Derek Sivers has lived many lives: musician, startup founder, TED speaker, minimalist nomad, and author of beloved books like Hell Yeah or No and Anything You Want.

In this conversation, we talk about:

– How to accumulate evidence for the life you want

– Tiny experiments that shape your identity

– Cities of the future, from China to South Korea

– Solopreneurship, uncertainty, and doing what scares you

We also talk about creative reinvention, raising children, and why retirement isn’t the end—it’s just another prototype.

💡 Favorite Derek quote from this episode:

“Whatever scares you—go do it.”

Because when you do, you collect evidence.You’ve done it once. You can do it again.

📚 Books Mentioned in This Episode

• The Art of Asking – Amanda Palmer → https://www.amazon.co.uk/Art-Asking-Learned-Worrying-People/dp/1455581089

• Selling the Invisible – Harry Beckwith → https://www.amazon.co.uk/Selling-Invisible-Field-Modern-Marketing/dp/0446672319

• You Can Negotiate Anything – Herb Cohen → https://www.amazon.co.uk/You-Can-Negotiate-Anything-Cohen/dp/0553281097

🌐 Where to Find Derek Sivers

• Website → https://sive.rs

• YouTube → https://www.youtube.com/user/dereksivers

• X (Twitter) → https://x.com/sivers

⏰ TIMESTAMPS

00:00:00 Intro

00:04:19 Two Truths & a Lie

00:11:29 Identity vs. What You Do

00:22:50 How 15 Years of Music Rewired His Mindset

00:28:38 Finding Your Voice From Scratch

00:43:20 Derek’s Current Goal

00:51:07 Failing Up

01:02:47 Adopting a New Persona

01:29:20 Lightning Round

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💌 WEEKLY LETTER – **Sunday Not Blue** Tools, tiny experiments, and behind-the-scenes stories → https://lydia-c-linzi.kit.com/

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#DerekSivers #Escape9to5Podcast #DoWhatScaresYou #RiskyPath #LifeDesign #Reinvention #CDbaby #TinyExperiments #CareerClarity #DigitalNomad---*

🧭 Take the “Escape 9 to 5” Quiz*Wondering if *you* should leave the default path?Take my free 30second quiz to discover what type of “escapee” you are:

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✨ Welcome to Escape 9 to 5 — the podcast for curious rebels*I’m Lydia — a former banker turned climate tech founder, nomadic creator, and podcast host.

🎯 About the Podcast

Escape 9 to 5 is for people who’ve left corporate life behind and never looked back. We talk about risk, reinvention, and what it takes to build a life you don’t need a vacation from.Let’s grow and glow together 🌱✨© 2025 Lydia C. Linzi. All Rights Reserved.