Olga Custodio
Olga Custodio
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Show notes
What does it take to keep pursuing a dream when the institution you want to join isn’t ready to welcome you?
In this episode, I talk with trailblazing military and airline pilot Olga Custodio about her memoir, Flight Path of Fortitude, and the remarkable journey that made her the first Latina and first Puerto Rican woman to become a U.S. Air Force pilot.
Olga grew up around the world as the daughter of an Army serviceman and knew from an early age that she wanted to wear a military uniform. But when she tried to join Air Force ROTC, women weren’t permitted to participate. A later attempt to enter the Air Force as an officer was similarly unsuccessful. It would take ten years, several career detours, and an extraordinary amount of determination before she finally found her opportunity.
By then, Olga was married and raising a young daughter. She entered military flight training at 26, navigating the demands of learning to fly high-performance jets while building a support system that made it possible to succeed as both a mother and a pilot.
Olga and I share our experiences of going through military flight training as mothers, discuss the importance of finding advocates and speaking up for ourselves, and explore the challenges of entering aviation environments where women were still very much the exception.
We follow her transition from Air Force instructor pilot to American Airlines, where she became a pioneering Latina airline captain, and talk about the unexpected places discrimination can come from—including other women.
But Olga’s story extends well beyond the flight deck. She’s a musician, a champion of Puerto Rican culture, a sought-after speaker, and a passionate advocate for the next generation. We talk about her appearance in Modelo’s Fighting Spiritcampaign, her induction into the Women in Aviation International Pioneer Hall of Fame, and why she waited until retirement to write her memoir.
Throughout our conversation, Olga returns to the importance of confidence, flexibility, mentorship, and staying open to opportunities that may not look anything like the original plan.
Her message is especially meaningful for anyone who has ever been told no, struggled to find a way forward, or wondered whether a dream is still worth pursuing.
In this episode, we explore:
- Olga’s childhood in Puerto Rico and around the world, and how those experiences shaped her confidence and worldview
- The institutional barriers that delayed her entry into the Air Force by a decade
- How she navigated the application process and found advocates willing to help
- Military flight training as a mother, including the family and community support that made it possible
- Becoming a T-38 instructor pilot and transitioning to the Air Force Reserve and American Airlines
- Discrimination, solidarity, and the complicated dynamics of women supporting other women
- Her work as a speaker, cultural advocate, and role model
- The process of writing Flight Path of Fortitude and preserving our experiences for future generations
Olga reminds us that role models need to be more than visible. They need to be accessible, willing to share their experiences and help others discover what might be possible.
And sometimes the most important thing we can do is take the next step, even when we can’t yet see the whole path.
