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.
Matt Yao Interviews Me
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, coaching, and several other side quests.Hope you enjoy this conversation.You can learn more about Matt here: Matt Yao
📘 GOOD WORK: LIVE! => Learn More📕 Buy
Building A Life Around Good Work (Paul Interviewed by Abel James)
You can follow Abel's podcast here: Abel James Show
📘 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 Way
Good Work is Live! (Audiobook preview)
Check out and purchase Good Work here: https://pmillerd.com/goodwork Or from Amazon directly: https://amzn.to/4gwRSCN
20 Families as a "Traveling Village - Nikolaj Astrup on his experiment living in Thailand, Vietnam, and Japan with 20 families from around the world
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Agency Is A Skill — Cate Hall on leaving law for poker, developing agency, deterministic vs probabilistic economy, risk, burnout, asking dumb questions, defining ambition, seeking real feedback, and the surface area of luck
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. O
1 Year Dad Reflections - Conversation with Sky King & Nat Eliason
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
📕Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to PathlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Pay
#173 Solopreneurship After Burnout — Justin Welsh on burnout, taking ownership of his time, struggling with a results oriented mindset, non-monetary success, becoming a top LinkedIn influencer, income goals, The Creator MBA, dealing with fears around money
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.🎥🍿 YOUTUBE: WATCH HERELinks:Personal website LinkedInX (Twitter): @thejustinwelshThe Creator MBAThe Saturday Solopreneur⌛TIMESTAMPS(00:00) - Intro
(00:56) - The scripts that Justin grew up with
(09:21) - Attention and social media
(11:05) - Liking your job, the
Success In The Second Half Of Life — Henry Oliver on John Stuart Mill, Samuel Johnson, Penelope Fitzgerald, why we shouldn't dismiss Gladwell, writing, late bloomers, the importance of finding the others, Tyler Cowen's help and the lessons from Audrey Sutherland
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.🎥🍿 YOUTUBE: WATCH HERELinks:Personal websiteSubstack: The Common ReaderX (Twitter): @HenryEOliverSecond Act⌛TIMESTAMPS(00:00) - Intro
(00:11) - Guest introduction
(00:57) - The scripts that Henry grew up with
(05:10) - John Stuart Mill
(07:41) - Samuel Johnson
(14:23) - "The common reader" &
#171 "All Work Is Noble," Montessori, and Kids & Work — Matt Bateman on starting growing up with the internet, digital and industrial literacy, studying philosophy and learning how to teach, starting the Guidepost school network, how to train teachers, how children learn and work, values in education, agency, and writing his new book
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.🎥🍿 YOUTUBE: WATCH HERELinks:Matt's Twitter — @mbatemanmontessorium.com guidepost⌛TIMESTAMPS(00:00) - Int
Apprenticeships, Sabbaticals & "Good Work" — Steve Schlafman & Matt Yao on slowing down, deprogramming, unlearning, learning from others, deciding to quit, going on a sabbatical, not being jealous anymore, competitiveness and enoughness, finding good work, ambition, the apprenticeship, Downshift, decelerator, marriage, family and reframing money
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 Do
"2M Subscribers, I love what I do, should I take a break?" — David Pakman on finding good work early, , how money and motivation changed over time, finding a balance in content creation, life after YouTube, his doubts about taking a sabbatical, having a daughter, dealing with public recognition and hateful comments, the lack of role models
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.🎥🍿 YOUTUBE: WATCH HERELinks:The David Pakman ShowX (Twitter): @dpakmanYouTube: David Pakman ShowInstagram: david.pakman⌛TIMESTAMPS(00:00) - Intro
(01:12) - The scripts that David grew up with
(03:26) - David
Building With "margin for life" — Justin Jackson on lessons from running a skate shop, optimizing for profit, running a "calm company," co-founding Transistor, having kids early, designing margins and how money actually does make him happy
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."🎥🍿 YOUTUBE: WATCH HERELinks:Personal websiteX (Twitter): @mi
#167 Wandering in the Wilderness — Dom Francks on confronting fragility, his love of nature, the disconnect from nature, working as a software engineer, viewing yourself as a piece of poetry, how we're always embedded in nature and being guided by intuition
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.🎥🍿 YOUTUBE: WATCH HERELinks:Personal websiteVIVIFY (Get $500 off if you mention this podcast)Substack⌛TIMESTAMPS(00:00) - Intro
(01
#166 Breaking Free of the Rules — Rick Lewis on being a child actor, dropping out of college, being a professional juggler, street performing and a clowning, the corporate world as an outsider, breaking rules, parenting and how to reinvent yourself
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 st
Gardening in the Digital Ecosystem — Kevin Espiritu on his fascination with the early Internet, how Poker broke his brain on money, starting his YouTube channel, Epic Gardening, taking a long term perspective, how to structure a video, transforming his YouTube channel, introducing new people to his audience, the probabilistic mindset and what he learnt from poker that helps him in his life
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 w
[Repost] My Nervous System Guru & Friend - Jonny Miller on His Own Pathless Path, Grief, Friendship, David Whyte & More
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.🍿Watch on
Transformation For High Achievers — Joe Hudson on growing up with an alcoholic father, living around the world, transformation and self-discovery, becoming comfortable with yourself, emotional fluidity, expressing emotions, and the art of parenting
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.🎥🍿 YOUTUBE: WATCH HERELinks:Art of AccomplishmentPodcastX (Twi
[Replay] Reinventing After Quitting A Top Job At Amazon - Christine Bader
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 Gi
[Replay] Taking a "structured sabbatical" & Calm Companies - Jacqueline Jensen
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 Answe
[Replay] Starting a "tribe" and living on an island with three kids - Ben Keene
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
Usin
[Replay] How "total work" took over the world - Andrew Taggart
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 writin
[Replay] We Adopted a 4-Day Workweek - Tash Walker
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
[Replay] Living On A Boat for 1.5 Years - John Zeratsky
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 u
[Replay] Packy McCormick on Injecting Fun To Newsletters
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 newslett
Luck Maximization — Jovian Gautama on being Indonesian in Taiwan, learning English from MTV and Reddit, graduating from a tourism high school, selling steel, podcasting, learning "tech" online, becoming the CEO of Castro
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.🎥🍿 YOUTUBE: WATCH HERE
Money, Work, Parenting & 1 Month In Taiwan - Angie & Paul on money scripts, cultural differences, being Taiwanese in the US, being American in Taiwan, perceptions of work in their families, life with a newborn, impostor syndrome, remote work and travel
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.🎥🍿 YOUTUBE: WATCH HERE⌛TIMESTAMPS
(00:00) - Podcast intro
(02:17) - How Angie & Paul think about work & money?
(10:12) - Cultural differences, ask vs guess
(14:58) - Defining work, feedback from the family
(22:22) - How are Angie & Paul thinking about having kids?
(29:09) - Angie's relationship with writing
(44:53) - Accepting complime
9 Year Identity Crisis?! - Tom Critchlow on being stuck, indecisiveness, going to wander, taking every 7th week off, strategically dropping the ball, hiring an editor, and fear of finishing his book
🥳 Join Find The Others: Learn More HereTom and Paul talk through Tom's challenges at this inflection point in his indie career, a book he's planning on shipping and how to think through indie consultant identity crises🎥🍿 YOUTUBE: WATCH HERELinks:Tom's Site: https://tomcritchlow.com/Strategic Independent: Book Draft
⌛TIMESTAMPS
(00:00) - Intro
(01:09) - Guest introduction
(03:33) - Tom's problem — indecisiveness
(07:47) - What does Tom think he should be doing?
