Airline Pilots Called It ‘Rolling the Dice’

Years of gambles and gut decisions shaped this American Airlines veteran’s trajectory.

Les Abend

Wednesday, August 19, 2026 at 08:00 AM ET

Verified

Edited By:

Travis Tingle

Les Abend’s first step toward an airline career as a Beech 99 copilot. [Credit: Les Abend]

Key Takeaways:

The author frames an aviation career as a series of unpredictable "dice rolls," starting from a childhood dream to join American Airlines and including strategic educational choices.
Throughout their early career, the author proactively sought opportunities, navigated challenges like furloughs and initial rejections, and persistently worked to gain experience and advance.
Key decisions, such as choosing American Airlines over Eastern Airlines despite pay differences, were based on long-term vision, intuition, and personal preference, culminating in a 34-year successful career.

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After typing a couple of paragraphs, it took a moment to realize that the topic I had originally intended for this column had disappeared. Instead, the words I had written became a trigger for reflection, which is not a process I often entertain.

The reflection involved decisions that significantly affected the trajectory of my career path. Perhaps the insight will help guide those following in similar footsteps.