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, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Join Paul as he shares his own reflections and tries to learn from others
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Tom and Paul talk through Tom's challenges at this inflection point in his indie career, a book he's planning on shipping and how to think through indie consultant identity crises
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⌛TIMESTAMPS
*** (00:00) - Intro
(01:09) - Guest introduction
(03:33) - Tom's problem — indecisiveness
(07:47) - What does Tom think he should be doing?
(10:10) - Not working, go and wonder, owning time
(14:27) - 7th week off, shaking things up
(18:36) - Strategically dropping the ball
(24:34) - Should Tom hire an editor?
(26:28) - The fear of finishing the book
(35:13) - The last 10% are the hardest
(37:30) - Writing the introduction, injecting the book with a personal story
(41:50) - Preselling his book as a motivation?
(43:24) - How Paul was pushing Tom to write his book
(45:13) - Closing remarks**
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Erin is a spiritual psychology and meditation teacher, with a background in clinical psychology. She believes in experiencing rather than explaining and because of that she has been drawn to travel to places like India and Israel, which have helped her connect to her roots and to what matters. Erin is passionate about discovering her true self, meditation, snapshot manifestation, and taking aligned action. She is finishing up a new book and is about to have her first child — a new chapter for which she prepares herself with her partner.
🎥🍿 YOUTUBE: WATCH HERE
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⌛TIMESTAMPS
*** (00:00) - Intro
(01:15) - The scripts that Erin grew up with
(05:36) - Early awakening & the inner guru connection &
(11:14) - Being lost, seeking the highest possible timeline
(19:51) - Snapshot manifestation & Aligned action
(32:44) - Travelling to get to know herself better
(37:12) - Women & work, misalignment and seeking freedom as entrepreneurs
(42:00) - Pregnancy & designing life around children
(50:44) - Pause, pray, pay attention - The PPP method
(55:55) - Erin's new book, her path role models & the new chapter of her life
(01:06:32) - Where can we find Erin?**
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Bilal was born in London to a family of Pakistani descent. A curious kid, with an interest in computers, he developed a successful website with over 500 000 readers in his teens. He ended up working at Google in the US. After a while Bilal has left the company to carve his own path. He has founded Creator Lab and discovered a passion for spoken word poetry, which enables him to better connect with his family
🎥🍿 YOUTUBE: WATCH HERE
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⌛TIMESTAMPS
*** (00:00) - Intro
(02:25) - The scripts Bilal grew up with
(08:08) - How video games got Bilal started with data analysis
(12:27) - Losing childhood curiosities
(19:00) - Google & moving to the US
(31:22) - The high highs and low lows of New York
(39:53) - Writing poetry & spoken word
(52:35) - What is enough? Money & Creativity
(01:11:37) - Travel vs Vacations
(01:21:58) - Rapid fire questions
(01:27:24) - Outro**
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Ben was a professional rugby player with an English literature degree — something not unheard of in the diverse rugby world, but also certainly not usual. After retiring from the sport, he was confronted with the task of redesigning his life. Although it was initially tough, he took the slow approach of focusing on the things he enjoys doing, which proved very beneficial in the long term. Ben has self-published 3 books so far, he is freelancing, running courses and he recently became a rising Tik Tok creator.
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📚 Ben's books:
⌛TIMESTAMPS
*** (00:00) - Intro
(01:38) - The scripts that Ben grew up with
(04:30) - School, University and Rugby
(17:51) - The transitional period in France
(25:05) - Transitioning to a new life
(38:01) - Getting into writing
(56:18) - Becoming a Tik Toker
(01:06:20) - What did Ben learn from sports
(01:09:16) - Closing remarks**
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I'm trying to convince Angie to do more episodes, so if you like it please let us know by e-mailing both of us here.
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Jenny is an author, international speaker, career and business strategist and executive coach. She has worked in a start up during her college years and then she worked at Google. At some point she decided to follow her passions and left her job. She has already written three books, she runs a business on intuition and she continues discovering her own path.
🎥🍿 YOUTUBE: WATCH HERE
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Jenny's Books:
⌛TIMESTAMPS
*** (00:00) - Podcast intro
(00:11) - Guest introduction
(01:32) - The scripts that Jenny grew up with
(08:45) - Google & Saying "no" to something good
(22:30) - Creating assets for yourself
(26:12) - Transparency & Making yourself discoverable
(30:34) - Free time & Aiming for longevity
(35:07) - "We'll see" — when things go wrong
(39:28) - Everything is a clue — running a business on intuition
(50:28) - Seeking advice — "the frientors"
(55:34) - Path role models & favourite podcasts
(59:09) - Where can we find Jenny?**
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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Dawn has a medical degree but she didn't pursue a traditional career as a doctor. She lives off grid with her husband and her homeschooled daughter. Dawn is passionate about finding a work-life balance and she wrote a book for professional women seeking to do so.
🎥🍿 YOUTUBE: WATCH HERE
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⌛TIMESTAMPS
*** (00:00) - Intro
(01:05) - The scripts Dawn grew up with
(02:49) - Medicine, engineering and rock climbing
(15:43) - Being diagnosed with a brain tumour
(20:22) - Shifting in a new direction
(25:42) - Infertility, having children & "leaning out"
(38:26) - Designing life with her husband
(47:43) - Moving off grid
(53:05) - Homeschooling & Dawn’s daughter
(01:01:31) - Where can we find Dawn?**
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Luke has a background on Wall Street and has founded 3 companies in Silicon Valley. He describes his adult life as a constant state of uncertainty. At some point, he took a classics course, which he completed in a 24-hour Starbucks in a couple of months while living in Las Vegas. This led to him to contemplate deeper questions, leaving "entrepreneur Luke" behind and spending 3 years in Rome. Luke is now a Professor at the Ciocca Center for Principled Entrepreneurship and has written a book — "WANTING: The Power of Mimetic Desire in Everyday Life." The book is one of the best ones I've read in the past couple of years and we talk about some of the ideas in the book and how they intersect with Luke and my life.
