Redefining success, money, and belonging...

Paul Millerd spent several years working in strategy consulting and on the “default path” 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:

• An explanation of the “default path” and the “pathless path”

• Signs you may be stuck on the default path

• How to inch your way toward the pathless path

• Why Paul suggests everyone should take a three-month sabbatical

• Tips for embracing fear and betting on yourself

• 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:

• X: https://twitter.com/p_millerd

• LinkedIn: https://www.linkedin.com/in/paulmillerd/

• Website: https://pathlesspath.com/

• Newsletter: https://newsletter.pathlesspath.com

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

• Podcast: https://think-boundless.com/podcast/

• Email: paul@strategyu.com

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Paul’s background

(04:33) An explanation of the “default path”

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

(07:35) Paul’s thoughts on “remixing your path”

(09:57) An explanation of the “pathless path” 

(12:06) Examples of the pathless path

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

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

(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 

(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 

(37:53) Lenny’s personal journey

(39:27) Advice on dealing with the naysayers 

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

(44:52) The “ship, quit, and learn” framework

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

(51:27) Paul’s response to criticism 

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

(55:42) Lightning round

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Referenced:

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

• David Autor on X: https://twitter.com/davidautor

• Tim Ferriss’s blog: https://tim.blog/

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

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

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

• StrategyU: https://strategyu.co/

• David Deming’s website: https://www.daviddeming.com/nyt-columns

• 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

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

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

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

• 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.