Aim High, Bounce Back, featuring Fiona Macaulay & Deborah Riegel

A seismic shift can wipe out a plan in five days—or hand you the clearest view you’ve ever had of your purpose. Fiona Macaulay opens up about what happens when an entire industry gets upended, and the funding model you relied on disappears overnight. Instead of shrinking, she chooses forward motion: staying true to the mission, redesigning the business model, and thinking bigger about impact. Deborah Grayson Riegel brings the conversation into the terrain many leaders quietly carry: anxiety, mental health, and the pressure to never slip. She shares how her daughter Sophie’s middle-school diagnoses became a family wake-up call—and how Sophie’s insistence on honesty pushed Deborah to be more public, more vulnerable, and more useful to others navigating the same realities. Together, Fiona and Deborah unpack the heart of their book, Aim High and Bounce Back: ambitious goals are supposed to be ambitious, which means setbacks are not an exception—they’re part of the process. They talk about the “messy middle,” how feedback can land differently for women, why perfection is a trap, and how leaders can reframe failure into learning without minimizing the pain of the moment. The result is an energizing, real-world playbook for anyone who wants to take bigger swings—without letting fear of failure call the shots.

CHAPTERS:
00:00 Welcome + why these two guests are “seismic shifters”x-up that led to a perfect co-author pairing
04:17 Fiona’s seismic shift: industry upheaval and a forced business pivot
06:33 “Add a zero”: using disruption to expand impact
08:59 The messy middle: small steps when everything feels unstable
10:53 Deborah on anxiety, advocacy, and leading with the truth
14:20 Thought leadership as activism and giving voice to others
15:57 How Fiona and Deborah met—and why “Me too” became the spark
18:34 Fear of failure as the hidden engine beneath leadership challenges
20:53 Deborah’s assignment: go fail on purpose (and build resilience)
22:46 Frances Frei’s on-stage moment and what authenticity looks like
24:54 Stories and insights from Frances Frei that shaped the book
31:08 What Aim High and Bounce Back is really for—and who needs it
33:30 The survey: 1,062 responses on failure from around the world
35:01 Rehumanizing leadership: imperfection, connection, and growth
36:43 Closing gratitude and send-off

Special thanks to our friend Brian Wayy for the theme music this season!
Track Title: My Heart's On Fire

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