Boundless: The Human Side Of Work

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.

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.

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortMatt 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.

Want To Become A Better Writer? Join Write of Passage's "Test Drive" WorkshopSteve 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.

Want To Become A Better Writer? Join Write of Passage's "Test Drive" WorkshopDavid 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.

Want To Become A Better Writer? Join Write of Passage's "Test Drive" WorkshopJustin 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."

Want To Become A Better Writer? Join Write of Passage's "How To Build Influence Online" WorkshopDom is the lead guide at the VIVIFY Regerative Leadership Program. He helps leaders develop by taking them on an 8-day backpacking expedition in the Sierra mountains. Dom is passionate about preserving the natural world, staying connected to it and practicing aliveness.

Want To Become A Better Writer? Join Write of Passage's "How To Build Influence Online" WorkshopRick Lewis could be succinctly described as "a speaker, author & professional consultant", but such technical labelling wouldn't paint a fair picture of who he really is. He describes what he's doing as "intelligent misbehavior". He's public appearances have a much deeper goal than just pure entertainment. Rick is passionate about discovering and breaking the hidden rules that rule our behavior and stifle our growth as people.

Want To Become A Better Writer? Join Write of Passage's "How To Build Influence Online" WorkshopKevin is the man behind the Epic Gardening channel. Although he had not read the Pathless Path at the time of the recording of this episode, he seems to be living it with every breath he takes. The only constant thing in his life seems to be that is constatly reinventing himself. From professional poker, gaming, web design, indie consulting, blogging to running a huge YouTube channel about gardening with almost 3 mil. subscribers, we meet at his next crossroads, after he's decided to take a step back from running the show personally day to day. 

Enroll In The 5th Cohort of Nervous System Mastery: You can get $250 OFF using the code PATHLESS => nsmastery.comJonny Miller is a dear friend and I've had the privilege to get to know him closely over the past four years on our own journeys. We've lived in Japan, Indonesia, and Mexico together. When we met we were both single but now are both married in cross-country relationships and have navigated finding work that matters, getting married, and living in foreign countries together.

Joe is an executive coach and the founder of the Art of Accomplishment. Having worked as a venture capitalist, a consultant and an international banker, Joe discovered meditation on a trip to Asia and has practiced it since for over 25 years since then. Meditating as well as a deep study of various spiritual, psychological and neurological traditions allowed him develop his unique ability to help others with personal transformation.

Join CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up HereChristine 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)

Join CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up HereJacqueline Jensen has been a digital nomad for 3.5 years, living and working globally. It might surprise you to find out then, that she's written a book called "Travel Isn't The Answer." While counter-intuitive, she argues for a return to awe and wonder with what is already around us. She talks about different moments of wonder she has experienced (including a breathtaking view in Montenegro) and different techniques for how people can "Live With a Sense of Curiosity, Passion, and Awe Anywhere and Everywhere" (the subtitle of the book).Last year, in a planned sabbatical she came face-to-face with the fact that work was the center of her world. While she almost "quit" the sabbatical, she pushed hers

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)

Andrew is a Practical Philosopher who believes that "there may be no greater vexation in our time than the question of how to make a living in a manner that accords with leading a good life." We dive deep into the questions of "what is the good life?" and what he means by "sustaining life." He also shares his perspective on the concept of "Total Work," a phrase first put forth in 1947 by the German Philosopher Josef Pieper, and shares how that phrase became central to his current writing on the topic and conversations he has with business leaders and executives.We also dive into his dichotomy of the three modes people could think about to make a living: Use what you've got Exchange what's in hand Offer what you can He reflects on our modern culture's over-reliance on exchanging our time for money while ignoring how we can live off the land and operate within the gift economy. Next, we talk about some of the different modes of living (whether it be a "settler", nomad or somewhere in between) and the implicatio

Tash Walker is the founder of a firm and spends her Fridays making marmalade.Before instituting a four-day workweek at her firm, The Mix, she barely had time for her relationships. She decided to start doing research about different ways of working. There had to be a better way than the default options of "Summer Fridays" and "flexible work," that never seem to make less anxiety or stress-ridden.In her research, she discovered many examples of Swedish companies embracing 4-day workweeks and also found that when they instituted it, they often helped improve productivity. After bringing the option to her team at The Mix, they decided to do a three-month trial. They didn't even tell their clients.The funny thing? The clients didn't even notice. Even better, when they shared it with their clients - they weren't offended. They were curious to learn more and impressed that they had prioritized their people. While many quickly reflex to "well that can't work here," Tash and her team went forward anyway and have show

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

Packy says that his differentiation "is that I’m going to be having more fun than most people”I've been a big fan of the energy he's brought to his writing over the past couple of years. But he didn't set out to have a popular newsletter.  His real plan was to launch an in-person community.  We chat about how the pandemic helped him figure out why that wasn't a good idea and how he's thinking about his solopreneur journey.The reason I asked him on the podcast is to talk about his recent newsletter on the future of work.  He argues that “Employees will ultimately make the decision” about what work looks like post-pandemic.  I think he is mostly right and we talk about what that might mean for people's lives.

Jovian is an Indonesian living in Taiwan, who is deeply immersed in the American pop culture through the power of the internet. His background in tourism helps him with problem solving and talking too people, he has learnt English from watching MTV, got one of his first jobs because he was browsing Reddit and he is now the CEO of Castro, the podcast app. Jovian is a magnet for opportunities, which apparently come to him simply because he just assumes that people are nice.

After a month spent in Taiwan and 6 months into parenthood Angie & Paul share their thoughts and take some deep dives into various other topics.