181 episodes
The Pathless Path with Paul Millerd Paul Millerd
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- Business
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4.8 • 61 Ratings
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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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#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
(00:56) - The scripts that Justin grew up with
(09:21) - Attention and social media
(11:05) - Liking your job, the interest curve & having goals
(15:17) - Justin's burnout, finding a new path & taking ownership of your time
(24:52) - Not starting earlier & struggling with a results oriented mindset
(31:08) - Creativity, non-monetary success & business as a creative act
(37:31) - Being the nr. 1 LinkedIn influencer
(41:52) - Income goals on the solo path
(46:31) - The Creator MBA & Brennan Dunn
(51:31) - Not making the solo career a job & fears around money
(57:09) - Avoiding emotions, confidence
(01:01:39) - What's Justin excited about
(01:03:20) - Closing remarks -
#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
(00:11) - Guest introduction
(00:57) - The scripts that Henry grew up with
(05:10) - John Stuart Mill
(07:41) - Samuel Johnson
(14:23) - "The common reader" & Why we shouldn't dismiss Gladwell
(17:41) - Writing
(21:25) - His book about the late bloomers
(28:10) - Penelope Fitzgerald
(33:38) - Is it too easy to share your writing?
(36:39) - The importance of finding the others
(40:42) - Conversations, talking to yourself and writing
(43:14) - Getting disappointed early
(47:52) - There is no actual average person, the importance of taking variability into account
(52:29) - How writing a book changes people
(55:10) - Tyler Cowen and the power of the internet
(57:47) - What Samuel Johnson would be working on today?
(59:36) - The lessons from Audrey Sutherland
(01:04:53) - Closing remarks -
#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
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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
(00:54) - The scripts that Matt grew up with
(04:40) - Growing up with the internet
(07:42) - Kids and technology, digital and industrial literacy
(13:33) - Babysitting, PhD in Philosophy and learning how to teach
(17:07) - Getting into Montessori
(19:02) - Starting the Guideposts & How to train good teachers
(23:50) - The pathological approach to work we learnt and how little children naturally want to help
(33:20) - “All work is noble”
(41:21) - The role of values in education through history
(49:03) - The Montessori system, differences in non-alphabetic writing systems
(54:11) - Agency as the aim of education
(59:22) - Advice for parents, the pros and cons of college
(01:06:02) - Matt’s new book & the hidden bad value system taught in modern schools
(01:10:16) - Closing remarks
📕Buy Paul’s Book (47k+ Sold): The Pathless Path
😁👉😁 Want To "Find The Others" On Pathless Paths? - Check out the 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 DescriptBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant 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
Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort
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
(02:14) - The scripts that Steve & Matt grew up with
(05:00) - Slowing down, deprogramming and unlearning
(11:52) - The cocoon stage
(14:05) - Deciding to quit
(18:25) - Learning from others on the path and having children
(25:18) - Trust
(28:29) - Matt's sabbatical, finding good work
(34:26) - No jealousy, competitiveness vs enoughness
(39:28) - Matt's apprenticeship with Steve
(48:37) - Putting yourself in a place where it's easy to help you
(52:35) - Downshift & Ambition
(01:03:06) - Marriage & Family
(01:10:54) - Reframing money, skiing and oatmeal
(01:17:15) - Launching decelerator
(01:21:26) - Closing remarks
📕Buy Paul’s Book (47k+ Sold): The Pathless Path
😁👉😁 Want To "Find The Others" On Pathless Paths? - Check out the 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 DescriptBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial -
#169 "2M Subscribers, I love what I do, should I take a break?" — David Pakman on finding good work early, , how money and motivation changed over time, finding a balance in content creation, life after YouTube, his doubts about taking a sabbatical, h
Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort
David Pakman is a political commentator and the host of The David Pakman Show. He joins the podcast to explore a possible paradigm shift in the way he approaches his work and life after the birth of his daughter.
