Reimagine Work

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.

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

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 herself to redefine her day and time to claim back some of herself from a sole focus on work.  She provides many actionable tips and perspectives that can help people question the role of work in their lives, take steps to increase the amount of awe in their lives and connect with people that matter to them.More About Jacqueline: TedX Talk Twitter: @JackieMJensen & LinkedIn: Jacqueline Jensen Book: Travel Isn't The Answer (Amazon) Recommendation on getting outside of your comfort zone: Check out local music: sofarsounds.com Go to an art museum Travel-as-a-service recommendations discussed: Hacker Paradise, Recess Labs, Roam, Outsite App for re-aligning your day: Today

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 implications for the community in society as a whole as well as how has dealt with that with his wife.Finally, Andrew offers three practical steps people can take to re-engage with life and try to understand what "a life worth living looks like" that does not include the advice to just quit your job. Dis-identify with the identity of the worker: Questioning whether you truly only are a worker, a CEO, a marketing manager, an accountant, etc... Begin an inquiry into the question "If I am not a worker, then who am I?": What else is worth living for? What practices do I want to have in part of my life? What relationships and conversations nourish me? The question whether or not the life you have defined is "sufficient": Are you thinking deeply enough about the question of who you are? Andrew's Writing & Site: Andrew's Newsletter On Total Work If Work Dominated Your Every Moment, Would Life Be Worth Living (Aeon) Andrew's Writing Other Writing Mentioned: Josef Pieper's Leisure, The Basis Of Culture Andre Gorz, Reclaiming Work David Graeber, Bullshit Jobs

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 shown that a 4-day work week can work and it can work in professional services - an industry where many take for granted the fact that you should always be available for your clients.Beyond improving the lives of the people at the firm, they achieved some incredible results: Revenues up 57% Absenteeism down 75% Productivity stayed the same Doubled the number of clients Client referrals up 50% Want to learn how to make this happen at your company? You can download their "4-day week" report which is one of the best reports I've seen on the future of work.

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

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.

Erin is a spiritual psychology and meditation teacher, with a background in clinical psychology. She believes in experiencing rather than explaining and because of that she has been drawn to travel to places like India and Israel, which have helped her connect to her roots and to what matters. Erin is passionate about discovering her true self, meditation, snapshot manifestation, and taking aligned action. She is finishing up a new book and is about to have her first child —  a new chapter for which she prepares herself with her partner.  

Bilal was born in London to a family of Pakistani descent. A curious kid, with an interest in computers, he developed a successful website with over 500 000 readers in his teens. He ended up working at Google in the US. After a while Bilal has left the company to carve his own path. He has founded Creator Lab and discovered a passion for spoken word poetry, which enables him to better connect with his family

Ben was a professional rugby player with an English literature degree — something not unheard of in the diverse rugby world, but also certainly not usual. After retiring from the sport, he was confronted with the task of redesigning his life. Although it was initially tough, he took the slow approach of focusing on the things he enjoys doing, which proved very beneficial in the long term. Ben has self-published 3 books so far, he is freelancing, running courses and he recently became a rising TikTok creator.

I'm trying to convince Angie to do more episodes, so if you like it please let us know by e-mailing both of us here. (00:16) - - Introduction and agenda for the podcast (03:16) - - Balancing work, fitness, health, and parenthood (13:16) - - Growth of their child and the emotional journey of parenthood (15:16) - - Financial situation and the concept of abundance (27:09) - - Sharing a parenting mistake they made and how they learned from it (38:11) - - Learning new skills and therapies (49:10) - - Angie's art business and the importance of a positive mindset (54:12) - - Future plans and dreams, including travel and education (56:11) - - Upcoming trip to Taiwan and the cultural differences they anticipate (01:04:10) - - Conclusion and plans for future podcast episodes

Jenny is an author, international speaker, career and business strategist and executive coach. She has worked in a start up during her college years and then she worked at Google. At some point she decided to follow her passions and left her job. She has already written three books, she runs a business on intuition and she continues discovering her own path.

Hannah is awesome and you should listen to this podcast.  She grew up homeschooled, is an endlessly curious person, has a deep sense of agency, and is a pro at carving her own path.  She's done a ton of things including writing, coaching, and working at startups and has created jobs for herself, negotiated working remotely (before it was cool), and has done a ton of other things.  She recently founded Rebel Educator which is a media brand that aims to share more about homeschooling and alternative education with a broader audience online.Follow Hannah: @HannahFrankman / Twitter @rebelEducator / Twitter

Dawn has a medical degree but she didn't pursue a traditional career as a doctor. She lives off grid with her husband and her homeschooled daughter. Dawn is passionate about finding a work-life balance and she wrote a book for professional women seeking to do so.