(10:10) - N
#160 - Why Manifesting Works — Erin Doppelt on how living in Israel and India changed her life, "snapshot manifestation", why women should work aligned with their menstrual cycle, entrepreneurship as freedom for women, pregnancy, and her new book
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 w
Living Intentionally After "Enough" - Bilal Zaidi on leaving Google, emigrating to the US, video games, the intensity of New York, writing poetry and spoken word, travel vs vacations, and money and creativity
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🎥🍿 YOUTUBE: WATCH HERELinks:
X (Twitter) — @bzaidi
Creator Lab Website
Not Investment
#158 From Rugby to TikTok Influencer — Ben Mercer on navigating the transitional periods in his life, being a professional athlete with an English literature degree, the diversity of the rugby world, various motivations in sports, his passion for rugby, his love of reading and writing, self-publishing and becoming a Tik Tok creator
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 Ti
#157 Parenting & Our Future - Paul & Angie Check-In on Five Months of Parenting, Unexpected Happiness, Parenting Scripts, and The Time Bucket Exercise from Die With Zero
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
(49:1
Saying "no" to something good — Jenny Blake on the inner CFO, spending every penny just to try, working at Google, running towards something vs. running away, creating assets for yourself, making yourself discoverable, and seeking advice from "friendtors"
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.🎥🍿 YOUTUBE: WATCH HERELinks:
itsfreetime.com
pivotmethod.com
Jenny's Books:
Life After College
Pivot
Free Time
⌛TIMESTAMPS
(00:00) - Podc
Homeschooling = Future of Education? - Hannah Frankman (Repost)
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 alternati
#154 Learning to "Lean Out" - Dr. Dawn Baker's Journey from Medicine to 'Leaning Out', Embracing Unconventional Paths, Living Off-Grid, and Homeschooling
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.🎥🍿 YOUTUBE: WATCH HERELinks:
Book: Lean Out
Twitter: @DLBakerMD
practicebalance.com
Instagram: practicebalance
⌛TIMESTAMPS
(00:00) - Intro
(01:05) - The scripts Dawn grew up with
(02:49) - Medicine, engineering and rock cli
Beyond Memetic Desires - Luke Burgis on the temptations of conformity, contemplating life in Starbucks, thick desires and thin desires, letting go of control, the importance of play, learning from different work cultures, his stay in Rome and becoming a father
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 — "WA
#152 The Creator Therapist - Melvin Varghese on Emigrating to Texas, his work as a clinical psychologist, starting a podcast, the birth of his daughter, re-evaluating life and money and detaching identity from work
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 acc
#151 Culture Without Culture War - Anna Gát on growing up in Hungary, emigrating at the age of 30, staying curious as we age, Interintellect, building a startup, bad advice and trusting your gut, her article in 2018, culture without culture war, creating your own gatekeepers, and success in the UK vs US
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.🎥🍿 YOUTUBE: WATCH HERELinks:
Interintellect
Twitter: @TheAnnaGat
Instagram: annagat_
Anna's Personal Website
Writing
⌛TIMESTAMPS
(00:00) - Intro
(01:20) - The sc
Why I Turned Down a $200k Book Deal (Solo Episode)
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
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow Paul
Twitter: @p_millerd
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#149 "I will sell out Madison Square Garden" - Danny Miranda on being on starting a blog at 14, following your intuition, discipline, meditation, his podcast, retreats, masculinity, compassion, "The True Path", thinking big, and trusting The Universe
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. 🎥🍿 YOUTUBE: WATCH HERELinks:
The Danny Miranda Podcast
Twitter: @heydannymiranda
Instagram: heydannymiranda
Embracing Post-Traumatic Growth - Jessica Depatie on her Korean background, shadow work, producing a documentary - "Dark Night of Our Soul", expanding your perspective through travel, what does it mean to rest, defining growth, the hero's journey, and memes
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".🎥🍿 YOUTUBE: WATCH HERELinks:
Link to Support The Movie - Dark Night of Our Soul
Jessica on IMDb
Instagram - jessicadepatie_
Hollywood Con Queen Podcast
Bill Plotkin’s Journey of Soul Initiation
@wordsarevibrations meme account
⌛TIMESTAMPS
(00:00) - Intro
(00:11) - Introduction
(01:19) - The scripts Jessica grew u
#147 You Can Love Cooking Too - Myles Snider on intuitive cooking, living in Argentina, working in Tulum, food industry scripts, health myths, the beauty of "slow cooking"
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.🎥🍿 YOUTUBE: WATCH HEREIf y
Separating Work & Identity - Simone Stolzoff on the myth of a "Dream Job," last-minute around the world trip, journalism, work, identity, writing his book, knowing when to quit, and the dangers of turning passion into a livelihood
Simone Stolzoff is an author and journalist from San Francisco. A former design lead at the global innovation firm IDEO, his work has been featured in The New York Times, The Atlantic, The Wall Street Journal, and various other publications.🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @SimoneStolzoff
Simone's Website: simonestolzoff.com
Happiness Lab
Recent every pieces
⌛TIMESTAMPS
(00:00) - Intro
(01:46) - The scripts that Simone grew up with
(06:46) - Anis Mojgani, copyrighting and travel
(
#145 Capitalist by Day, Spiritual by Night - Alex Hardy on achievement, Wall Street, tech startups, exiting his company, pride & suffering, his sabbatical, suppressing his curiosity and rediscovering his passions
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. 🎥🍿 Y
#144 The Creator Pivot - Khe Hy on laying people off, collapsing course demand, seasons of creativity, having zero change in net worth in eight years, competitiveness, investing, coaching, and marriage on the pathless path
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.🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @khemaridh
radreads.co
Down
#143 The Art of Living - Kyle Kowalski on how to have an existential crisis, synthesizing the art of living, curiosity as fuel, his relationship with money, "killing himself to work" and "purpose washing" in big companies
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".🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @KyKow
Sloww: sloww.co
Happiness Book
Igikai 2.0
⌛TIMESTAMPS
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create &
#142 Goofing Off On Purpose - Kevin Kelly on why we should subsidize travel for young people, owning his time, a rest ethic, riding his bike across US, his love of YouTube, staying optimistic about the future, raising children and his new book
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.🎥🍿 YOUTUBE: WATCH HERELinks:
Kevin's website: kk.org
Kevin's articles on Wired
Excellent Advice on Living: Amazon
⌛TIMESTAMPS
(01:01) - Taiwan and t
#141 Ryan Holiday's Secret Weapon - Billy Oppenheimer on growing in Philadelphia, almost going to law school, role models, working with Ryan Holiday, his research process, the notecard system, skiing, and the downsides to fame
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. 🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @bpoppenheimer
Website: billyoppenheimer.com
Billy's Newsletter
⌛TIMESTAMPS
#140 Tom Peters - Fired from McKinsey to Top Business Thought Leader
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
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow Paul
Twitter: @p_millerd
Paul’s Newsletter: Subscrib
#139 Compounding Memes - Trung Phan on his great grandfather, living abroad, the expat community in Asia, writing, working at The Hustle, children and work, balancing his various activities, going solo, and playing the long game
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.🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @TrungTPhan
Website: trungtphan.com
Bearly.AI
Podcast: Not Investment Advice
Trung's writing at Bloomberg and Workweek
Trung's Newsletter
⌛TIMESTAMPS
(02:12) - College and getting up late
(04:06) - Trung's great grandfather - Vietnamese hero
(08:53) - V
#138 Money & The Creator Economy - Steph Smith on our lack of wisdom about money, reaching "ice cream freedom", The Hustle, balancing employment and side gigs, unconventional paths, opportunities in the creator economy and how not to get disappointed at your wedding
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...🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @stephsmithio
Steph's book: doingcontentright.com
a16z Podcast
The Sh*t You Don't Learn in School Podcast
Blog: stephsmith.io
⌛TIMESTAMPS
(01:19) - The scripts that Steph grew up with
(03:09) - Perceptions of money over time
(28:37) - Working at The Hu
#137 Life as Conversation - Russ Roberts on his relationship with his father, starting the EconTalk podcast in 2006, Adam Smith, why people want to be "lovely", aiming high, why it's hard to have fun, misunderstandings of the academic world, and moving to Israel in his 60's
🥳 Join Find The Others: Learn More HereRuss is an economist, a research fellow at Stanford University's Hoover Institution and president of Shalem College in Jerusalem. One of pioneers of podcasting, he's been hosting EconTalk since 2006.🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @EconTalker
EconTalk Website: www.econtalk.org
EconTalk YouTube Channel
⌛TIMESTAMPS
(03:25) - The influence of Russ' father
(11:33) - What modern economics often fails to observe
(16:35) - Adam Smith and huma
#136 Complexity & Complicatedness - Sam Spurlin on playing hockey, why he quit teaching, studying at Claremont, leaving a PhD program, working pro bono too start his career, complicated vs complex systems, how to deal with ego in organizations, remote work failures, podcasting with his brother, and the importance of a retrospective meeting
🥳 Join Find The Others: Learn More HereSam is a partner at The Ready - an organizational design consultancy operating fully remotely. He is also a prolific writer, passionate about personal development, self-managing organizations and adopting a more human, adaptive, and meaningful way of working.🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @samspurlin
Instagram: samspurlin
LinkedIn: linkedin.com/in/samspurlin
Sam's writing: samspurlin.com/writing
Sam's writing on Medium: samspurlin.med
#135 Beyond Comfort - Derek Sivers on why great musicians shake things up, ambition, and moving to a new country as a superpower, lessons from Singapore, and the scripts around having children