🎥🍿 YOUTUBE: WATCH HERE
Links:
The David Pakman ShowX (Twitter): @dpakmanYouTube: David Pakman ShowInstagram: david.pakman⌛TIMESTAMPS(00:00) - Intro
(01:12) - The scripts that David grew up with
(03:26) - David's first steps on the internet
(06:13) - Finding an alternative path
(11:11) - Advice for young YouTubers
(13:17) - Money, motivation, workflows and how they changed over time
(18:15) - Imagining life after YouTube, doubts about taking a sabbatical
(27:57) - Having a child
(31:23) - Taking time off and fans
(35:08) - Divisive politics, public recognition and hateful comments
(42:20) - Growth ceiling, YouTube colleagues and the lack of clear role models
(47:32) - The dynamics of creator economy, YouTube & other creative projects
(53:49) - David's inspirations, what does he read
(57:47) - Closing remarks
📕Buy Paul’s Book (47k+ Sold): The Pathless Path
😁👉😁 Want To "Find The Others" On Pathless Paths? - Check out the 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 DescriptBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial -
#168 Building With "margin for life" — Justin Jackson on lessons from running a skate shop, optimizing for profit, running a "calm company," co-founding Transistor, having kids early, designing margins and how money actually does make him happy
Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort
Justin is the co-founder of Transistor, a podcast hosting platform on which The Pathless Path podcast is hosted. Justin is passionate about designing his company so that all the team benefits. He achieves that by making sure that there is always a financial margin as well as a "margin for our emotional health, margin for our physical health, margin for life."
🎥🍿 YOUTUBE: WATCH HERE
Links:
Personal websiteX (Twitter): @mijustinJustin's podcastTransistor⌛TIMESTAMPS(00:11) - Guest introduction
(02:30) - The scripts that Justin grew up with
(07:21) - Lessons from running a skate shop
(13:15) - Optimizing for profit in business
(25:49) - The opportunities on the internet, staying in the water, the survivor bias
(36:00) - Getting into digital business
(43:02) - The importance of the customer support
(45:21) - "A calm company" — designing the company to make their lives better
(54:28) - How Transistor has changed Justin's life?
(54:52) - Having kids early and how more money actually made him happy
(57:13) - How Justin approaches money
(59:45) - Navigating the changes in the podcasting platforms
(01:08:22) - The next chapter for Justin
(01:10:14) - Where can we find out more about Justin?
(01:11:15) - Closing remarks
📕Buy Paul’s Book (47k+ Sold): The Pathless Path
😁👉😁 Want To "Find The Others" On Pathless Paths? - Check out the 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 DescriptBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Teachable is what I recommendWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
Customer Reviews
Good guests with unique stories and insights to share
I first learned about Paul from another writer and blogger I follow. I enjoy the way Paul brings a diverse set of people with interesting perspectives, it helps to decondition one from the standard scripts and ideas that often unknowingly govern our lives.
Be prepared to lose all interest in your job
This podcast and “The Pathless Path” book have made it EXTREMELY hard to work my regular, boring job 😂 For better or for worse, though I think it’s a good thing. I feel like I’ve woken up after 2 years of sticking my head in the sand. I LOVED entrepreneurship when I was in college, but lost my passion as I got my first job, started a family, bought a house, etc. But now I’ve been slapped in the face and reminded that there is more to life than a paycheck. I’m now deeply contemplating my passions and gaps where I can add value to others lives, and hope to launch my own solopreneur journey in the next month or 2. Thank you for waking me up Paul. And thank you for colabing with others in this podcast doing similar things, their stories are inspiring.
Great podcast
"The Pathless Path with Paul Millerd" is a super cool podcast that totally shakes up the traditional career journey. I really appreciate how it pushes you to think outside the box and question the usual norms around work and success. Millerd's conversations are thought-provoking and inspire you to find your own unique path to happiness and fulfillment in your professional life.
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