This episode features Leslie (Stein) Riley, a 1997 graduate from the U.S. Military Academy. In this episode, Leslie dives deep into the many struggles she had, both at the Academy and in the Army. Usually these struggles surrounded her weight and the negative messages she received about her femininity and being a woman in the military. Ultimately, Leslie found strength in adversity and built a career out of helping people communicate more effectively. Despite all the hardships, Leslie also had some major highlights and views her time at the Academy as a foundational step on her journey towards who she is today. Enjoy the show!


  • Receiving negative messages about women in the military.
  •  Struggling with her weight throughout her time at the Academy.
  • Making the decision to leave the military.
  • Building her own business as a facilitator.


  • 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?

1:55 PART I:

  • What made you choose a Service Academy – and what made you specifically choose the U.S. Military Academy?
  • How did your family feel about you applying to the military academies and then getting in?
  • What did you envision your life would look like when you graduated from West Point?

9:50 PART II:

  • Did the military lifestyle bother you – traveling, going away, even being on the other side of the country for school?
  • Tell me about that first summer and first day. How did that go?
  • Having her definition of camaraderie crushed on the first day of Beast Summer. 
  • Struggling with physical fitness.

19:58 PART III:

  • Getting a fresh start during the academic year.
  • Let’s dive into the highlights at the Academy.
  • Her experiences at the glee club.
  • How were academics going for you at this time?
  • Going to Brazil as part of her major.

28:07 PART IV:

  • What did you plan to do with this degree in Portuguese?
  • Deciding she wanted to fly.
  • Lowlights at the Academy.
  • Struggling with an eating disorder.
  • Did you question whether or not you should continue on at the Academy?

39:21 PART V:

  • Struggling with the physical assessment to graduate.
  • If you had to sum up your time at the Academy in one word, what would it be?
  • Getting an aviation slot.
  • What happened after graduation?
  • Struggling through flight school.
  • Being challenged about her femininity and her weight.
  • Having a review board about her ability to succeed in flight school.
  • Being told she’s a liability and not an asset.


  • What did you do for the rest of your career in the Army?
  • Did you enjoy your time in the Army?
  • How do you currently feel about your decision to attend an Academy?
  • Do you have any parting words for listeners? Perhaps a key message to your fellow Service Academy sisters?
  • What’s next for you?
  • What’s one random fun fact about you?
  • Where can people reach you?



Instagram: @leadlikeagirl

Twitter: @leadlikeagirl


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