Derek Sivers Book Recommendations

Robert Cialdini―New York Times bestselling author of Pre-Suasion and the seminal expert in the fields of influence and persuasion―explains the psychology of why people say yes and how to apply these insights ethically in business and everyday settings. Using memorable stories and relatable examples, Cialdini makes this crucially important subject surprisingly easy. With Cialdini as a guide, you don’t have to be a scientist to learn how to use this science.

Written by Roman Emperor Marcus Aurelius, Meditations is a series of personal reflections on Stoic philosophy. It offers insights on resilience, humility, and the nature of human existence, emphasizing self-discipline, rationality, and virtue. Composed as a private journal, the work reveals how to maintain inner peace amid external chaos, making it a timeless guide for personal growth. Its concise wisdom and ethical clarity continue to influence leaders, thinkers, and individuals seeking meaning in a turbulent world.

This curated guide distills Naval Ravikant’s wisdom on wealth, happiness, and self-improvement, drawn from his tweets, podcasts, and essays. It blends philosophy, mental models, and practical advice for living a rich life—both materially and emotionally. The Almanack encourages clear thinking, long-term decision-making, and personal freedom, becoming a go-to for entrepreneurs and thinkers.

Essentialism is a manifesto for simplicity in an increasingly busy world. Greg McKeown advocates for doing less, but better—focusing only on what is truly important. He challenges the idea that we must do everything and instead teaches readers how to identify their highest priorities, eliminate non-essential tasks, and reclaim control of their time and energy. With practical tips and clear frameworks, the book empowers readers to make deliberate choices, say no more often, and live with intention. Essentialism is about creating space for what really matters—professionally and personally—by embracing the power of focus and clarity.

Anything You Want is a concise, unconventional guide to entrepreneurship drawn from Derek Sivers’ experience founding and running CD Baby. Rejecting traditional business advice, Sivers advocates for simplicity, personal fulfillment, and customer-centric thinking. He emphasizes doing what feels right rather than chasing external validation or scale for its own sake. The book combines practical insights with reflective storytelling, highlighting the value of independence, generosity, and clarity of purpose. With its direct tone and minimalist philosophy, Anything You Want is an inspiring read for entrepreneurs who want to build meaningful businesses on their own terms—not by following a blueprint.

The War of Art is a motivational call to overcome the internal resistance that blocks creativity and achievement. Steven Pressfield breaks the creative struggle into three sections: identifying resistance, turning pro, and embracing higher purpose. He argues that fear, procrastination, and doubt are universal forces that sabotage our potential, and success requires discipline and persistence. Blending personal anecdotes with spiritual undertones, Pressfield challenges readers to treat creative work as a daily practice. The book is especially resonant for writers, artists, and entrepreneurs, offering tough love and encouragement to push through fear and self-sabotage in pursuit of meaningful creation.

In How to Live, Derek Sivers offers 27 radically different philosophies for living a meaningful life—each chapter presenting a distinct worldview with confidence and conviction. From “Be independent” to “Commit fully,” the book explores contradictory yet compelling ideas, encouraging readers to reflect on what matters most. Rather than offering a single path, Sivers embraces complexity, suggesting that the truth of how to live may lie in navigating these contradictions. Written in his signature minimalist, thought-provoking style, How to Live is part philosophy, part self-inquiry, and part creative manifesto—ideal for readers seeking clarity, flexibility, and personal growth.

Rework is a no-nonsense guide to building and running a business differently—smarter, leaner, and with less bureaucracy. Written by the founders of Basecamp, the book dismantles traditional startup myths and offers fresh advice on productivity, marketing, hiring, and growth. Each chapter is short and punchy, advocating for simplicity, speed, and authenticity. Rework encourages readers to launch quickly, ignore competitors, and focus on real value rather than business plans or investor pitches. Whether you're an entrepreneur, freelancer, or team leader, this book provides a practical, counterintuitive perspective on what really matters when creating something meaningful.

The E-Myth Revisited challenges the assumption that most small businesses are started by entrepreneurs. Michael E. Gerber argues that many founders are actually “technicians” who struggle with running a business. The book offers a clear framework for building a business that can scale and function independently of the owner. Gerber emphasizes the importance of systems, standardization, and working “on” the business rather than just “in” it. Through the fictional story of a struggling bakery owner, he illustrates common pitfalls and provides actionable solutions. This book is a foundational read for anyone seeking to grow a sustainable, replicable business.

In Principles, billionaire investor Ray Dalio shares the core life and work principles that guided him in building Bridgewater Associates into one of the world’s largest hedge funds. The book is split into three sections: a personal journey, life principles, and work principles. Dalio emphasizes radical transparency, meritocracy, and continuous learning. He advocates for clear decision-making frameworks and a systematic approach to solving problems. Combining autobiography, management philosophy, and practical advice, Principles serves as a handbook for both personal growth and organizational excellence. It's especially relevant for leaders, investors, and anyone seeking to improve decision-making through reflection and structure.

This marketing classic distills decades of experience into 22 concise rules for building and maintaining strong brands. Al Ries and Jack Trout argue that marketing success comes from perception, not product, and each “law” illustrates a key principle—such as the Law of Leadership, the Law of the Category, and the Law of Focus. The book warns against common marketing pitfalls and emphasizes clarity, consistency, and positioning. Though first published in the 1990s, its ideas remain highly relevant in a crowded, fast-moving marketplace. It’s a sharp, digestible guide for marketers, entrepreneurs, and business owners seeking long-term strategic advantage.

The Untethered Soul is a spiritual and psychological exploration of consciousness, identity, and inner freedom. Michael A. Singer invites readers to observe their thoughts and emotions without attachment, helping them transcend internal limitations and live in the present moment. Drawing from mindfulness and Eastern philosophy, the book emphasizes awareness as the key to personal liberation. Through practical guidance and reflective questions, Singer teaches how to release fear, embrace stillness, and cultivate peace regardless of external circumstances. The Untethered Soul offers a deeply calming and transformative approach for anyone seeking to quiet their mind and reconnect with their deeper self.

In The Art of Learning, chess prodigy and martial arts champion Josh Waitzkin shares his journey of mastering two disciplines to reveal universal principles of performance and personal growth. Blending autobiography with actionable insights, he discusses focus, resilience, and the psychology of peak performance. Waitzkin emphasizes the importance of incremental progress, embracing adversity, and turning setbacks into growth. His philosophy integrates Eastern and Western approaches to learning and competition. Whether applied to sports, business, or creative pursuits, The Art of Learning is a compelling guide to developing mastery through mindfulness, self-awareness, and continuous refinement of one’s process.