Orthogonal · February 7, 2019

127: Buckets of Insanity (feat. Christopher DeCaro)

On an important episode of Orthogonal Brett and Andrew discuss (with their friend Chris) the mental stresses of being a freelancer. And no one talks about it. And we should.

High points include:

  • Remote workers and freelancers - anyone working in isolation need to manage that scenario
  • Successful freelancer have a series of tools to manage mental health and you need to be aware of that
  • Is your "default setting" - "WORK"?
  • Is a predisposition to anxiety correlated to a predisposition to freelancing?
  • Is the "working less as a freelancer" really a thing?
  • The good side of the drive is you get joy from creating new things
  • The bad side of the drive is you are never "content"
  • What is enough?
  • Chris' #lifehack to managing your business.

Quote 'Are you a crazy person so you decided to become a freelancer? Or are you a crazy person because you decided to become a freelancer?"



  • We didn't mention this, but you should definitely watch DHH's Startup School talk because it relates directly to our point.

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