🎥🍿 YOUTUBE: WATCH HERE
Links:
⌛TIMESTAMPS
*** (00:00) - Intro
(01:18) - The scripts that Luke grew up with
(14:59) - Book publishing the temptations of conformity
(22:24) - The memetic desires & The romantic lie of our own desires
(27:54) - Doing the classics course after hours
(32:42) - The importance of play & Feeding the spirit
(35:29) - Thick Desires & Thin Desires
(46:05) - Creativity, Being open & Letting go of control
(50:31) - Learning from different work cultures & transcending the system
(57:41) - "The Three Cities Problem" — Reason, Faith & Technology
(01:06:02) - What’s next, preparing to be a father
(01:14:30) - Luke's path role models
(01:17:28) - Closing remarks**
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
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Melvin has a PhD in psychology but to call him just "a psychologist" would be trying to fit him in too small of a box. He has left a successful clinical career to build his online "healthy business" – he is the person behind "Selling the Couch" podcast, he does sessions with entrepreneurs and he runs an online course where he helps therapists to move their business online. Everything he does is designed to allow him to be fully present as a father and a husband because, "What's the point of accomplishing all of this if we can't be fully present with the people that we love the most?"
🎥🍿 YOUTUBE: WATCH HERE
Links:
⌛TIMESTAMPS
*** (00:00) - Intro
(01:25) - The scripts that Melvin grew up with
(11:42) - From Psychology PhD to Content Creator
(20:53) - The beginnings of "Selling The Couch"
(28:29) - Finding long-term sustainability in podcasting
(40:43) - Slowly going all in
(43:12) - Re-evaluating money and life - The birth of Melvin's daughter
(57:26) - Detaching identity from work
(58:56) - Lessons from therapy sessions
(01:01:19) - Melvin's path role models & routine
(01:07:26) - Closing remarks**
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Anna is the founder and CEO of Interintellect - a global community of thinkers. She grew up in Hungary and emigrated to London at the age of 30 and later to the US where she built her startup. She is passionate about staying curious as we age. While for some their late 20's are the end, she has chosen to treat it as the beginning.
🎥🍿 YOUTUBE: WATCH HERE
Links:
⌛TIMESTAMPS
*** (00:00) - Intro
(01:20) - The scripts Anna grew up with
(10:39) - Anna's writing influences
(13:53) - Emigrating to London at 30, entering the survival mode
(17:29) - Startups - following bad advice vs trusting your guts
(23:20) - Anna's article in 2018, Culture without culture war
(30:52) - "Unbossing" - Are the gatekeepers dead?
(37:43) - Success - UK vs US
(42:08) - Interintellect
(44:32) - Staying curious as you age
(51:58) - Conformism, nonconformism & feedback
(01:06:13) - Rapid fire questions with Anna
(01:10:27) - Closing remarks**
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This is a solo episode of my podcast, inspired by Jenny Blake. I will do more of these if people like them. Let me know!
For Video: YouTube
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Danny Mirands is the host of The Danny Miranda Podcast. He's been hanging out on the internet since he was 14. We talk about his journey, almost getting sidetracked by the default path in college, and then betting on himself with his podcast. Danny is a friend, and he inspired me by how true he is to his own path, his ability to dream big in creative ways and spread love in the world.
🎥🍿 YOUTUBE: WATCH HERE
Links:
⌛TIMESTAMPS
*** (00:00) - Intro
(00:11) - Introduction
(01:21) - The Scripts That Danny Grew Up With
(09:13) - First Steps On The Internet
(12:59) - College, Addictions & Taking Responsibility
(21:12) - Danny's podcast
(26:10) - Podcast Role Models & Learning from Procrastination
(31:45) - Talent scouting - "Lookig at life through the lens of love
(37:09) - "The True Path" & Goals
(46:58) - Learning from feedback and reps
(51:45) - Reconnecting & The Importance of Rituals
(57:55) - Thinking Big
(01:02:52) - The Business Side & Trusting The Universe
(01:09:55) - Masculinity & Compassion
(01:14:59) - Closing Remarks**
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
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Jessica is a producer and a podcaster. She is passionate about shadow work and is currently working on her documentary on post traumatic growth - "Dark Night of Our Soul".
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⌛TIMESTAMPS
*** (00:00) - Intro
(00:11) - Introduction
(01:19) - The scripts Jessica grew up with
(08:22) - The shadow work, memes, addictions & the hero's journey
(25:00) - Expanding your perspective through travel
(28:11) - Gifts in the shadows & how to rest
(36:52) - The Dark Night of The Soul & post traumatic growth
(51:15) - Producing a documentary
(59:48) - How to watch & support Jessica's project
(01:03:04) - Closing remarks**
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
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Adam Braff grew up in a house where writing was always encouraged. His mother published a newsletter, and his father was a data analytics consultant. He started out as a lawyer, but after the dot-com boom led to a surge in demand for consultants, he decided to make the switch. He now runs his own consulting firm and writes regularly on a variety of topics. Braff himself became interested in consulting during the first dot-com boom. He transferred from MIT to Brown in order to study linguistics, and eventually became a strategy consultant at McKinsey.
Relevant Links:
Timestamps
0:00 Audio Intro
0:48 The scripts Adam grew up with
3:54 Shifting from MIT to Brown
5:33 Becoming interested in consulting
7:25 What was it like from 1999 to 2002?
9:08 Adam's path to becoming a partner at McKinsey
11:56 Leaving McKinsey
14:05 What kept Adam at McKinsey for 10 years?
16:06 What do people get wrong about McKinsey?
18:49 Decentralization and the emergent order
21:46 The new ideas in customer experience Adam helped shape
24:06 Going into the finance industry in 2009
25:23 Turning data into insights
27:20 How to influence other executives to embrace the "hypothesis first" framing?
28:44 The 2 skills from the consulting world that are missing elsewhere
30:28 Teaching the importance of feedback
33:22 Development Group Leaders
35:21 Lessons from working at a hedge fund
42:01 Did the world of billions inspire Adam to go solo?
42:56 Becoming a freelancer
46:52 Should you clearly define the services you're offering as a freelance consultant?
50:18 The role of Adam's writing
51:44 Did the nature of Adam's projects shift over time?
53:14 The best part of the self-employed life Adam didn't expect
54:15 AI & The Future
58:10 The forecasting contest
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This episode was a delight. Venkatesh Rao is the creator of Ribbonfarm and has been writing about the internet, technology, and gig life. This conversation focuses on his recently published book, The Art of Gig.
If you are thinking about working independently, becoming a freelancer, or are interested in consulting, you should definitely buy his book:
You can find Venkatesh:
Links Mentioned:
We talked about:1:00 The scripts Venkatesh grew up with
5:05 Preparing for the leap, Dan Pink's books
10:48 Predictable income vs adventure
18:58 Is $100 enough to build confidence in a project?
21:08 Understanding the big consulting companies
27:18 The positioning vs people's school
33:34 "Avoid polished deliverables"
42:17 Helping the executives take a step back
47:54 Systematic doubt and systematic confidence
51:40 What is "the clutch class" and why does it matter?
