Episode 009 – Madeleine, Pilot

What does a 30-year career in the cockpit really look like?

In this episode, I sit down with Madeleine, a United pilot who has been flying professionally for over three decades. We talk about how her love of aviation started at just 16 years old after her very first flight lesson over the San Francisco Bay Area — and how that spark turned into a lifelong career.

Madeleine shares what it was like moving across the country to study Aeronautical Science at Embry-Riddle, waiting tables at a pizza place to make ends meet during her early flying jobs, and eventually starting a plane management and charter business with her husband. After selling the business, she made the leap back into commercial aviation — returning to what she truly loves.

We also talk about navigating career pivots during COVID, exploring new opportunities (including a potential master’s degree), and how that period of reflection ultimately brought her back to flying.

Along the way, Madeleine shares:

• What a pilot’s schedule actually looks like

• How flight routes are assigned

• What she packs for work

• Memorable flights and destinations

• The mentors who supported her as a woman in a male-dominated field

• Balancing family, health, and time off

Listen to full episode :