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.

Follow Malcolm:

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:

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:

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:

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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:

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:

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.

More:

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:

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:

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:

" 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:

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:

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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

Links Mentioned:

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 was not possible in the past.  Reflecting on her path she admits “this field just sort of emerged.”  As her career has shifted more towards speaking, she has been able to design her life around learning.  Through her talks, she is able to get feedback and combined with her own curiosity, it helps her focus on what to learn next.  

In the working world, she focuses on how we can think about learning and work in a more holistic way and traces many challenges back to education.  She cites research from Gallup showing that: “while 74% of surveyed fifth-graders are engaged with school, just 32% of surveyed 11th-graders are engaged.”  Perhaps some of that disengagement is because people aren’t too excited about their job prospects.  She worries that organizations in the short-term are still too focused on productivity, which depersonalizes the experience of work.  As work increasingly becomes specialized - she calls it “atomization” - she fears that we will increasingly only focused on “explicit knowledge” instead of the deeper tacit knowledge that makes us special. 

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 of two books Joy, Inc. and Chief Joy Officer. 

Hear about his company has achieved gender diversity in the workforce, introduced pay transparency, embraces pair-working methods across all functions and other transformative principles.

Links/Books Mentioned

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 of learning and adventure.

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 mornings to a morning advocate over the past 7 years.  He defines the morning effect as:

He’s experimented with 100 morning rituals over that time and now works with people to help them take back their mornings and find “another 20 hours” a week as he did.

His story is more than another “hustle” hack - its grounded on bringing more presence, joy and creativity to ones life and is why I hope you check out the podcast this week!

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 their way.  However, deep down both wanted something a little more. Some of Tanya’s challenges working as a freelance graphic designer on the side convinced them they should try to think a little deeper about building a brand and a business, instead of just helping other people.

As they found themselves thinking about the business all day at their full-time jobs and coming home ready to work on it, they realized they finally had to go all-in. Over the past year they have worked on the business and are starting to find some traction.  As they’ve dealt with the challenges of running a business, they have also had to constantly reflect on how to manage a relationship both as committed partners and co-founders. 

Check Out Nimble Made (unsponsored):

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 magical and adventurous life.”  Two of the lessons she has found:

We explore these a bit and she shares some examples from fantasy that have inspired her. Check out the show!

We talk about:

Her Top 3 Magic Podcasts:

A quick little update from Taipei.

A couple links from the podcast:

 Gabi Macra was a top Canadian basketball player that never really thought about the "life after basketball" before dealing with a major injury towards the end of her college career.

Instead of following any sort of traditional path, she headed East to Japan where she came to teach English.  She loved her experience there and now reflects on the immense value of learning how to teach and coach others helped her in the following years.

Instead of heading back to Canada, she headed to London where she had a successful career and journey as an actuary.  She was a leader in her company but reached a point where she was dealing with health challenges and finding that her career was no longer giving her the fulfillment that it once was. 

She ended up deciding to take some time off and told her boss that she was leaving.  However, she ended up staying another 18 months as she helped the team transition with some other internal changes.  Just knowing she was leaving enabled her to approach everything completely different and think about how she could best serve her team while also taking care of her own health.

She finally took the leap in 2018 and after several months of sabbatical, including some time in Bali, she realized that becoming a Yoga Therapist was something she was ready to commit to over the next few years.  While preparing for that program, she also created a learning internship for herself in London (stealing this from Lydia Lee's podcast episode!) by taking 8 people interested in Yoga and creating a customized program for them.  Her only goals: to learn a ton about how she can serve people and learn what to do next.

What we covered:

Links

Tyler Tringas is an entrepreneur and traveler.  He's started two companies (one worked!) and now is founding Earnest Capital where he wants to help companies avoid going into $50,000 of credit card debt (like he did) to start technology companies.  We talk about how this type of investing vehicle can help transcend some of the pressures to "scale at all costs" in ways that may not be suitable for most companies.

