The Pathless Path with Paul Millerd

“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!

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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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SUPPORT BOUNDLESS

Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.

🆕 I launched Freelance Consulting Skills Course.  You can find out more and sign up here.

If you'd like to support the podcast, consider using my affiliate links

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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SUPPORT BOUNDLESS

Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.

I launched Freelance Consulting Skills Course.  You can find out more and sign up here.

If you'd like to support the podcast, consider using my affiliate links

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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SUPPORT BOUNDLESS

Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.

I launched Freelance Consulting Skills Course.  You can find out more and sign up here.

If you'd like to support the podcast, consider using my affiliate links

Jenni and Lisa Dazols read an essay six years ago which made them question their frantic & busy lifestyle.  They could barely take care of their dog.  They decided to take a break from a work.  We dove into their story of deciding to move abroad, taking a sabbatical, having kids, moving to Taiwan, launching a passion project, coaching people on their money fears, and what they've learned along the way.

They run a business called Modern Family Finance and help people think about finances in a way that lets them live the life they want to live.  They also run a charity bike ride in Taiwan supporting LGBTQ rights called Rainbow Ride.

Links:

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I'm launching a Freelance Consulting Skills Course that launches July 1.  You can sign up here and get a $50 discount.

If you'd like to support the podcast, consider using my affiliate links

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.

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Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.

I'm launching a Freelance Consulting Skills Course that launches July 1.  You can sign up here.

I had a conversation with Ali Abdaal about his year away from medicine, how he grapples with his identity, the challenges of veering off the course of traditional metrics of success, enjoying the journey, and the challenges he faces.

More from Ali here: https://aliabdaal.com/

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I talked with Michael Ashcroft six months before he was planning to quit his job.  We talked about his plan to quit his job, what was going through his mind, his fears and what he expected might happen.

We then chatted again three months later after he submitted his notice and checked in on how he felt

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The best way you can support me is to join in the conversation. Share thoughts on Twitter, send me an e-mail and tell me what resonated or what you’d add or refer a friend:

If you’d like to support further you can use my affiliate link for some of the platforms I recommend.

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

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

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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