🥳 Join Find The Others: Learn More HereDerek Sivers has been a musician, producer, circus performer, successful entrepreneur, TED speaker, and book publisher. He has lived all around the world and has never let himself be too comfortable - constantly changing and following his inner ambition.🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @sivers
Website: sive.rs
My Favorite Derek Book: Anything You Want
⌛TIMESTAMPS
(00:54) - The scripts that Derek grew up with
(06:05) - Comfort as a platea
#134 The Office-Based Reality is Over - Dror Poleg on entrepreneurship in Israel, studying in Australia, working in China, Future of Remote Work and The Real Estate Business, How To Write A Top 5 Book in Almost Any Category, The Disappearance of The Middle-Skilled Job, Inequality and The End of The Offices
Dror worked as a real estate private equity exec, startup founder, front-end developer, parliamentary advisor, and soldier. Having lived all around the world he is now based in NYC, writing as an “Economic Historian”.Having predicted that remote work is going to become the new norm back in 2015, he has just published a survival guide titled "After Office".🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @drorpolegWebsite: drorpoleg.comAfter Office ⌛TIMESTAMPS (13:30) - Living in Australia and Chi
#133 Creation Without The Ego - Isabel Unraveled on writing, "the chronic state of performing", detaching your sense of self from the work, finding the inner child, paying attention to your emotions, trusting your intuition and why people should stop pretending
Isabel is a writer who is very passionate about the creative process. She has some powerful original ideas about the relationship between the artist and their creation, trusting one's intuition, and why people should stop pretending.🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @isabelunraveled
Isabel's Writing: https://mindmine.substack.com
⌛TIMESTAMPS(0:11) Introduction (5:41) "The chronic state of performing" (12:00) Missing and rediscovering her passion for writing (34:38) Detaching you
#132 Making Money Simple & Smart - Nick Maggiulli on blogging into a new career, writing for smart people, building relationships in the finance world, the lifestyle creep myth, dying with too much money, and money emotions
Nick Maggiulli is a finance data analyst and writer. He is the author of "Just Keep Buying" and has a blog titled "Of Dollars and Data".🎥🍿 YOUTUBE: WATCH HERELinks:
Twitter: @dollarsanddata
Blog: Of Dollars and Data
Nick's Book: Just Keep Buying
⌛TIMESTAMPS(0:47) The scripts nick grew up with(5:35) Writing books and blogging(32:44) Building relationships in the NYC finance scene(36:07) Why the writers shouldn't dumb down their books(37:33) Perceptions of money(1:07:26) Closing th
#131 The Art of Sabbaticals - Cécile and Michelle on finding "forgotten hobbies", writing online, improving their relationship with money, abundance mindset and rediscovering joy
Cécile has had a successful career in consulting, acquiring a senior position in a big company that has taken a leadership role in the energy transition in the UK. Although she was passionate about her job she decided to go on a yearlong sabbatical from work, traveling around the world and writing - creating space for her curiosity & creativity.Michelle has a background in sales but after a couple of years in the business she decided to go on a sabbatical that doesn't seem to have a
#130 You Have One Life - David Senra on finding his life's work, trial & error, the necessity of talking risks, mortality, balancing his entrepreneurial endeavours and family life and what can be learned from reading hundreds of biographies.
David Senra has sponsored a $1,000 giveaway of copies of my book. You can grab a copy of The Pathless Path Here or https://tally.so/r/n0V0XZ (Check out Founders Podcast!)David Senra is the creator of Founders Podcast and is obsessed with bringing alive the knowledge of the most driven, curious, courageous, and interesting founders throughout history. He has spent almost all his time reading, re-reading, and recording one of the best podcasts on the planet right now. Links:
Follow his p
#129 Friendly Ambitious Nerd World-Building - Visakan Veerasamy on Long-Orbit Friendships, Preemptive Defensiveness, "Hot Streaks," Writing A Book, Making $1000 for one copy & Negative Comments
Visakan Veerasamy is an internet creator and writer, he is passionate about the future of the internet, ideas, and how people can be bolder on their creative journeys. His mission is to build the greatest social graph of friendly, ambitious nerds that the world has ever seen.This is our second conversation and dives much more into his current work and how he thinks about the internet. 🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @visakanvWebsite: visakanv.com Buy Introspect: On Gumroad⌛TIMES
#128 Crafting A Life You Love - Amy Tangerine on working in fashion, carving her own path, starting a business, a third-life crisis, scrapbooking as contemplation and learning from and inspiring her children
🥳 Join Find The Others: Learn More HereAmy Tangerine is a long-time creator, entrepreneur, and mother. We talk about her path, starting a business that took off, her "third-life" crisis, learning to inject rest into her path, her relationship with her mother, having children, scrapbooking and building a business around work she loves. WATCH On YouTubeFOLLOW AMY
Her Website: amytangerine.com
Twitter: @amytangerine
Instagram: @amytangerine
Facebook: @amytangerine
TIMESTAMPS0:00 Audio
#127 The Art of Quitting & Reinvention - Nina Simon on living "off the grid" in an intentional community, taking "turns" in marriage and work, having kids on an unconventional path & leaving her dream job at NASA
At each professional crossroad, Nina Simon has made the choice most likely to disappoint her mother. She left an electrical engineering job at NASA to design spy museum exhibits, said goodbye to a museum directorship to start a global movement for more inclusive cultural organizations, and now has put down her CEO hat to write crime fiction. Her first novel, Mother-Daughter Murder Night, will be published in 2023 by William Morrow. Nina lives off the grid in the Santa Cruz mountains wit
#126 Hearts on Fire - David Perell on curiosity, being a citizen of the internet, taking himself seriously, childhood obsessions, building Write of Passage, ambition, and money
This episode was a delight. I've been following David's journey since 2017 and he was one of the fellow internet weirdos I saw on a similar path that didn't quite make sense. I've been inspired by how many people David has helped onboard as "citizens of the internet" through his course Write of Passage. I'm rooting for David and I think you'll want to as well by the end of this episode. We filmed this in David's epic studio - I highly recommend watching this one on YoutubeLinks Mention
#125 Angie & Paul - We're Having a Kid (and other life updates)
Get CASH to move to cities in the US: MakeMyMove.comAngie and I talked about our journey (mostly hers) over the last two years including her leaving fitness, moving to the US, enrolling in Write of Passage, finding her community, and initial traction as a freelancer.🍿 WATCH ON YOUTUBELinks:
Angie's Site: Angie Creates
Her Experience in Write of Passage: From Fear To Thriving
Angie's Podcast: Angie Creates (English & Chinese)
Timestamps0:00 Introduction0:15 Introduction & Angi
#124 Can You Ever "Make It" While Self-Employed - David Kadavy on Doing Work You Love, Self-Publishing, Traveling & Perspective, Mini-Lives & Living as An Expat
David talks about his self-employment journey, discussing topics such as graphics design, studying abroad, work identity and engagement, self-publishing books, and advertising on Amazon. He reflects on his experiences and explains how he shifted from a traditional job to self-employment, including how he experienced a new reality after leaving his job. We talk about how hard it is to ever "make it" on a solo journey and how you are constantly starting from day 1.🍿YOUTUBE: https://youtu
#123 McKinsey Partner to Indie Freelancer - Adam Braff on writing online, the gig economy, consulting skills, consulting
Adam Braff grew up in a house where writing was always encouraged. His mother published a newsletter, and his father was a data analytics consultant. He started out as a lawyer, but after the dot-com boom led to a surge in demand for consultants, he decided to make the switch. He now runs his own consulting firm and writes regularly on a variety of topics. Braff himself became interested in consulting during the first dot-com boom. He transferred from MIT to Brown in order to study lin
#122 Indie Life & The Future of Work - Venkatesh Rao
This episode was a delight. Venkatesh Rao is the creator of Ribbonfarm and has been writing about the internet, technology, and gig life. This conversation focuses on his recently published book, The Art of Gig. If you are thinking about working independently, becoming a freelancer, or are interested in consulting, you should definitely buy his book:
The Art of Gig, Foundations
The Art of Gig, Superstructures
WATCH ON YOUTUBE: https://youtu.be/KC63HrF8V4EYou can find Venkatesh:
on Twit
#121 Carving Your Own Path In a "Vibecession" - Kyla Scanlon on leaving her job, writing online, TikToks as Poetry, and The Passion Crisis
I believe that Kyla Scanlon is one of the most talented all-around creators. She is transcending the assumptions about what people want, especially with things like short-form videos. Her TikToks are synthesized, thoughtful, and funny, setting a new bar for what people want in an information age.We talked about her journey growing up in Kentucky, writing online, hacking into the finance industry from a non-target school, and ultimately deciding to become self-employed with less than two
#120 How Do You Buy A Home While Self-Employed? Catherine Cusick on her path, acting, economics of Broadway, longreads, independent book sales, buying a home, digital media & how to navigate hostile US self-employment regulations,
The legible story is that Catherine is a writer, producer, and digital media consultant. She helps creative people connect with new audiences, usually writers, usually online. But she hasn't had a W-2 job since 2017. Before that she worked as an actor, worked at a company called Longreads, and then has done a bunch of solopreneur experiments over the past five years.Her recent interest is writing and speaking about how to navigate systems that make self-employment harder in the United S
#119 Goosebump-inducing Waves of Knowingness - Jonny Miller on grief, friendship, living abroad, founding a company, remote work, Rolf Potts, David Whyte, poetry, and finding work that matters.