59:34 "What the clutch class is doing on evenings and weekends everyone will be doing in 10 years"
1:01:54 Keeping a 10-foot pole between your public identity and freelance gigs
1:03:38 How does Venkatesh work with clients?
1:07:53 The Yak collective and the future of indie consulting
1:12:34 Why the gig economy will outgrow the paycheck economy?
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I believe that Kyla Scanlon is one of the most talented all-around creators. She is transcending the assumptions about what people want, especially with things like short-form videos. Her TikToks are synthesized, thoughtful, and funny, setting a new bar for what people want in an information age.
We talked about her journey growing up in Kentucky, writing online, hacking into the finance industry from a non-target school, and ultimately deciding to become self-employed with less than two years of work experience. Someone at her company told her she wouldn't "make it"
Kyla's Website: Educator, Creator, Investor
Follow Kyla: @kylascan on Twitter, Instagram, and TikTok
Path Role Model: Cody Ko
⌛TIMESTAMPS
1:09 The scripts that Kyla grew up with
2:26 Writing her first book
5:01 Finding out that people actually want deeper ideas
7:31 Kyla's mindest when she was graduating
9:24 Why Kyla didn't like her "cool" job in LA?
11:50 DMing Paul and quitting her job
16:05 Approach to work in Kyla's age cohort
17:19 Kyla's parents on her leaving her job
18:05 Pushback and skepticism
19:27 Positive surprises after going on her own path
20:27 "The passion crisis"
23:24 How to find things you care about?
25:26 Gatekeeping and aging out
27:27 Kyla's short vertical videos
33:09 AI and the future of writing
35:58 Doing, not doing, and bike riding
38:17 Remembering the good ideas
38:48 The vibes of the economy
41:20 Influence and responsibility
42:58 Favourite financial leader?
43:50 Why Kyla doesn't like what the Fed is doing?
45:33 Generations living in different realities
47:00 How did the "vibes" of Kyla's path change?
50:51 Kyla's biggest supporters
51:23 Putting herself out there
52:04 Fame, success, and imposter syndrome
54:03 Charts in Kyla's videos
54:50 Kyla's TikTok's as poems
55:48 What do people get wrong about short-form videos?
56:46 Going from TikTok to YouTube
57:27 Bread
58:32 "Money is not our moral compass".
59:15 What does Kyla need help with?
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Check out David Senra's Podcast: Founders on Apple Podcasts
The legible story is that Catherine is a writer, producer, and digital media consultant. She helps creative people connect with new audiences, usually writers, usually online. But she hasn't had a W-2 job since 2017. Before that she worked as an actor, worked at a company called Longreads, and then has done a bunch of solopreneur experiments over the past five years.
Her recent interest is writing and speaking about how to navigate systems that make self-employment harder in the United States, like housing, healthcare, taxes, and insurance.
Links:
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Audio Timestamps:0:00 Audio intro
2:10 What were the scripts Catherine grew up with?
8:46 The differences in the experience of work between generations
12:19 Applying to Emerson - the cold, unwelcoming Boston
16:02 How Vassar teaches acting
16:41 Auditioning in New York City after graduating
17:16 Becoming disillusioned with a career path as an actress
20:24 Producing her first play
23:34 The American Booksellers Association
30:24 Creating jobs for herself
33:15 Working at Longreads
38:00 Leaving Longreads
39:30 After Longreads - moving to Austin
44:17 Designing life with her husband
48:18 How the system is incompatible with the new ways of life
48:52 Leaving the US as a way to gain perspective
49:42 "I'm breaking some law right now, I just don't know which one"
50:37 Does work equal suffering? The IRS' definition of a hobby
51:44 Why Catherine doesn't think in long time horizons
52:59 Getting a mortgage as a self-employed person
59:12 Small Bets & Dan Vassallo
1:01:55 LLC vs. S Corp
1:12:24 Healthcare in different states
1:16:55 Catherine's course
1:17:20 Tennessee Williams - The Catastrophe of Success
1:23:24 Cathrine's path role models?
Join 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
Jonny Miller is a dear friend and I've had the privilege to get to know him closely over the past four years on our own journeys. We've live in Japan, Indonesia, and Mexico together. When we met we were both single but now are both married in cross-country relationships and have navigated finding work that matters, getting married, and living in foreign countries together.
This conversation was really special.
I also recommend his course: Nervous System Mastery which wraps up enrollment for the 2nd cohort this week.
Links:
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Andy Schoonover is the CEO of one of the sponsors of this podcast. After talking with him I actually thought he'd be a great guest on the podcast. He has a fascinating story from going from search-funder post-MBA grad to forming his own healthcare company. Can his company fix healthcare? Can anyone? Time will tell but I'm rooting for him.
Join 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 (Sponsored Link, Includes discount)
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🍿 Watch on YouTube
Ali Green has been a remote worker since 2014. It took her a couple of attempts to fully unpair from the office and even when she had a fully remote job it took her another year to lean into her freedom. Now she's writing a book about what she's learned leading teams, living in different countries, and working remotely.
Learn more:
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Dr. Corey Wilks is a Licensed Clinical Psychologist and Executive Coach with over 15 years of psychological experience.
In 2020, he stopped practicing therapy and ventured into entrepreneurship. Now, he coaches entrepreneurs and creates content to help people be more intentional with how they live, work, and create.
His latest project is Intentional Life Design, a 5-week live cohort-based course focused on helping people overcome limiting beliefs, think bigger, and do work that matters.
Find More About Corey
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
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Dr. Corey Wilks is a Licensed Clinical Psychologist and Executive Coach with over 15 years of psychological experience.
In 2020, he stopped practicing therapy and ventured into entrepreneurship. Now, he coaches entrepreneurs and creates content to help people be more intentional with how they live, work, and create.
His latest project is Intentional Life Design, a 5-week live cohort-based course focused on helping people overcome limiting beliefs, think bigger, and do work that matters.
