049: Christine Hassler | Cutting Through the BS

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Christine Hassler is the author of Expectation Hangover: Overcoming Disappointment in Work, Love, and Life and the host of the top-rated Over It & On With It podcast, and I wanted to bring her on the show for one main reason: Christine has the uncanny ability to cut through the BS and find the truth of what someone is really after faster than I’ve ever seen before. I witnessed this brilliance firsthand when I saw her speak during one of my mastermind weekends and I wanted to share it with all of you.

In This Conversation We Cover:

  • [2:20] Christine’s childhood, when she wanted to be something between a mermaid & a dolphin trainer
  • [7:20] Mom guilt & why it’s so important to have your own purpose and passions as a parent
  • [12:50] What Christine heard on an elevator that pushed her to quit being a Hollywood agent
  • [16:50] Working on The Man Show
  • [18:50] What it means to be “living by a checklist” (and how this limits your opportunities)
  • [22:45] Interrupting your behavioral patterns & connecting your mind with your heart
  • [32:40] Being authentic VS strategic
  • [45:20] Not being so hard on yourself
  • [51:50] Why Christine chose to coach people live in her podcast, Over It & On With It
  • [56:10] Accidentally going on a date with Jerry Springer
  • [58:05] How Christine ended up spending New Year’s Eve with George Clooney
  • [58:30] Christine’s awesome Play Hard life

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Hi, I’m Rob!

Hi, I’m Rob! It has been said “You are not what you have learned, but what you’ve overcome.”


I have overcome my share of obstacles in order to architect the life of my dreams and uncover the key to lasting, meaningful success. Growing up in Queens (literally on the wrong side of the tracks), my early years were tumultuous, marked by hardship and violence.

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