Jonny 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.🍿Watch on YouTubeThis conversation was really special.I also recommend his course: You can get 10% off using the c
#118 A Better Future for Healthcare - Andy Schoonover on Crowdfunding for Healthcare, Search Funds, Buying A Company, Work-Life Balance, Bitcoin & Problems With Healthcare
Andy Schoonover is the CEO of one of the sponsors of this podcast. After talking with him I actually thought he'd be a great guest on the podcast. He has a fascinating story from going from search-funder post-MBA grad to forming his own healthcare company. Can his company fix healthcare? Can anyone? Time will tell but I'm rooting for him.Join CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability
#117 The Truth About Remote Work - Ali Greene on being a remote leader, leaving the default path, stories and taking breaks, living in different countries, & writing a book
🍿 Watch on YouTubeAli Green has been a remote worker since 2014. It took her a couple of attempts to fully unpair from the office and even when she had a fully remote job it took her another year to lean into her freedom. Now she's writing a book about what she's learned leading teams, living in different countries, and working remotely.
Quitting her job and inventing a "story"
Experiences working remotely since 2014
Working full-time remotely for Duck Duck Go
What people get wrong abo
#116 From The "Holler" to Therapist to Creator Coach - Corey Wilks Psy. D. On Helping People Thrive
Dr. Corey Wilks is a Licensed Clinical Psychologist and Executive Coach with over 15 years of psychological experience.In 2020, he stopped practicing therapy and ventured into entrepreneurship. Now, he coaches entrepreneurs and creates content to help people be more intentional with how they live, work, and create.His latest project is Intentional Life Design, a 5-week live cohort-based course focused on helping people overcome limiting beliefs, think bigger, and do work that matters.Fi
#115 Creativity as a Compass - Anne-Laure Le Cunff on Leaving Google, Freelancing, and Combining Creativity & Neuroscience,
In this episode, I talk with fellow creator and curious human Anne-Laure Le Cunff. She left her job at Google and embarked on an entrepreneurial journey about one month before I did in April 2017. We compare the lessons we have learned over the past five years as well as talk about:
How her mother's experience as an immigrant influenced her work scripts
Her creative interests vs. practical career choices
Getting into google and getting sucked into the tech world
Quitting her job and th
#114 Training Elite Wall Street Traders - Michael Steiner on his time at SIG, using games to train market makers & becoming a high school teacher
Mike Steiner found himself on Penn’s campus at a young age not really knowing what he was supposed to do next. Thanks to helpful roommates, he started to figure out how to take advantage of the opportunities around him. He started getting more interested in math, statistics, and finance. He eventually ended up interviewing in New York and ending up at the famous training firm Susquehanna Investment Group (SIG). As a part-time trainer at first and then in a more central role, Mike starte
#113 Beyond Hustle Culture & Helping Creators Make Money - Justin Moore from Creator Wizard on his journey as a Youtuber, creator, brand agency founder, musician, and now Sponsorship Coach
Today I’m talking with Justin Moore - he and his wife was what he calls “OG Youtubers.” From creating content to landing sponsorships to building his own agency, he’s seen every angle of the creator economy. a lot over the last ten years. In the past couple of years, he walked away from the agency and has stumbled into a new path, one he’s finding a lot of joy following - helping other creators getting paid as a sponsorship coach.He turned down a buyout offer for his course and newslett
The Power of Play In Work & Life - Gary Ware is Leading A Playful Rebellion
Gary Ware is someone that inspires me. I've seen him give two walks, both at the World Domination Summit in 2018 and then in 2022. In each, he stood out for his ability to show up as himself and share playful and powerfully true stories about his journey. I love when I get to meet people like Gary and this interview was no different. You can feel his positive energy flowing through the screen (or earbuds!).🍿🎞️ Watch This Episode on Youtube Links Mentioned:
📕Gary's book: Playful Re
#111 The Art of Self-Management - Claire Emerson on Quiet Achievers, Her Unconventional Path, Finding Digital Mentors & Overcoming Procrastination
Claire Emerson is a writer and project consultant who helps business owners execute their best ideas. She is the curator of Flourish newsletter and the creator of Implement My Course — a free 10-day email course on how to apply what you learn without procrastination poisoning your progress. Links Mentioned:
Anna Macko - Crypto Queen (@lovingnotworking) • Instagram photos and videos
We Don't Just Teach Content Marketing ... We Built Our Company With It (copyblogger.com)
About The Kolbe A
The Very Online Quasi-Wandering Monk - Tasshin Fogleman on Metta, Monasteries, Leisure, Work, Twitter and Finding Work That Matters
I spoke with Tasshin Fogelman about his life's work to bring more love into the world, how he navigates life as a modern online monk, what he learned from spending time at the monastic academy, and what he see's as work worth doing.You can learn more about his work here: https://tasshin.com/📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow Paul
Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe
🙏Further Ways To Support T
Autism at Work, Early Blogging & Unconventional Paths - Tara McMullin
Tara McMullin is a writer, host of the What Works Podcast, and also cofounder of a podcast production studio. She's been working with small business owners for more than 13 years and has a deep understanding of what makes them tick. She’s recently written about realizing she was autistic and how that has impacted her role in the workplace.🍿 Watch On Youtube🔗 Links:
Tara's Site: Explore What Works
Twitter: @taragentile
How learning I’m autistic changed the way I work
Finding A Way
The Nonlinear Life Path: College at 16, Med School in Cuba & Starting Over After Kids - Aida Alston
Aida Alston is no stranger to alternatives to the default path. From testing out of high school at 15, to finishing college with no debt, then going to medical school for free in Cuba, Aida has been walking her version of a pathless path for a long time. But she's at a transition point now. She decided not to pursue clinical practice as a physician—again turning away from the default path right in front of her. She's been a full-time stay-at-home mother since then to her two children, r
Fixing The Healthcare System For Indies x Web3 - John Paller
John Paller is a Denver-based entrepreneur and the Founder of Opolis, a Digital Employment Cooperative for independent workers. He is also the founder of ETH Denver, the world’s largest Web3 and Ethereum festival. Prior to discovering Ethereum in 2015, John spent more than 15 years in talent acquisition, HR Technology, and employment systems, building multiple successful enterprises. John brings a breadth of experience in fundraising, investor relations, community outreach and crypto ec
How To Set Goals & Do Things That Matter - Malcolm Ocean
Malcolm ocean is a fellow wanderer of the pathless path and as is such - is hard to describe. He runs a software company, Complice which helps people turn big goals into day-to-day actions. More broadly from my vantage point, Malcolm appears to be one of the most deeply curious humans alive about how we make things happen at the individual and group levels.Follow Malcolm:
Website
Twitter @Malcolm_Ocean
Sign Up For Complice and get one bonus week
CrowdHealth: You ditched the traditional
Lessons From Homeschooling, Skipping College & Carving Her Own Path - Hannah Frankman
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
What Do Digital Nomads Tell Us About The Future? - Lauren Razavi (Executive Director, Plumia)
Lauren and I first talked when I was locked down in Taiwan in 2021. It was amazing to connect with another nomad and writer after weeks of not seeing people. I was also a bit stuck in my book writing process and she gave me a ton of helpful hints to take my book to the next level.
I was excited to interview Lauren because she just finished her own book, Global Natives about her own experience as a nomad (since 2013!) and also the past, present, and future of the movement. I think she
Growing up in Hawaii, Corporate Detours & The Future of Audio - Sky King
This episode is with Sky King, the founder of Modern Stoa, a podcast advertising company for podcasters. His path is fascinating - he grew up in Hawaii, rarely wore shoes, was heavily influenced by Asian culture, had a father who was retired, and somehow ended up in a massive corporation right after college. In 2016. he became fascinated by how the media was shaping the 2016 US election and decided it was time to act. From a cold email to Ryan Holiday to helping build Aubrey Marcus'
The Arc of The Practical Creator - Lawrence Yeo
Being an undeclared major till his senior year of college, Lawrence didn’t really know what he wanted to do. After looking up which jobs make the most money, he decided to declare as an economics major, leading him to explore Investment Banking. While he didn’t end up working in investment banking, he was still pulled by the power of prestige, something he says “is a drug, and is most potent” when you are young and looking at schools. Over a number of years and experiments with music an
Podcast Update! Re-branded as The Pathless Path & LIVE Q&A From Youtube
I offer a short little update on the next steps for the podcast and include a live Q&A I did on youtube last week.
