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The Pathless Path with Paul Millerd

The Pathless Path with Paul Millerd

By Paul Millerd

The Pathless Paul is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Khe Hy, Ben Hunt, Wade Foster, Dan Vassallo, Kris Abdelmessih, Steph Smith, Amir Salihefendić, Alex Pang, Visakan Veerasamy, and more.
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Packy McCormick - Bringing Fun To Newsletters Since 2019

The Pathless Path with Paul MillerdDec 04, 2020

00:00
42:27
How To Set Goals & Do Things That Matter - Malcolm Ocean

How To Set Goals & Do Things That Matter - Malcolm Ocean

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:

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📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

🙏Further Ways To Support The Podcast:

Jul 12, 202201:35:55
Lessons From Homeschooling, Skipping College & Carving Her Own Path - Hannah Frankman

Lessons From Homeschooling, Skipping College & Carving Her Own Path - Hannah Frankman

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.

Follow Hannah:

Links Mentioned:

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📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

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Jun 28, 202201:18:48
What Do Digital Nomads Tell Us About The Future? - Lauren Razavi (Executive Director, Plumia)

What Do Digital Nomads Tell Us About The Future? - Lauren Razavi (Executive Director, Plumia)

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.

Currently, Lauren is Executive Director of Plumia, the mission to build an internet country for digital nomads at SafetyWing, a Y Combinator company that raised a $35 million Series B in 2022. She is also author of the book Global Natives and writes the Counterflows newsletter) about borderless living. She tweets @LaurenRazavi.

SPONSOR: CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here

Links Mentioned

Timestamps

  • 2:01 Introduction
  • 3:22 Lauren's Influences Growing Up
  • 6:30 Lauren's Idea of Home
  • 9:00 Paul on International Couples
  • 10:24 Lauren on how she sees "place" & digital citizenship
  • 12:44 Becoming a Digital Nomad
  • 17:26 Paul's experience in Bali
  • 19:34 Digital Nomads being self-reflective
  • 23:51 The fear of asking questions about life
  • 30:10 How everything changed in 2020
  • 31:52 Why the remote work is here to stay
  • 34:21 Asking better questions - Nomads and Settlers
  • 43:52 Lauren's approach to writing - working with an editor
  • 51:21 The most interesting experiments with countries/policies
  • 58:23 The problem with the real estate
  • 1:02:28 Rapid fire questions with Lauren

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

🙏Further Ways To Support The Podcast:

Jun 22, 202201:08:10
Growing up in Hawaii, Corporate Detours & The Future of Audio - Sky King

Growing up in Hawaii, Corporate Detours & The Future of Audio - Sky King

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

CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here

Timestamps

  • 1:41: Intro to Sky and where his name came from
  • 5:03: Sky's influences growing up
  • 11:34 Why he went to the corporate world
  • 17:12 Cold emailing Ryan Holiday & vision for 
  • 19:47 Sky's "quake moment"
  • 25:15 Moving to Austin and working for Aubrey Marcus
  • 30:44 Sky's desire to help people 
  • 32:55 Growing up in Hawaii
  • 36:10 Going to China at 10
  • 39:30 Everything anywhere all at once reflections
  • 44:40 The "true default path"
  • 47:30 Hiring someone & responsibility
  • 48:30 "what are you uniquely positioned to do?"
  • 49:20 Advertising Subsidy & Media incentives
  • 57:20 Meme farming & future of audio
  • 1:01:30 Bucky Fuller & specialization

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path 

📲Connect + Follow Paul

🙏Further Ways To Support The Podcast:


Jun 14, 202201:06:31
The Arc of The Practical Creator - Lawrence Yeo

The Arc of The Practical Creator - Lawrence Yeo

Being an undeclared major till his senior year of college, Lawrence didn’t really know what he wanted to do. After looking up which jobs make the most money, he decided to declare as an economics major, leading him to explore Investment Banking. While he didn’t end up working in investment banking, he was still pulled by the power of prestige, something he says “is a drug, and is most potent” when you are young and looking at schools. Over a number of years and experiments with music and creating and writing, he slowly started to figure out a better path forward for him. After leaving the corporate world for a second time, Lawrence finally found a calling - writing on his blog: More To That where he uses visual storytelling to express his ideas of pursuing alternative paths, sharing ideas, and creating online. 