Find More About Corey
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
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Join 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
In this episode, I talk with fellow creator and curious human Anne-Laure Le Cunff. She left her job at Google and embarked on an entrepreneurial journey about one month before I did in April 2017. We compare the lessons we have learned over the past five years as well as talk about:
Her personal site: Anne-Laure Le Cunff | Wellness, Creativity & Culture
Her newsletter & community: The Maker Mind Newsletter by Anne-Laure Le Cunff (nesslabs.com)
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
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In this episode, I talk with fellow creator and curious human Anne-Laure Le Cunff. She left her job at Google and embarked on an entrepreneurial journey about one month before I did in April 2017. We compare the lessons we have learned over the past five years as well as talk about:
Her personal site: Anne-Laure Le Cunff | Wellness, Creativity & Culture
Her newsletter & community: The Maker Mind Newsletter by Anne-Laure Le Cunff (nesslabs.com)
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
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Mike Steiner found himself on Penn’s campus at a young age not really knowing what he was supposed to do next. Thanks to helpful roommates, he started to figure out how to take advantage of the opportunities around him. He started getting more interested in math, statistics, and finance. He eventually ended up interviewing in New York and ending up at the famous training firm Susquehanna Investment Group (SIG). As a part-time trainer at first and then in a more central role, Mike started to experiment with different ways of teaching things like market making, probability, thinking in bets, and the behaviors needed to "make it" in the trading pits.
This conversation was a delight and I think you'll enjoy it. We cover:
Prefer Video? 👉 Watch on Youtube
Learn more about stockslam:
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Mike Steiner found himself on Penn’s campus at a young age not really knowing what he was supposed to do next. Thanks to helpful roommates, he started to figure out how to take advantage of the opportunities around him. He started getting more interested in math, statistics, and finance. He eventually ended up interviewing in New York and ending up at the famous training firm Susquehanna Investment Group (SIG). As a part-time trainer at first and then in a more central role, Mike started to experiment with different ways of teaching things like market making, probability, thinking in bets, and the behaviors needed to "make it" in the trading pits.
This conversation was a delight and I think you'll enjoy it. We cover:
Prefer Video? 👉 Watch on Youtube
Learn more about stockslam:
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
📲Connect + Follow Paul
🙏Further Ways To Support The Podcast:
Today I’m talking with Justin Moore - he and his wife was what he calls “OG Youtubers.” From creating content to landing sponsorships to building his own agency, he’s seen every angle of the creator economy. a lot over the last ten years. In the past couple of years, he walked away from the agency and has stumbled into a new path, one he’s finding a lot of joy following - helping other creators getting paid as a sponsorship coach.
He turned down a buyout offer for his course and newsletter because he enjoys it so much. Check out this convo as we explore:
Justin's mission is to enable creators big and small to land 1 million paid brand partnerships by 2032.
You can find Justin here ⇒ Creator Wizard or Twitter
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Gary Ware is someone that inspires me. I've seen him give two walks, both at the World Domination Summit in 2018 and then in 2022. In each, he stood out for his ability to show up as himself and share playful and powerfully true stories about his journey. I love when I get to meet people like Gary and this interview was no different. You can feel his positive energy flowing through the screen (or earbuds!).
🍿🎞️ Watch This Episode on Youtube
Links Mentioned:
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Claire Emerson is a writer and project consultant who helps business owners execute their best ideas.
She is the curator of Flourish newsletter and the creator of Implement My Course — a free 10-day email course on how to apply what you learn without procrastination poisoning your progress.
Links Mentioned:
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I spoke with Tasshin Fogelman about his life's work to bring more love into the world, how he navigates life as a modern online monk, what he learned from spending time at the monastic academy, and what he see's as work worth doing.
You can learn more about his work here: https://tasshin.com/
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Tara McMullin is a writer, host of the What Works Podcast, and also cofounder of a podcast production studio. She's been working with small business owners for more than 13 years and has a deep understanding of what makes them tick. She’s recently written about realizing she was autistic and how that has impacted her role in the workplace.
🍿 Watch On Youtube
🔗 Links:
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Aida Alston is no stranger to alternatives to the default path. From testing out of high school at 15, to finishing college with no debt, then going to medical school for free in Cuba, Aida has been walking her version of a pathless path for a long time.
But she's at a transition point now. She decided not to pursue clinical practice as a physician—again turning away from the default path right in front of her. She's been a full-time stay-at-home mother since then to her two children, raising them bilingually after becoming bilingual in Spanish herself during her time in Cuba.
She's a self-described early AND late bloomer, having sped through milestones early on but now slowly figuring out what's next for her work and family. She understands many of the challenges of going off the default path—like the paradox of choice—and how decision-making and prototyping are skills to be learned and practiced while building a pathless path.
She is from San Francisco originally but now lives in New York with her husband and kids.
👉 Follow Aida on Twitter and Read Her Writing
Links Mentioned:
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John Paller is a Denver-based entrepreneur and the Founder of Opolis, a Digital Employment Cooperative for independent workers. He is also the founder of ETH Denver, the world’s largest Web3 and Ethereum festival.
Prior to discovering Ethereum in 2015, John spent more than 15 years in talent acquisition, HR Technology, and employment systems, building multiple successful enterprises. John brings a breadth of experience in fundraising, investor relations, community outreach and crypto economies, guiding his vision of democratizing employment and growing decentralized communities. In 2014, John was awarded “40 Under 40” by the Denver Business Journal for his contribution to shaping the future of business.
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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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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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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.
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Links Mentioned
Timestamps
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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 how people reacted to the 2016 US election and decided he wanted to try to make it better. From a cold email to Ryan Holiday to helping build Aubrey Marcus' podcast, Sky learned a ton that helped him build an agency FOR podcasters. 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
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Timestamps
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Connect + Follow Paul
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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:
How To Find Lawrence:
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Audio Timestamps
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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
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?
Learn More About Tim’s work here 👉 Different Space - Transformational learning & development by Tim Malnick
New to Reimagine Work? Learn more about Paul here
JUST LAUNCHED: 📕The Pathless Path
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.
He also hosts Tech News for MBAs
New to Reimagine Work? Learn more about Paul here
JUST LAUNCHED: 📕The Pathless Path
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.
Check out Sasha here: Sasha Chapin (imsashachapin.com)
& Buy Paul's Book https://think-boundless.com/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
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.
Kris Abdelmessih has one of the most unique perspectives on life and works I've stumbled across in the past few years. He uses his experience as a trader to look at decision-making and work investments through the lens of options, pricing, and other financial models. I enjoy his perspective because unlike other financial types, he seems to have a proper appreciation of non-work / non-productive time.
We explore his recent break from trading, his creative journey writing on the internet, and finding his people, and he challenges me to think differently about how I'm spending my time with my work.
The conversation dramatically shifted how I'm thinking about the possibilities of my path. If you are on a self-employed path, this is a must-listen:
For Kris' newsletter: Party at the Moontower - (moontowermeta.com)
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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
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“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:
You can buy his book the Fail Safe Solopreneur on Amazon
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In parts 1 and 2, I interviewed Michael about his plan to quit his comfortable consulting job and start a new path creating and selling courses online.
