183 episodes
The Pathless Path with Paul Millerd Paul Millerd
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- Business
The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Khe Hy, Ben Hunt, Wade Foster, Dan Vassallo, Kris Abdelmessih, Steph Smith, Amir Salihefendić, Alex Pang, Visakan Veerasamy, and more.
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Agency Is A Skill — Cate Hall on leaving law for poker, developing agency, deterministic vs probabilistic economy, risk, burnout, asking dumb questions, defining ambition, seeking real feedback, and the surface area of luck
Cate seemed to be fully entrenched on the default path — she had graduated from Yale and became the Supreme Court advocate on her way to becoming a partner in her law firm. But she didn't want to live the lives of the people around her. She pivoted hard, you could almost hear car brakes squeaking as she made the turn, and over a year she became the number one female poker player in the world. She later started art and perfume companies and led operations at Avlea — a pandemic medicine company. One might think she's simply a superhuman, and what she did is beyond the grasp of mere mortals, but Cate claims that agency is learnable and joins the podcast to tell us how.
🎥🍿 YOUTUBE: WATCH HERE
Links:
X (Twitter): @catehallLinkedInCate's Article — How to be More Agentic⌛TIMESTAMPS(00:00) - Intro
(02:29) - The scripts that Cate grew up with
(06:54) - Doors-opening credentials?
(10:45) - Leaving law for poker
(18:59) - Developing agency, learning form the others
(24:04) - Deterministic vs probabilistic economy
(27:15) - Risk and the diminishing prestige of the traditional paths
(31:32) - Burnout
(37:42) - Asking dumb questions
(42:21) - Defining ambition
(44:01) - Seeking actual feedback and how everything is learnable
(50:33) - The surface area of luck
(58:07) - Closing remarks
📕Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
Twitter: @p_millerdPaul’s Newsletter: Subscribe to PathlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:
Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereEpic transcription & text-based video editing via DescriptWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial -
1 Year Dad Reflections - Conversation with Sky King & Nat Eliason
This is from Sky King's podcast: https://skmp.supercast.com/
Guest info:Nat: https://www.nateliason.com/
Nat also has an amazing book coming out which I highly recommend, "Crypto Confidential": https://amzn.to/44BJ74I
📕Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
Twitter: @p_millerdPaul’s Newsletter: Subscribe to PathlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:
Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereEpic transcription & text-based video editing via DescriptWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial -
#173 Solopreneurship After Burnout — Justin Welsh on burnout, taking ownership of his time, struggling with a results oriented mindset, non-monetary success, becoming a top LinkedIn influencer, income goals, The Creator MBA, dealing with fears around
Justin is a former startup executive who helped build two startups past valuations of $1B, teams of 150+ people, and raise over $300M in venture capital. Now he’s building his one-person knowledge business toward $5M in annual profit.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Personal website LinkedInX (Twitter): @thejustinwelshThe Creator MBAThe Saturday Solopreneur⌛TIMESTAMPS(00:00) - Intro
(01:56) - The scripts that Justin grew up with
(10:21) - Attention and social media
(12:05) - Liking your job, the interest curve & having goals
(16:17) - Justin's burnout, finding a new path & taking ownership of your time
(25:52) - Not starting earlier & struggling with a results oriented mindset
(32:08) - Creativity, non-monetary success & business as a creative act
(38:31) - Being the nr. 1 LinkedIn influencer
(42:52) - Income goals on the solo path
(47:31) - The Creator MBA & Brennan Dunn
(52:31) - Not making the solo career a job & fears around money
(58:09) - Avoiding emotions, confidence
(01:02:39) - What's Justin excited about
(01:04:20) - Closing remarks
📕Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
Twitter: @p_millerdPaul’s Newsletter: Subscribe to PathlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:
Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereEpic transcription & text-based video editing via DescriptWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial -
#172 Success In The Second Half Of Life — Henry Oliver on John Stuart Mill, Samuel Johnson, Penelope Fitzgerald, why we shouldn't dismiss Gladwell, writing, late bloomers, the importance of finding the others, Tyler Cowen's help and the lessons from A
Henry is a writer, speaker and brand consultant. He joins the podcast to discuss his upcoming book — Second Act — in which he analysises the phenomenon of late bloomers and what we can learn from them.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Personal websiteSubstack: The Common ReaderX (Twitter): @HenryEOliverSecond Act⌛TIMESTAMPS(00:00) - Intro
(01:11) - Guest introduction
(01:57) - The scripts that Henry grew up with
(06:10) - John Stuart Mill
(08:41) - Samuel Johnson
(15:23) - "The common reader" & Why we shouldn't dismiss Gladwell
(18:41) - Writing
(22:25) - His book about the late bloomers
(29:10) - Penelope Fitzgerald
(34:38) - Is it too easy to share your writing?
