031: Jill Coleman | Gaining Unstoppable Clarity

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Everyone I know has been telling me that I have to interview Jill Coleman, who is like a fitness model and captain of industry all rolled into one. Jill is the owner of the hugely successful brand JillFit, where she helps people in the areas of mindset, physique, and business.

In This Conversation We Cover:

  • [2:40] Growing up in a big Irish family
  • [6:10] Launching JillFit
  • [7:25] Deeply personal stories about marriage
  • [10:40] The mindset Jill developed to create her hugely successful international brand
  • [13:10] Working smarter instead of harder
  • [16:50] A crazy story about running into your ex-husband, staying friends, & the power of mindset
  • [29:20] Forgiveness & trust
  • [31:10] How stoicism philosophy entered Jill’s life & how she applies it to the play hard part of her life
  • [38:25] Getting out of “blame & complain” and into relentless positivity
  • [40:40] Using practical pessimism as a productivity tool
  • [42:10] Why Jill created JillFit & what she’s doing next
  • [45:20] What Play Hard looks like for Jill
  • [54:10] Jill’s evening wind down routine
  • [58:00] Your questions for Jill

Stoic Philosophy & Playing Hard

Memento Mori translates to remember death, and it’s a phrase at the heart of Stoic philosophy.

For Jill, it really means creating or living life to the fullest. “Remember Death reminds me that this is finite. I have a limited amount of days or hours or minutes that I get to live and be in this space, and for me, it reminds me to take action, to do the scary stuff, to invest, to make a choice when I’m scared.”

Practical Pessimism & Productivity

Practical pessimism is really just a systematic way of looking at all of the scenarios that could happen if you take a big leap.

Say you’re going to start a business. Ask yourself, what is the worst thing that could possibly happen? Most people might go to I’m broke, homeless, or have to move back in with their parents.

Then ask yourself two more questions: If that happened, could you handle it? And if that did transpire, what is one single step you could take to get back to baseline?

There’s actually a lot of freedom in the worst-case scenario because it’s almost never as bad as you think it’s going to be.

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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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