Video link: https://youtu.be/CGbw7Q8hoys
The Money Path or The Life Path? - Tim Malnick
Tim Malnick has always lived between the two worlds of business and creative/activist circles. In his twenties, he stumbled into a creative group of young people, of which “none of them following the obvious path.” This gave him a lot of confidence that different kinds of paths were possible and enabled him to offer a diversity of perspectives that he was able to bring to many different environments.
One of the things he spends a lot of time on now is helping people transcend their re
Music, Entrepreneurship & Embracing Non-Work - Paul Canetti
Paul Canetti is a professor at Columbia Business School and sits on the Strategic Advisory Board of Riverside Acceleration Capital. We explore his initial passion for music growing up, how he became an accidental founder, and how he's exploring his relationship with work after exiting his startup.
He was named one of Inc.'s “30 Under 30” and has founded multiple software businesses including MAZ and ClickEasy (originally Bounce House), both of which were acquired in 2021. He is an an
The Magic of Writing with Sasha Chapin
I talked with writer and writing coach Sasha Chapin about the role of writing in our lives, how we think about writing, and how he specifically helped with my process in the book.
Check out Sasha here: Sasha Chapin (imsashachapin.com)
& Buy Paul's Book https://think-boundless.com/the-pathless-path/
Khe Hy - Tales From The Pathless Path
Join Khe's Supercharge Your Productivity course: https://10k.radreads.co/join-syp11/yzrsv (affiliate)Get access to Khe's $10k training which will help you wander towards the pathless path: https://radreads.co/millerdFrom a live event where Paul & Khe talk about their shared journeys of self-employment, creating online & more
The Pathless Path Launched! (reading of the introduction)
Just launched my book, The Pathless Path!
Purchase the book here.
This is the introduction of the book.
I'll be releasing some clips of me reading the book and will eventually publish an audio book.
Valuing Options & Possibilities On The Solo Creator Path with Kris Abdelmessih
Kris Abdelmessih has one of the most unique perspectives on life and works I've stumbled across in the past few years. He uses his experience as a trader to look at decision-making and work investments through the lens of options, pricing, and other financial models. I enjoy his perspective because unlike other financial types, he seems to have a proper appreciation of non-work / non-productive time.We explore his recent break from trading, his creative journey writing on the internet
The Formless Path - Money, Fatherhood & Creativity (Howard Gray)
Howard Gray is the founder of Wavetable, a studio that helps brands and companies come together to develop fan-based experiences to help teams teach and share ideas.
The two things that drive him are to "create space for people to do the work they want to do" and to help people "make sense of the world and overcome the tension of putting things out in the world"
We dive into his idea of the formless path, why the creator economy is in danger of being hijacked, how he sees himself as a g
The Shadow Side of Solopreneurship - Darren Joe
“You can’t study or learn your way into a new identity” - I love this quote from Darren Joe. He’s been thinking about carving a different path from 2003 to 2004. He said that he was driven by a natural drive to be independent and do his own thing. I found this pretty impressive because in those years not many people were doing what he was doing.
He recently published a book titled The Fail-Safe Entrepreneur. In it he argues that almost all solopreneurs strive for three things: Freed
Six Months In The Creator Economy - Michael Ashcroft (Part 3)
In parts 1 and 2, I interviewed Michael about his plan to quit his comfortable consulting job and start a new path creating and selling courses online.
Let's see how he reacts to his own quotes from a year earlier!
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The best way you can support me is to join in the conversation. Share thoughts on Twitter, send me an e-mail, and tell me what resonated or what you’d add or refer a friend:
If you’d like to support further you can use my affiliate link for some of th
Accidental Freelancer To Brand Consultant, Founder & Freelance Coach (Austin Church)
Austin Church thought he was going to be a poet. When that didn't go as planned, he joined the business world. Six months later he was laid off in the 2008 recession. Luckily, his firm hired him back as a freelancer and that completely changed his perspective on work. Ever since he's been hacking a living, shifting roles as a freelancer, founder, entrepreneur, and coach. We chat about his journey and more.
Learn more about Austin and his great writing on freelancing here.
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Burnout & "Living At Work" In 2020 - Natalie Rachel
Natalie Rachel went through her own experience with burnout before turning to help others. She found that "with burnout, rest doesn't touch it," you need a deeper strategy. We compare notes on our own journeys where we were surprised by burnout. We thought it was something that resulted from working long hours. Natalie says a better way to think about it is as "self-neglect of reflection."
Resources Mentioned:
Natalie On Twitter
Natalie on the James Altucher Show
Dr. Geri Puleo
Narratives, Work & What Matters - Ben Hunt
Ben Hunt is a father, husband, former academic, author turned blogger, former hedge fund analyst, investment advisor, and farmer.
And he’s also my podcast guest in this episode.
His writing has been an inspiration to me as I try to carve my own path after leaving what he calls “Team Elite.” His philosophy of make, protect, teach focuses on local and bottom-up change in the world. In addition, we also discuss:
How losing his father changed his relationship with time
Industrially nece
Money Fears, Self-Employment & Living Abroad With Kids - Jenni & Lisa Dazols
Jenni and Lisa Dazols read an essay six years ago which made them question their frantic & busy lifestyle. They could barely take care of their dog. They decided to take a break from a work. We dove into their story of deciding to move abroad, taking a sabbatical, having kids, moving to Taiwan, launching a passion project, coaching people on their money fears, and what they've learned along the way.
They run a business called Modern Family Finance and help people think about fina
A Sabbatical Every Seven Weeks - Sean McCabe
Sean McCabe runs seanwes and in 2014 he was working seven days per week. Yup, no breaks. He knew he needed to make a chance but the problem? All of his friends and even his wife worked at the company. He decided he would take every seven weeks off. He quickly realized it was a bit unfair to his team and extended it to everyone in the company. He's found that not only has his life gotten better but his business has continued to grow and they have figured out how to build mandatory
Ali Abdaal on Identity, Prestige, Creativity & Meaning and Deciding To Leave Medicine
I had a conversation with Ali Abdaal about his year away from medicine, how he grapples with his identity, the challenges of veering off the course of traditional metrics of success, enjoying the journey, and the challenges he faces.More from Ali here: https://aliabdaal.com/---------Subscribe to Paul's Weekly Newsletter: http://boundless.substack.com
What happens six months (and three months) before you quit? - Michael Ashcroft
I talked with Michael Ashcroft six months before he was planning to quit his job. We talked about his plan to quit his job, what was going through his mind, his fears and what he expected might happen.
We then chatted again three months later after he submitted his notice and checked in on how he felt
Fear Setting Exercise
Michael's Website
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The best way you can support me is to join in the conversation. Share thoughts on Twitter, send me an e-mail and tell me what resona
The Self-Employment Meta-Game (Dan Vassallo)
I had a delightful conversation with Daniel Vassallo a self-employed creator for the last three years who seems to have gone through many of the same "a-has" as I have. He walked away from Amazon despite making an absurd salary of $500,000 a year. We talk about why he made that leap, why he would never go back and some of the unexpected lessons and insights he's learned from becoming self-employed.
You can learn more about Dan at his site => Dan Vassallo
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To follow alon
Who are digital nomads? (Professors Rob Litchfield & Rachael Woldoff)
Robert Litchfield & Rachael Woldoff have recently written a book titled "Digital Nomads: In search of Freedom, Community, and Meaningful Work in the new economy"
A married couple and both professors, they bring an interesting combination of perspectives. Rachel is a sociologist specializing in urban communities and Rob is a management professor specializing in creativity and motivation.
They both moved to Bali for three months with their kids and immersed themselves in this world.
Quitting To Teach History to 500k+ on TikTok (Michael McBride, Creator of Idea Soup)
Michael Mcbride left his job almost a year ago to work on building out Idea Soup, an instagram and TikTok channel focused on helping re-inspire people’s passion for history and knowledge.
We talk about his creations over the years, how he has felt since leaving his job over the last year, what he’s learned from engaging with young people on TikTok and how he sees the future of education emerging from things like TikTok and other online platforms.
