All Episodes
Displaying episodes 91 - 120 of 184 in total
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. T...
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 ...
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 h...
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...
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 str...
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 thi...
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 ...
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 ...
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 metr...
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...
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...
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 mar...
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 hi...
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 nom...
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 p...
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 fo...
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. ...
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 s...
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 pla...
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 li...
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. ...
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 o...
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 s...
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 wa...
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 f...
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 mov...
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...
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 t...
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 shif...
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. T...