The Pathless Path with Paul Millerd

John Zeratsky was a designer in the tech industry has worked with hundreds of startups in his time at Google Ventures.  He’s also obsessed with redesigning time and thinking about what matters in life.  Earlier this year he just got back from 18 months living on his boat "Pineapple" with his wife sailing around Central America, which he wrote about in an article titled “What quitting my job to sail around central america taught me about fulfillment.”  In this conversation we talk about: Growing up in a small lake community His love of sailing growing up Why him and his wife change their mind on taking the trip in 2015 Rethinking convenience and comfort What comforts are worth paying for Belonging and community How his relationship with money has changed How him and his wife are structuring their life to work how they want The one change that helps people be less addicted to their phones Links Mentioned: Designing Your Life Sprint: How To Solve Big Problems and Test New Ideas In Just Five Days Make Time: How To Focus On What Matters Every Day Twitter: @jazer Want to support the podcast?  Offer a one-time or recurring donation on Boundless.   📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

Hannah Wei has been living as a digital nomad for the last four years traveling across the US, Canada and Southeast Asia.  When she is not working as a product consultant, she trains in Muay Thai, photographs people, and collaborates on local initiatives.   In our conversation we touch on many things, including: Her upbringing in China and move to the US Her creative inspirations as a child and how that evolved as she got older Her experiment to code a bot to swipe on Tinder and tell people’s stories What she has learned from Muay Thai Her decision to compete in a professional Muay Thai fight in Thailand What Muay Thai that has taught her about burnout, performance and success How she defines success as a nomad depending on the region she is in Follow Hannah Hannah’s Website Hannah on Twitter: @herlifeinpixels Her personal review Notion group How to pack up your life in eight steps Tinder Photography Bot Experiment  Want to support the podcast?  Offer a one-time or recurring donation on Boundless.   📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

I talked to Alastair Humphreys after he had returned the previous night from a micro-adventure.  It wasn't a four year biking trip or a challenging long walk across the desert (he's done that though!), but instead a short overnight camping trip with himself to re-connect with nature and his adventurous spirit.  He helps others think about how they can design similar micro-adventures to find joy in the "5 to 9" rather than doing everything in service of the 9 to 5. Links Mentioned: Alastair Humphries Subscribe to his newsletter "living adventurously" His new book: My Midsummer Morning: Rediscovering How to Live Adventurously Hardcover – May 30, 2019  Want to support the podcast?  Offer a one-time or recurring donation on Boundless.  📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

After attending a few corporate recruiting sessions, he didn't take for granted that his path was to enter the corporate world.  Twenty years later, he is still carving his own path and has recently returned from Koh Lanta, where he lived with his three children in Thailand for the last six months.  We Talked About Ben starting a "tribe" in Fiji Early internet adventures His experiences coaching people with career transition The decision to move to Thailand with his three kids for six months Using "no code" tools to start things like Rebel Book Club How to think about a career in today's world How finding a friend is one of the most important things to head in a new direction Links Mentioned: Ben Keene's site Rebel Book Club Tribe Wanted Fiji Right to Dream Escape The City Moving to Koh Lanta with three kids His experience after the six-months in Thailand The 100 year life (book) Curiosity Conversations with Paul Want to support the podcast?  Offer a one-time or recurring donation on Boundless. 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

Heather McGowan is the most thoughtful writer and speaker I follow on the future of work. She is able to connect the dots between work, culture, society and identity in a way that has captured the attention of many individuals, companies and universities around the world.  Heather’s career is also a perfect example of the type of path and work that was not possible in the past.  Reflecting on her path she admits “this field just sort of emerged.”  As her career has shifted more towards speaking, she has been able to design her life around learning.  Through her talks, she is able to get feedback and combined with her own curiosity, it helps her focus on what to learn next.   In the working world, she focuses on how we can think about learning and work in a more holistic way and traces many challenges back to education.  She cites research from Gallup showing that: “while 74% of surveyed fifth-graders are engaged with school, just 32% of surveyed 11th-graders are engaged.”  Perhaps some of that disengagement is because people aren’t too excited about their job prospects.  She worries that organizations in the short-term are still too focused on productivity, which depersonalizes the experience of work.  As work increasingly becomes specialized - she calls it “atomization” - she fears that we will increasingly only focused on “explicit knowledge” instead of the deeper tacit knowledge that makes us special.  Find out more about Heather's work here or follow her on Linkedin. ---- Boundless Support Reimagine Work Read About The Future of Work 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