Let's see how he reacts to his own quotes from a year earlier!
The best way you can support me is to join in the conversation. Share thoughts on Twitter, send me an e-mail, and tell me what resonated or what you’d add or refer a friend:
If you’d like to support further you can use my affiliate link for some of the platforms I recommend.
Or if you want to fund my crypto house, you can send me some crypto here.
Austin Church thought he was going to be a poet. When that didn't go as planned, he joined the business world. Six months later he was laid off in the 2008 recession. Luckily, his firm hired him back as a freelancer and that completely changed his perspective on work. Ever since he's been hacking a living, shifting roles as a freelancer, founder, entrepreneur, and coach. We chat about his journey and more.
Learn more about Austin and his great writing on freelancing here.
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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:
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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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Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
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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.
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:
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.
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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.
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.
I had a conversation with Ali Abdaal about his year away from medicine, how he grapples with his identity, the challenges of veering off the course of traditional metrics of success, enjoying the journey, and the challenges he faces.
More from Ali here: https://aliabdaal.com/
Subscribe to Paul's Weekly Newsletter: http://boundless.substack.com
I talked with Michael Ashcroft six months before he was planning to quit his job. We talked about his plan to quit his job, what was going through his mind, his fears and what he expected might happen.
We then chatted again three months later after he submitted his notice and checked in on how he felt
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:
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Or if you want to fund my crypto house, you can send me some crypto here.
I had a delightful conversation with Daniel Vassallo a self-employed creator for the last three years who seems to have gone through many of the same "a-has" as I have. He walked away from Amazon despite making an absurd salary of $500,000 a year. We talk about why he made that leap, why he would never go back and some of the unexpected lessons and insights he's learned from becoming self-employed.
You can learn more about Dan at his site => Dan Vassallo
To follow along with Paul subscribe to his newsletter => Boundless
Paul is also working on a book to launch later this year titled The Pathless Path
Robert Litchfield & Rachael Woldoff have recently written a book titled "Digital Nomads: In search of Freedom, Community, and Meaningful Work in the new economy"
A married couple and both professors, they bring an interesting combination of perspectives. Rachel is a sociologist specializing in urban communities and Rob is a management professor specializing in creativity and motivation.
They both moved to Bali for three months with their kids and immersed themselves in this world. I share some of my perspectives and they share what they learned, how it impacted how they lived their life and how they see these trends impacting modern work and institutions.
If you'd like to subscribe to the weekly newsletter on the modern world of work, please subscribe: Boundless Newsletter
If you want to support the podcast you can do so by using my affiliate link for one of the products I use and endorse.
Michael Mcbride left his job almost a year ago to work on building out Idea Soup, an instagram and TikTok channel focused on helping re-inspire people’s passion for history and knowledge.
We talk about his creations over the years, how he has felt since leaving his job over the last year, what he’s learned from engaging with young people on TikTok and how he sees the future of education emerging from things like TikTok and other online platforms.
On his foundational belief: “If I had a thesis it's that education really does work and education really does matter”
His motivation and secret to his success: He said, “I find history so crazy and weird and fascinating that I think that;s contagious. If I had a mission it’s not to make them more educated, it’s to make them go. “How did roman's wipe their ass, that’s crazy,”
Listen to the episode to find the answer to this!
Uri Bram is the CEO of The Browser which runs regular newsletters to help people find good articles, podcasts, and videos to read. He has been living as a digital nomad for over seven years and also runs The Browser as a remote company.
We chat about Uri’s own journey, what it's like working with Robert Cottrell (who reads 10-12 hours a day), his early experiences becoming a kindle best-selling, how he thinks about running a remote company and some of his favorite reads worth checking out.
Articles/Books mentioned
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Packy says that his differentiation "is that I’m going to be having more fun than most people”
I've been a big fan of the energy he's brought to his writing over the past couple of years. But he didn't set out to have a popular newsletter. His real plan was to launch an in-person community.
We chat about how the pandemic helped him figure out why that wasn't a good idea and how he's thinking about his solopreneur journey,
The reason I asked him on the podcast is to talk about his recent newsletter on the future of work. He argues that “Employees will ultimately make the decision” about what work looks like post-pandemic. I think he is mostly right and we talk about what that might mean for people's lives.
You can find ways to support Paul through affiliate links, newsletter sponsorship or direct gifts here
If you want to subscribe to Paul's weekly newsletter on the modern state of work, the solopreneur journey and creating online, you can subscribe here.
I decided to record a short little update with my friend Travis. What have I been up to, where have I been living throughout the pandemic and what is in store next for Reimagine Work.
If you'd like to watch on YouTube, you can do that here: https://www.youtube.com/watch?v=7Xlqe6D-HfM
I interviewed my wife, Angie, who has gone through a major career change and has launched a number of creative experiments and projects over the past couple of years. She reflected on what its been like going along this journey alongside me and grappling with success, identity, being a woman in Taiwan and creating in public.
Video Version Of The Interview: Watch The Interview on Youtube
If you like conversations like this, join my weekly e-mail which is an exploration of life, work, creativity and a contemplation on what matters: Boundless Newsletter
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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.
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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.
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:
Learn More: StephSmith.io
Oshan sums up his worldview as:
"We’re all going to die, but in the meantime, the world is far more mysterious, wonderful, and stimulating than human consciousness plagued by economic precarity can experience.”
We explore that possibilities might emerge if we can imagine a life beyond work.
Be brave and join us on this episode?
Oshan's Work: Musing Mind
Subscribe to boundless: Subscribe
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.
Our full conversation, including Q&A can be found here: YouTube Link
Subscribe to Paul's weekly newsletter on work & what matters: Boundless @ Substack
Buy Amy's Book: Reclaiming Control @ Amazon
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
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:
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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
For more on Andrew: His Website
Music: Deliberate Thought by Kevin MacLeod
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.
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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.
She then took a 2 month unpaid sabbatical to walk the Camino de Santiago (a 500 mile trek across northern Spain). She also bought a house, adopted a dog, and found herself a midwestern gentleman. Diania founded EconoMe, a one day event at the University of Cincinnati on March 7th, 2020, to make the ideas that inspired her more accessible to others.
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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:
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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:
See the episode notes here
Follow Visa on twitter
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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.
Read more about Alex and get a copy of his book here
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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.