Some of the topics we explore in this conversation include: 

  • The influence of money and prestige 
  • Burnout and reflection
  • The importance of the right partner 
  • Finding the right medium 
  • The Arc of the Practical Creator

How To Find Lawrence:

CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here 

Audio Timestamps 

  • 2:26: Intro/Who is Lawrence 
  • 3:47: Scripts around creativity 
  • 5:37: Prestige and Money 
  • 8:56: Fear of ending up broke and homeless 
  • 16:55: Knowledge Work & Burnout 
  • 21:20: Having the right partner supporting you 
  • 29:38 How writing emerged as something important 
  • 32:44: The Arc of the Practical Creator: Stage 1 
  • 42:15: The Arc of the Practical Creator: Stage 2 
  • 50:48: The Arc of the Practical Creator: Stage 3 
  • 59:10: Rapid-fire questions with Lawrence 
  • 1:03:35: Outro/Where to find Lawrence 

Buy Paul’s Book (Published Jan 2020): The Pathless Path 

Connect + Follow Paul 

Further Ways To Support The Podcast: I support the following services and recommend and/or use all of the following 

Jun 07, 202201:04:23
Podcast Update! Re-branded as The Pathless Path & LIVE Q&A From Youtube

Podcast Update! Re-branded as The Pathless Path & LIVE Q&A From Youtube

I offer a short little update on the next steps for the podcast and include a live Q&A I did on youtube last week.

Video link: https://youtu.be/CGbw7Q8hoys

Jun 01, 202233:25
The Money Path or The Life Path? - Tim Malnick
Mar 28, 202201:06:47
Music, Entrepreneurship & Embracing Non-Work - Paul Canetti
Mar 21, 202257:03
The Magic of Writing with Sasha Chapin
Feb 12, 202245:00
Khe Hy - Tales From The Pathless Path

Khe Hy - Tales From The Pathless Path

From a live event where Paul & Khe talk about their shared journeys of self-employment, creating online & more

Get access to Khe's $10k training which will help you wander towards the pathless path: https://radreads.co/millerd

Feb 09, 202201:00:12
The Pathless Path Launched! (reading of the introduction)

The Pathless Path Launched! (reading of the introduction)

Just launched my book, The Pathless Path! 

Purchase the book here.

This is the introduction of the book.

I'll be releasing some clips of me reading the book and will eventually publish an audio book.

Jan 27, 202206:49
Valuing Options & Possibilities On The Solo Creator Path with Kris Abdelmessih
Nov 10, 202101:49:12
The Formless Path - Money, Fatherhood & Creativity (Howard Gray)
Sep 27, 202101:11:23
The Shadow Side of Solopreneurship - Darren Joe

The Shadow Side of Solopreneurship - Darren Joe

Sep 19, 202101:02:34
Six Months In The Creator Economy - Michael Ashcroft (Part 3)

Six Months In The Creator Economy - Michael Ashcroft (Part 3)

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!

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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.

Or if you want to fund my crypto house, you can send me some crypto here.

Aug 19, 202122:37
Accidental Freelancer To Brand Consultant, Founder & Freelance Coach (Austin Church)
Aug 04, 202156:16
Burnout & "Living At Work" In 2020 - Natalie Rachel
Jul 22, 202157:39
Narratives, Work & What Matters - Ben Hunt
Jul 06, 202153:35
Money Fears, Self-Employment & Living Abroad With Kids - Jenni & Lisa Dazols

Money Fears, Self-Employment & Living Abroad With Kids - Jenni & Lisa Dazols

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:

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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 links

Jun 24, 202101:02:44
A Sabbatical Every Seven Weeks - Sean McCabe
Jun 17, 202144:40
Youtuber and Doctor - Ali Abdaal on Identity, Prestige, Creativity & Meaning

Youtuber and Doctor - Ali Abdaal on Identity, Prestige, Creativity & Meaning

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/

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Subscribe to Paul's Weekly Newsletter: http://boundless.substack.com

May 03, 202101:00:02
What happens six months (and three months) before you quit? - Michael Ashcroft

What happens six months (and three months) before you quit? - Michael Ashcroft

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

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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.