On his foundational belief: “If I had a
Curating Goodreads Remotely (Uri Bram, CEO of The Browser)
Uri Bram is the CEO of The Browser which runs regular newsletters to help people find good articles, podcasts, and videos to read. He has been living as a digital nomad for over seven years and also runs The Browser as a remote company.
We chat about Uri’s own journey, what it's like working with Robert Cottrell (who reads 10-12 hours a day), his early experiences becoming a kindle best-selling, how he thinks about running a remote company and some of his favorite reads worth checking
Packy McCormick - Bringing Fun To Newsletters Since 2019
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 rec
Podcast Update Nov 2020 - The Pathless Path
I decided to record a short little update with my friend Travis. What have I been up to, where have I been living throughout the pandemic and what is in store next for Reimagine Work.
If you'd like to watch on YouTube, you can do that here: https://www.youtube.com/watch?v=7Xlqe6D-HfM
Angie Wang - My Partner On This Crazy Journey
I interviewed my wife, Angie, who has gone through a major career change and has launched a number of creative experiments and projects over the past couple of years. She reflected on what its been like going along this journey alongside me and grappling with success, identity, being a woman in Taiwan and creating in public.
Video Version Of The Interview: Watch The Interview on Youtube
If you like conversations like this, join my weekly e-mail which is an exploration of life, work, cr
Carving a 21st Century Life & Career - Steph Smith
Steph has a hard time identifying as anything. Remote worker, writer, or coder don't really do it justice. The thing that stands out when you talk to Steph is that she is a LEARNER. Through competing in chess as a child she learned the valuable meta-skill of how to improve and never really saw any reason why she couldn't just take something up.
This mindset is invaluable in today's world and this is demonstrated by the way Steph landed her job at The Hustle (hint: it didn't involve a
The Possibilities Of Life Beyond Work with Oshan Jarow
Oshan sums up his worldview as:
"We’re all going to die, but in the meantime, the world is far more mysterious, wonderful, and stimulating than human consciousness plagued by economic precarity can experience.”
We explore that possibilities might emerge if we can imagine a life beyond work.
Be brave and join us on this episode?
Oshan's Work: Musing Mind
Subscribe to boundless: Subscribe
Amy McMillen - Wandering In Uncertainty & Writing A Book (Mid Pandemic)
I had a great conversation with Amy McMillen via a live group conversation and we talked about her journey of leaving her full-time job WITHOUT a plan, what it felt like, what she learned and how she ended up documenting it in a beautiful book during the pandemic.
Our full conversation, including Q&A can be found here: YouTube Link
Subscribe to Paul's weekly newsletter on work & what matters: Boundless @ Substack
Buy Amy's Book: Reclaiming Control @ Amazon
Will Bachman: Building an Independent Consulting Practice With a 5-Decade Success Mindset
Will Bachman is the creator of a community-first talent platform for management consultants, Umbrex and hosts a podcast for independent consultants called Unleashed. We talk about the recent course he created called the Guide To Setting Up Your Consulting Practice course ($100 off with the code: boundless), which is a product of his 12 years as an independent consultant and his work helping hundreds (perhaps thousands) become thriving solo consultants. We talk about
How he thought a
Reflection with Andrew Taggart on Work & Life
A conversation and reflection with Andrew Taggart on total work, the role of the human amid our current crisis and an exploration of philosophical questions
For more on Andrew: His Website
Music: Deliberate Thought by Kevin MacLeod
Laurel Farrer: The Global WFH Experiment & Long-Term Promise Of Remote Work
Laurel and I decided to jump on a video call to talk about the world emerging work-from-home experiment amid the evolving Covid-19 pandemic. We wanted to talk about some of the deeper principles & opportunities that remote work offers and talk about how companies might think about it in the next month and over the next few years. We talk about:
The short-term mindset companies should take in the next few weeks (hint: don't overdo the tools right now)
What the broader opportunity
Imagining A New American Dream (Diania Merriam, Econome Conference)
In 2015, Diania Merriam discovered the Mr. Money Mustache blog about financial independence and reading it was like a refreshing punch in the face. At the time, she was living in NYC and $30k in debt. She got out of that debt in 11 months and started saving 60% of her income. This newfound grip on her finances gave her a huge boost of confidence to pursue goals that previously felt out of reach. In 2017, she moved to Cincinnati after negotiating a remote working arrangement with her emp
Longform Thoughts: Why Organizations Undermine Creativity & Potential
For the re-launch of the Boundless podcast, I'm releasing a previously Patreon-only audio discussion of a piece I wrote - Crisis at Work - which was published in the fall of 2017. *You can read the piece here*: Crisis At WorkI talk through six key reasons why organizational fail to unlock human potential:
We're defaulting to the wrong goals (shareholder value)
We're mistaking authority for performance (the Tom Brady principle)
We aren't providing a connection to purpose
We don't underst
A Remote Company With 40 Vacation Days?! (Amir Salihefendić, CEO Doist)
Amir Salihefendić is the Founder and CEO of Doist, a fully distributed, remote company that creates productivity tools (Todoist & Twist). We dive into his story of moving from Bosnia to Denmark as a child and how he started Doist while in college. He’s built a growing technology company in a fully remote setting, often experimenting with different ways of working and sharing the thinking behind the decisions as he goes on the doist blog as a major supporter of the remote work movem
The Lazy Person's Guide To Freedom, Generosity & Creative Work (Moataz Ahmed)
Moataz Ahmed otherwise known as “motizzy” is a graphic designer, consultant and hand lettering artist. He recently published Part 1 of his book titled, “Lazy Person’s Guide to Freedom” and we talked about his journey and book in this conversation.
We also talk about:
How we naturally started freelancing by helping people
His embrace of the “gift mindset”
How he improved his will-power and motivation
How he thinks about freedom and justice
How freedom should also be about speak
Twitter Friends & Threads, Self-Employment & Curiosity (Visakan Veerasamy)
I connected with Visa on twitter, where he’s made many friends over the past several years. I wanted to interview Visa to talk about his leap to self-employment over the past couple of years, but we talked about so much more. We talk about:
What the word “nourish” means to him
His evolution on procrastination and getting started
How to find like-hearted humans on twitter
The “asshole problem”
The curious humans of twitter
How he creates his own work
See the episode notes her
Rest, Leisure, Working Less & The 4-Day Workweek (Alex Pang)
Alex Pang is the author of Rest about how you can do more while working less and is author of the forthcoming Shorter, which shares stories of companies that have shifted to a four day workweek.
Hear about Alex's own sabbatical, how he changed his relationship to rest and what he's learning now.
Read more about Alex and get a copy of his book here
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Want to support the Boundless Podcast? Join as a Patron here
Geography & Culture Side Hustle Experiments w/ Rohith
I'm experimenting with some shorter episodes where I explore side hustles and creative experiments with people taking action on experiments they are excited about.
This one features Rohith Amruthur, creator of the Lost Geographer, which you can learn more about here. If you have any suggestions or want to come on the podcast, shoot me an e-mail.
If you'd like to support this podcast you can do so here.
The Phases & Emotional Journey Of Making A Work Shift (Stephen Warley)
I had a 2nd conversation with Stephen about the phases and emotional experiences of what a shift looks like. He's coached hundreds of people so has a good understanding of what people typically face.
I created this as part of my curious exploration of making sense of what it takes to reinvent in the modern world.
If you want to support the podcast, you can go here.
Good Writing & Doing Work That Matters (Andy Sparks, CEO Holloway)
Andy Sparks founded a company called Holloway, which is trying to solve the problem of sharing knowledge online. He shared how his startup is trying to combine beauty, writing & deep knowledge to complex topics like Venture Capital and Hiring.
We talk about his journey, how he started writing, the professor that changed his life in college and how his father has influenced his approach to work & life. He also shares how he thinks about "a lake" as a metaphor for life and how
Coworking That Works & The 10k Independents Project - Alex Hillman, Indy Hall
" coworking at its best isn’t an occupancy based business at all. If the only time your members can get value from their membership is when they’re in the room, you’re limiting the potential of your community "
Alex Hillman runs one of the longest running co-working spaces in the world - Indy Hall - in Philadelphia. He thinks the word "coworking" has lost some of its meaning and that many companies are running "spreadsheet businesses" rather than cultivating community.
"That level of d
Should Everyone Have A Coach? (Ben Brooks, Founder of Pilot)
Years ago, Ben wrote that his personal mission statement was “to help people reach their full potential” and our conversation touches on this theme in many different ways. Ben is a former car rental pro turned consultant turned HR executive. His work in HR landed him on the cover of Human Resource Executive but instead of staying on the path to CEO he decided to carve his own path.
