The Pathless Path with Paul Millerd

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:

• Total USD spent: $24,740
• Total days on the road: 338
• Total countries visited: 38 (including the USA)
• Most days in a single country: 30 (Vietnam)
• Total number of miles traveled: 68,307 (109,925 km) – equivalent to circling the earth 2.7 times
• Air Travel: 51,044 mi (82,143 km)

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.

Link to Video Version Of Interview (Dumplings Included)

------------------

For More With Boundless:

1. Consider supporting the podcast on Patreon
2. Join 110+ People Carving Their Own Paths In The Slack Community
3. Set Up A Curiosity Conversation With Paul
4. Join The Free 3-Week Self-Employment Challenge
5. Sign up For The Strategy Toolkit - Learn The Secrets Of Strategy Consulting

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.

• Twitter: @tedbauer2003
• Ted's Writing & Blog: The Context Of Things

Join The Conversation

• Join the exclusive Slack Boundless Community & engage with other people carving their own path
• Signup for the newsletter

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:

1. Write down the ideas, make it real
2. Share your dumb idea as widely as possible (don't worry if people steal it)
3. Get as much feedback as possible (even the negative!)
4. Continue to tweak and re-work the dumb idea (don't get too tied to the original idea)

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!

• Dumb Idea Project
• Shayne Spencer (LinkedIn)

Boundless Links:

• Subscribe to the newsletter
• Support On Patreon
• Freelance Consulting Playbook

Jacqueline Jensen has been a digital nomad for 3.5 years, living and working globally. It might surprise you to find out then, that she's written a book called "Travel Isn't The Answer." While counter-intuitive, she argues for a return to awe and wonder with what is already around us. She talks about different moments of wonder she has experienced (including a breathtaking view in Montenegro) and different techniques for how people can "Live With a Sense of Curiosity, Passion, and Awe Anywhere and Everywhere" (the subtitle of the book).

Last year, in a planned sabbatical she came face-to-face with the fact that work was the center of her world. While she almost "quit" the sabbatical, she pushed herself to redefine her day and time to claim back some of herself from a sole focus on work.  She provides many actionable tips and perspectives that can help people question the role of work in their lives, take steps to increase the amount of awe in their lives and connect with people that matter to them.

More About Jacqueline:

• TedX Talk
• Twitter: @JackieMJensen & LinkedIn: Jacqueline Jensen
• Book: Travel Isn't The Answer (Amazon)

Recommendation on getting outside of your comfort zone:

• Check out local music: sofarsounds.com
• Go to an art museum
• Travel-as-a-service recommendations discussed: Hacker Paradise, Recess Labs, Roam, Outsite
• App for re-aligning your day: Today

------------------------------------------------

Boundless Links:

• Subscribe to the newsletter
• Support On Patreon
• Join The VIP Facebook Group (upcoming book club on Bullshit Jobs in September 2018)

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:

------------------------------------------------

Boundless 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:

1. Use what you've got
2. Exchange what's in hand
3. Offer what you can

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.

• Dis-identify with the identity of the worker: Questioning whether you truly only are a worker, a CEO, a marketing manager, an accountant, etc...
• Begin an inquiry into the question "If I am not a worker, then who am I?": What else is worth living for? What practices do I want to have in part of my life? What relationships and conversations nourish me?
• The question whether or not the life you have defined is "sufficient": Are you thinking deeply enough about the question of who you are?

Andrew's Writing & Site:

• Andrew's Newsletter On Total Work
• If Work Dominated Your Every Moment, Would Life Be Worth Living (Aeon)
• Andrew's Writing

Other Writing Mentioned:

• Josef Pieper's Leisure, The Basis Of Culture
• Andre Gorz, Reclaiming Work
• David Graeber, Bullshit Jobs

------------------------------------------------

For More With Boundless:

1. Consider supporting the podcast on Patreon
2. Join 110+ People Carving Their Own Paths In The Slack Community
3. Set Up A Curiosity Conversation With Paul
4. Join The Free 3-Week Self-Employment Challenge
5. Sign up For The Strategy Toolkit - Learn The Secrets Of Strategy Consulting

------------------------------------------------

Detailed Bio

Andrew Taggart is a practical philosopher. He asks and seeks to answer the most basic questions

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. 

*You can read the piece here*: Crisis At Work

I talk through six key reasons why organizational fail to unlock human potential:

1. We're defaulting to the wrong goals (shareholder value)
2. We're mistaking authority for performance (the Tom Brady principle)
3. We aren't providing a connection to purpose
4. We don't understand how organizations operate (Chaos theory)
5. We aren't giving people autonomy
6. We're choosing comfort over growth

Boundless Links:

• Subscribe to the newsletter
• Support On Patreon
• Join The VIP Facebook Group (upcoming book club on Bullshit Jobs in September 2018)

Paul provides a summer update:

1. Shifting the podcast from making sense of the future of work => "The Human Side Of The Future Of Work"
2. Early lessons from the digital course experiment, Solopreneur Shift
3. I'm moving to Asia...

Boundless Links

• My article on beanie babies and doing things that don't make sense = > yes, please
• Check out the latest tools, including the Freelance Target Income Calculator
• Want an e-mail of 5 good reads every Sunday? Subscribe to #boundlessreads

**This podcast is supported via micro-donations. Consider supporting the 10+ other patrons on Patreon**

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.

Find Tony Here => Tony Triumph

Full Bio: Is a contributing Life & Style Editor, Brand Entrepreneur, and the Founder & Editor of The Triumphant Scoop website. As a Creative Entrepreneur and international Brand Ambassador, he is the CEO & Founder of The Triumphant Group, having successful collaborations with top brands: Barney's New York, PUMA, Macy's Inc., Lord & Taylor, Pirelli, Sunglass Hut, and SONY among many others.

----------------------------------------------

Boundless Links

• Interested in taking the leap to self-employment? Join the first cohort of the Solopreneur Shift Program, starting July 30th
• Check out the latest tools, including the Freelance Target Income Calculator
• Want an e-mail of 5 good reads every Sunday? Subscribe to #boundlessreads

**This podcast is supported via micro-donations. Consider supporting the podcast on Patreon**

--------------------------------