the entire time you’re inhabiting Dostoyevsky’s creative world, nothing else exists.
Would I murder an evil old woman and redistribute her ill-gotten wealth to people who were more deserving? Would you? What’s stopping us?
Crime and Punishment was also the very first book I finished, ever since I decided to track the number of books I read, beginning in 2014 and continuing up to the present day.
It started me on a path to read more than 1,000 books before I turned 30. And after engaging with it, pondering it, pushing through it to the end, Dostoyevsky’s brilliant philosophical novel helped give me the confidence to imagine that I could read 1,000+ books: difficult ones, the greatest ones; and that if I could finish this masterpiece, there were also potentially thousands of others that I would eventually come to love too.
Difficulty Rating: Moderate
Deep Questions It Addresses: Questions of morality and justice abound in this one, as well as...just about everything else. This is a novel (and novelist) that touches on sooo many aspects of the human experience, and he’ll have you questioning your entire life up until this point before you even hit chapter 5.
"Regret is not dangerous or abnormal, a deviation from the steady path to happiness. It is healthy and universal, an integral part of being human. Regret is also valuable. It clarifies. It instructs. Done right, it needn't drag us down; it can lift us up."
It's more or less a universal human experience to look back on the path we never followed and feel a nagging, painful, sometimes sinking, sickening feeling that we've somehow missed our chance, that we've traded our many unlived lives for this one, real life, and that it could have been so much better had we simply acted differently.
Virtually everyone has experienced something to the same effect, ranging from the "that might have been nice," to the "damn, I really should have done that," all the way to the "I've thrown it all away and I'll never, ever recover from this."
Anyone who says that they have no regrets is also usually viewed with suspicion by most people who have taken the time to reflect on their own personal history.
In this book, The Power of Regret, Daniel Pink refers to regret as our most misunderstood emotion and shows how it can potentially be transformed, transmuted into something extraordinarily valuable. We can reflect on our regret, reorganize it in our minds, reconceptualize it, and then use it to live better with all the time we have left.
What's more, navigating regret (and life) is always an ongoing process of closing certain opportunities while at the same time opening new ones. Every action we take determines the possibilities that are available to us in the next moment, and we are always choosing, even when we do nothing.
But we are not helpless against regret, as Daniel Pink argues in this book. We can enlist this misunderstood, potentially painful emotion in service of living a larger life, gaining redemption, and reclaiming at least a portion of our remaining unlived lives.
Difficulty Rating: Easy (But Potentially Painful)
Deep Questions It Addresses: Obviously this book will help you think more deeply about regret and the path not taken, but it’ll also give you clarity and insight when it comes to how you should live from this day forward.
“All the analysis in the world doesn't allow the person to find out who he is, why he is here on earth, why he has to die, and what he can do to make his life a triumph.”
This book about the subconscious fear of death and how it motivates much of human behavior won the Pulitzer Prize in 1974, but the man behind the book was just as interesting as its subject matter. I never met the guy, but he might just be one of my favorite university professors.
Becker taught at the University of California, Berkeley, where he was so beloved by his students that they once got together and offered to pay his salary after learning that the university wasn’t going to renew his contract!
Many times - while teaching, for example, King Lear, anthropology, and whatever else - he’d come to class in full costume, full of life and energy and enthusiasm for learning. When he died at the age of 49 from colon cancer, the academic world lost someone very special, and I’d personally recommend several of his other books too, including The Birth and Death of Meaning, and Escape from Evil.
The Denial of Death is one of my favorite books, and its main thrust is that being alive - as fragile beings with no satisfying explanation for why we’re here - is so terrifying that in response to this realization, the majority of people retreat into a socially constructed self that basically forms a psychological defense against the reality of death.
Becker also believed that these psychological defenses prevent us from discovering who we really are, and not only that, are also responsible for much of the evil that’s present in the world.
It’s not an “easy” read, by any means, and one of its strengths is that it gives a person very little room to hide, or rationalize away his conclusions.
With brilliantly reasoned arguments, he shows how this subconscious fear of death limits our lives, prevents accurate self-knowledge, and, if not surmounted through the pursuit of “genuine heroism,” casts a dark shadow across our full human potential.
Difficulty Rating: Moderate
Deep Questions It Addresses: Connecting with your own death can help bring clarity and focus to the potential meaning of your life. The potential meaning. Other philosophers like Heidegger pointed out that we’re just “thrown” into this world, but the fact is that we’re here, we don’t know for how long the privilege will be ours, and we’re forced to come to terms with how we can make our lives matter for having taken place.
