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:

  • Grappling with the achiever identity
  • Longing for independence and freedom
  • Parental approval
  • Building Community
  • Experiments
  • Defining success

You can buy his book the Fail Safe Solopreneur on Amazon

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What is 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.