#22 Whatever Scares You—Go DO It | Derek Sivers on Reinventing Yourself

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Escape 9 to 5

Lydia.CLinzi

32 episodes

3 days ago

Freedom, Agency and Meaning. Ever thought about ditching the regular 9 to 5 to chase what truly lights you up? I'm on this path to. This podcast is all about that leap of faith—no guides, no guarantees, just real stories from those brave enough to pursue a life beyond the ordinary. Join me as we uncover the untold journeys of dreamers and doers who are carving their own paths. Let's figure out this together.

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#22 Whatever Scares You—Go DO It | Derek Sivers on Reinventing Yourself

Escape 9 to 5

1 hour 35 minutes 47 seconds

5 months ago

#22 Whatever Scares You—Go DO It | Derek Sivers on Reinventing Yourself

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

🎧 LISTEN ON THE GO Spotify · Apple · all links → https://www.dayzeroproduction.com/escape-9-to-5

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

☕ SUPPORT THE SHOW Buy me a Not-So-Blue Brew → https://lydia-c-linzi.kit.com/products/buy-me-a-not-so-blue-brew

#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:

👉 https://tally.so/r/nG7ZbQ*

✨ 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.