254: Heather Monahan | How to Create Indestructible Confidence for Our New World

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Heather Monahan was running the advertising department for one of the largest radio networks in the country… until she suddenly found herself out of a job. She decided to tweet about it, and what came next was no less than remarkable. If you’re someone who has thought about writing a book or becoming a sought-after speaker — but you have no idea how to do it — this interview is packed with super-actionable advice for how to reinvent yourself.

In This Conversation We Cover: 

  • [03:56] The foundations of your childhood
  • [07:22] Being forced to reinvent yourself
  • [12:28] Advice on writing a book
  • [15:36] Entering the world of speaking
  • [24:55] The difference between confidence and cockiness
  • [28:30] Coming up with Boss in Heels
  • [31:49] The best and worst part of living in South Beach, Miami
  • [36:04] Talking about fulfillment

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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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