Topics

Related Links:

"I didn't think I'd be turning down work and choosing not to grow"

I spoke with Chris Donohoe one year ago about his just-announced launch of his consulting firm, Uncommonly. He's more committed to carving his own path than ever and we walk through some of the lessons learned, pivots and his long-term strategy. Chris breaks down what he's learned over the past year, how he has started coaching people one-on-one and how he is thinking about structuring his time and day.

Topics Discussed:

This episode is a special treat from friends of Boundless, Cody Royle, who came on the podcast last year to talk about what the business world can learn from sports.

I wanted to share a special episode from his podcast that was just launched featuring the NBA great Joe Dumars and workforce research great Adam Grant. I thought the three of them had a special conversation. If you want to subscribe to Where Others Won't do so here:

Mike was always a self-driven creator, developing TI-83 apps for his classmates to keep track of their grades from an early age. He spent a lot of time "head in in the clouds, making things." It is no surprise then, that he eventually found that self-employment was the right fit after several years of trying to make it work in the corporate world.

Mike and I dive into his path in which he slowly made sense of the fact that it was time to take the leap to self-employment. As he was about to take the leap, his company ended up laying him off anyway. Reflecting back, he has found many valuable lessons in his journey and has brought these together in a self-published a workbook called Clear Path Forward. The workbook helps people re-assess their relationship with work. We talk about the process he took to publish the book and where he sees his work taking him over the next couple of years.

He now lives and works around the tagline "making business more human" which he is using to run workshops with clients and have deep conversations with people around what really matters.

Topics Discussed:

Books That Influences Mike (That We Discuss)

Jeff Hittner of Your Project X and Paul talk about their favorite 10 career myths. They dive deep into the beliefs and mindsets that drive these beliefs while making an argument for people to reflect at a deeper level to shift past the default to contemplate a wide range of options

In this short episode, I talk about the five lessons I've found that help people make the leap to self-employment:

Tash Walker is the founder of a firm and spends her Fridays making marmalade.

Before instituting a four-day workweek at her firm, The Mix, she barely had time for her relationships. She decided to start doing research about different ways of working. There had to be a better way than the default options of "Summer Fridays" and "flexible work," that never seem to make less anxiety or stress-ridden.

In her research, she discovered many examples of Swedish companies embracing 4-day workweeks and also found that when they instituted it, they often helped improve productivity. After bringing the option to her team at The Mix, they decided to do a three-month trial. They didn't even tell their clients.

The funny thing? The clients didn't even notice. Even better, when they shared it with their clients - they weren't offended. They were curious to learn more and impressed that they had prioritized their people. While many quickly reflex to "well that can't work here," Tash and her team went forward anyway and have shown that a 4-day work week can work and it can work in professional services - an industry where many take for granted the fact that you should always be available for your clients.

Beyond improving the lives of the people at the firm, they achieved some incredible results:

Lydia Lee was a self-described "multi-potentialite" growing up and loves to experiment and play games growing up. You can probably draw a straight line from her hosting television shows for the stuffed animals in her room to her current YouTube channel Screw The Cubicle TV. However, life is never that simple.

Lydia is based in Bali where she is the Founder and Corporate Escape Coach of Screw The Cubicle, a movement to inspire people to break free from the shackles of conventional work.

From building businesses to forging freelance careers, she’s helped hundreds of talented professionals repurpose their skills to create better versions of their careers and become better versions of themselves.

Topics Covered:

Wade Foster was graduating during the worst recession in the past 100 years and traditional employers were simply not hiring anyone. He reached out to a local software company in Missouri and talked them into hiring him to work on marketing. The experience "opened his eyes" to the digital world and the enormous opportunities that were beginning to emerge. He also tapped into a "thirst for developing new skills" that pushed him to learn how to code.