(37:39) - The importance of finding the others
(41:42) - Conversations, talking to yourself and writing
(44:14) - Getting disappointed early
(48:52) - There is no actual average person, the importance of taking variability into account
(53:29) - How writing a book changes people
(56:10) - Tyler Cowen and the power of the internet
(58:47) - What Samuel Johnson would be working on today?
(01:00:36) - The lessons from Audrey Sutherland
(01:05:53) - Closing remarks
📕Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
Twitter: @p_millerdPaul’s Newsletter: Subscribe to PathlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:
Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereEpic transcription & text-based video editing via DescriptWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial -
#171 "All Work Is Noble," Montessori, and Kids & Work — Matt Bateman on starting growing up with the internet, digital and industrial literacy, studying philosophy and learning how to teach, starting the Guidepost school network, how to train teacher
Matt Bateman has a PhD in philosophy. He has abandoned the academic career, to pursue education in the Montessori system. A dad of three, he is passionate about educating children. Having worked a lot with training the teachers in the Montessori approach, he has now taken a step back to focus on writing his book.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Matt's Twitter — @mbatemanmontessorium.com guidepost⌛TIMESTAMPS(00:00) - Intro
(01:54) - The scripts that Matt grew up with
(05:40) - Growing up with the internet
(08:42) - Kids and technology, digital and industrial literacy
(14:33) - Babysitting, PhD in Philosophy and learning how to teach
(18:07) - Getting into Montessori
(20:02) - Starting the Guideposts & How to train good teachers
(24:50) - The pathological approach to work we learnt and how little children naturally want to help
(33:28) - “All work is noble”
(41:29) - The role of values in education through history
(49:11) - The Montessori system, differences in non-alphabetic writing systems
(54:19) - Agency as the aim of education
(59:30) - Advice for parents, the pros and cons of college
(01:06:10) - Matt’s new book & the hidden bad value system taught in modern schools
(01:10:24) - Closing remarks
📕Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
Twitter: @p_millerdPaul’s Newsletter: Subscribe to PathlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:
Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereEpic transcription & text-based video editing via DescriptWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial -
#170 Apprenticeships, Sabbaticals & "Good Work" — Steve Schlafman & Matt Yao on slowing down, deprogramming, unlearning, learning from others, deciding to quit, going on a sabbatical, not being jealous anymore, competitiveness and enoughness, finding
Steve is a professional coach and the founder of Downshift — the world's first decelerator. He has left a career in venture, but he remains ambitious, it's just that his ambition is now to have a good, multidimentional life, where he can be a good dad for his kids.Matt has left a traditional path early on to write, travel and discover his own path. When he met Steve, he offered him to become his apprentice and joined Downshift.
🎥🍿 YOUTUBE: WATCH HERE
Links:
DownshiftSteve's websiteSteve's TwitterMatt's TwitterMatt's blog — Game of OneMatt's blog — Build in ClimateDownshift on Twitter⌛TIMESTAMPS(00:00) - Intro
(03:14) - The scripts that Steve & Matt grew up with
(06:00) - Slowing down, deprogramming and unlearning
(12:52) - The cocoon stage
(15:05) - Deciding to quit
(19:25) - Learning from others on the path and having children
(26:18) - Trust
(29:29) - Matt's sabbatical, finding good work
(35:26) - No jealousy, competitiveness vs enoughness
(39:36) - Matt's apprenticeship with Steve
(48:45) - Putting yourself in a place where it's easy to help you
(52:43) - Downshift & Ambition
(01:03:14) - Marriage & Family
(01:11:02) - Reframing money, skiing and oatmeal
(01:17:23) - Launching decelerator
(01:21:34) - Closing remarks
📕Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
Twitter: @p_millerdPaul’s Newsletter: Subscribe to PathlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:
Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereEpic transcription & text-based video editing via DescriptWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial