

The Pathless Path with Paul Millerd
Paul Millerd
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, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.
Episodes
Mentioned books

Mar 13, 2019 • 48min
From the basketball court to the yoga mat via the corporate world (Gabi Macra)
Gabi Macra was a top Canadian basketball player that never really thought about the "life after basketball" before dealing with a major injury towards the end of her college career.
Instead of following any sort of traditional path, she headed East to Japan where she came to teach English. She loved her experience there and now reflects on the immense value of learning how to teach and coach others helped her in the following years.
Instead of heading back to Canada, she headed to London where she had a successful career and journey as an actuary. She was a leader in her company but reached a point where she was dealing with health challenges and finding that her career was no longer giving her the fulfillment that it once was.
She ended up deciding to take some time off and told her boss that she was leaving. However, she ended up staying another 18 months as she helped the team transition with some other internal changes. Just knowing she was leaving enabled her to approach everything completely different and think about how she could best serve her team while also taking care of her own health.
She finally took the leap in 2018 and after several months of sabbatical, including some time in Bali, she realized that becoming a Yoga Therapist was something she was ready to commit to over the next few years. While preparing for that program, she also created a learning internship for herself in London (stealing this from Lydia Lee's podcast episode!) by taking 8 people interested in Yoga and creating a customized program for them. Her only goals: to learn a ton about how she can serve people and learn what to do next.
What we covered:
Her drive and motivation as a basketball player
Her experience living and working in Japan after university
Starting her actuarial career and what she enjoyed about work
Becoming successful but questioning her role as a successful worker as the center of her life
Her decision to take a sabbatical and leave the company (and how she ended up staying for 18 months but doing so with a completely different mindset)
Her recent creative projects, "learning experiments" and decision to start a long-term Yoga therapist training program
Links
Instagram: Gabi Macra and Real People Do Yoga
Website: Real People Do Yoga
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📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Mar 6, 2019 • 46min
Learning To Quit & Life Reinvention (Christine Bader)
Christine Bader is currently living in Bali, Indonesia, where she is spending time focused on her family and self. She is the author of The Evolution of a Corporate Idealist: When Girl Meets Oil and the former head of CSR for Amazon before leaving in 2017, a journey she details in an amazing essay titled “The year I learned to quit.”
She talks about leaving the corporate world and shifting her focus from building a career to building a life.
Topics Discussed:
Corporate social responsibility
Taking a sabbatical in Bali
Building a life
The greek concept of Kairos
Working in Asia
Working at Amazon
Recommended Reading
Can a business of any size be good?
The Year I Learned To Quit (New York Times)
📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Feb 13, 2019 • 1h 1min
Building & Investing In Calm Companies (Tyler Tringas)
Tyler Tringas is an entrepreneur and traveler. He's started two companies (one worked!) and now is founding Earnest Capital where he wants to help companies avoid going into $50,000 of credit card debt (like he did) to start technology companies. We talk about how this type of investing vehicle can help transcend some of the pressures to "scale at all costs" in ways that may not be suitable for most companies.
Topics
Digital nomads
Starting a company
Bootstrapping
How to sell a company
The four-hour workweek
Calm companies
Flaws with the VC model
Taking leaps
Transitions
Meaningful work while traveling
Related Links:
Earnest Capital
Tyler Tringas
His Journey Selling StoreMapper
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For More With Boundless:
Consider supporting the podcast on Patreon
Join 125+ People Carving Their Own Paths In The Slack Community
Set Up A Curiosity Conversation With Paul
Join The Free 3-Week Self-Employment Challenge
Sign up For The Strategy Toolkit - Learn The Secrets Of Strategy Consulting
📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Feb 8, 2019 • 46min
Paul on success, storytelling, learning & experiments (UX Gorilla Interview)
I joined the amazing Jagriti Pande for a fun conversation around a number of different topics. You can subscribe to her master series on UX designers and other creatives here.
Her amazing editing, way-too-kind-intro and fun clip at the beginning were such an amazing gift.
Let me know what you think!
📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Jan 30, 2019 • 33min
Launching Uncommonly: One Year Later (Chris Donohoe)
"I didn't think I'd be turning down work and choosing not to grow"I spoke with Chris Donohoe one year ago about his just-announced launch of his consulting firm, Uncommonly. He's more committed to carving his own path than ever and we walk through some of the lessons learned, pivots and his long-term strategy. Chris breaks down what he's learned over the past year, how he has started coaching people one-on-one and how he is thinking about structuring his time and day.Topics Discussed:Selling time versus projectsWorking a max 40-hour workweekTaking a coaching programThings he didn't expect 1 year into building his own firmWorking with an amazing co-founderHis reflections on leadership and his goalsUncommonly: Website-------For More With Boundless:Consider supporting the podcast on PatreonJoin 125+ People Carving Their Own Paths In The Slack CommunitySet Up A Curiosity Conversation With PaulJoin The Free 3-Week Self-Employment ChallengeSign up For The Strategy Toolkit - Learn The Secrets Of Strategy Consulting
📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Jan 23, 2019 • 1h 8min
Guest Episode: Joe Dumars x Adam Grant x Cody Royle
This episode is a special treat from friends of Boundless, Cody Royle, who came on the podcast last year to talk about what the business world can learn from sports.I wanted to share a special episode from his podcast that was just launched featuring the NBA great Joe Dumars and workforce research great Adam Grant. I thought the three of them had a special conversation. If you want to subscribe to Where Others Won't do so here:ItunesOvercastWebsite
📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Jan 16, 2019 • 50min
Learning, Self-Employment & Making Business More Human (Mike Tannenbaum)
Mike was always a self-driven creator, developing TI-83 apps for his classmates to keep track of their grades from an early age. He spent a lot of time "head in in the clouds, making things." It is no surprise then, that he eventually found that self-employment was the right fit after several years of trying to make it work in the corporate world.Mike and I dive into his path in which he slowly made sense of the fact that it was time to take the leap to self-employment. As he was about to take the leap, his company ended up laying him off anyway. Reflecting back, he has found many valuable lessons in his journey and has brought these together in a self-published a workbook called Clear Path Forward. The workbook helps people re-assess their relationship with work. We talk about the process he took to publish the book and where he sees his work taking him over the next couple of years.He now lives and works around the tagline "making business more human" which he is using to run workshops with clients and have deep conversations with people around what really matters.Topics Discussed:Building his first program on TI-83Creativity & WritingMindfulness & awarenessHis relationship with workMoney and the fear of going brokeLearning & readingDiversity of viewpoints Embracing uncertaintyMaking work more humanBooks That Influences Mike (That We Discuss)The AlchemistLiving BeautifullyThe War of ArtSo You Want To Talk About RaceSapiensDaring GreatlyConnect With Mike:Personal Blog — LinkBusiness — Enjoy HumanityWorkbook — Clear Path ForwardDownload a Free Worksheet — Link Offer: 25% off either edition of Clear Path Forward with code “Boundless” — LinkFor More With Boundless:Consider supporting the podcast on PatreonJoin 110+ People Carving Their Own Paths In The Slack CommunitySet Up A Curiosity Conversation With PaulJoin The Free 3-Week Self-Employment ChallengeSign up For The Strategy Toolkit - Learn The Secrets Of Strategy Consulting
📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

4 snips
Jan 9, 2019 • 1h 15min
10 Career Myths We Should Stop Believing (Jeff Hittner)
Jeff Hittner of Your Project X and Paul talk about their favorite 10 career myths. They dive deep into the beliefs and mindsets that drive these beliefs while making an argument for people to reflect at a deeper level to shift past the default to contemplate a wide range of optionsReadable Version: Top 10 MythsMyth #1 - "Once I land my dream job / make $X a year, I'll be happy" (2:35)Myth #2 - "I need to find my passion" (7:15)Myth #3 - "I should never take a pay cut" (14:15)Myth #4 - "You should have a 'steady' income" (20:40)Myth #5 - "I have to know what I need to do before I change directions" (26:15)Myth #6 - "An extended break is irresponsible" (32:30)Myth #7 - "It's fine to take a risk when young, but not when you have kids" (40:35)Myth #8 - "I should go to grad school to figure out what I want to do" (46:15)Myth #9 - "I can't make a change now after years in this field" (55:20)Myth #10 - "I'll be happy once I'm running my own business" (1:04:54)Links Mentioned:How to Get Unstuck In The New Year, Jeff Hittner On QuartzSelf-Determination Theory, Deci & RyanComparing Passion & Purpose, Thrive GlobalJeff Hittner leads Your