Rich fell in love with coding as a child but lost that passion when coding just turned into a job in the late 1990s.  As he looked around and saw everyone overwhelmed in his industry, he decided to take a different path.  He co-founded of Menlo Innovations in 2001 with a personal mission to end human suffering in the workplace.  He is also the author of two books Joy, Inc. and Chief Joy Officer.  Hear about his company has achieved gender diversity in the workforce, introduced pay transparency, embraces pair-working methods across all functions and other transformative principles. Links/Books Mentioned Menlo Innovations Extreme Programming, Beck The Fifth Discipline, Senge Chief Joy Officer, Sheridan Joy, Inc. Sheridan Boundless (Learn More Here) Support Think-Boundless 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

Jerel calls himself one of the original "job-hoppers."  While he never found a great fit in the corporate world, in the 1980s, he was inspired by Steven Covey to develop a "personal mission statement."  He used this to shape his decisions in life. In the early 2000's he decided to shake it up and headed to China for what turned into a 14 year journey of learning and adventure. To learn more about Jerel click here. ---------- Boundless => Reimagine Work 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

I met Craig at a conference called The World Domination Summit and when he introduced himself he gave me a pack of tea with his business card on it. Everything he does is like this - packed with thoughtfulness and humor. Craig is also the creator of the Morning effect, something he ended up being passionate about after going from someone that hated mornings to a morning advocate over the past 7 years.  He defines the morning effect as: "the principle that what you choose to do in the morning can have an amazing impact on other parts of your life. It leads you to get up and be productive, do more of the things you wish you were doing, and embark on your days already feeling accomplished. All of that is a HUGE win, but honestly, it’s just the tip of the iceberg…" He’s experimented with 100 morning rituals over that time and now works with people to help them take back their mornings and find “another 20 hours” a week as he did. His story is more than another “hustle” hack - its grounded on bringing more presence, joy and creativity to ones life and is why I hope you check out the podcast this week! For More => The Morning Effect Boundless Page Books/Articles Mentioned: When by Daniel Pink The Power of Habit by Charles Duhigg 127 Morning Rituals How to Schedule Your Workday 9 Lessons from a 9 Day Silent Meditation Retreat  Boundless / Reimagine Work: Support the podcast on Patreon  Subscribe to the free weekly newsletter on our modern conception of work  📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

Wesley Kang and Tanya Zhang are the co-founders of Nimble Made, an e-commerce clothing brand that makes “actually slim” dress shirts.   Before taking the leap to work full-time on their business, they worked in the corporate world in New York City.  As first generation Asian-Americans, they had achieved “success” - good jobs, good salary.  They were on their way.  However, deep down both wanted something a little more. Some of Tanya’s challenges working as a freelance graphic designer on the side convinced them they should try to think a little deeper about building a brand and a business, instead of just helping other people. As they found themselves thinking about the business all day at their full-time jobs and coming home ready to work on it, they realized they finally had to go all-in. Over the past year they have worked on the business and are starting to find some traction.  As they’ve dealt with the challenges of running a business, they have also had to constantly reflect on how to manage a relationship both as committed partners and co-founders.  Check Out Nimble Made (unsponsored): Interested in their shirts? Check out more at Nimble Made.  For their past reflections check out Wesley's guest post on entrepreneurship and Tanya's post on how her father inspired her to start the company.   Boundless / Reimagine Work: Support the podcast on Patreon  Subscribe to the free weekly newsletter on our modern conception of work  📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here

Chris Kirkland is a bootstrapped entrepreneur who has been living nomadically since 2006 and is the founder of several web businesses including artweb.com and tokyocheapo.com. We talk about how he has experimented with money, creativity, health and his lifestyle over the past 13 years.  His nomadic journey started when he took a trip to Japan and after two days decided "fuck it," I'm going to stay a bit longer.  We talk about his journey, entrepreneurship and his life experiments Why entrepreneurs are really risk averse His learnings from living nomadically and stoic exercises of living minimally  Prioritizing time over money as a bootstrapper  How running an online business was different in 2006 and why he "felt like he was cheating" His experiments with becoming a "breatharian" and trying polyphasic sleep (do not try these at home) How he thinks about running an online media business in 2019 His recommendations for cheap eats in Tokyo More about Chris: TokyoCheapo Chris' Personal Site & Writings Headstands Across The World Boundless / Reimagine Work: Support the podcast on Patreon  Subscribe to the free weekly newsletter on our modern conception of work  📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): 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 Here