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Episode 334: Endless Curiosity with Derek Sivers

by Mike Vardy

After decades of following his own interests, today’s guest Derek Sivers has gone down many interesting rabbit holes. With an ambitious title for his new book, ‘How To Live’, we explore what makes a good life.

This episode is sponsored by BetterHelp. BetterHelp offers you access to a your own licensed professional therapist – all from the comfort of wherever you are. You can arrange weekly video chats or phone calls, text with your carefully curated counsellor, and do so at an affordable price. And anything you share is confidential. I’ve been using BetterHelp for a while and I am highly impressed. It’s been a huge help for me and I know it can be the same for you. Start living a happier life today with BetterHelp. As a listener, you’ll get 10% off your first month by visiting betterhelp.com/timecrafting. Give BetterHelp a try today.

This episode is sponsored by Fundrise. Fundrise is an investing platform that makes investing in high-quality, high-potential real estate as easy as investing in your favourite stock or mutual fund. Whether you’re looking to add stable cash flow via dividends or prefer long-term growth through appreciation, Fundrise has you covered. Fundrise’s team of real estate professionals carefully vets and actively manages all of their real estate projects. And with their easy-to-use website you can track your portfolio’s performance and watch as properties across the country are acquired, improved, and operated via asset updates. Want to get started? All you need to is visit fundrise.com/timecrafting to do that… and when you do you’ll have your first NINETY days of advisory fees waived. Start building your better portfolio with Fundrise today!

This episode is sponsored by TextExpander. With TextExpander, you can unlock your productivity with its many features. With TextExpander you can make everything you write repetitively available everywhere you type: text documents, spreadsheets, web forms, and more. Unlock your productivity with TextExpander. Visit TextExpander.com/podcast for 20% off your first year.

Derek Sivers is best known as a writer, musician, programmer and the founder of CD Baby, an online CD store for independent musicians. For the past 12 years he’s been living a nomadic lifestyle and pondered a lot about what makes a good life. 

In this episode we explore his new book he’s currently writing ‘How To Live’ – and how there is no one ‘right’ way to live. Derek’s life philosophy of being curious is infectious, and I enjoy going down a few rabbit holes with him in this interview. Join us as we explore how time is personal, setting creative constraints, and the surprising conclusion from his book. Get ready for a few Star Wars references too.

Talking Points

  • The reason why he wrote his new book ‘How To Live’ (2:16)
  • The role curiosity plays in his life (5:55)
  • How setting constraints gives your freedom (9:00)
  • Thinking beyond New Year’s Eve: how time is personal (17:30)
  • The big phases throughout Derek’s life (28:30)
  • Is Derek always having fun? (45:39)
  • His relationship with email (48:54)

“Constraints free you from the daunting prospect of infinite possibility”

– Derek Sivers

Helpful Links

  • How To Live
  • American History X
  • The Listening Book | Amazon
  • Quiet | Amazon
  • The 4-Hour Workweek | Amazon
  • Akimbo podcast by Seth Godin
  • Conversations with Tyler
  • John McWhorter
  • The Art of Noticing | Amazon
  • The Good Place
  • Comedian
  • Hugo Jacomet’s YouTube channel
  • Salt | Amazon
  • Cod | Amazon
  • Curious with Josh Peck
  • Monthly Self-Expansion Project
  • Chris Guillebeau
  • Sivers.org

Enjoy the show? Want to keep up with the podcast? You can subscribe to the podcast feed by clicking the “Share” button in the player above – and you can share it further using the same button as well. You can take things even one step further by rating and reviewing the show wherever you listen to podcasts. (FYI: I use Overcast on iOS.)

About Mike Vardy

Mike Vardy is a writer, speaker, productivity strategist, and founder of Productivityist. He is the author of The Front Nine: How to Start the Year You Want Anytime You Want, The Productivityist Playbook, and TimeCrafting: A Better Way to Get the Right Things Done, coming soon from Mango Publishing.

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