The idea for Zapier emerged from some work Wade was doing with his friend Brian to connect different apps on the internet. They brought the idea to Startup Weekend in Missouri and ended up building a prototype of what would later form the foundation of Zapier. By Monday morning, they were committed to spending time on it and seeing where it would go.

Seven years later, Wade is the CEO of that company and he is leading it as a remote company. Wade shares reflections on building a remote company and the fact that you have to default to trust and be very intentional about building a connection between people. In traditional companies, he notes that "The default for most companies is that they don't trust you."

I highly recommend checking out the resources Wade and his team have put together on running a remote company:

Nemo Ashong's bold vision is "a truly inclusive and empowered world" He helps people to be fully expressed and to be more authentic, be more unique and be more powerful.

This conversation brought out some vulnerability in both of us and we barely scratched the surface around some tough topics like diversity, & inclusion. I live for this type of tough conversation and appreciate that podcasts give the kind of space to explore topics with nuance. I'm not sure we ended up with any clear answers, but I think had the type of conversation filled with respect and curiosity that can enable us to go deeper with each other and with other people.

Connect With Nemo:

Ervin Ling followed the default path as an actuary, passing test after test. After passing all the tests, he found himself working harder than he was ever working. As he stared at the television and saw his friends on TV during a weekend trip to the Final Four, he realized he didn't want to keep doing this. He declared (after a few drinks, nonetheless) to his friends, "If UConn wins the national championship, I'm going to quit my job."

As any good number-driven actuary would, he didn't quit his job immediately. He took about 18 months to plot his escape from the corporate world. During this time, he re-thought his relationship with money, his possessions and his relationships with friends and family. He ended up traveling around the world for 12 months. Here are some stats from his trip:

After this trip, he still felt a pull towards living abroad and now lives and teaches English in Taiwan. This journey has helped him discover and invest a life he could be proud of.

Ted Bauer is a freelance writer and content strategist who writes prolifically about the future of work. In this episode, he talks about some of his experiences in the corporate world. He shares a story of how he broke the record for the number of story ideas when he first joined ESPN which both captures his frustrations with the corporate world and also illuminates his process of how he generates new ideas for his writing.  We talk a bit about technology and his view is that people are using technology not to engage with people but to hide from them. His view of the future of work is simple - it's about moving back to in-person, human to human engagement and questioning a lot of the things we take for granted in modern organizations.

While Shayne has built a successful marketing consulting firm, there was no "plan" to do this. His first exposure to marketing was out of necessity - his professor let students boost their low economics grades by joining the marketing group he ran. Shayne quickly applied the lessons to his DJ gigs on the side in college and became more interested in how to build real relationships with people through incredible experiences. He brings this same passion to his work today.

Shayne has had many "dumb" ideas, but he would argue that most ideas (good and bad) start out as dumb ideas. The difference is the people with the courage to keep moving and respond to feedback. He has called the entrepreneurship journey "one of the most humbling things he has done in his life." From this humility and willingness to stay vulnerable, Shayne has been able to build a successful digital marketing firm. So what's his secret? He shares four key steps to turn your own "dumb idea" into something that might work:

Shayne wants more people to follow their silly ideas and see what they can make of it. In 2010, he decided to start his own business during a recession and with no money to his name. Eight years later, he has no regrets and couldn't imagine taking a different path. It may not have made sense at the time - but its the decisions that don't make sense that often turn into something meaningful. If it made sense, people would already be doing it!

Dr. Laura Gallaher joins me from Serbia, where she is part of Remote Year, a community that travels to twelve locations within a year with a cohort of people working remotely. Laura is an organizational psychologist who studied humor and communication in the workplace and notably completed a dissertation with "that's what she said" in the title (office fans, anyone?). With a title like that it was probably clear that Academia would be too limiting for her.

We talk a bit about humor and how it can be helpful or destructive in an organization. She first points out that "aggressive" humor - even if you mean well is rarely a way to strengthen bonds. We then talk about how leaders can embrace humor, especially to show their vulnerability, and give their teams more freedom to make mistakes, be open and be themselves.

