Career Exploration

Career Resilience, Risk, and Reinvention with the Force behind Gap and J.Crew

If you’ve ever shopped at Gap, Old Navy, J.Crew, or Madewell, you’ve experienced the influence of Mickey Drexler.

A retail visionary and the former CEO of both Gap and J.Crew, Mickey is known for transforming American brands into global icons through bold decisions, deep customer insight, and fearless leadership. In this exclusive conversation with Hello Monday host Jessi Hempel, Mickey reflects on decades at the helm of iconic brands, unpacking the risks that paid off, insights from his time on Apple’s board alongside Steve Jobs, and how he continues to shape the fashion industry as Chairman of Alex Mill.

Whether you’re navigating change, building staying power, or stepping into a senior leadership role, Mickey shares perspective-shifting lessons that you can apply to your own career to move forward with clarity.

This is a recording of a live event and features audience participation and an unscripted Q&A. Visit linkedin.com/events for more can’t-miss conversations featuring prominent leaders.

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