Could your drive to succeed actually be the thing keeping you stuck?

Phil sits down with clinical psychologist and author Dr. Kelly Flanagan, whose work has resonated most with an unexpected audience: high-achieving entrepreneurial men.

Dr. Flanagan breaks down the difference between guilt and shame, and how shame quietly hijacks careers, marriages, and parenting. He explains why achievement does not resolve the original wound of “something is wrong with me,” and how success can actually intensify it.

He also shares the pivotal question he and his wife asked themselves before walking away from prestigious paths to build a different kind of life…one shaped by worthiness instead of proving.

You’ll hear them unpack:

• The question that reveals whether your next move is driven by freedom or the need to prove
  

• Why success often strengthens shame instead of resolving it
  

• Why passion always involves suffering, and why that is not a signal to quit
  

• The three stage cycle of worthiness, belonging, and purpose
  

• How to build relationships where you feel less pressure to perform and more freedom to be yourself

If achievement hasn’t quieted the voice that says you’re not enough, this conversation explains why.

0:00 Intro

02:21 Who Lovable Was Written For

06:59 Shame as the Original Wound

10:16 Guilt vs. Shame

13:22 Parenting Triggers and Self Grace

19:05 Meeting His Wife

23:22 The Freedom Question That Changed Everything

29:19 The Cycle of Worthiness, Belonging, Purpose

32:04 Why Relationships Come First

39:22 How Passion, Pain, and Purpose Connect

42:21 Why Resistance Is Not a Sign to Quit

44:28 The Road Less Triggered

Dr. Kelly Flanagan’s books:

📚 Lovable

📚 The Unhiding of Elijah Campbell

📚 The Road Less Triggered Available now for pre-order with bonuses: https://lesstriggered.com

➡️ Download the Purpose Matrix tool for FREE:https://www.thepurposematrix.com/

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