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The Pathless Path with Paul Millerd

180 EpisodesProduced by Paul MillerdWebsite

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, … read more

1:02:34

The Shadow Side of Solopreneurship - Darren Joe

“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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