Project X, a social venture with a mission to help 1 million people find more purposeful work. He has more than 18 years experience as an entrepreneur, consultant and changemaker. He is the founder of five social ventures, including IBM’s Corporate Social Responsibility (CSR) consulting practice globally. In 2011, he developed the curriculum for one of the first MBA’s in Sustainability in the US, at Bard College, where he was the Leadership professor. He was also two-time Chairman of the Carnegie New Leaders at the Carnegie Council for Ethics in International Affairs.Jeff’s passion has always been at the intersection of education and entrepreneurship. Prior to your Project X, he ran a career transition program for 64 New Yorkers, built global education programs including a blended learning initiative for high school dropouts in Latin America and career discovery programs for youth in Europe. Jeff received his Masters in Cultures and Development Studies from the Katholieke Universiteit Leuven in Belgium, and a Bachelor of Business Administration from The College of William and Mary in Virginia where he was an elite gymnast. As a thought leader, Jeff has been published in a dozen major publications, including Forbes. Jeff lives in NYC with his wife, Grace, and one-year-old son, Rivington.For More With Boundless:Consider supporting the podcast on PatreonJoin 110+ People Carving Their Own Paths In The Slack CommunitySet Up A Curiosity Conversation With PaulJoin The Free 3-Week Self-Employment ChallengeLearn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Dec 21, 2018 • 8min
Mini Episode: Five Things Before You Leap: Lessons From The Self-Employed
In this short episode, I talk about the five lessons I've found that help people make the leap to self-employment:Find a friend taking a different pathRe-define your relationship with moneyBuild up your "eff you" fundTeach others somethingFind a way to make money other than full-time incomeFull Article | This episode is also a YouTube videoFor More With Boundless:Consider supporting the podcast on PatreonJoin 110+ People Carving Their Own Paths In The Slack CommunitySet Up A Curiosity Conversation With PaulJoin The Free 3-Week Self-Employment ChallengeSign up For The Strategy Toolkit - Learn The Secrets Of Strategy Consulting
📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Dec 12, 2018 • 51min
Bryan Victor's Education: wedding planning, year-long travel & building a visual animation studio
Bryan Victor has never taken a traditional path but he doesn’t know any other way. Perhaps that is why he started his own podcast in Singapore, Misfits, which interviews unconventional Singaporeans. At 20, he saved up $10,000 while he was serving required military time and decided he would travel the world for a year. During the trip, he realized this was all the “schooling” he needed (see 10 things I learned). After learning how he could live simply on very little money, he knew that this opened up many options for him. He knew that he would always value flexibility over maximizing income, learning this lesson earlier than others.Regardless of any position towards “formal” schooling, his chosen path, wedding planning, wasn’t something you learned at school. He knew he had to create his own internship. So before his trip, he wrote to 50 American wedding planners (the best, he says), to ask if he could work with them. One person gave him a chance and he was able to learn while making enough money to live.Going back to Singapore, he couldn’t get anyone to hire him, so he realized he was “forced” to create his own wedding planning business. In the process, he became named one of Singapore’s Top 10 Wedding Planners (though he argues there weren’t that many anyway!).After proving he could make it, he started dabbling with a side business, 2D animation and founded Sage Animation. He decided to give the wedding planning business away as a gift and was able to find one person (out of 40) that he thought would do a great job.Bryan has been fascinated with understanding what makes him happy. As he was on another trip in the United States, he was drawn to another project (motivated by the #vanlife movement) to build a liveable van for himself. While he accomplished the feat, he found that he was overcome with a “something-like depression” feeling after he achieved it. While he thought he had everything, it led to a new and deeper curiosity in what actually leads to happiness. Books & Other Resources Mentioned:Jose Villa – Wedding PhotographerSeth GodinTim FerrissAntifragileNaval Ravikant Podcast on Farnham StreetSolve For HappySEO That Works CourseVanessa Van Edwards – People School---------------------------------------------------------For More With Boundless:Consider supporting the podcast on PatreonJoin 110+ People Carving Their Own Paths In The Slack CommunitySet Up A Curiosity Conversation With Paul
📘 My 2nd Book Good Work: LIVE! => Learn More📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path😁 Join 500+ In My Cozy Community: Pathless Path Community📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial