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The Pathless Paul 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, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Join Paul as he shares his own reflections and tries to learn from others
 
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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…
 
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 fo…
 
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 p…
 
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…
 
“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…
 
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! ------------------------ The best way you can support me is to join in the conversation. Share thoughts on Twitter, send me an e-mail, …
 
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, e…
 
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 ab…
 
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 an…
 
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 …
 
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 …
 
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.substac…
 
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 -------…
 
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…
 
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 spe…
 
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 …
 
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 e…
 
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 t…
 
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 In…
 
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. Thi…
 
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…
 
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 Pau…
 
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 …
 
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…
 
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…
 
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 …
 
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 mi…
 
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-he…
 
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 …
 
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…
 
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,…
 
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 …
 
" 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" h…
 
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…
 
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 i…
 
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…
 
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 ca…
 
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 Earl…
 
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 …
 
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 …
 
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…
 
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…
 
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…
 
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 af…
 
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 magica…
 
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