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Paul Millerd spent several years working in strategy consulting and on the \u201cdefault path\u201d before deciding to walk away to work on his own in 2017. His book, The Pathless Path, chronicles his own journey and deep dive into the history of work and has been read by more than 40,000 people. His podcast, The Pathless Path Podcast, highlights conversations with others following unconventional paths. He also runs the online training business StrategyU, helping people learn the skills of consulting without having to work in the industry. In our conversation, Paul shares:

\u2022 An explanation of the \u201cdefault path\u201d and the \u201cpathless path\u201d

\u2022 Signs you may be stuck on the default path

\u2022 How to inch your way toward the pathless path

\u2022 Why Paul suggests everyone should take a three-month sabbatical

\u2022 Tips for embracing fear and betting on yourself

\u2022 How to work through the fear of losing money and prestige

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Find the full transcript at: https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/

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Where to find Paul Millerd:

\u2022 X: https://twitter.com/p_millerd

\u2022 LinkedIn: https://www.linkedin.com/in/paulmillerd/

\u2022 Website: https://pathlesspath.com/

\u2022 Newsletter: https://newsletter.pathlesspath.com

\u2022 YouTube: https://www.youtube.com/channel/UCofS_FvauuHc-x6mq7yz6nA

\u2022 Podcast: https://think-boundless.com/podcast/

\u2022 Email: paul@strategyu.com

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Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 X: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Paul\u2019s background

(04:33) An explanation of the \u201cdefault path\u201d

(06:32) Questions to help clarify which path you are on

(07:35) Paul\u2019s thoughts on \u201cremixing your path\u201d

(09:57) An explanation of the \u201cpathless path\u201d\xa0

(12:06) Examples of the pathless path

(13:54) Why meaning is hard to find and sustain on a traditional career path\xa0

(16:05) A case for the three-month sabbatical\xa0

(18:16) A mindfulness and self-reflection exercise

(20:18) Why Paul recommends three months

(22:28) Advice to founders on offering sabbaticals

(23:40) Other tactics for self-discovery

(27:08) The variability of income in self-employed roles\xa0

(29:12) Methods for staying afloat after leaving your job

(30:42) Tips for reframing your thoughts around money

(33:19) Why betting on yourself usually works out

(34:46) The importance of setting aside time for creative pursuits

(36:22) How to dip your toes in and find your path\xa0

(37:53) Lenny\u2019s personal journey

(39:27) Advice on dealing with the naysayers\xa0

(40:22) How to acknowledge and tame your fears

(44:52) The \u201cship, quit, and learn\u201d framework

(46:39) Why the pathless path is one of constant reinvention

(51:27) Paul\u2019s response to criticism\xa0

(58:02) First steps for getting started on your journey

(55:42) Lightning round

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Referenced:

\u2022 The Pathless Path: Imagining a New Story for Work and Life: https://www.amazon.com/Pathless-Path-Imagining-Story-Work/dp/B09QF6Q421

\u2022 David Autor on X: https://twitter.com/davidautor

\u2022 Tim Ferriss\u2019s blog: https://tim.blog/

\u2022 Why you should define your fears instead of your goals | Tim Ferriss: https://www.youtube.com/watch?v=5J6jAC6XxAI

\u2022 How Lenny Rachitsky Got 531,000 Substack Subscribers: https://www.youtube.com/watch?v=DMZem1NYfpM

\u2022 The Lindy effect: https://en.wikipedia.org/wiki/Lindy_effect

\u2022 StrategyU: https://strategyu.co/

\u2022 David Deming\u2019s website: https://www.daviddeming.com/nyt-columns

\u2022 The Great Work of Your Life: A Guide for the Journey to Your True Calling: https://www.amazon.com/Great-Work-Your-Life-Journey/dp/0553386077

\u2022 Wanting: The Power of Mimetic Desire in Everyday Life: https://www.amazon.com/Wanting-Power-Mimetic-Desire-Everyday/dp/1250262488

\u2022 Roadrunner: A Film About Anthony Bourdain: https://www.hbo.com/movies/roadrunner-a-film-about-anthony-bourdain

\u2022 Nuna travel stroller: https://nunababy.com/usa/trvl-easy-fold-compact-stroller

\u2022 Build Your Own Chatbot with OpenAI GPT-3 and Streamlit: https://medium.com/@avra42/build-your-own-chatbot-with-openai-gpt-3-and-streamlit-6f1330876846

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.