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#668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life”

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Apr 21, 2023

Guest

Derek Sivers

Derek Sivers, an author and former musician known for his unique insights, discusses the joys of living an un-optimized life and embracing tech independence. He shares personal anecdotes about minimalism, overcoming fear, and the value of spontaneity in life choices. Derek emphasizes the importance of owning email and managing personal data for security. He explores skepticism and the fluidity of identity, urging listeners to redefine success on their own terms. His thoughts on happiness and mentorship highlight the journey towards personal fulfillment.

02:54:25

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volunteer_activism

ADVICE

People Compass

If unsure of your direction, consider your heroes, as they reflect your ideal self.
Build a business serving people you love being around, prioritizing emotional fulfillment over potential monetary gains.

insights

INSIGHT

Tech Independence

The cloud's convenience comes at the cost of self-reliance and control over your data.
Tech independence, achieved by managing your own servers and software, offers better security, privacy, and flexibility.

volunteer_activism

ADVICE

Setting Up Your Server

For tech independence, get a server from Vulture.com, a dedicated server, or a used Thinkpad.
Install OpenBSD, encrypt a partition, use SSH with a private key, disable password logins, and set up a firewall.

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Exploring Un-Optimized Living and Tech Independence

03:52 • 3min

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Embracing Minimalism and Overcoming Fear

06:48 • 12min

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The Fluidity of Identity and Tech Independence

18:51 • 16min

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Setting Up Personal Servers and Financial Security Insights

34:24 • 3min

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Setting Up Secure Servers

36:57 • 4min

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Enhancing Server Security and Embracing Independence

41:20 • 2min

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Empowering Tech Independence

43:42 • 11min

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Taking Control: The Importance of Email Independence

54:19 • 2min

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Taking Control of Your Email

56:11 • 4min

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Navigating Email Challenges and Reflecting on Tech Investments

59:55 • 2min

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The Journey of Optimization and Spontaneity

01:01:42 • 15min

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Embracing Skepticism and Personal Beliefs

01:16:42 • 22min

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Breaking Down Tribalism in Beliefs

01:39:08 • 4min

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The Pursuit of Happiness and Personal Transformation

01:42:50 • 17min

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Navigating Mentorship: Insights and Strategies

02:00:10 • 17min

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Redefining Success and Validation

02:17:13 • 6min

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Satisficing for Personal Fulfillment

02:23:10 • 21min

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Emotional Connections in Parenting

02:43:47 • 5min

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Emotional Reflections and Weekly Recommendations

Ruby is a novel that tells the story of a young woman's struggle to survive against insurmountable odds during the Great Depression. The story explores themes of resilience, hope, and the fight for freedom in a historical context.

#13654

• Mentioned in 5 episodes

Saga

volume one

Brian K. Vaughan

Saga is a critically acclaimed comic book series that combines elements of science fiction and fantasy. It follows the story of Alana and Marko, lovers from opposing sides of a galactic conflict, as they flee with their daughter Hazel. The series explores themes of family, love, and survival amidst war, drawing inspiration from classics like 'Star Wars' and 'Romeo and Juliet'.

#1233

• Mentioned in 44 episodes

Excellent Advice for Living

Wisdom I Wish I'd Known Earlier

Kevin Kelly

Excellent Advice for Living is a compilation of Kevin Kelly's life wisdom, initially written for his young adult children on his 68th birthday. The book features 450 aphorisms that cover a wide range of topics, from setting ambitious goals and optimizing generosity to cultivating compassion and practical advice on career, relationships, parenting, and finances. Kelly's advice is designed to be accessible and applicable to all ages, emphasizing the importance of kindness, decency, and generosity of spirit. The book is praised for its straightforward and memorable guidance, making it an ideal companion for anyone seeking to navigate life with grace and creativity.

#2796

• Mentioned in 23 episodes

Genghis Khan and the Making of the Modern World

Jack Weatherford

This book, written by Jack Weatherford, challenges the traditional Western view of Genghis Khan as a ruthless destroyer. Instead, it portrays Khan as a secular leader who promoted egalitarianism, religious tolerance, and free trade. The Mongol Empire, under Khan's leadership, subjugated vast lands and people, but also facilitated cultural communication, expanded trade routes, and contributed to the blossoming of civilization. Weatherford argues that the Mongols' rule was less burdensome than that of European nobility, with lighter taxes, tolerance of local customs and religions, and universal education for boys. The book also explores how the Mongols encouraged scientific advances, improved agriculture, and sponsored lucrative international trade, thereby influencing European civilization and the modern world.

