This episode features Ann Holder, a 1989 graduate from the U.S. Military Academy. In this episode, you’ll learn how a comment that was made to Ann at a young age sent her on a mission to attend a federal service academy; what it was like to be a woman at West Point in the ‘80’s; how Ann navigated the many challenges she faced at the Academy, some of which made her question whether or not she wanted to continue on; and how ultimately – while she’s grateful to have graduated from West Point – her decision to leave the military allowed her to tap into her entrepreneurial spirit while also building a family. Enjoy the show!


  • Being a woman applying to the Academy in the 1980’s
  • Not getting a nomination to her number one choice of Federal Service Academies 
  • Having a challenging first year at the Academy
  • Struggling with test anxiety
  • Deciding to leave the military earlier than expected
  • Embracing entrepreneurship


  • 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?

2:03 PART I:

  • What made you choose a Service Academy – and what made you specifically choose the U.S. Military Academy?
  • What was it about the Academies and the military that hooked you?
  • If you wanted to fly, what was the goal if you were going to attend West Point?
  • Did you visit West Point before you went there?

15:00 PART II:

  • Arriving on campus for the first time for R-Day.
  • Struggling with her hair.
  • Managing homesickness during her first summer.
  • What was the transition like going into the academic year?
  • Wanting to leave the Academy.

25:26 PART III:

  • If you had to sum up your time at the Academy in one word, what would it be?
  • What were some of the highlights of your time at the Academy?
  • What were some of the challenges you faced at the Academy during your last year?

37:50 PART IV:

  • As you approached graduation, what was the plan?
  • Getting sent to Germany and her involvement in the Gulf War.
  • Having a baby while her husband was deployed.

44:40 PART V:

  • Did you decide to stay in the military or did you decide to get out?
  • Making the decision to leave the military.
  • Moving through different corporate jobs at General Mills, M&M-Mars, and Pepsi.


  • How do you currently feel about your decision to attend an Academy?
  • 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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