This one features Rohith Amruthur, creator of the Lost Geographer, which you can learn more about here. If you have any suggestions or want to come on the podcast, shoot me an e-mail.
If you'd like to support this podcast you can do so here.
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.
If you want to support the podcast, you can go here.
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:
Learn more about Holloway here or subscribe to Good Work
REINVENT: Learn more about the course here or lurk on my progress here
Patreon: Become a supporter here and get access to the curious rebel club for $1/month
" 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)
Subscribe to the weekly Boundless newsletter - much more than a link drop - a deep dive into our modern relationship with work.
I'm launching Reinvent on October 1st and updating people on my content creation process here or purchase now for early bird access.
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:
Boundless:
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:
Links Mentioned:
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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:
Follow Hannah
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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:
Want to support the podcast?Offer a one-time or recurring donation on Boundless.
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:
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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.
Find out more about Heather's work here or follow her on Linkedin.
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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
Boundless (Learn More Here)
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.
To learn more about Jerel click here.
Boundless => Reimagine Work
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:
"the principle that what you choose to do in the morning can have an amazing impact on other parts of your life. It leads you to get up and be productive, do more of the things you wish you were doing, and embark on your days already feeling accomplished. All of that is a HUGE win, but honestly, it’s just the tip of the iceberg…"
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!
For More => The Morning Effect Boundless Page
Books/Articles Mentioned:
Boundless / Reimagine Work:
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):
Boundless / Reimagine Work:
Chris Kirkland is a bootstrapped entrepreneur who has been living nomadically since 2006 and is the founder of several web businesses including artweb.com and tokyocheapo.com.
We talk about how he has experimented with money, creativity, health and his lifestyle over the past 13 years. His nomadic journey started when he took a trip to Japan and after two days decided "fuck it," I'm going to stay a bit longer.
We talk about his journey, entrepreneurship and his life experiments
More about Chris:
Boundless / Reimagine Work:
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:
Mythology Studios: Work With Martha
Boundless / Reimagine Work:
A quick little update from Taipei.
A couple links from the podcast:
Would love any feedback - e-mail Paul.
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
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Christine Bader is currently living in Bali, Indonesia, where she is spending time focused on her family and self. She is the author of The Evolution of a Corporate Idealist: When Girl Meets Oil and the former head of CSR for Amazon before leaving in 2017, a journey she details in an amazing essay titled “The year I learned to quit.”
She talks about leaving the corporate world and shifting her focus from building a career to building a life.
Topics Discussed:
Recommended Reading
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:
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I joined the amazing Jagriti Pande for a fun conversation around a number of different topics. You can subscribe to her master series on UX designers and other creatives here.
Her amazing editing, way-too-kind-intro and fun clip at the beginning were such an amazing gift.
Let me know what you think!
"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:
Uncommonly: Website
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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)
Connect With Mike:
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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
Readable Version: Top 10 Myths
Myth #1 - "Once I land my dream job / make $X a year, I'll be happy" (2:35)
Myth #2 - "I need to find my passion" (7:15)
Myth #3 - "I should never take a pay cut" (14:15)
Myth #4 - "You should have a 'steady' income" (20:40)
Myth #5 - "I have to know what I need to do before I change directions" (26:15)
Myth #6 - "An extended break is irresponsible" (32:30)
Myth #7 - "It's fine to take a risk when young, but not when you have kids" (40:35)
Myth #8 - "I should go to grad school to figure out what I want to do" (46:15)
Myth #9 - "I can't make a change now after years in this field" (55:20)
Myth #10 - "I'll be happy once I'm running my own business" (1:04:54)
Links Mentioned:
Jeff Hittner leads Your Project X, a social venture with a mission to help 1 million people find more purposeful work. He has more than 18 years experience as an entrepreneur, consultant and changemaker. He is the founder of five social ventures, including IBM’s Corporate Social Responsibility (CSR) consulting practice globally. In 2011, he developed the curriculum for one of the first MBA’s in Sustainability in the US, at Bard College, where he was the Leadership professor. He was also two-time Chairman of the Carnegie New Leaders at the Carnegie Council for Ethics in International Affairs.
Jeff’s passion has always been at the intersection of education and entrepreneurship. Prior to your Project X, he ran a career transition program for 64 New Yorkers, built global education programs including a blended learning initiative for high school dropouts in Latin America and career discovery programs for youth in Europe. Jeff received his Masters in Cultures and Development Studies from the Katholieke Universiteit Leuven in Belgium, and a Bachelor of Business Administration from The College of William and Mary in Virginia where he was an elite gymnast. As a thought leader, Jeff has been published in a dozen major publications, including Forbes. Jeff lives in NYC with his wife, Grace, and one-year-old son, Rivington.
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In this short episode, I talk about the five lessons I've found that help people make the leap to self-employment:
Full Article | This episode is also a YouTube video
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Bryan Victor has never taken a traditional path but he doesn’t know any other way. Perhaps that is why he started his own podcast in Singapore, Misfits, which interviews unconventional Singaporeans. At 20, he saved up $10,000 while he was serving required military time and decided he would travel the world for a year. During the trip, he realized this was all the “schooling” he needed (see 10 things I learned). After learning how he could live simply on very little money, he knew that this opened up many options for him. He knew that he would always value flexibility over maximizing income, learning this lesson earlier than others.
Regardless of any position towards “formal” schooling, his chosen path, wedding planning, wasn’t something you learned at school. He knew he had to create his own internship. So before his trip, he wrote to 50 American wedding planners (the best, he says), to ask if he could work with them. One person gave him a chance and he was able to learn while making enough money to live.
Going back to Singapore, he couldn’t get anyone to hire him, so he realized he was “forced” to create his own wedding planning business. In the process, he became named one of Singapore’s Top 10 Wedding Planners (though he argues there weren’t that many anyway!).
After proving he could make it, he started dabbling with a side business, 2D animation and founded Sage Animation. He decided to give the wedding planning business away as a gift and was able to find one person (out of 40) that he thought would do a great job.
Bryan has been fascinated with understanding what makes him happy. As he was on another trip in the United States, he was drawn to another project (motivated by the #vanlife movement) to build a liveable van for himself. While he accomplished the feat, he found that he was overcome with a “something-like depression” feeling after he achieved it. While he thought he had everything, it led to a new and deeper curiosity in what actually leads to happiness.
Books & Other Resources Mentioned:
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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:
Want to learn how to make this happen at your company? You can download their "4-day week" report which is one of the best reports I've seen on the future of work.