Our conversation touches on a number of issues including coaching, entrepreneurship, how his relationshi
What living on a boat for 18 months can teach you about work & life (John Zeratsky)
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:
Hannah Wei on her nomadic life, Muay Thai fights, Tinder experiments & community
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 tel
Microadventures, Long-term Travel & Busking Through Europe (Alastair Humphreys
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:
Ala
Dreaming, starting a tribe & living on an island with three kids (Ben Keene)
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
Heather McGowan on learning, adapting & identity in the future of work
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
Building A Company And Life Filled With Joy (Rich Sheridan, CEO)
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 trans
A Mission-Driven Life & Career (Jerel Bonner)
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.
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Boundless => Reimagine Work
How To Fill Your Morning With Purpose & Joy (Craig Kulyk)
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 mo
Beyond Average: Co-Creating A Life & Company (Tanya Zhang & Wesley Kang, NimbleMade.com)
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 o
Lessons from 13 years of entrepreneurship & living nomadically (Chris Kirkland)
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
Creating Art Filled With Magic (Martha Balaile)
Martha Balaile is a fantasy illustrator living in Cape Town, South Africa originally from Tanzania. Her mission is to figure out how magic, mythology and fantasy can have an impact on real life. She’s also the wonderful creator of the new cover art for this podcast.
Martha aspired to create “art that is filled with subtle lessons on living a magical and adventurous life.” Two of the lessons she has found:
Go with the flow
Be aware of fear
We explore these a bit and she shares s
Reimagine Work & A Short Update From Paul
A quick little update from Taipei.
A couple links from the podcast:
Revisiting Keynes Prediction for a Post-Work 2030 in “Economic Possibilities for Our Grandchildren”
Luke Kanies Podcast Interview
Curiosity Conversation With Paul
Would love any feedback - e-mail Paul.
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 Lon
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 resp
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 c
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!
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:
S
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:
Itunes
Overcast
Website
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
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 - "
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 path
Re-define your relationship with money
Build up your "eff you" fund
Teach others something
Find a way to make money other than full-time income
Full Article | This episode is also a YouTube videoFor More With Boundless:
Consider supporting the podcast on Patreon
Join 110+ People Carving Their Own Paths In The Slack Community
Set Up A Cu
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
Why every company should adopt the 4-day workweek (Tash Walker)
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
The Humans Behind The Gig Economy (Sarah Kessler, Quartz)
Amid all the buzzwords and reports on the future of work, I find Sarah Kessler's stories about the gig economy to be the most insightful and the most human. Her stories and her book, Gigged, give an accurate picture of some of the upsides of the gig economy, but also some of the downsides. She shares stories of people that are sleeping in their office making five cents per task on Amazon's Mechanical Turk to creative freelancers who can make six-figure salaries working from anywhere.
Screw The Cubicle (Lydia Lee)
Lydia Lee was a self-described "multi-potentialite" growing up and loves to experiment and play games growing up. You can probably draw a straight line from her hosting television shows for the stuffed animals in her room to her current YouTube channel Screw The Cubicle TV. However, life is never that simple.Lydia is based in Bali where she is the Founder and Corporate Escape Coach of Screw The Cubicle, a movement to inspire people to break free from the shackles of conventional work.Fr
How A Remote Company Enables Freedom, Trust & Digital Dance Parties (Wade Foster, CEO of Zapier.com)
Wade Foster was graduating during the worst recession in the past 100 years and traditional employers were simply not hiring anyone. He reached out to a local software company in Missouri and talked them into hiring him to work on marketing. The experience "opened his eyes" to the digital world and the enormous opportunities that were beginning to emerge. He also tapped into a "thirst for developing new skills" that pushed him to learn how to code.The idea for Zapier emerged from some w
"My Name Is Nemo and I Don't Do Small Talk"
Nemo Ashong's bold vision is "a truly inclusive and empowered world" He helps people to be fully expressed and to be more authentic, be more unique and be more powerful.This conversation brought out some vulnerability in both of us and we barely scratched the surface around some tough topics like diversity, & inclusion. I live for this type of tough conversation and appreciate that podcasts give the kind of space to explore topics with nuance. I'm not sure we ended up with any clear
Ervin Ling On Escaping The Corporate World At 30 To Travel The World
Ervin Ling followed the default path as an actuary, passing test after test. After passing all the tests, he found himself working harder than he was ever working. As he stared at the television and saw his friends on TV during a weekend trip to the Final Four, he realized he didn't want to keep doing this. He declared (after a few drinks, nonetheless) to his friends, "If UConn wins the national championship, I'm going to quit my job."As any good number-driven actuary would, he didn't q
Ted Bauer: The Absurdity Of The Corporate World & Real Future Of Work
Ted Bauer is a freelance writer and content strategist who writes prolifically about the future of work. In this episode, he talks about some of his experiences in the corporate world. He shares a story of how he broke the record for the number of story ideas when he first joined ESPN which both captures his frustrations with the corporate world and also illuminates his process of how he generates new ideas for his writing. We talk a bit about technology and his view is that people are
Shayne Spencer on the dumb idea project and how failing econ helped him start his firm
While Shayne has built a successful marketing consulting firm, there was no "plan" to do this. His first exposure to marketing was out of necessity - his professor let students boost their low economics grades by joining the marketing group he ran. Shayne quickly applied the lessons to his DJ gigs on the side in college and became more interested in how to build real relationships with people through incredible experiences. He brings this same passion to his work today.Shayne has had ma
YuTing Chiu on cultural sound differences, building instruments & creative expression
Jacqueline Jensen on sabbaticals, rethinking work and building a "calm company"
Jacqueline 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 A
Dr. Laura Gallaher on using humor at work, leadership at NASA after crisis, and building a business traveling the world
Dr. Laura Gallaher joins me from Serbia, where she is part of Remote Year, a community that travels to twelve locations within a year with a cohort of people working remotely. Laura is an organizational psychologist who studied humor and communication in the workplace and notably completed a dissertation with "that's what she said" in the title (office fans, anyone?). With a title like that it was probably clear that Academia would be too limiting for her.
We talk a bit about humor and
Andrew Taggart, Practical Philosopher, on how "total work" is taking over our lives
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
Podcast Update, Digital Course Experiment & Moving To Asia
Paul provides a summer update:
Shifting the podcast from making sense of the future of work => "The Human Side Of The Future Of Work"
Early lessons from the digital course experiment, Solopreneur Shift
I'm moving to Asia...
