Run Your Life Show With Andy Vasily

#269: Beyond True: Multiple Perspectives and Living Well with Derek Sivers

Feb 19, 2025

Derek Sivers, an entrepreneur and author known for founding CD Baby, shares his insights on embracing diverse perspectives in life. He discusses his latest books, exploring 27 conflicting philosophies that encourage personal reflection. Sivers emphasizes the transformative power of learning and the importance of questioning beliefs. He also recounts a near-fatal accident in Cambodia, illustrating how random events shape our interpretations of life. With a belief that life is a blank canvas, he inspires listeners to seek their own paths and redefine meaning through experience.

01:41:06

Episode guests

Derek Sivers

AI Summary

AI Chapters

Episode notes

Podcast summary created with Snipd AI

Quick takeaways

Derek Sivers emphasizes the transformative power of embracing new experiences to foster personal and professional growth throughout life.

Through his experience with CD Baby, Sivers illustrates how unexpected ventures can lead to meaningful contributions and inspire philanthropy.

In his book 'How to Live,' Sivers highlights the complexity of life's choices by presenting conflicting viewpoints, encouraging readers to forge their own paths.

Deep dives

A Life-Altering Experience

At 17, the speaker was involved in a car crash that changed the course of his life. Blowing through a yield sign, he collided with another vehicle, resulting in severe consequences for the other driver, who was left unable to walk. This incident haunted him for years, as he grappled with guilt over the harm he caused. The story sets the stage for a powerful exploration of how our past traumas can shape our identities and perspectives.

Intro

3min

The Journey of Perspective and Growth

23min

Cultural Perspectives and Personal Anecdotes

11min

Dueling Philosophies of Life

11min

Threads of Fate

11min

Embracing the Blank Slate of Life

31min

Connecting Through Literature: Charitable Impact of Direct Engagement

2min

Unlocking Potential: A Journey Through Reflection

9min

Send us a text

In today's episode, I'm thrilled to welcome Derek Sivers, a remarkable individual whose openness to new experiences has profoundly shaped both his personal and professional journey. What I appreciate the most about Derek is how he's taken important life's lessons and transformed them into wisdom about the things that truly matter.

Derek's passion for learning is infectious, but what's truly fascinating is his refusal to be boxed into any single worldview. This philosophy has served him well throughout his diverse career as an entrepreneur, writer, and musician. Many know him as the founder of CD Baby, which he started in 1998. The company grew to become the largest seller of independent music online, generating over $100 million in sales before Derek sold it in 2008 for $22 million. In a remarkable act of generosity, he donated the entire proceeds to a charitable trust for music education.

But Derek's impact extends far beyond CD Baby. Through his blog and five books, he's become known for his concise, thought-provoking writing on business, life, and decision-making. In our conversation, we dive deep into his two latest works. The first, "HOW TO LIVE," presents 27 conflicting approaches to life, each making a compelling case for a different way of living. Rather than providing easy answers, Derek challenges readers to find their own path based on their unique circumstances and perspectives.

We also explore his newest book, "Useful NOT True," which examines the powerful concept of reframing. Derek makes a fascinating case that success begins with perspective, which then shapes our strategy and actions. He argues that while our initial thoughts might feel true, they're often obstacles we need to overcome. By recognizing that no single perspective holds absolute truth, we can make more informed choices in our lives.

Many of you might know Derek from his three compelling TED Talks, including my personal favorite about the dancing guy on a hill – a brilliant metaphor for how movements begin. Our conversation weaves through various aspects of his life, from his early days to his writing, but what really resonated with me was our discussion about the importance of changing our minds. Derek believes that what we consider absolute truths can actually restrict our growth and shut us off from new learning experiences.

His insights about the power of changing one's mind have particularly influenced my own thinking about life and work, making it one of the highlights of our conversation. I genuinely enjoyed my time with Derek, and I believe this discussion will offer you fresh perspectives on your own life, work, and what matters most to you.

Connect with Derek:

Website

His books can be found below:

Useful Not True

How to Live

Hell Yeah or No

Your Music and People

Anything You Want

As well you can see any of Derek's Ted Talks below:

Derek’s Ted Talks