Boundless: The Human Side Of Work

Derek 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.

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".

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.

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".

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 an end. When she isn't busy fending off people who constantly try to hire her, she runs a podcast with her sister - "Status Post Adulting Podcast" and she has written multiple essays, while slowly "getting famous for not working" in the meantime.

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 podcast: @FoundersPodcastListen: Founders Podcast or Itunes⏳TIMESTAMPS2:58 The scripts David grew up with8:09 Working full time while in high school and during college20:47 Trial and error, finding his life’s work33:24 Why David thinks keeping his podcast behind a paywall was a mistake51:15 Nobody understands the scale of the Internet54:15 The time needed to succeed1:03:56 Ed Thorp - balancing being an entrepreneur with one's family life1:14:02 Lessons from David Ogilvy and Marvin Bower1:24:57 The necessity of taking risks

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.

Amy 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 AMYHer Website: amytangerine.comTwitter: @amytangerineInstagram: @amytangerineFacebook: @amytangerineTIMESTAMPS0:00 Audio intro0:12 Introduction1:10 The scripts Amy grew up with2:35 Amy's parent's path and the ancestral trauma6:00 How Amy's parents inspired her11:03 Amy's vision of her future after graduating college13:50 The seeds of doubt about her path14:57 The 1/3 life crisis17:43 Keeping in touch with your creative side24:57 Scrapbooking & contemplation29:33 Suffering a miscarriage and writing a book37:13 The 3 F's - Fulfillment, Freedom, and Fun39:07 Creative freedom42:39 The challenges of working creatively44:39 Having kids48:16 Overthinking and worrying

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 with 20 people, 16 chickens, 2 trampolines, and 1 zipline.We talk about:Leaving her dream jobLiving in an intentional "off the grid" communityWhat she learned from her ambitious days as a museum industry leaderMarriage & kids on an unconventional pathWriting her novelWATCH On YouTubeFOLLOW NINAHer Website: NinaSimon.comTwitter: @ninaksimonTIMESTAMPS0:00 Audio intro0:12 Introduction1:37 The scripts Nina grew up with4:43 Did Nina see herself as creative growing up?5:39 Nina's education and why she hated her dream job at NASA12:1

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 Mentioned:@david_perell (Twitter)David's course Write of PassageFriday Find's LinksAct of Creation (Koestler)Denial of Death (Becker)Art of Loving (Fromm)Gutenberg Galaxy (McLuhan)The Managerial Revolution (Burnham)Tribe (Junger)Bullshit Jobs (Graeber)@culturaltutor (Twitter)

Angie 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.

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.

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 linguistics, and eventually became a strategy consultant at McKinsey.Relevant Links:Adam's Website and McKinsey EssayTom Critchlow's WritingVenkatesh Rao's The Art of GigTimestamps0:00 Audio Intro0:48 The scripts Adam grew up with3:54 Shifting from MIT to Brown5:33 Becoming interested in consulting7:25 What was it like from 1999 to 2002?9:08 Adam's path to becoming a partner at McKinsey11:56 Leaving McKinsey14:05 What kept Adam at McKinsey for 10 years?16:06 What do people get wrong about McKinsey?18:49 Decentralization and the em

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, FoundationsThe Art of Gig, SuperstructuresWATCH ON YOUTUBE: https://youtu.be/KC63HrF8V4EYou can find Venkatesh:on Twitter @vgron RibbonFarm (blog and substack)His consulting website: venkateshrao.comLinks Mentioned:How Karate Kid Ruined The Modern World (Cracked)Lords of StrategyWhat Theorising Is, Theorising Is NotTempo, by VenkateshJim KellerSquad WealthWe talked about:1:00 The scripts Venkatesh grew up with 5:05 Preparing for the leap, Dan Pink's books 10:48 Predictable income vs adventure18:58 Is $100 enough to build confidence in a project?21:08 Understanding the big consulting companies 27:18 The positioning vs people's school33:34 "Avoid po

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 years of work experience.  Someone at her company told her she wouldn't "make it"

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 States, like housing, healthcare, taxes, and insurance.

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.

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 of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here (Sponsored Link, Includes discount)------------------

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.Find More About CoreyWriting on Psychology TodayHis personal website ------------------