The Pathless Path with Paul Millerd

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.

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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 alternative education with a broader audience online.

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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 is one of the most thoughtful perspectives on the future of work and global mobility.

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' podcast, Sky was on his way.  His long-term vision is to build an alternative to traditional advertising in audio.

We talk about this and a lot more including:

• Why he quit a good job to work at a smoothie bar
• How a cold email to Ryan Holiday changed his life
• Growing up in Hawaii
• Serendipitous events that lend to him moving to Austin
• The future of Audio

Links Mentions

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 relationship with money.  He runs The Money Workshop with people helping them explore the scripts people have with money and realized that people have one of two orientations towards the world:

#1 The Money Path: “One day when I sorted this out I’ll get to do what I want”

#2 The Life Path: “Do what you love and the more you follow it you will have your needs met with and without money”

Which one are you?

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 angel investor, startup advisor, and the author of an upcoming book about the business implications of augmented reality.

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.

Just launched my book, The Pathless Path! 

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:

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

“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

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.

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:

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

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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.

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.

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

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.  

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.

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Packy says that his differentiation "is that I’m going to be having more fun than most people”

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.

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.

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

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?

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.

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

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 is for remote work over the next 10 years
• The role of trust in remote work and what happens when it breaks down
• How to think about meetings and how to design your day and re-think productivity
• Examples of companies who have been innovating in this space for 10+ years
• Experience from Laurel's 10+ years as a remote team leader

As the Founder of Distribute Consulting and the Remote Work Association, Laurel Farrer starts, strengthens, and leverages virtual workforces to solve corporate and socioeconomic concerns. A global thought leader on the topic of remote work, Laurel collaborates with the world's leading businesses and governments to eliminate virtual worker discrimination, prevent policy retraction, increase remote job accessibility, train distributed leaders, and design economic initiatives. Additionally, she also shares her expertise as a Forbes contributor, subject matter expert for business education curriculum, and virtual software product advisor.

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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 employer.  

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. 

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 movement.

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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 speaking out for other people’s freedom
• Learning new languages and the benefit of cross-cultural insight for design work

You can learn more:

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

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.

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.  

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.

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 he stays in touch with friends in a vulnerable way.

We talk about:

• Andy's writing practice
• Teaching & modern education system
• A college professor that inspired him to think differently
• Unlocking wisdom from books on the internet
• Grappling with success & status in the modern world
• How he stays in touch with the people that matter to hi

" 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 dependence on a single employer is brittle at best and dangerous at worst. And that single source of 50,000 jobs being Amazon, who is notoriously one of the most ruthless businesses in the world, is the WORST worst way to generate those jobs. "

We also dive into Alex's working model of a new project, the 10k independents project.  Hear about why he thinks self-sufficient independents are better than Amazon (I tend to agree)

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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 relationship with work has evolves, management versus leadership and what he wants written on his tombstone.  Some other topics we touch on:

• Ben’s motivation to work at Enterprise Rent-a-Car after college and what he learned
• His early entrepreneurial “ventures” starting at 12 years old
• How his mindset about work shifted as he became successful in the corporate world
• His experience hiring working with an executive coach in his late 20s
• His experience coaching and favorite exercises
• Why companies are scared of trusting their people
• Why being a manager is actually an incredible opportunity for people
• The learning and ownership upside of carving your own path
• The value of having advisors, friends of confidants to celebrate “wins”
• Balancing life & work and his personal sustainability
• Deciding to give himself a raise as an entrepreneur

Links Mentioned:

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 tell people’s stories
• What she has learned from Muay Thai
• Her decision to compete in a professional Muay Thai fight in Thailand
• What Muay Thai that has taught her about burnout, performance and success
• How she defines success as a nomad depending on the region she is in

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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:

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
• Using "no code" tools to start things like Rebel Book Club
• How to think about a career in today's world
• How finding a friend is one of the most important things to head in a new direction

Links Mentioned: