Boundless: The Human Side Of Work

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, and finding his people, and he challenges me to think differently about how I'm spending my time with my work.The conversation dramatically shifted how I'm thinking about the possibilities of my path.  If you are on a self-employed path, this is a must-listen:For Kris' newsletter: Party at the Moontower - (moontowermeta.com)------------SUPPORT BOUNDLESSSubscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.

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 guide rather than as a creator, and why fatherhood is helping him "sharpen" his focus. Links Mentioned Howard Homepage Labels In, Labels Out Jobs, Vocations, Careers SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.

“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: Freedom, Adventure, Meaning.  I definitely agree.  However, he says many fail to reach these aims because they ignore the shadow side of this path.  He details four things - FAIL: Failure, anxiety, instability, loneliness. We explore many things in this conversation including: Grappling with the achiever identity Longing for independence and freedom Parental approval Building Community Experiments Defining success You can buy his book the Fail Safe Solopreneur on Amazon ------------------------ SUPPORT BOUNDLESS Subscribe

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, 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 the platforms I recommend. Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Or if you want to fund my crypto house, you can send me some crypto here.

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. --------- SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.

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 --------- SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. I launched Freelance Consulting Skills Course.  You can find out more and sign up here. If you'd like to support the podcast, consider using my affiliate links Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Charles Schwaab No International ATM Fees

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 necessary scripts and "the good egg" Why writing about work elicits strange responses How he thinks about narratives and politics related to work --------- SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. I launched Freelance Consulting Skills Course.  You can find out more and sign up here. If you'd like to support the podcast, consider using my affiliate links Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed fo

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 finances in a way that lets them live the life they want to live.  They also run a charity bike ride in Taiwan supporting LGBTQ rights called Rainbow Ride. Links: Rushed and Tired (Portrait of a Modern Family) Money Script Quiz --------- Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. I'm launching a Freelance Consulting Skills Course that launches July 1.  You can sign up here and get a $50 discount. If you'd like to support the podcast, consider using my affiliate lin

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 (not like "unlimited vacation...) sabbaticals into the operating rhythm of the company.  His mission is to help every company globally (yes, really) embrace this model by 2047.  I'm on board. Learn more about Sean Sean's Sabbatical Blog My Essay On Sabbaticals --------- Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. I'm launching a Freelance Consulting Skills Course that launches July 1.  You can sign up here. Podia - 14-day free trial Teachable - 14-day fr

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

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 ---------- 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 the platforms I recommend. Podia - 14 day free trial Teachable - 14 day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Or if you want to fund my crypto house, you can send me some crypto here.

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 ---------- To follow along with Paul subscribe to his newsletter => Boundless  Paul is also working on a book to launch later this year titled The Pathless Path

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.  I share some of my perspectives and they share what they learned, how it impacted how they lived their life and how they see these trends impacting modern work and institutions. -------------- If you'd like to subscribe to the weekly newsletter on the modern world of work, please subscribe: Boundless Newsletter If you want to support the podcast you can do so by using my affiliate link for one of the products I use and endorse.

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 thesis it's that education really does work and education really does matter” His motivation and secret to his success:  He said, “I find history so crazy and weird and fascinating that I think that;s contagious.  If I had a mission it’s not to make them more educated, it’s to make them go. “How did roman's wipe their ass, that’s crazy,” Listen to the episode to find the answer to this!

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 out. Articles/Books mentioned In Praise of Idleness and Other Essays, Bertrand Russell Derek Parfit, Reasons and Persons Leadership & Solitude, William Deresiewicz Disadvantages of an Elite Education, William Deresiewicz Seeing Like a State, James Scott How Ghost Is Structured for the Long-Term The Great Works of Your Life, Cope Ada Palmer, Ex Urbe Susan Bryson, Aftermath Salary Negotiation: Make More Money, Be More Valued, Patrick McKenzie ------------------------- To find ways to support Boundless, Click her

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 newsletter on the future of work.  He argues that “Employees will ultimately make the decision” about what work looks like post-pandemic.  I think he is mostly right and we talk about what that might mean for people's lives. ---- You can find ways to support Paul through affiliate links, newsletter sponsorship or direct gifts here If you want to subscribe to Paul's weekly newsletter on the modern state of work, the solopreneur journey and creating online, you can subscribe here.

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

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, creativity and a contemplation on what matters: Boundless Newsletter ................................... Ways to support Boundless You can use one of the several products I endorse and I'll receive a small affiliate fee from the company. ConvertKit I tried Mailchimp and a few others before landing on ConvertKit for e-mail automation.  The UX is intuitive and easy to manage.  I really like it a lot though I'm probably not even maximizing its potential.  If you sign up using this link I'll get 30% of your monthly fee forever (which

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 formal application.  This conversation was a lot of fun and explores: Digital nomadism myth vs. reality How she chooses where to live What she learned traveling the world competing in chess as a child How she thinks about work and her identity One of her favorite topics - words that don't translate Learn More: StephSmith.io 

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