Or if you want to fund my crypto house, you can send me some crypto here.

Apr 13, 202151:26
The Self-Employment Meta-Game (Dan Vassallo)
Jan 26, 202157:40
Who are digital nomads? (Professors Rob Litchfield & Rachael Woldoff)
Jan 19, 202101:02:19
Quitting To Teach History to 500k+ on TikTok (Michael McBride, Creator of Idea Soup)

Quitting To Teach History to 500k+ on TikTok (Michael McBride, Creator of Idea Soup)

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!

Jan 11, 202156:44
Curating Goodreads Remotely (Uri Bram, CEO of The Browser)

Curating Goodreads Remotely (Uri Bram, CEO of The Browser)

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

  1. In Praise of Idleness and Other Essays, Bertrand Russell
  2. Derek Parfit, Reasons and Persons
  3. Leadership & Solitude, William Deresiewicz
  4. Disadvantages of an Elite Education, William Deresiewicz
  5. Seeing Like a State, James Scott
  6. How Ghost Is Structured for the Long-Term
  7. The Great Works of Your Life, Cope
  8. Ada Palmer, Ex Urbe
  9. Susan Bryson, Aftermath
  10. Salary Negotiation: Make More Money, Be More Valued, Patrick McKenzie

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Dec 24, 202039:58
Packy McCormick - Bringing Fun To Newsletters Since 2019

Packy McCormick - Bringing Fun To Newsletters Since 2019

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.

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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.

Dec 04, 202042:27
Podcast Update Nov 2020 - The Pathless Path
Nov 03, 202021:08
Angie Wang - My Partner On This Crazy Journey

Angie Wang - My Partner On This Crazy Journey

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

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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 is kind of crazy!).

Podia

I also use Podia for my Reinvent Course. I like both Teachable and Podia but Podia is probably better if you are just getting started and don't want to get lost in customizing the pages. Their referral deal is super generous for me 30% of your monthly fees forever, so I'll be a huge supporter of your course ;-) Pro Tip: Click my link and then sign up for a free trial. If you wait a few days to commit, then they'll offer you a 15% lifetime discount in the first two weeks.

Teachable:

I also use Teachable for my Think Like A Strategy Consultant course. It works quite well as well, though Podia is a little more slick for more recent design and using a simple editor. If you click here I'll get a 30% cut of your monthly fee - same deal as Podia!

Charles Schwab No International ATM Fee Checking

This card is a must have if you plan on living or traveling abroad. Easy to withdraw money and not worry about fees anywhere in the world. This link will give me $100 if you deposit $1,000 within 45 days.

Wealthfront

I use Wealthfront for my SEP IRA which is like a 401k for self-employed creators. If you use this link you'll get $15,000 managed for free and I'll get an additional $5,000

Quickbooks Self-Employed

I do all my own finances, accounting and axes using Quickbooks which makes things quite simple. If you use this link you'll get 50% off and I'll get $30.

Oct 19, 202001:01:17
Carving a 21st Century Life & Career - Steph Smith
Sep 16, 202048:24
The Possibilities Of Life Beyond Work with Oshan Jarow
Sep 08, 202001:19:52
Amy McMillen - Wandering In Uncertainty & Writing A Book (Mid Pandemic)
Aug 31, 202025:47
Will Bachman: Building an Independent Consulting Practice With a 5-Decade Success Mindset

Will Bachman: Building an Independent Consulting Practice With a 5-Decade Success Mindset

Will Bachman is the creator of a community-first talent platform for management consultants, Umbrex and hosts a podcast for independent consultants called Unleashed.  We talk about the recent course he created called the Guide To Setting Up Your Consulting Practice course ($100 off with the code: boundless), which is a product of his 12 years as an independent consultant and his work helping hundreds (perhaps thousands) become thriving solo consultants.  We talk about

