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 Hu ...
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Khe Hy Podcasts
Here’s a scary fact about adulthood. We stop asking questions. We lose the playful curiosity and creativity that we had as children. And it’s a shame. Questions are gateways to our deepest desires, insecurities and dreams. Reflecting on a deep question takes us one step closer to a life well-lived. Each week, we’ll ponder and debate one of life’s thorniest questions. We’ll explore ambition, careers, money, relationships, productivity and psychology — all in the pursuit of living an Examined ...
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FWD: Thinking is a podcast about bold professionals who have challenged the status quo to recreate their careers. They've grown out of the cracks in the org chart, punched above their titles, and when all else failed, started their own companies. Hosted by Khe Hy and created by Quartz, this podcast traces the blueprints that lead to a more fulfilling work life.
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A show for creators, by creators. Every Wednesday, hosts Charli Prangley, Miguel Pou, and Haley Janicek explore the creator economy, discussing the topics and questions facing creators and creative hopefuls alike.
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Josh Gonsalves hosts in-depth conversations with some of the brightest people in the known universe. Guests include entrepreneurs, artists, creators, innovators, scientists, and more. The aim is to spark deep conversations around interesting topics to find the tools, tactics, and philosophies that listeners can use in their personal and creative lives.
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Explore the unseen paths to success with Erika & Abi. Our guests range from industry leaders, innovators, and artists each with a story that will inspire and inform. Subscribe to join our community of curious and passionate listeners. Erika: NYC Affordable Housing Director turned full-time land investor and entrepreneur. Her company, Gokce Capital, buys and sells land throughout the United States. Don't miss her insightful book, "Land Investing Mistakes," now on Amazon. Abi: Wall Street tech ...
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Latitude is an interview show about all the non-business parts of running a successful online business. I interview freelancers and founders about how they are building their businesses and (mostly) maintaining their sanity.Latitude is about finding the space to do real, meaningful, creative work. Work that inspires others and motivates yourself. I interview creators like you to discover what it actually takes to show up and define work on your own terms. Doing creative work is hard. Making ...
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The Life Well Lived Project is motivated by this: There is so much unhappiness, anxiety and depression in the world, and this work is about trying to make things better, tiny bit by tiny bit, one day at a time. The vision of the Life Well Lived Project is a world where this cycle of unhappiness, anxiety and depression does not have to be handed down across multiple generations and accepted as an unavoidable fact of life. The vision is a world where everyone is liberated to know, embrace and ...
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Click here to watch a video of this episode. Mentioned in the episode Andrew Taggart’s website Pathways to the Dao (Andrew’s Substack) Leisure: The Basis of Culture by Josef Pieper Secular Monks (article by Andrew Taggart) Why Buddhism is True by Robert Wright Pierre Hadot (Philosophy as a Way of Life) The Pathless Path by Paul Millerd (00:00) - In…
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AMA Episode 200 - I answer questions on parenting, courage, being a prophet, taking risks, and money
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29:55
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29:55I took questions from people for episode 200. Enjoy! Click here to watch a video of this episode. (00:00) - Introduction and Podcast Background (03:08) - Future of Education and Teaching (05:29) - Thoughts on Being a Prophet (06:09) - Current Pulling Forces and Changes (08:30) - Special Hardcover Edition Plans (10:05) - Managing Financial Anxiety (…
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How To Retire Well: Dennis Owen on Moving Abroad, Building Community, Volunteering, Adapting to New Cultures, Creating Routine, Consulting After Retirement, Managing Money Mindset Shifts, Staying Current ...