Boundless Links
My article on beanie babies and doing things that don't make sense = > yes, please
Check out the latest tools, including the Freelance Target Income Calculator
Want an e-mail of 5 good reads every Sunday? Subscribe to #boundlessreads
**This p
Tony Triumph on growing up entrepreneurial, moving to NYC with $300 and building incredible relationships
Tony grew up around entrepreneurs but did not use the label at the time. At age 19, he was going to college in Maryland and felt the pull to something bigger. He decided to move to New York City with $300 to his name and started modeling to pay the bills. He got a lot of pushback from the people in his life about the move but knew he had to take the leap. Despite many setbacks and almost running out of many several times, he kept his head down and stayed in the city, saying to himself
Rohan Rajiv on learning through 3500+ daily blog posts, writing and parenting
Reflections: One year of freelancing, experiments & other people's reactions
In this short "reflection" episode, I check in on where my head is at one year into my freelance journey and share some of the opportunities I have had, how I have changed my mindset over the last year and how people have reacted to me carving a different path in the world. Some things mentioned in the show:Links:
Awakening - Quitting The Default Path
Questioning Work
Luke Kanies on his journey from commune to CEO and why people hate working for big companies
Luke grew up on a commune and then ended up as a co-founder and CEO of a startup that raised $87 million. He talks about his unique path and how that shaped his thoughts about building an organization. He raises the central tension of organizations in a free market economy - the fact that our corporations are run more like authoritarian states with centrally planned economies than free-markets. We talk about lessons he learned as he built his company and his perspective that he shares i
Candace Cabrera Moore, fearless yoga entrepreneur on building a global business, brand and community
Candace was first inspired by her mother who always looked for solutions to problems rather than admitting defeat so always had an entrepreneurial spirit. She had also been practicing yoga for several years (also with her mother) before deciding to invest more time and signing up for a Yoga workshop in Thailand while recovering from a challenging case of lyme disease. This leap of faith led to her thinking about yoga more seriously and starting to experiment with different projects such
Stephen Warley on the biggest shift since the industrial revolution (Episode 19)
Stephen has been self-employed for more than 18 years. At first, it was by accident. He referred to himself as a “reluctant freelancer.” We talk about how that mindset evolved into one where he now sees self-employment as THE option for today’s world. He is the founder of Life Skills That Matter, a platform, and community to help people to build the real skills they need to build a life they are proud of.There are many future of work “thought leaders” but that title would sell Stephen t
Nita Baum on how to "be free" and self-employed (Episode 18)
Nita Baum is a rock star self-employed freelancer. She has been working on her own for over a decade and now splits her time across many domains, describing herself as an "entrepreneur, co-creator, facilitator, mentor-coach, and community-builder." A lot of her current work focuses on supporting and working with people who are carving their own paths as freelancers, which evolved from her helping hundreds of people informally over the year. In 2013, she turned this into a business, laun
Boundless/Unleashed: Paul on the future of work, freelancing and his media diet (Episode 17)
This was an interview of Paul on the Unleashed podcast hosted by Will Bachman, who is the founder of Umbrex, a platform for independent consultants.Will's podcast interviews many freelancers who are working independently and I can't recommend it enough. Check out the unleashed Podcast => Subscribe Today------Weekly #BoundlessReads Newsletter - 5 Things Every Week: Subscribe NowBook Recommendations Mentioned:Designing Your Life, BurnettHow Will You Measure Your Life, ChristensenTuesda
Damien Peters on blogging, wealth, and building a remote business from Spain (Episode 16)
Damien Peters is a self-described "personal finance nerd" - which explains how he ended up founding WealthNoir.com, a platform to preach and teach about the importance of financial freedom and generational wealth to Black millennial professionals. He started blogging over ten years ago and has recently focused more on writing as he increases his focus on building Wealth Noir. Damien is also a big fan of travel and recently made the decision to move out of San Francisco and move with his
Connor Gillivan on entrepreneurship, selling on Amazon and working with freelancers (Episode 15)
Connor's path as an entrepreneur began when he was in college via an AIM chat with a classmate in one of his classes. What started as a textbook e-commerce business led him to build a sizeable business selling things on Amazon.com. Through his work on that, he ended up working with many freelancers across the globe on a variety of different projects. Realizing that he had developed skills in recruiting and working effectively with freelancers led him to start FreeUp.com. where he vets t
Jen Morilla on breaking plates and traveling the world with purpose (Episode 14)
Jen Morilla is an impact travel influencer. What does that mean? It means she travels the world and writes about her experiences but also has a central mission. At first, she started out with the mission to "change the world" that has since gotten more specific. She has been bringing water filters to many different villages across the globe and impacted an estimated 12,000 people globally What has been meaningful for her is not bringing the water filters, but teaching people how to solv
Romy Rost on leadership, freelancing & coaching as a skill (Episode 13)
Romy is an employee engagement consultant turned coach. She built her career consulting for and working in Fortune 100 companies on all challenges employee-related. Her mission is to drive meaningful and behavior-based change for mid-level leaders that helps them operate in a more productive and human way in the workplace. There are a lot of coaches out there, but what makes Romy stand out is that she has a lot of experience working with senior executives in her consulting career and sh
Tanya Alvarez on entrepreneurship, community & redefining failure (Episode 12)
Tanya Alvarez is the Co-Founder, and CEO of OwnersUP is a platform which advances solopreneurs business through accountability, goal setting, and community. Over the past fifteen years, Tanya has accumulated marketing experience with international & US companies such as Nike and US Olympics. She started her first company at the age of 25 and grew it to be a profitable company from credit card debt to over $1mm in gross revenue the first year. Since then, she has founded, bootstrappe
Pauri Pandian on tennis as a career, coaching & healthy masculinity (Episode 11)
Pauri started playing Tennis when he was seven and it has turned into a clear passion. He wasn't always sure that was the path he wanted to take, but when a job as a teacher fell through because he decided to attend his sister's wedding, he picked up some coaching work to make some money. One thing turned into another and he is now the head women's and men's coach at Wheaton College. As a coach, he is in the position of constantly having to think about how to motivate different types of
Ben Dubow - From State Department Rejection To Propaganda-Fighting Startup Founder (Episode 10)
Ben is the founder and COO of Omelas, a startup that is focused on using technology to fight propaganda. Ben's journey, however, does not start there. His journey is a classic case of "do not try this at home" - as we walk through Ben's story, I found myself impressed at the number of rejections and roadblocks he faced. Early in his career, he thought he landed his dream job, at the State Department, only to have the offer reneged. This led him to put his passion (which was diplomac
Paul Millerd on Finding Work That Matters To You (Episode 9)
This is a copy of the interview I did with Stephen Warley on the Life Skills That Matter Podcast. Stephen is a bit of a role model for me. We have similar missions and ways of seeing the world. He interviewed me on Facebook live and I thought we had an interesting discussion on doing things that matter, defining priorities and how to figure out the answer "what do you want to do?" (which I think is an absurdly bad question!)Show Notes: Life Skills That Matter (Episode 174)Podcast Inf
Amma Marfo on Combining Humor, Creativity & Writing (Episode 8)
Amma Marfo cracked me up several times on this podcast. It is no surprise then, that she describes herself as "thoughtful yet incurably silly." She also defines herself by three words: humor, creativity, and energy - something we talk about at the beginning of the podcast. Like many freelancers, she does so many things - she is a speaker, teacher, coach, and podcaster and has a lot of insight around the future of education and what helps people succeed in school. If you are interest
Tom Critchlow on Personal Branding, Freelance Consulting & The Future of Work (Episode 7)
I discovered Tom by reading a piece he wrote on freelance consulting. I was fascinated with his approach and how similar it was to mine - especially coming from a completely different perspective - digital marketing & content. We talk in depth about how he thinks about content in today's world, his thoughts on personal branding, how writing helps him create and leads to serendipitous connections and how he manages a diversity of interests. We also geek out about our love of all t
Cody Royle on The Talent & Performance Secrets of The Sports World (Episode 6)
Growing up all Cody thought about was sports. He saw his path as becoming a professional Aussie Rules Football player. However, after competing at the highest level of the sport, he quickly saw felt his “talent just fell away” at the age of 18. He struggled to live in the moment and stewed on the fact that everyone around him seemed much more talented. While this period would help him realize that he was better suited as a coach than a player, it took him a few years to make that realiz
Janet Matta - Rock Star Career Coach On The Alternative Paths We Fail To See (Episode 5)
Janet is one of my favorite people. We have a similar belief that people are capable of more than they believe and that alternative paths are more realistic and the reality than people realize.Not a fan of default paths from an early age, one quote stood out from Janet that she has continuously asked herself throughout her life:“The conventional path is not going to work for me, what can I do instead?”Janet first started “hacking” life in high school when she decided that the standard c
Super Bowl Minisode - Cody Royle on The Patriots and what business can learn from sports
In this episode Cody Royle and I discuss what sets high performing NFL organizations like the Patriots and the Giants (and others apart from the rest). Cody is the author of Where Other’s Wont: Taking People Innovation from the Locker Room into the Boardroom. His book is available here: http://amzn.to/2E5R88kCONTEST DETAILS: I am giving away two of Cody's books for free. Just retweet this episode with the hashtag #boundlesspod or send a screenshot of you subscribed to the podcast to
Chris Donohoe on "uncommon" leadership, starting his own firm and "limitless creation" (Episode 4)
Chris is the founder of uncommonly and an avid fan of the long-running CBS television show Survivor. A former teacher, marketer, and management consultant, Chris has an eclectic mix of skills and professional experience. Chris has worked with over a dozen Fortune 500 clients spanning multiple industries including Media & Entertainment, Publishing, Insurance, Pharmaceuticals, and Corporate Social Responsibility. He is obsessed with inspiring great leadership and creating incredible l
David Vaucher on Ending His Career to Start His Life (Episode 3)
David was born abroad then moved to the US at a young age, all while being raised to believe that the path to success rests solely on going to school and getting a “safe” job with a big company. For the last 11 years he did just that, and by traditional measures of success, it looked like things were going well. Unfortunately, starting on Day 1 of his first job, he could never shake one, recurring feeling: “I really, really, really don’t like this”.In December 2017, after a lot of savin
Noel Boyland on “doing the things you want to do” in your career (Episode 2)
Although Noel claims he lacks wisdom, he has a lot of it. He describes his career as “eclectic.” Starting his career in the 1980’s the environment around him (greed, money) influenced him to question what he was really trying to accomplish. He took a long term perspective and tried to focus on what he did not want his career to be at sixty — which he put simply as not doing “the things he wanted to do”. Although on a more corporate track early on in his career, he tried to continuously
Episode 1 - Why do I care about the future of work?
Paul talks about why he is passionate about the future of work and shares some of his personal journey