“What we are, of that we make the world.”
This book was my first introduction to Krishnamurti, and he took me completely by surprise with his total rejection of authority, and his insistence on seeking the truth for oneself, not relying on any external sources of knowledge or truth.
The Revolution from Within is a collection of public talks he gave throughout the world in the 1950s, where he asks, again and again, whether or not the mind can be free of its own projections, and whether the limited human mind can ever perceive the unlimited nature of ultimate truth.
In fact, Krishnamurti speaks mostly in questions. He proceeds very slowly, and uncovers more and more questions in slowly escalating stages, the whole point of which is to provoke independent thought and objectless awareness in the minds of his listeners.
If Jiddu Krishnamurti had a dominant message, it would be that there must be a revolution in our thinking. Not an outward revolution, which is just the continuation of conditioned thought, slightly adapted according to some other philosophy (whatever it may be), but a complete and total rejection of external authority, ideology, and belief.
The whole book is just incredible, covering ideas as diverse as war and global conflict, parenting and relationships, education, spiritual belief, critical thinking, self-awareness, and personal freedom.
After I finished reading the transcript of each lecture - and even while I was reading them - I could feel myself being transformed. I knew that I’d never live the same way again, see the world the same way again, and sure enough, I never did.
Difficulty Rating: Moderate
Deep Questions It Addresses: Again, Krishnamurti was just one of those people who could, with a simple question, shake your most deeply-held beliefs. This book will cause cracks to form in your existing worldview and ask you to face your life without having any “safe” beliefs to fall back on. Your life will never be the same.
“Reasonableness and generosity do not remake an intrinsically meaningless universe, but they have their own dignity.”
Martha Nussbaum is one of the most brilliant thinkers I’ve ever discovered in all my wide reading, and, just as the title would suggest, this book is about something that not only surrounds us, but can also overtake us, causing even the best of us to lose a bunch of IQ points: anger.
I was a nightclub bouncer for over a decade, and so I’ve seen some anger in my day. I’ve felt its corrosive influence in my own life, and I’ve seen its deleterious effects on the wider society.
So I’m especially grateful for someone of Nussbaum’s brilliance to come along and show us what we’ve all been missing when we talk about anger - and its equally misunderstood corollary, forgiveness.
Nussbaum claims in her book that people are generally confused about anger: about when they should be angry, if ever, and about the role it plays in both public and private life.
Most striking (no pun intended) of all for me was her dissection of the current, retributive criminal justice system. We seem to have this erroneous belief that if we make someone else suffer for what they’ve done to us, or to our community, this will make the first injury somehow disappear.
But even in the private sphere, we have so many ill-conceived notions about anger, so many half-formed thoughts and vague ideas about what it’s good for and where its limitations lie, which make it so urgently necessary that we clarify our thinking before we let anger spin out of control, and let forgiveness lose its redemptive power.
For example, if you don’t get angry, do you really care? Do you have an ethical obligation to get angry at injustice? Or does your anger invariably cloud your judgment? If you don’t get angry, will you ever have the requisite motivational drive to change and improve your life? These are just a few of the questions she raises.
Where forgiveness is concerned, is it really the best way of transcending anger? Or does it sometimes cheapen itself by disposing us towards projects of humiliation and diminishment of the “other” as a condition of abolishing our anger? Is forgiveness always good everywhere, and anger always bad everywhere?
We need a closer look. We need Nussbaum.
She’s clear-thinking and wise and kind and generous, and she’s exactly the kind of guide you should wish for when you’re looking to understand the all too human emotion of anger.
Currently, she's the Ernst Freund Distinguished Service Professor of Law and Ethics at the University of Chicago; she also has more honorary degrees than I’ve been alive, and I absolutely loved her thought-provoking book.
Difficulty Rating: Moderate
Deep Questions It Addresses: Nussbaum focuses here on questions of anger, revenge, and retribution, and asks what place they have within our criminal justice system and society at large.
“The difference between people more or less intelligent is like the difference between prisoners condemned to life in prison whose cells are more or less large. An intelligent man who is proud of his intelligence is like a prisoner who is proud of having a big cell.”
I’d like to introduce you to one of my favorite people ever. Her name is Simone Weil, and I’ve learned more from her than almost anyone I’ve ever read or been in contact with, ever. That’s three “evers” I just used. That shows you how serious I am!
She might actually be one of the greatest and most compassionate human beings who ever lived, and whenever I think of truth, or goodness, or beauty, or justice, I tend to think of her.