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Amid all the buzzwords and reports on the future of work, I find Sarah Kessler's stories about the gig economy to be the most insightful and the most human. Her stories and her book, Gigged, give an accurate picture of some of the upsides of the gig economy, but also some of the downsides.
She shares stories of people that are sleeping in their office making five cents per task on Amazon's Mechanical Turk to creative freelancers who can make six-figure salaries working from anywhere. She also shares the story of companies that see limits to the gig economy, like Dan Teran's company Managed by Q who is following Zeynep Ton's Good Jobs Strategy and looking at people as valuable and investing in them as full-time employees and partners in the businesses success.
Our conversation dives deeper into some of the stories she shares as well as some of the current challenges with platforms, the PR machine (all the firms say people want flexibility, but fail to mention they are happy to give it up for more pay!).
One of her subjects in the book puts it most powerfully, Kristy Milland, “I am a human, not an algorithm”
More From Sarah:
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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:
Connect With Lydia* Screw The Cubicle * Bali Retreat: April 2019
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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."
Connect With Wade & Zapier:I highly recommend checking out the resources Wade and his team have put together on running a remote company:
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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:
Empjoyment
1-On-1 Coaching With Nemo
World Joy Movement
Boundless
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.
Link to Video Version Of Interview (Dumplings Included)
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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.
Join The Conversation
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!
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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:
Recommendation on getting outside of your comfort zone:
Boundless Links:
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:
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:
Other Writing Mentioned:
For More With Boundless:
Detailed Bio
Andrew Taggart is a practical philosopher. He asks and seeks to answer the most basic questions
Paul provides a summer update:
Boundless Links
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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
This podcast is supported via micro-donations. Consider supporting the podcast on Patreon
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:
Luke grew up on a commune and then ended up as a co-founder and CEO of a startup that raised $87 million. He talks about his unique path and how that shaped his thoughts about building an organization. He raises the central tension of organizations in a free market economy - the fact that our corporations are run more like authoritarian states with centrally planned economies than free-markets. We talk about lessons he learned as he built his company and his perspective that he shares in his article: "Why People Hate Working For Big Companies" on Medium.
Lukes long-term interests are software that helps people, making better founders, the intersection of organizations and economics, and improving inclusion in the information economy. You can find his work at http://lukekanies.com/.
Podcast Information: #BoundlessPod
Become a Supporter Of The Podcast for $1 a month: Patreon
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:
Podcast Information: #BoundlessPod
Show Notes: Candace
Join the conversation: #boundless VIP facebook group
Want To Support The Pod? => Patreon / One-Time Gift
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."
To connect with Stephen => Life Skills That Matter
Podcast Information: #BoundlessPod
Show Notes: Stephen Warley
Join the conversation: #boundless VIP facebook group
Want To Support The Pod? => Patreon: Support Paul
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.
Podcast Information: #BoundlessPod
Patreon: Support Paul
Show Notes: Nita Baum
Join the conversation: #boundless VIP facebook group
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.
Will's podcast interviews many freelancers who are working independently and I can't recommend it enough. Check out the unleashed Podcast => Subscribe Today
Weekly #BoundlessReads Newsletter - 5 Things Every Week: Subscribe Now
Book Recommendations Mentioned:
Course: 60 Minute Dream Job Resume & Personal Story Course
Damien Peters is a self-described "personal finance nerd" - which explains how he ended up founding WealthNoir.com, a platform to preach and teach about the importance of financial freedom and generational wealth to Black millennial professionals. He started blogging over ten years ago and has recently focused more on writing as he increases his focus on building Wealth Noir. Damien is also a big fan of travel and recently made the decision to move out of San Francisco and move with his family and son to Spain, where he will focus on building his company remotely. We talk about a range of topics including his passion for writing, how he defines success, his influences, how to run a remote company and his relationship with money.
Book Recommendations:
Personal Finance Influences:
Podcast Information: #BoundlessPod
Patreon: Support Paul
Show Notes: Damien Peters
Join the conversation: #boundless VIP facebook group
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.
Connor Gillivan is the CMO of FreeUp.com. He has sold over $30 million online, has hired hundreds of freelancers to build his companies, is a published author, and is the owner of ConnorGillivan.com. Connor is driven by making a positive impact on others through the companies that he builds. He currently lives in Denver, CO.
Podcast Recommendation: Marketing School with Neil Patel and Eric Siu
Connect With Connor: Contact Connor
Podcast Information: #BoundlessPod
Patreon: Support Paul
Show Notes: Connor Gillivan
Join the conversation: #boundless VIP facebook group
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:
Organizations She Admires:
Influences:
Her Book Recommendation:
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...
Romy Rost - Website
Empower Your Conversations - Work With Romy
Podcast Information: #BoundlessPod
Support: Support The Podcast For $1 a Month
Show Notes: Romy Rost
Join the conversation: #boundless VIP facebook group
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.
OwnersUp - Website & Twitter
Tanya's Recent Book Recs
My Book Recommendations: Boundless Top Reads on Amazon
Podcast Information: #BoundlessPod
Support: Become a Patron For $3 a Month
Show Notes: Tanya Alvarez
Join the conversation: #boundless VIP facebook group
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.