After getting her Ph.D., she worked with NASA after the Columbia explosion and worked on some of the toughest "they fell victim to the same thing that could happen in any organization." She notes that these factors are prevalent across many organizations, but the stakes are often not life or death. Her work with a small tech company found that two key elements can help companies transcend hierarchy. First, the leader is willing to be vulnerable and second, the leader demonstrates both through words and actions that they care deeply about all the people in the organization.

"We hire people for what they think....what we care about is your ability to learn, your ability to think, your ability to grow...creating an environment where the employees opinion and input has value and you ask for it and you seek it out and you actually listen to it, this is where really, really engaged organizations are born and powerful cultures are created"

Links:

Andrew is a Practical Philosopher who believes that "there may be no greater vexation in our time than the question of how to make a living in a manner that accords with leading a good life." We dive deep into the questions of "what is the good life?" and what he means by "sustaining life." He also shares his perspective on the concept of "Total Work," a phrase first put forth in 1947 by the German Philosopher Josef Pieper and shares how that phrase became central to his current writing on the topic and conversations he has with business leaders and executives.

We also dive into his dichotomy of the three modes people could think about to make a living:

He reflects on our modern cultures over-reliance on exchanging our time for money while ignoring how we can live off the land and operate within the gift economy. Next, we talk about some of the different modes of living (whether it be a "settler", nomad or somewhere in between) and the implications for the community in society as a whole as well as how has dealt with that with his wife.

Finally, Andrew offers three practical steps people can take to re-engage with life and trying to understand what "a life worth living looks like" that does not include the advice to just quit your job.

Andrew's Writing & Site:

Paul provides a summer update:

Boundless Links

Tony grew up around entrepreneurs but did not use the label at the time. At age 19, he was going to college in Maryland and felt the pull to something bigger.  He decided to move to New York City with $300 to his name and started modeling to pay the bills.  He got a lot of pushback from the people in his life about the move but knew he had to take the leap. Despite many setbacks and almost running out of many several times, he kept his head down and stayed in the city, saying to himself "you cannot leave."

His path only makes sense looking backward. He has had a wide range of jobs and gigs over the last ten years in New York and is now starting to see all the pieces come together into something that makes sense with who he is and what he has to offer to the world. We talk a lot about how he thinks about building relationships and connections and how some surprising relationships have come back around (including a job he was fired from!) to help him in his current entrepreneurial adventures.

In this short "reflection" episode, I check in on where my head is at one year into my freelance journey and share some of the opportunities I have had, how I have changed my mindset over the last year and how people have reacted to me carving a different path in the world. Some things mentioned in the show:

Links:

Candace was first inspired by her mother who always looked for solutions to problems rather than admitting defeat so always had an entrepreneurial spirit. She had also been practicing yoga for several years (also with her mother) before deciding to invest more time and signing up for a Yoga workshop in Thailand while recovering from a challenging case of lyme disease. This leap of faith led to her thinking about yoga more seriously and starting to experiment with different projects such as a DVD and online videos. Over the past few years, this has taken off and YogaByCandace has evolved into a community, a company with a team and has enabled her to teach workshops all over the world (including to 1,000+ people in the middle east), write a book called Namaslay and have a chance to personally impact many people. Check out this episode to hear lessons learned, challenges and her perspective on gratitude, setting intentions and generosity.

Connect With Candace:

Stephen has been self-employed for more than 18 years. At first, it was by accident. He referred to himself as a “reluctant freelancer.” We talk about how that mindset evolved into one where he now sees self-employment as THE option for today’s world. He is the founder of Life Skills That Matter, a platform, and community to help people to build the real skills they need to build a life they are proud of.

There are many future of work “thought leaders” but that title would sell Stephen too short. He has been in the weeds experimenting in his own life and has helped hundreds of people carve their own paths in the world that I would instead call him the wise elder statesman of the freelance economy. If you have ever thought about working for yourself, I recommend Stephen’s work over my own.

Stephen puts the emerging trends bluntly: “The only work left is managing yourself. If your going to manage yourself, you mine as well work for yourself.”

To get started, he pushes people to “work on creating…you’re not just going to get paid right off the bat, just enjoy the freedom of creation of whatever it is that you want to do, whatever form that is, however you want to do it without judgement…just start doing that.” Because that’s what really gets people interested when you can share your creations and there’s nothing more human than that."

Nita Baum is a rock star self-employed freelancer. She has been working on her own for over a decade and now splits her time across many domains, describing herself as an "entrepreneur, co-creator, facilitator, mentor-coach, and community-builder." A lot of her current work focuses on supporting and working with people who are carving their own paths as freelancers, which evolved from her helping hundreds of people informally over the year. In 2013, she turned this into a business, launching b*free in 2013 as a platform "by freelancers for freelancers" to help people with the transition to self-employment as the future of work evolves.

One of her core beliefs is that you can "design the contribution you want to give from the inside out." We discuss this and more including her perspective coaching freelancers, working as an independent consultant, some of the blocks people face when taking a leap and much more about the evolving future of work.

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This was an interview of Paul on the Unleashed podcast hosted by Will Bachman, who is the founder of Umbrex, a platform for independent consultants.

Connor's path as an entrepreneur began when he was in college via an AIM chat with a classmate in one of his classes. What started as a textbook e-commerce business led him to build a sizeable business selling things on Amazon.com. Through his work on that, he ended up working with many freelancers across the globe on a variety of different projects. Realizing that he had developed skills in recruiting and working effectively with freelancers led him to start FreeUp.com. where he vets the best freelancers in the world and helps companies tap into this global talent pool.

Jen Morilla is an impact travel influencer. What does that mean? It means she travels the world and writes about her experiences but also has a central mission. At first, she started out with the mission to "change the world" that has since gotten more specific. She has been bringing water filters to many different villages across the globe and impacted an estimated 12,000 people globally What has been meaningful for her is not bringing the water filters, but teaching people how to solve problems. Her own journey is an experience of learning as well - spending time on youtube and learning from others to develop skills in video editing, writing and more. She never saw this as a risky move and saw that if she was at the same job in five years (although her view of the empire state building was pretty nice!), that she would always regret not having tried.

Find Jen Here:

Romy is an employee engagement consultant turned coach. She built her career consulting for and working in Fortune 100 companies on all challenges employee-related. Her mission is to drive meaningful and behavior-based change for mid-level leaders that helps them operate in a more productive and human way in the workplace. There are a lot of coaches out there, but what makes Romy stand out is that she has a lot of experience working with senior executives in her consulting career and she has deeply studied what works and what doesn't. Hear more in our conversation...

Tanya Alvarez is the Co-Founder, and CEO of OwnersUP is a platform which advances solopreneurs business through accountability, goal setting, and community. Over the past fifteen years, Tanya has accumulated marketing experience with international & US companies such as Nike and US Olympics. She started her first company at the age of 25 and grew it to be a profitable company from credit card debt to over $1mm in gross revenue the first year. Since then, she has founded, bootstrapped, sold and invested in several companies.

Pauri started playing Tennis when he was seven and it has turned into a clear passion. He wasn't always sure that was the path he wanted to take, but when a job as a teacher fell through because he decided to attend his sister's wedding, he picked up some coaching work to make some money. One thing turned into another and he is now the head women's and men's coach at Wheaton College. As a coach, he is in the position of constantly having to think about how to motivate different types of people and how he wants to lead. We also discuss his role in the healthy masculinity project and his work with college students.

His Advice For Careers: Go work somewhere interesting rather than something that is safe. Earlier in your career, Tom pushes people to sacrifice revenue or stability in favor of learning and growth.