#635

• Mentioned in 72 episodes

The art of learning

An Inner Journey to Optimal Performance

Josh Waitzkin

The Art of Learning takes readers through Josh Waitzkin’s unique journey to excellence in both chess and Tai Chi Chuan. The book explains how a well-thought-out, principled approach to learning separates success from failure. Waitzkin discusses how achievement is a function of a lifestyle that fuels a creative, resilient growth process. He shares his methods for systematically triggering intuitive breakthroughs, honing techniques, and mastering performance psychology. The book also emphasizes the importance of embracing defeat, making mistakes work for you, and turning weaknesses into strengths. It is divided into sections that cover his rise in chess, his transition to Tai Chi, and the similarities in preparation and execution between the two disciplines.

#710

• Mentioned in 65 episodes

Do the Work

Steven Pressfield

#1863

• Mentioned in 32 episodes

The Moral Landscape

How Science Can Determine Human Values

Sam Harris

In this book, Sam Harris challenges the traditional separation between scientific facts and human values. He argues that morality can be understood in terms of human and animal well-being, and that science can provide objective answers to moral questions. Harris contends that moral relativism is false and that science can tell us how we ought to live to achieve the greatest well-being. He uses his expertise in philosophy and neuroscience to make a case for a science of morality, emphasizing that moral values should be grounded in empirical facts about what causes people to flourish.

#561

• Mentioned in 78 episodes

The paradox of choice

Why More Is Less

Barry Schwartz

In 'The Paradox of Choice,' Barry Schwartz argues that the abundance of choices in modern Western society, while seemingly beneficial, can actually be detrimental to our psychological and emotional well-being. He explains how the explosion in choices, from mundane decisions like buying jeans to profound challenges like balancing career and family, has paradoxically become a problem rather than a solution. Schwartz synthesizes current research in social sciences to make the counterintuitive case that eliminating choices can reduce stress, anxiety, and busyness. He offers practical steps to limit choices, focus on important ones, and derive greater satisfaction from decision-making. The book also introduces the concepts of 'maximizers' and 'satisficers,' highlighting the differences in their decision-making processes and outcomes.

#676

• Mentioned in 68 episodes

How to Get Rich

Felix Dennis

In 'How to Get Rich,' Felix Dennis shares his insights and experiences on building wealth. The book is distinct from other self-help or get-rich-quick guides as it emphasizes the importance of hard work, calculated risks, and ownership. Dennis discusses the necessity of execution over great ideas, the role of luck, and the need to overcome fear and embarrassment of failure. He also highlights the importance of maintaining control over one's business and the sacrifices required to achieve significant wealth. The book is known for its blunt and practical advice, reflecting Dennis's own journey from a college dropout to a multi-millionaire.

#2161

• Mentioned in 28 episodes

Useful Not True

Derek Sivers

In 'Useful Not True', Derek Sivers challenges readers to question their beliefs and adopt thoughts based on their usefulness rather than their inherent truth. The book emphasizes the power of reframing perspectives, recognizing that most statements are subjective rather than objective facts. Sivers argues that beliefs and meanings are tools that should serve us, helping us to take effective actions and navigate life more effectively. He encourages readers to separate events from their interpretations, question their thoughts and memories, and choose beliefs that lead to positive outcomes. The book is known for its concise and empowering approach, using practical examples and stories to illustrate its points.

#4004

• Mentioned in 16 episodes

The myths of happiness

Sonja Lyubomirsky

In 'The Myths of Happiness', Sonja Lyubomirsky challenges common assumptions about what brings happiness and misery. She argues that our misconceptions about the impact of major life events, such as marriage, children, wealth, and failures like divorce or illness, can significantly affect our long-term well-being. The book emphasizes the concept of hedonic adaptation, which shows that people tend to return to their initial happiness level after significant life changes. Lyubomirsky provides scientific evidence and practical lessons to help readers make wiser choices and find happiness by looking beyond their initial emotional responses and focusing on their mindset rather than circumstances.

#1401

• Mentioned in 40 episodes

A Guide to the Good Life

William B. Irvine

#1105

• Mentioned in 47 episodes

How to Stop Worrying and Start Living

Dale Carnegie

In 'How to Stop Worrying and Start Living', Dale Carnegie provides a set of practical formulas and techniques to help readers overcome their worry habits. The book, first published in 1948, has been updated and remains highly relevant today. It offers advice on how to eliminate business and financial worries, avoid fatigue, improve sleep, and cultivate a mental attitude that brings peace and happiness. Carnegie's approach includes rules such as living in 'day-tight compartments', accepting the worst-case scenario, and keeping busy to crowd out worry. The book is filled with inspiring examples and stories of people who have successfully applied these principles to achieve a more enjoyable and fulfilling life.

#1345

• Mentioned in 41 episodes

Anything you want

Derek Sivers

In 'Anything You Want,' Derek Sivers shares 40 powerful lessons learned from his experience of accidentally starting and growing CD Baby into a successful business. The book emphasizes the importance of creating a business that is a 'utopia' or perfect world, where the focus is on making dreams come true for both the entrepreneur and the customers. Sivers stresses that business is not just about money but about helping people and making them happy. He also highlights the advantages of starting with no money, the irrelevance of traditional business plans, and the importance of prioritizing customer needs over personal gain. The book includes memorable stories of his mistakes and successes, including his interactions with Steve Jobs and the impact of his decisions on his business.

#610

• Mentioned in 73 episodes

Stumbling on Happiness

Daniel Gilbert

In 'Stumbling on Happiness,' Daniel Gilbert delves into the human capacity to imagine the future and why we are often poor at predicting what will make us happy. Gilbert argues that our imagination is flawed in several ways: it adds or removes details, extrapolates from the present, and fails to account for the psychological immune system that helps us cope with undesired outcomes. The book uses scientific research from psychology, cognitive neuroscience, and behavioral economics to explain why we consistently misjudge our future satisfaction and how this affects our decisions. Gilbert also suggests that understanding these biases can help us make better choices and gain more control over our pursuit of happiness.

#1367

• Mentioned in 40 episodes

How to Live

27 conflicting answers and one weird conclusion

Derek Sivers

In 'How to Live', Derek Sivers presents a collection of 27 independent chapters, each offering a different philosophy on how to live. These chapters often contradict each other, arguing for various approaches such as being completely independent, committing to one career or person, being fully present, or delaying gratification. The book is designed for reflection as much as instruction, providing actionable directives without quoting philosophers or naming specific ideologies. It invites readers to consider multiple perspectives and find their own way, emphasizing that there is no one right way to live life.

#5871

• Mentioned in 12 episodes

Your Music and People

Derek Sivers

In 'Your Music and People,' Derek Sivers shares a philosophy on getting your work to the world by emphasizing creativity, consideration, resourcefulness, and connection. Although the book uses music as an example, its principles are applicable to any creative field. Sivers discusses how marketing is an extension of your art, the importance of being considerate and helpful, and how persistence and specificity are key. The book is praised for its practical advice and inspiring perspective on building a successful creative career.

#1708

• Mentioned in 34 episodes

Hell Yeah or No

What's Worth Doing

Derek Sivers

This book by Derek Sivers is a collection of short, concise chapters offering practical wisdom on decision-making, prioritization, and living a fulfilling life. The central philosophy is that one should only commit to things that elicit a 'hell yeah' response, and say 'no' to everything else. This approach helps in avoiding burnout and ensuring time and energy are dedicated to the most important and exciting activities. The book covers themes such as what’s worth doing, fixing faulty thinking, and making things happen, providing numerous mental models and life lessons to apply in daily life.

Brought to you by Allbirds incredibly comfortable shoes, Wealthfront high-yield savings account, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business.

Derek Sivers (@sivers) is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. He is a former musician, programmer, TED speaker, and circus clown, who sold his first company, CDBaby, for $22 million and gave all the money to charity.

Derek’s books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: sive.rs. His upcoming book is Useful Not True.

Please enjoy!

P.S. To follow the exact step-by-step "Tech Independence" instructions from Derek, please visit sive.rs/ti.

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[06:16] The Derek Sivers School of Enough.

[11:24] Scuba diving and empathy lessons in Iceland.

[16:13] Categories we apply to ourselves and others.

[22:46] Derek’s people compass.

[28:14] How to secure your tech independence.

[1:05:19] The unoptimized life.

[1:16:37] The meaning of Derek’s upcoming book, Useful Not True.

[1:32:55] The problem with moral relativism and other -isms.

[1:51:24] Giant leaps.

[2:00:10] Finding and asking mentors for help.

[2:08:18] Games.

[2:12:26] The wisdom of quitting when you’re ahead.