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1:02:39
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1:02:39In this episode, I talk with Dennis Owen about his journey from a long career in the airline industry to building a purposeful and active retirement in Chiang Mai, Thailand. Dennis shares how he intentionally “retired to” a new life filled with volunteering, consulting, and community involvement, rather than just leaving work behind. We discuss the…
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Worldschooling 2.0: Rekha Magon on Location-Independent Schooling, co-founding Boundless Life, Lessons during bed rest, rethinking family in a digital age, travel, freedom, and raising global citizens
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1:05:54In this video, I talk with Rekha about Boundless Life and the idea of location-independent education. We cover her background, what led her to start Boundless Life, and how the program works for families who want a different approach to learning and community. For more: Boundless Life Boundless Education Rekha on LinkedIn Rekha on Instagram (00:00)…
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The Inner Game of Work: Pranab Sachi on Codependent Origination, Rob Burbea, Quake Books, Attentional Co-Piloting, Michael Taft, and "Non-Success"
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1:21:31
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1:21:31In this episode, I interview my friend Pranab Saachi, and we get specific about the ideas and influences that have shaped his thinking. We talk about codependent origination from Buddhist philosophy, the concept of “quake books” that have shifted his worldview, and his own approach to “attentional co-piloting” as a practical alternative to traditio…
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How much money do you need to quit? I debate with Nick Maggiulli (and rabbit holes: wealth > income, why COAST FIRE rocks, and more...)
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1:19:11In this episode, I'm pumped to welcome back Nick Maggiulli to the podcast (https://youtu.be/deMXbaI-Ir4). We dive into various topics about money and financial independence, with a focus on Nick's endorsement of the 'COAST Fire' strategy, something I accidentally embraced after quitting my job. Nick shares his personal stories of financial challeng…
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Following Your Inner Compass - Lawrence Yeo on his creative journey, sharing ideas, self-publishing, and playing the long game
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1:11:12Lawrence is one of my favorite creators. He shares with passion, vulnerability and care. I chatted with Lawrence Yeo about his new book, 'The Inner Compass,' exploring themes of self-reflection, creativity, and the journey of writing and self-publishing. We discuss the importance of engaging with the world to gain a deeper understanding of oneself,…
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Hustle & Flow - Jack Moses on dropping out of school, hustle culture, spiritual paths, finding flow, and travel as transformation
1:15:22
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1:15:22In this episode, I have a conversation with my friend Jack Moses. Three years ago, Jack emailed me after reading my book, declaring he was dropping out of college. Over time, I've been amazed by his life's actions, from embracing hustle culture to diving deep into spirituality. Recently, Jack led a retreat in Thailand, inspiring me with his courage…
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Does anybody want to be an influencer anymore? [Paul Millerd]
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1:15:05What if the secret to creative freedom isn't making more money but wanting less? Paul Millerd has mastered the art of living well on very little — spending $2,000 a month in Austin, driving a used cars, and now raising his toddler in Thailand. Paul and Khe discuss making creative trade-offs, the toxicity of social media, parenting outside of tradit…
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Paul Q&A Episode - Moving to Asia, Parenting, Preparing for Kids, Pathless Hardcover Art Edition
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28:04
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28:04Personal updates about life, including his recent move back to Asia, reflections on work and career paths, parenting experiences, and insights into education and self-publishing. I share the challenges and joys of parenting, how I think about decisions in regards to kids, and evolving thoughts on publishing and creative projects. Topics 00:00 Intro…
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I asked AI to roast me. It wasn’t pretty. Then it said, “Do you want me to be meaner?” The exchange was testy and agitating. It then asked, if I want it to go “nuclear.” Is this an AI slippery slope? Who owns our memories? Is creativity at risk? And should we let our kids interact with ChatGPT? [Episode 104] References from the show: • Subscribe to…
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Should we be avoiding our uncomfortable emotions? Clinical psychologist, Emily Anhalt explores how we consistently avoid feelings like shame, grief, and sadness through work, substances, or disassociation. Emotional fitness isn't about eliminating these emotions but learning to become comfortable with discomfort. [Episode 103] Dr. Emily Anhalt is a…
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Was it worth it? (10 years of leaving Wall Street) [Khe Hy]
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32:59I left Wall Street 10 years ago. Was it the right decision? What would I have done differently? 10 years is a long time — and comes with a lot of data points to assess the decision. [Episode 102] References from the show: • Walking away from a $2 million salary on Wall Street (with no plan): https://youtu.be/sy4FGaYK_l0 • I Left a $2 Million Job. H…
