“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 when he graduated college. This was before Tim Ferriss’ 4-Hour Workweek and before becoming a digital nomad was a thing. I asked him what his inspirations were and he wasn’t quite sure. He just always had a natural drive to be independent and do his own thing.  

He recently published a book titled The Fail-Safe Entrepreneur.  In it, he argues that almost all solopreneurs strive for three things: Freedom, Adventure, and 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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