She taught me how to listen, how to really “see” other people, how to demand the most from myself, and how to give the most of myself. In fact, Albert Camus called her “the only great spirit of our time.”
This was back in the middle of the 20th century, as she died in 1943 at the age of 34. Why so young? The answer is that she starved herself to death - defying her doctor’s orders to eat - in solidarity with the French citizens living under Nazi occupation during World War II.
She refused to eat any more food than the French people were allowed to eat (she was living in England at this time) under German rule, and with eating such a small amount of food, she died of malnutrition.
I have mixed feelings about this.
Of course, what she did was so completely selfless and incredible and totally in line with who she was as a person and with what she believed to be true.
On the other hand, what could such a brilliant philosopher like her have contributed through her works that would have had a much larger positive impact on the future health of humanity? No one knows, and that’s part of the tragedy and absurdity of her death.
What you almost have to respect about her though is her total commitment to her ideals. Unlike pseudo-intellectuals like Karl Marx and friends, she actually spent time working in factories herself so that she could understand more about the life of the urban poor and gain insight into what they were actually like and what they needed.
She didn’t disdain physical labor but instead embraced it as a chance to get closer to what’s most real. She thought it unusual - as I do - that we complain about low pay, but not about soul-crushing work itself. It’s like saying, “That’s not enough money! My soul is worth at least twice that amount!” Ridiculous, right?
As I hope you’ll see from these book notes below, Simone Weil was a very special philosopher, a woman of unimpeachable intellectual honesty, and the possessor of the type of limitless compassion - and stubbornness - that could have only ended with her death. In so many ways, I just wanna be like her!
Difficulty Rating: Moderate
Deep Questions It Addresses: Simone Weil was a Christian “mystic” of sorts, and so a lot of the themes she deals with in her work have to do with religious faith, redemption, ethics, virtue, and compassion. But you don’t have to identify with a particular religion to be profoundly changed by her positive influence.
“Socrates exposed himself to death for the sake of virtue. He preferred to die rather than renounce the demands of his conscience, thus preferring the Good above being, and thought and conscience above the life of his body. This is nothing other than the fundamental philosophical choice."
If you took a few required philosophy courses in university, hated it, and subsequently wrote off philosophy forever as “not really my thing,” then it probably wasn’t philosophy.
You might have heard some version of this joke where a doctor is asked what he specializes in, and the doctor replies, “I specialize in the treatment of the left earlobe.” The joke is that medicine has become so ultra-specialized and exact - finely technical - that you could have a specialization like that and no one would know if you’re even joking or not!
Well, it’s kind of the same thing in philosophy nowadays. It’s become so unbelievably stuffy and academic that you could present a thesis on “Semiotic De-Temporalization in Abstract Existentialist and Metaphysical Meta-Realities” and you’d probably get your doctorate! Did I make that up? Or is it a real thing? Who knows!
Anyway, it’s so far away from the actual philosophy that real people used to practice to, you know, improve their lives! Hadot’s book is about real, honest to goodness philosophy (a word that means love of wisdom), and it’s about real people (everyone from slaves to Roman Emperors) who used it to become mentally stronger, more joyful, less afraid, and more fully alive.
I won’t say that this is an easy read because it’s not. It’s more of a philosophy textbook than something you’d bring with you to the beach, but the whole purpose is to show you that philosophy’s a real, live activity, that can actually improve your one and only life.
Reading it, you’ll see why people like Socrates felt that real communication with other human beings was infinitely superior to knowledge gained from books, how Marcus Aurelius used philosophy to help him run the Roman Empire without losing his mind, and how you can go from where you are now, to where you want to be.
Difficulty Rating: Moderate
Deep Questions It Addresses: This book draws attention to the wonder and magic available to witness all around us - literally at any moment, no matter where we are, who we’re with, or what we’re doing. It’s a philosophy book about how to live, but it’s also about why is worth living, and about all the fascinating questions and experiences we can open ourselves up to if we’d just notice they’re there.
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OK, that’s it for now…
I’ve got plenty more excellent book recommendations coming your way soon though!
There’s also my YouTube channel, where I publish book reviews, reading updates, and more each week.
And if you want to learn how I’ve built an audience of 170,000+ followers across social media, became a full-time creator, and how I’m rapidly growing my audience and scaling my profits in 2025, join us inside Creator Launch Academy and that’s exactly what I’ll teach you — we’d love to have you in the community!
With that said, I hope you enjoyed this edition of The Reading Life, and enjoy the rest of your day!
Until next time…happy reading!
All the best,
Matt Karamazov
P.S. Whenever you're ready, here are two more ways I can help you:
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