Our host Thomas Haffenden sits down with Anna Jackson, Head of Creative Excellence at Telstra, for a raw and refreshingly honest conversation about trusting your gut, letting go of “the shoulds,” and taking the scenic route to a fulfilling career.

Before leading Telstra’s creative vision, Anna was on a very different path, training as an architect in one of the toughest degrees you can do. But a brutally hard year working in London forced her to confront a truth: she was in the wrong profession. That so-called “mistake” became the first step into a whole new world of creativity, storytelling, and leadership.

They discuss:

• How a chance encounter in a Kings Cross nightclub led her to advertising
• Why kids make the best critics (and sometimes the best boardroom consultants)
• The power of making decisions with your gut, even when it makes no sense on paper
• Building trust to take creative leaps in large organisations
• Why you should audit your life as often as your car
• The leader who changed her career trajectory
• The role other people play in helping you find your place, and why job descriptions are often BS

This one’s for anyone who’s ever felt stuck, misaligned, or on the wrong path. Anna’s story is a powerful reminder that it’s never too late to pivot and that the best careers are often built on the boldest decisions.

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