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:

An airline career path is inherently unpredictable, requiring individuals to "roll the dice" on major decisions, from initial training programs to employer choices.
The author's successful 34-year career was a blend of early ambition, relentless perseverance in educational pursuits and job seeking, and strategic networking.
Key career transitions involved overcoming challenges like furloughs and rejections, while proactively pursuing new opportunities through initiative.
Crucial "dice rolls" included making difficult choices, such as selecting American Airlines based on long-term aspiration and intuition, despite immediate financial considerations elsewhere.

See a mistake? Contact us.

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.