Chad James Reading List – 2025 Edition
My most recommended books for entrepreneurs and small business owners.
It’s been a while since I overhauled this list—and it was overdue.
This is my freshly sharpened 2025 reading guide. I kept the core titles that still punch above their weight and cut the ones that now feel dated, fluffy, or off-purpose. I also added newer books, published mostly in the last five years, that go deeper, hit harder, and align with the level you're operating at now.
Some are tactical. Some are strange. All of them are meant to provoke movement, not just reflection.
Oh, and I added a fiction section, too. Because some truths don’t land through frameworks or formulas. They have to be felt.
Timeless & Seminal (Keepers)
These books earned their place and kept it. I didn’t keep them out of sentimentality or habit, but because they still hit with force. Their relevance hasn’t faded; it’s deepened. In fact, with everything that’s changed in the world (and in how we build, lead, and live), these titles feel even more essential now than when I first picked them up. They speak to fundamentals—creativity, discipline, integrity, awareness—that don’t go out of style.
The War of Art – Steven Pressfield
The battle isn't out there—it's in here. A field manual for facing down Resistance and finally doing your real work.Turning Pro – Steven Pressfield
The life-changing moment isn’t when you "make it." It’s when you decide. Becoming a pro is a choice—and a war against distraction, numbing, and shadow comforts.Awareness – Anthony de Mello
Part spirituality, part slap in the face. This book wakes you up to how asleep you really are—and how simple, honest awareness can change everything.Love is Letting Go of Fear – Gerald Jampolsky
Short, strange, and potent. It’s about the radical idea that most of what you call “problems” are just fear in disguise. Forgiveness becomes a power move here.The Way of the Superior Man – David Deida
A masculine operating manual that doesn’t pull punches. Cringe in a few spots, sure—but the core message about purpose, polarity, and grounded integrity is fire.The Obstacle is the Way – Ryan Holiday
A modern Stoic classic. The things you’re trying to avoid? They’re actually the path. Flip adversity into advantage.Deep Work – Cal Newport
How to build a fortress for your attention and go monk-mode on what matters. A cornerstone book for the distracted entrepreneur.Extreme Ownership – Jocko Willink & Leif Babin
No blame. No excuses. Just total ownership. Turns leadership from a concept into a way of life.The Dip – Seth Godin
Don’t quit too early. But also—don’t waste your life in a dead-end. Learn the difference. Master it.How to Win Friends and Influence People – Dale Carnegie
Still the best book on being human in business. Simple truths that outlast every platform, funnel, and algorithm.The 7 Habits of Highly Effective People – Stephen R. Covey
Old-school but evergreen. Mastering habits, priorities, and values gives you a durable edge.
Updated Core Additions (Post-2020)
Modern weapons for high-agency thinkers. These are important now. If you are my client, you are either already hearing about this titles from me, or you will be soon…
Wealth, Time, and Aliveness
Lately, two books have been reshaping the conversations I’m having with entrepreneurs…especially those in their 40s, 50s, and beyond. They challenge the old financial script we’ve been sold for decades: make as much as you can, save obsessively, and hope you have enough ime, energy, health left to enjoy it someday.
But I think that model is broken. It delays life in service of a future that may never arrive. Worse, it teaches us to equate security with fulfillment, and accumulation with freedom. These two books offer a sharp counterpoint: they argue for intentional living now. For using your money, your time, and your health while you have all three. For building a life you’re not constantly deferring.
If you’ve ever caught yourself grinding with no finish line in sight, or saving out of fear instead of purpose, these books will resonate.
Let’s Retire Retirement – Michelle Silver
Retirement is a 20th-century invention—and a bad one at that. This book dismantles the assumption that age = irrelevance. Silver explores how purpose, mastery, and contribution still matter deeply past traditional “retirement age.” A must-read if you're thinking long game about your identity, not just your income.Die with Zero – Bill Perkins
More than a finance book—it’s a framework for memory-making, not money-hoarding. Perkins challenges you to stop deferring your life, stop chasing a never-ending number, and start allocating your time and energy toward experiences you’ll actually remember. Especially powerful if you're driven, ambitious, and secretly terrified of wasting your shot.
Self-Perception, Identity & Change
These three books are on the list because they get under the surface of why we do what we do, especially as leaders. Not in a motivational, “find your why” kind of way, but in a deeper, more uncomfortable sense: they expose the hidden drivers most of us don’t want to admit are running the show. Status. Approval. Envy. Mimicry. The need to be seen a certain way.
If you’ve ever wondered why your goals shifted the second someone else succeeded… or why you’re crushing it on paper but still restless underneath… these books will light that up. They’re not about achievement—they’re about reclaiming agency from the forces that quietly hijack it.
The Status Game – Will Storr
Shows how status—not money or power—is the real driver. Learn the games you’re playing (or losing) without even knowing it.The Courage to Be Disliked – Ichiro Kishimi & Fumitake Koga
An elegant slap that helps you detach from praise, criticism, and the need to be liked. Unclench your life.Wanting – Luke Burgis
Reveals how mimetic desire—copying what others want—runs your decisions. Once you see it, you can choose differently.
Business + Psychology
These three books are here because they sharpen your edge where it matters most: strategy, growth, and value creation. Not theoretical fluff—real, actionable insight for entrepreneurs who are actually building something.
If you’re tired of vague business advice and want to build with precision—these are for you.