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Becoming A Writer - Nat Eliason on his upcoming fiction release, traditional publishing vs. self-publishing, AI tools, tinkering, readers, launch plans
1:16:19
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1:16:19Hello! I'm back! Expect a slow ramp, but there are new episodes coming! I talked with Nat Eliason about his journey as a writer, from early experiments with ideas to fully embracing writing as a career. We discussed the challenges and rewards of moving from nonfiction to fiction, the trade-offs between traditional and self-publishing, and the impor…
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How do you become a millionaire? [Sam Dogen]
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58:06Can you achieve the American Dream by saving half your paycheck? Sam Dogen, founder of Financial Samurai, left Wall Street at 34 with a seven-figure nest egg after a demanding investment banking career. He saved “until it hurts” but would he do it differently? We discuss real estate, generational wealth, and financial freedom. [Episode 101] Sam Dog…
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Should men fear mid-life? [Greg Scheinman]
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1:06:48What happens when men hit their 40s with all the trappings of success but a gnawing emptiness inside? Greg Scheinman shares his awakening at 47 — the same age his father died — when he realized professional achievement alone wasn't enough. He introduces his "six F's" framework (family, fitness, finance, food, fashion, and fun) as a roadmap for midl…
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A parent’s worst nightmare: losing a child [Mary Anne Keegan]
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59:30What happens when your world shatters with the unimaginable loss of a child? Mary Anne Keegan shares her raw journey after her healthy 20-year-old son Matthew was suddenly diagnosed with cancer and passed away just ten months later. She discovered that grief doesn't follow a playbook — giving yourself grace becomes essential when navigating between…
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How do you get your parents to be vulnerable? [Dorothy Chow]
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1:02:05Can capturing untold stories heal decades-old wounds? When Dorothy Chow set up a makeshift podcast studio to record her father's Khmer Rouge survival story, she had no idea what would unfold. What began as a historical preservation project transformed into profound healing for both father and daughter. [Episode 98] Dorothy Chow is the Host of the D…
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To understand today’s market turmoil we need to take a page out of history. This a deep-dive (and front row perspective) on the global financial crisis from 2008. You’ll learn about excess leverage, liquidity crisis, the failure of risk models, and Wall Street impacting Main Street. This will help you decide if you should “do anything.” [Episode 97…
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I was wrong about the FIRE movement [Khe Hy]
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30:38
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30:38The economy is broken and everything is going to sh*t. That’s the current narrative. But I attended a FIRE (Financial Independence, Retire Early) conference and discovered a thriving community completely defying this narrative. These professionals, not bankers or FANG engineers were nurses, teachers, IT managers. They save aggressively, embrace fru…
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Should you be weird and manipulative at work? [Jenny Wood]
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48:49
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48:49What happens when career advancement requires you to be manipulative, bossy, and a bit reckless? Jenny Wood's meteoric rise at Google reveals that success often demands breaking unspoken rules. From strategically meeting your boss's boss to mastering the Monday MiniFesto, Jenny shares how walking the line between authentic boldness and calculated s…
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Is your identity preventing you from making a necessary change? The golden child, the one who spent decades climbing the corporate ladder, often stays miserable because they can't separate who they are from what they do. Annie Duke reminds us that even the toughest career pivots are surprisingly reversible, and encourages us to imagine what we'd do…
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"Dirtbag Rich" - Blake Boles & I Talk About Extracting More Freedom From Life
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1:05:25
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1:05:25Links: 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, pres…
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Markets are selling off. Quick, how do you react? I’ve been long (i.e. no selling) since 1999. Yup, 25 years. But that doesn’t mean that major sell-offs don’t test my resolve. It’s particularly hard given our unique financial situation: lots of financial assets, no cash, low income and high spending. So how do we do it? [Episode 93] References from…
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How do you navigate career uncertainty? [Anne-Laure Le Cunff]
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51:19What happens when you hit a career crossroads and don't know which path to take? Anne-Laure Le Cunff discusses navigating "liminal spaces" – those uncomfortable in-between periods where you've left something behind something familiar but haven't yet found what's next. Instead of rushing to the nearest known thing or following the obvious sequel to …
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What’s next after a brain tumor? [Steven Mallouk]
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1:01:40
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1:01:40What happens when a brain tumor forces you to actually take a break and stop? After decades in management consulting and startups, Steve Mallouk's diagnosis made him confront the difference between chasing "enough" money versus "enough" life experiences. His journey from BCG partner to embracing vulnerability reveals how facing mortality can have u…