Luke has a background on Wall Street and has founded 3 companies in Silicon Valley. He describes his adult life as a constant state of uncertainty. At some point, he took a classics course, which he completed in a 24-hour Starbucks in a couple of months while living in Las Vegas. This led to him to contemplate deeper questions, leaving "entrepreneur Luke" behind and spending 3 years in Rome. Luke is now a Professor at the Ciocca Center for Principled Entrepreneurship and has written a book — "WANTING: The Power of Mimetic Desire in Everyday Life." The book is one of the best ones I've read in the past couple of years and we talk about some of the ideas in the book and how they intersect with Luke and my life.

Melvin has a PhD in psychology but to call him just "a psychologist" would be trying to fit him in too small of a box. He has left a successful clinical career to build his online "healthy business"  – he is the person behind "Selling the Couch" podcast, he does sessions with entrepreneurs and he runs an online course where he helps therapists to move their business online. Everything he does is designed to allow him to be fully present as a father and a husband because, "What's the point of accomplishing all of this if we can't be fully present with the people that we love the most?"

Anna is the founder and CEO of Interintellect - a global community of thinkers. She grew up in Hungary and emigrated to London at the age of 30 and later to the US where she built her startup. She is passionate about staying curious as we age. While for some their late 20's are the end, she has chosen to treat it as the beginning.

This is a solo episode of my podcast, inspired by Jenny Blake. I will do more of these if people like them.  Let me know!For Video: YouTube

Danny Mirands is the host of The Danny Miranda Podcast. He's been hanging out on the internet since he was 14. We talk about his journey, almost getting sidetracked by the default path in college, and then betting on himself with his podcast. Danny is a friend, and he inspired me by how true he is to his own path, his ability to dream big in creative ways and spread love in the world. 

Jessica is a producer and a podcaster. She is passionate about shadow work and is currently working on her documentary on post traumatic growth - "Dark Night of Our Soul".

Myles is a chef and a farmer's market enthusiast. He studied economics and was pursuing many other interests like filmmaking on the side. During his stay in Argentina, he realized that he wanted to follow his true passion - cooking. Although he hasn't gone to a fancy cooking school, he managed to get a position working under a former Michelin star chef in Tulum and now he's sharing his love for cooking on the Internet, making it approachable for other people.

Simone Stolzoff has worn many hats. He's worked as a writer, designer, and now, Author. He grew up with "four parents", each having a unique influence on him,  He grew up being told he could do whatever he wanted but realized there were assumptions behind that. Over the last couple of years, he's contemplated how we can design a life not centered around work (which obviously interests me as well) and has come to some interesting conclusions.

Alex was crushing it early in his career, ending up on Wall Street after getting a combined JD/MBA.  But after a few years, he went looking for his next mountain, aiming his ambition at the tech sector. He ended up co-founding LiveOak, a company he eventually sold in 2020. After that, he struggled to determine what was next and finally decided to walk away from more than a million dollars. Now he's embracing non-doing, reconnecting with his passions, and figuring out what's next.

In 2015 Khe left a Wall Street carrier to pursue his own path of "uncomfortable introspection", reevaluating his life. This is a constant process - Khe is always being emergent to himself. Now he finds himself at a crossroads - after a great initial success in 2020, he recently had to scale down his cohort-based course. Although laying people off was tough, Khe welcomes the change as entering a new season of creativity.

Kyle was a marketing executive who believed in the "hard work" ethic. After an existential crisis, he decided to carve his own path as a solopreneur and started Sloww - "a trusted resource of lifelong learning". Kyle describes his purpose as "synthesizing the art of living for students of life".

Kevin is the founding executive editor of Wired magazine, a writer and a photographer. When he was young he dropped out of college and travelled to Taiwan, which he describes as a live changing experience. Kevin is passionate about owning his time, the importance of goofing off and staying optimistic about the development of technology.

Billy used to be an avid skier, working odd jobs and traveling between the northern and southern hemispheres trying to catch the best skiing. In 2018 he e-mailed Ryan Holiday and pitched him on doing some work for him for free. In a couple of months, he was hired as Ryan's research assistant.  Billy is one of the most curious people I know and we dive into his journey.

I'm sharing this conversation I had a couple of months ago with Tom Peters. Our convo got cut a bit short but it was a fun conversation reflecting on his trajectory, why he got kicked out of McKinseyTo learn more about Tom: His Website

Trung is a writer at Workweek, cofounder of bearly.ai, and co-host of the Not Investment Advice podcast. He is passionate about playing the long game and unleashing the power of compounding.

Steph Smith is the host of the  a16z podcast and is an online creator, former consultant, former digital nomad and all-around badass.  We talk about money, work, relationships, and weddings...