  • How he thought about independent consulting in 2008 versus now in 2020
  • How his talent platform, Umbrex, was born and how it has remained community focused
  • What led him to create his course and some of the
  • What makes him want to “keep playing the game” of self-employment
  • How independent consultants can think about finding new clients
  • How he designs experiments to keep his learning journey alive
  • How he builds his virtual team to help him succeed as a consultant
  • How he filters everything he does through a 5-decade time horizon

If you want to connect with Will, connect with him on LinkedIn or Twitter,

If you want to get the Guide To Setting Up Your Consulting Practice:

Books Mentioned:

Support Boundless:

May 28, 202054:38
Reflection with Andrew Taggart on Work & Life
Mar 26, 202044:09
Laurel Farrer: The Global WFH Experiment & Long-Term Promise Of Remote Work

Laurel Farrer: The Global WFH Experiment & Long-Term Promise Of Remote Work

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.

More:

Mar 18, 202051:07
Imagining A New American Dream (Diania Merriam, Econome Conference)
Jan 08, 202056:03
Longform Thoughts: Why Organizations Undermine Creativity & Potential

Longform Thoughts: Why Organizations Undermine Creativity & Potential

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:

Jan 02, 202029:21
A Remote Company With 40 Vacation Days?! (Amir Salihefendić, CEO Doist)
Dec 10, 201945:35
The Lazy Person's Guide To Freedom, Generosity & Creative Work (Moataz Ahmed)
Dec 02, 201950:55
Twitter Friends & Threads, Self-Employment & Curiosity (Visakan Veerasamy)
Oct 30, 201901:14:15
Rest, Leisure, Working Less & The 4-Day Workweek (Alex Pang)
Oct 22, 201901:01:08
Geography & Culture Side Hustle Experiments w/ Rohith
Oct 17, 201921:38
The Phases & Emotional Journey Of Making A Work Shift (Stephen Warley)
Sep 19, 201947:31
Good Writing & Doing Work That Matters (Andy Sparks, CEO Holloway)
Sep 04, 201901:04:52
Coworking That Works & The 10k Independents Project - Alex Hillman, Indy Hall
Aug 21, 201901:02:07
Should Everyone Have A Coach? (Ben Brooks, Founder of Pilot)

Should Everyone Have A Coach? (Ben Brooks, Founder of Pilot)

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:

Boundless: 

  1. Want to support the podcast?  Offer a one-time or recurring donation on Boundless.  
  2. Check out Boundless - The Site For Creative & Curious Rebels
Jun 19, 201901:02:55
What living on a boat for 18 months can teach you about work & life (John Zeratsky)

What living on a boat for 18 months can teach you about work & life (John Zeratsky)

John Zeratsky was a designer in the tech industry has worked with hundreds of startups in his time at Google Ventures.  He’s also obsessed with redesigning time and thinking about what matters in life.  Earlier this year he just got back from 18 months living on his boat "Pineapple" with his wife sailing around Central America, which he wrote about in an article titled “What quitting my job to sail around central america taught me about fulfillment.” 

In this conversation we talk about:

  • Growing up in a small lake community
  • His love of sailing growing up
  • Why him and his wife change their mind on taking the trip in 2015
  • Rethinking convenience and comfort
  • What comforts are worth paying for
  • Belonging and community
  • How his relationship with money has changed
  • How him and his wife are structuring their life to work how they want
  • The one change that helps people be less addicted to their phones

Links Mentioned:

Want to support the podcast?  Offer a one-time or recurring donation on Boundless.  

Jun 12, 201901:04:28
Hannah Wei on her nomadic life, Muay Thai fights, Tinder experiments & community
Jun 05, 201947:19
Microadventures, Long-term Travel & Busking Through Europe (Alastair Humphreys
May 22, 201940:11
Dreaming, starting a tribe & living on an island with three kids (Ben Keene)
May 15, 201958:45