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In this episode of OFFBounds, Paula Macaggi sits down with retail leader, five-time Top Retail Expert, NRF Top Voice, and Retail Women in Tech founder Shannon Flanagan to discuss the launch of her new book, Choose, Don't Chase Your Career. After being laid off four times between 2016 and 2024, Shannon shares how those experiences forced her to rethink success, identity, and the stories we tell ourselves about work. Together, they explore why career transitions are about far more than finding the next job—they're opportunities to redefine who we are and what truly matters.
The conversation dives into fear, comparison, burnout, financial insecurity, and the courage to pause instead of rushing into the next opportunity. Shannon explains why the traditional definition of success is no longer enough, how to recognize the "scripts" that shape our decisions, and why choosing purpose over chasing titles can lead to a more meaningful career and life. Whether you're navigating a layoff, considering a career change, or simply questioning what success looks like, this episode offers practical wisdom and an honest reminder that sometimes the greatest transformation happens in the space between chapters.
You can buy Shannon's book here!
You can buy Shannon's book here!
Creators and Guests
What is OFFBounds Retail?
OFFBounds is where the world’s retail and commerce leaders go beyond headlines to talk about the decisions, strategies, and ideas shaping the future of the industry.
Every week, Paula Macaggi sits down in person with executives from leading brands, retailers, and technology companies for candid conversations about leadership, innovation, growth, and the realities behind building modern commerce businesses.
More than a traditional interview show, OFFBounds explores the human side of leadership: the risks taken, the lessons learned, the moments of reinvention, and the perspectives that rarely make it into press releases or conference stages.
Recorded in person with premium audio and video production, OFFBounds brings global commerce executives together in conversations designed to inform, challenge, and inspire the next generation of industry leaders.