The Cold Start Problem – Andrew Chen
Network effects decoded. Especially sharp if you’re building anything that grows via community or referrals.$100M Offers / Leads / Sales – Alex Hormozi
Ignore the TikTok fanboys. The man knows how to package, position, and price. Tactical, no-BS, field-tested business building.Playing to Win – A.G. Lafley & Roger L. Martin
Corporate playbook clarity that adapts surprisingly well to small biz. Sharpens your thinking on positioning and strategy.
Inner World, Shadow Work, & Growth
This set of books is about doing the real inner work—not the trendy kind, but the raw, sometimes uncomfortable kind that actually shifts you. They’re not quick reads or clever reframes. They’re practices. Invitations to slow down, turn inward, and face the emotional patterns and protective strategies that quietly shape your choices, your leadership, and your capacity to enjoy what you’ve built.
If you feel stuck in loops you can’t name, if you’re constantly bracing for impact even when life is good, or if you’re hungry for clarity that doesn’t come from thinking harder. These books meet you there. They won’t give you the answers, but they will strip away the noise until you hear your own.
The Presence Process – Michael Brown
A practical 12-week journey that’s somewhere between therapy, breathwork, and emotional exorcism. Not easy. But real.The Mountain Is You – Brianna Wiest
Gentle entry point into shadow work. Helps you name and unwind the patterns that quietly run your life.Living Untethered – Michael A. Singer
Goes deeper than The Untethered Soul. A powerful companion for surrendering the noise and creating from stillness.
Contrarian & Critical Thinking
These books are here to stretch your thinking about society, meaning, and the systems shaping our decisions. They offer clarity in a noisy, reactive world. Each one tackles a different dimension of modern life: how crowds lose their minds, how virtue can be practiced without dogma, and how technology outpaces our values if we’re not paying attention.
If you care about building something that lasts, these will challenge your frameworks. Not to overwhelm you, but to deepen your discernment. Because clear thinking is a competitive and (and ethical) advantage.
The Psychology of Totalitarianism – Mattias Desmet
Breaks down how “mass formation” arises—and why smart people fall for collective delusions.The Good Life Method – Meghan Sullivan & Paul Blaschko
Philosophy made punchy. Centers on virtue, purpose, and meaning through a lens that doesn’t feel like a lecture.The Alignment Problem – Brian Christian
AI isn’t the enemy. Misaligned incentives are. If you want to think clearly about intelligence and ethics, read this.
Fictional Power + Literary Intensity (Optional but Soulful)
These aren’t business books in the traditional sense. There are no frameworks, no tactics, no guarantees of a better quarter. But they build something more foundational: your soul, your emotional depth, your capacity to hold nuance and make meaning. And whether you realize it or not, that’s what actually drives your business.
Shantaram – Gregory David Roberts
A sprawling, brutal, romantic novel of redemption, criminality, and spiritual seeking. Like reading a fire. Get the audio version; the narration is the single best I’ve ever heard.The Overstory – Richard Powers
A mind-expanding, heart-breaking exploration of trees, connection, and time. It changes how you see the world.The Paper Palace – Miranda Cowley Heller
If you know me, you know I rarely read books with a female protagonist. It’s not that I’m being toxicly masculine, but just that I don’t relate male and female experiences interchangeably. However, this book is beautiful, raw, and haunting. An intimate portrait of choice, trauma, and the weight of memory.
Removed or Deprecated
I took several books off this list this year.
Some of these books were once staples for me—and probably still land for the right person at the right time. Like, if you haven’t read them, it would still be good to do so. But for this guide, they no longer belong. Not because they’re bad, but because they’re no longer essential. The thinking has evolved. The bar has risen. We’ve grown.
Think and Grow Rich helped introduce millions to mindset work, but its mystical tone and formulaic repetition haven’t aged well. Make Your Bed went viral for a reason—it’s neat, tidy, and motivational—but it reads more like a commencement speech than a playbook. Greenlights is a vibe-heavy memoir with some beautiful moments, but it’s more campfire story than catalytic tool. And books like The Greatest Salesman in the World or Modern Chess Openings may still have value, but they’re either too wrapped in fable or too niche to warrant a spot on a high-impact list like this.
Some removals are about tone and focus. Bukowski’s grit and poetry are legendary, but not aligned with the work this list is meant to support. 12 Rules for Life is complex, at times profound, but has become so polarizing and over-discussed that it no longer sparks the kind of clarity or challenge this guide aims for. Good to Great was gospel in its time, but many of its “great” companies failed to stay great—and its conclusions, while once illuminating, now feel overfitted to a specific era. As for The 5 Dysfunctions of a Team, it’s still a solid model, but better, sharper tools now exist to help you build trust and performance in modern teams.
In short, the list isn’t just what worked once. It’s what works now.
That’s the list—for now. Hopefully it won’t take me another five years to update it again, but this time around, I’m treating it as a living, evolving tool. As new books emerge that challenge assumptions, deepen clarity, or unlock sharper ways of building and leading, I’ll add them. Maybe even release a few focused mini-lists around topics like team-building, wealth, or spiritual endurance. We’ll see.
And if you’re one of my coaching clients, know this: these aren’t just recommendations. These are the books I’ll reference in sessions, quote mid-conversation, or push you to engage with when you hit a wall. This isn’t shelf candy. It’s source material for your next leap.
– love, Chad