
The Pathless Path with Paul Millerd
The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.
Latest episodes

Dec 4, 2020 • 44min
Packy McCormick - Bringing Fun To Newsletters Since 2019
Packy says that his differentiation "is that I’m going to be having more fun than most people”
I've been a big fan of the energy he's brought to his writing over the past couple of years. But he didn't set out to have a popular newsletter. His real plan was to launch an in-person community.
We chat about how the pandemic helped him figure out why that wasn't a good idea and how he's thinking about his solopreneur journey,
The reason I asked him on the podcast is to talk about his recent newsletter on the future of work. He argues that “Employees will ultimately make the decision” about what work looks like post-pandemic. I think he is mostly right and we talk about what that might mean for people's lives.
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You can find ways to support Paul through affiliate links, newsletter sponsorship or direct gifts here
If you want to subscribe to Paul's weekly newsletter on the modern state of work, the solopreneur journey and creating online, you can subscribe here.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Nov 3, 2020 • 23min
Podcast Update Nov 2020 - The Pathless Path
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
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Oct 19, 2020 • 1h 3min
Angie Wang - My Partner On This Crazy Journey
I interviewed my wife, Angie, who has gone through a major career change and has launched a number of creative experiments and projects over the past couple of years. She reflected on what its been like going along this journey alongside me and grappling with success, identity, being a woman in Taiwan and creating in public.
Video Version Of The Interview: Watch The Interview on Youtube
If you like conversations like this, join my weekly e-mail which is an exploration of life, work, creativity and a contemplation on what matters: Boundless Newsletter
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Ways to support Boundless
You can use one of the several products I endorse and I'll receive a small affiliate fee from the company.
ConvertKit
I tried Mailchimp and a few others before landing on ConvertKit for e-mail automation. The UX is intuitive and easy to manage. I really like it a lot though I'm probably not even maximizing its potential. If you sign up using this link I'll get 30% of your monthly fee forever (which is kind of crazy!).
Podia
I also use Podia for my Reinvent Course. I like both Teachable and Podia but Podia is probably better if you are just getting started and don't want to get lost in customizing the pages. Their referral deal is super generous for me 30% of your monthly fees forever, so I'll be a huge supporter of your course ;-) Pro Tip: Click my link and then sign up for a free trial. If you wait a few days to commit, then they'll offer you a 15% lifetime discount in the first two weeks.
Teachable:
I also use Teachable for my Think Like A Strategy Consultant course. It works quite well as well, though Podia is a little more slick for more recent design and using a simple editor. If you click here I'll get a 30% cut of your monthly fee - same deal as Podia!
Charles Schwab No International ATM Fee Checking
This card is a must have if you plan on living or traveling abroad. Easy to withdraw money and not worry about fees anywhere in the world. This link will give me $100 if you deposit $1,000 within 45 days.
Wealthfront
I use Wealthfront for my SEP IRA which is like a 401k for self-employed creators. If you use this link you'll get $15,000 managed for free and I'll get an additional $5,000
Quickbooks Self-Employed
I do all my own finances, accounting and axes using Quickbooks which makes things quite simple. If you use this link you'll get 50% off and I'll get $30.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Sep 16, 2020 • 50min
Carving a 21st Century Life & Career - Steph Smith
Steph has a hard time identifying as anything. Remote worker, writer, or coder don't really do it justice. The thing that stands out when you talk to Steph is that she is a LEARNER. Through competing in chess as a child she learned the valuable meta-skill of how to improve and never really saw any reason why she couldn't just take something up.
This mindset is invaluable in today's world and this is demonstrated by the way Steph landed her job at The Hustle (hint: it didn't involve a formal application.
This conversation was a lot of fun and explores:
Digital nomadism myth vs. reality
How she chooses where to live
What she learned traveling the world competing in chess as a child
How she thinks about work and her identity
One of her favorite topics - words that don't translate
Learn More: StephSmith.io
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Sep 8, 2020 • 1h 22min
The Possibilities Of Life Beyond Work with Oshan Jarow
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
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Aug 31, 2020 • 27min
Amy McMillen - Wandering In Uncertainty & Writing A Book (Mid Pandemic)
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
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

May 28, 2020 • 56min
Will Bachman: Building an Independent Consulting Practice With a 5-Decade Success Mindset
Will Bachman, creator of Umbrex and host of the Unleashed podcast, discusses his experience in independent consulting. Topics include the evolution of consulting from 2008 to 2020, community-focused platforms, finding new clients, building a virtual team, and a mindset with a 5-decade time horizon.

Mar 26, 2020 • 46min
Reflection with Andrew Taggart on Work & Life
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
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Mar 18, 2020 • 53min
Laurel Farrer: The Global WFH Experiment & Long-Term Promise Of Remote Work
Laurel and I decided to jump on a video call to talk about the world emerging work-from-home experiment amid the evolving Covid-19 pandemic. We wanted to talk about some of the deeper principles & opportunities that remote work offers and talk about how companies might think about it in the next month and over the next few years. We talk about:
The short-term mindset companies should take in the next few weeks (hint: don't overdo the tools right now)
What the broader opportunity is for remote work over the next 10 years
The role of trust in remote work and what happens when it breaks down
How to think about meetings and how to design your day and re-think productivity
Examples of companies who have been innovating in this space for 10+ years
Experience from Laurel's 10+ years as a remote team leader
As the Founder of Distribute Consulting and the Remote Work Association, Laurel Farrer starts, strengthens, and leverages virtual workforces to solve corporate and socioeconomic concerns. A global thought leader on the topic of remote work, Laurel collaborates with the world's leading businesses and governments to eliminate virtual worker discrimination, prevent policy retraction, increase remote job accessibility, train distributed leaders, and design economic initiatives. Additionally, she also shares her expertise as a Forbes contributor, subject matter expert for business education curriculum, and virtual software product advisor.
More:
Episode Link & Show Notes
5 Tips For Remote Work (Boundless)
CEO of Doist & CEO of Zapier on Remote Work
Laurel on Twitter & LinkedIn
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Jan 8, 2020 • 58min
Imagining A New American Dream (Diania Merriam, Econome Conference)
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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📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here