Podcast Information: #BoundlessPod
Support: Support The Podcast For $1 a Month
Show Notes: Pauri Pandian
Learn More: Helathy Masculinity @ Wheaton
Join the conversation: #boundless VIP facebook group
Ben is the founder and COO of Omelas, a startup that is focused on using technology to fight propaganda. Ben's journey, however, does not start there. His journey is a classic case of "do not try this at home" - as we walk through Ben's story, I found myself impressed at the number of rejections and roadblocks he faced. Early in his career, he thought he landed his dream job, at the State Department, only to have the offer reneged. This led him to put his passion (which was diplomacy), to the side, while he pursued a "practical" career. A job from Google appeared just at the last minute, where he found himself in a role to help redirect terrorist search results. This helped re-awaken something he was passionate about and led to the founding of his current company.Podcast Information: #BoundlessPodSupport: Support The Podcast For $1 a MonthShow Notes: Ben DubowBoundless Facebook Group: Join the #boundless community
This is a copy of the interview I did with Stephen Warley on the Life Skills That Matter Podcast. Stephen is a bit of a role model for me. We have similar missions and ways of seeing the world. He interviewed me on Facebook live and I thought we had an interesting discussion on doing things that matter, defining priorities and how to figure out the answer "what do you want to do?" (which I think is an absurdly bad question!)Show Notes: Life Skills That Matter (Episode 174)Podcast Information: #BoundlessPodSupport: Support The Podcast For $1 a Month
Amma Marfo cracked me up several times on this podcast. It is no surprise then, that she describes herself as "thoughtful yet incurably silly." She also defines herself by three words: humor, creativity, and energy - something we talk about at the beginning of the podcast. Like many freelancers, she does so many things - she is a speaker, teacher, coach, and podcaster and has a lot of insight around the future of education and what helps people succeed in school. If you are interested in writing, education, and creativity check out this episode.Show Notes: Amma Marfo - Episode 8
Podcast Information: #BoundlessPod
Support: Support The Podcast For $1 a Month
Links:
Formal Bio
Amma Marfo is a thoughtful yet incurably silly independent higher education professional, writer, and editor based in Boston, MA. She holds a Bachelor’s degree in Communication Studies from the University of Rhode Island, and a Master of Education from the University of South Florida. Amma is a dynamic and sought-after speaker on topics such as leadership, group dynamics, learning and optimizing the temperament of your organization, cultivating environments that encourage creativity, and incorporating your values into your work and larger goals- and has written three books on those topics since 2014. She speaks on college and university campuses across the country, at regional and national conferences, and has partnered with organizations like HubSpot, Wayfair, Startup Institute Boston, and General Assembly. She is an outspoken advocate for creativity, believes strongly in the power of humor, and looks forward to helping you find the way you live and work best. Her other interests include live comedy, surfing, trivia, and gluten-free cooking/baking. You can follow her on Twitter @ammamarfo.
I discovered Tom by reading a piece he wrote on freelance consulting. I was fascinated with his approach and how similar it was to mine - especially coming from a completely different perspective - digital marketing & content. We talk in depth about how he thinks about content in today's world, his thoughts on personal branding, how writing helps him create and leads to serendipitous connections and how he manages a diversity of interests. We also geek out about our love of all things Ribbon Farm and Venkatesh Rao.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.
Podcast Information: #BoundlessPod
Support: Support The Podcast For $1 a Month
Links:
Growing up all Cody thought about was sports. He saw his path as becoming a professional Aussie Rules Football player. However, after competing at the highest level of the sport, he quickly saw felt his “talent just fell away” at the age of 18. He struggled to live in the moment and stewed on the fact that everyone around him seemed much more talented. While this period would help him realize that he was better suited as a coach than a player, it took him a few years to make that realization.Show NotesSupport the Podcast: PatreonPodcast Information: #BoundlessPodPaul: @p_millerd & Cody: @codyroyle
Cody's Book: Where Others WontBook Recommendations:* Legacy: What The All Blacks can teach us about the business of life
* Originals by Adam Grant and A Dozen Things I Learned From Adam Grant
Links:* altMBA * Simon Sinek: Start With Why * Netflix Culture * How Netflix's Culture Got Patty McCord Fired * Boundless Podcast: Episode 3
Janet is one of my favorite people. We have a similar belief that people are capable of more than they believe and that alternative paths are more realistic and the reality than people realize.Not a fan of default paths from an early age, one quote stood out from Janet that she has continuously asked herself throughout her life:“The conventional path is not going to work for me, what can I do instead?”Janet first started “hacking” life in high school when she decided that the standard curriculum wasn’t for her. Despite pushback from parents, teachers, and peers, she followed her curiosity and negotiated an alternative path — avoiding things like Math to go deeper with teachers in social studies, religion and politics.Her next “hack” was to apply to college in Canada. Starting with the constraints that she wanted to avoid debt and that her parents would support the equivalent of in-state tuition she looked for different options and found a way when her uncle convinced her to look at Canadian universities. Although taking a non-conventional path, she learned a lot about being able to adapt that would help her later on in her career. Full writeup: https://think-boundless.com/2018/02/07/934/Janet: http://www.careerjanet.comLinks: www.boundlesspod.comSupport the podcast & join the community: www.patreon.com/thinkboundless
In this episode Cody Royle and I discuss what sets high performing NFL organizations like the Patriots and the Giants (and others apart from the rest). Cody is the author of Where Other’s Wont: Taking People Innovation from the Locker Room into the Boardroom. His book is available here: http://amzn.to/2E5R88kCONTEST DETAILS: I am giving away two of Cody's books for free. Just retweet this episode with the hashtag #boundlesspod or send a screenshot of you subscribed to the podcast to paul@think-boundless.comLinks: www.boundlesspod.com www.whereotherswont.comSupport the podcast & join the community:* www.patreon.com/thinkboundless
Chris is the founder of uncommonly and an avid fan of the long-running CBS television show Survivor. A former teacher, marketer, and management consultant, Chris has an eclectic mix of skills and professional experience. Chris has worked with over a dozen Fortune 500 clients spanning multiple industries including Media & Entertainment, Publishing, Insurance, Pharmaceuticals, and Corporate Social Responsibility. He is obsessed with inspiring great leadership and creating incredible learning experiences that change the way people think and operate.Learn More:Chris' Website: www.un-commonly.comHis Youtube Channel: https://www.youtube.com/user/TopherDean87Links:Podcast: www.boundlesspod.comSupport: www.patreon.com/boundless*Show Notes: https://wp.me/p9AOW1-cY
David was born abroad then moved to the US at a young age, all while being raised to believe that the path to success rests solely on going to school and getting a “safe” job with a big company. For the last 11 years he did just that, and by traditional measures of success, it looked like things were going well. Unfortunately, starting on Day 1 of his first job, he could never shake one, recurring feeling: “I really, really, really don’t like this”.In December 2017, after a lot of saving and planning, he worked up the courage to quit his job, build his retirement house in France, and focus on building a life around a freelance career.Forget the big house and fancy cars, his new measure of success is the amount of control he has over his time. He is using his time to explore his passion for learning new things, particularly in technology and programming, as well as helping others who are also looking to forge their own path away from the cubicle farm.Support the podcast: https://www.patreon.com/thinkBoundlessCheck out more episodes: https://www.think-boundless.com/podcastIdeas, questions, guest ideas? paul@think-boundless.com
Although Noel claims he lacks wisdom, he has a lot of it. He describes his career as “eclectic.” Starting his career in the 1980’s the environment around him (greed, money) influenced him to question what he was really trying to accomplish. He took a long term perspective and tried to focus on what he did not want his career to be at sixty — which he put simply as not doing “the things he wanted to do”. Although on a more corporate track early on in his career, he tried to continuously reflect on what mattered — even if it raised some eyebrows in among his peers.
Paul talks about why he is passionate about the future of work and shares some of his personal journey