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What if your job actually kills you? [Lou Marchetti]
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1:13:41
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1:13:41Is your drive for success killing you? Lou Marchetti was a private equity Master of the Universe until he dropped dead during a CrossFit workout. (Yes, he had a heart attack.) Despite this wake-up call, it took getting fired two years later to finally confront the deeper void his relentless achievement was trying to fill, leading him on a journey f…
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What the heck happened to the Internet? [Khe Hy]
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26:50
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26:50What the heck is happening to the internet? Why does everything feel so different now? Between algorithmic feeds optimizing for outrage, AI-generated content flooding our feeds, and the commodification of our attention, we're watching the entire digital landscape transform in real-time. What does this mean for connection, authenticity and truly exp…
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Is the 40 hour work week dead? [Elle Griffin]
1:02:39
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1:02:39Is the 40-hour work week dead? Elle Griffin’s research shows that 70% of salaried workers clock less than 40 hours. But here's the twist: as AI and automation make us more efficient, we're not necessarily working less – we're choosing to create more. From remote software engineers to newsletter writers, the future isn't about less work, it's about …
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How do you create leverage as an entrepreneur? [Bart Egnal]
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55:40
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55:40Are solopreneurs destined to be stuck trading time for money? Serial entrepreneur Bart Egnal breaks down the traps of scaling a service business — where more revenue often leads to lower profits and bigger headaches. As entrepreneurs hit different revenue breakpoints, they face crucial decisions about hiring, systematizing their IP, and most import…
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What happens when a founder walks away from $60 million after selling his company? Post-achievement entrepreneurs often find themselves chasing bigger highs yet nothing fills the void of being without a rudder. Loom co-founder Vinay Hiramath's candid story reveals a deeper truth about conditional love and validation that many children of immigrants…
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What’s it like being married to an entrepreneur? [Anonymous]
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56:52
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56:52What happens when your spouse's startup explodes and you're suddenly worth $20 million? The anonymous spouse of a successful founder shares the real truth about identity earthquakes, unconscious power shifts, and the loneliness of being the "hidden partner" in entrepreneurial marriages. She candidly reveals how couples navigate the psychological wh…
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How do you prepare for retirement? [Christine Benz]
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1:00:42What if we've been thinking about retirement planning all wrong? Christine Benz, Morningstar's personal finance expert, breaks down how our obsession with the financial aspects of retirement often overshadows other priorities like relationships and purpose. Drawing from her new book "How to Retire," she challenges the conventional wisdom that you'l…
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50 insights that will change your life [Khe Hy]
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33:48
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33:48If you’re looking to ditch anxiety, overwhelm and comparison — this episode’s for you. Executive coach Joe Hudson put out a list of steps to develop your emotional resilience and Khe reacts to the entire list. I promise you’ll find a handful that resonate. [Episode 83]And if you have a Big Decision to make in 2025 check out Joe Hudson’s Great Decis…
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Is searching for your life's purpose causing more anxiety than fulfillment? Jordan Grumet, a former doctor turned author and podcaster, discovered that chasing "Big P" purpose – those audacious, society-approved goals – often leads to burnout and emptiness. Instead, he advocates for embracing "Little P" purpose: the small, joy-filled activities tha…
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Should you move out of the US? [Tiago and Lauren]
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1:07:10We would love to live in another country with my kids. But there’s inertia, logistics and — let’s be honest — a baked in view (for Americans) that despite its warts, life is pretty good here. I’m inspired by families who challenge conventions and blow things up a bit — especially if they have kids. Tiago Forte and Lauren Valdez left comfy Southern …
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How do you conduct an annual review? [Khe Hy]
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35:23
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35:23Modern life doesn’t allow us to take a pause, zoom out and reflect on our lives. We’re always putting out the latest fire drill or reacting to an endless stream of work messages — but how do we know if we’re doing life right? Follow along with this 16-part interactive Q&A. [Episode 80] —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep…
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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, coachin…
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