This episode features Karen Deschaine, a class of 1997 graduate from The United States Military Academy (USMA) at West Point. You’ll get to hear all about her journey from living in the suburbs of Detroit to becoming a competitive skydiver at West Point to eventually ending up as a corporate lawyer and mother of two in Southern California. Enjoy the show!


  • The difficulties with extreme competition and building real relationships
  • Dealing with survival mode and dysfunctional habits 
  • The importance of relationships and confronting loneliness/false camaraderie at service academies
  • Knowing when it’s the right time to leave the military and change course
  • Learning how to transition skills learned in the Army to a law career
  • Ambition and making sure you’re climbing the right mountain


  • Can you tell everyone where you’re from? What school you went to and when you graduated?
  • Can you give everyone 1-2 lines about who you are?

2:15 PART I:

  • What made you choose a service academy – and what made you specifically choose USMA?

12:30 PART II:

  • If you had to sum up your time at USMA in one word – what would it be?
  • What are some of the highlights/most memorable moments from your time there?
  • What were your goals while you were at the Academy?

22:56 PART III:

  • What were some of the lowlights/most difficult times at the Academy?
  • What are some of the lessons you learned?

30:30 PART IV:

  • Tell me about your life post-graduation. 
  • How do you feel going to a service academy influenced the trajectory of your life?
  • How do you feel about serving in the military while having a baby?

40:12 PART V:

  • What made you decide to get out of the Army?
  • When considering law school were you still thinking you wanted a political career?
  • How did you learn to transition your skills?
  • How do you feel about your decision to attend West Point? 


  • What’s next for you?
  • Do you have any parting words for listeners? Perhaps a key message to your fellow Service Academy sisters?
  • What’s one random fun fact about you?
  • Where can people reach you?

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