Clocking Out with Raymond Lee

In this episode of Clocking Out, we meet Anna McDougall — an award-winning engineering leader, author, and former opera singer whose career is anything but ordinary.

Born in Sydney and raised by an academic mother and a creative father, Anna was a curious child who loved writing, performing, and—at just eight years old—taught herself to code from a book on HTML. That early spark of curiosity would guide her through a remarkable life of reinvention: from corporate boardrooms to opera stages, and eventually, to the world of tech.

Her path was anything but linear. There were moments of burnout, side jobs, and starting over from scratch in a new country. She’s lived through long nights balancing ambition with survival, chasing both purpose and stability in equal measure. But whenever Anna dives into something, she’s all in—and each leap taught her something new about resilience, creativity, and courage. 

Today, she leads global engineering teams and mentors others navigating transformation. In this conversation, Anna shares how she built a career that feeds both her heart and her mind—and what it truly takes to follow curiosity wherever it leads. Her story is a reminder that your next chapter might be the one that finally feels like home.