Links:

• Podcast
• Blake Boles
• Dirtbag Rich Site: https://www.blakeboles.com/dbr/

Episode Desription
Paul Millerd is a 39-year-old writer, ex-consultant, and advocate for ditching the default path in favor of what he calls “the pathless path.” (pmillerd.com / @p_millerd)

Paul walked away from a promising corporate consulting career—think McKinsey, prestige, and six-figure salaries—to pursue a life of writing, experimenting, and global wandering. He describes how he initially struggled with unlearning his achievement-oriented mindset, why the idea of good work (work that energizes) became his guiding principle, and how his first self-published book, The Pathless Path, briefly and unexpectedly earned six figures.

We discuss the philosophical basis of work and money, how to avoid the traps of both scarcity and overachievement, and how the value of exercising your freedom is limited by how others exercise their own freedom. (In other words: if you're free to hike on a sunny Wednesday afternoon, and no one's available to go with you, are you really free?)

Paul and his wife have a young daughter, and they struggle to find and live near other, like-minded families. We talk about how online communities help Paul stay connected while living nomadically between Texas and Taiwan and how online self-education was invaluable to his success. We conclude with a discussion of navigating fear and uncertainty on the pathless path.

Throughout the conversation, Paul stays refreshingly honest about the tensions between freedom and stability, the allure of easy money, and the ever-present temptation to fall back into old habits of achievement and validation. Energized by this conversation, I ended up talking more than usual about the tricky balance of factors that leads to a Dirtbag Rich existence.

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

• Twitter: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (23k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here

This was a fun episode. A friend, Matt Yao, reached out to see if he could interview me about my recent book, Good Work.

We first connected when he called me in the summer of 2022. He was in the middle of my book and knew he needed to quit his job.

Over the last few years, he's been on a transformational journey, experimenting with writing, coaching, and several other side quests.

Hope you enjoy this conversation.

You can learn more about Matt here: Matt Yao

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

• Twitter: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (23k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here

You can follow Abel's podcast here: Abel James Show

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

• Twitter: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (23k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here

Check out and purchase Good Work here: https://pmillerd.com/goodwork

Or from Amazon directly: https://amzn.to/4gwRSCN

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): @catehall
• LinkedIn
• Cate's Article — How to be More Agentic

⌛TIMESTAMPS

• (00:00) - Intro
• (02:07) - The scripts that Cate grew up with
• (06:32) - Doors-opening credentials?
• (10:23) - Leaving law for poker
• (18:37) - Developing agency, learning form the others
• (23:42) - Deterministic vs probabilistic economy
• (26:53) - Risk and the diminishing prestige of the traditional paths
• (31:10) - Burnout
• (37:20) - Asking dumb questions
• (41:59) - Defining ambition
• (43:39) - Seeking actual feedback and how everything is learnable
• (50:11) - The surface area of luck
• (57:45) - Closing remarks

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

• Twitter: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (23k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here

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

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

• Twitter: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (23k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here

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
• LinkedIn
• X (Twitter): @thejustinwelsh
• The Creator MBA
• The Saturday Solopreneur

⌛TIMESTAMPS

• (00:00) - Intro
• (01:34) - The scripts that Justin grew up with
• (09:59) - Attention and social media
• (11:43) - Liking your job, the interest curve & having goals
• (15:55) - Justin's burnout, finding a new path & taking ownership of your time
• (25:30) - Not starting earlier & struggling with a results oriented mindset
• (31:46) - Creativity, non-monetary success & business as a creative act
• (38:09) - Being the nr. 1 LinkedIn influencer
• (42:30) - Income goals on the solo path
• (47:09) - The Creator MBA & Brennan Dunn
• (52:09) - Not making the solo career a job & fears around money
• (57:47) - Avoiding emotions, confidence
• (01:02:17) - What's Justin excited about
• (01:03:58) - Closing remarks

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

• Twitter: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (23k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here