Identifying the Patterns and Underlying Threads of Your Life’s Work with Josh Long

To say that Josh Long is an entrepreneur who keeps himself busy is an understatement. He’s the creator of the to-do list app Cheddar, the podcasting service Simplecast, and oversees sponsorship at the Great Discontent. In this interview he talks to me about the underlying themes and threads of his life’s work and how to identify yours. 

  • Josh’s exposure to entrepreneurship at a very early age
  • Why entrepreneurship is all about creating value
  • The innate entrepreneurial spirit within all of us 
  • Why our low points teach us so much about ourselves
  • Learning to put things in perspective when you’re challenged
  • Why facing your fears head on is the best way to deal with them
  • Looking at your whole life through the lens of design 
  • Finding the things that make you weird to develop your own frameworks
  • The concept of design as a religion 
  • Stripping things down to a core idea 
  • Why should build and create things that you wish existed 
  • Josh’s role in getting projects and funded for The Great Discontent
  • What separates the risk takers from the ones who play it safe
  • A look at the work that Josh did with Seth Godin
  • The cathartic drive that comes from pain 
  • Leveraging the patterns of successful people you admire
  • The difference between getting A’s in life 
  • Why Josh is only focused on serving 1000 people 
  • The role that the story plays in everything you create

Josh Long is a designer and writer with a degree in philosophy and three books under his belt: Execute, Jenius, and Design Evolution. He co-hosts the Happy Monday podcast with Sarah Parmenter, is building the to-do app Cheddar, coordinates sponsorships for The Great Discontent, and is the co-founder of Simplecast.


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