How To Turn Awkward Moments Into Confidence, Connections, and Career Success w/ Henna Pryor

How To Turn Awkward Moments Into Confidence, Connections, and Career Success w/ Henna Pryor

From ReLaunch to a Rich Life by Hilary DeCesare

March 25, 2026 · 36 min · Season 1 · Episode 312

About this episode

Henna Pryor shares her journey from a corporate career to entrepreneurship, discussing confidence and handling awkward moments.

Henna Pryor is a globally recognized workplace performance expert, TEDx speaker, and bestselling author of “Good Awkward”. She is also one of the rare female entrepreneurs to successfully scale beyond seven figures and now helps leaders and professionals build the mental and social fitness needed to perform, communicate, and lead at the highest level. In today’s episode, Henna joins me to share her powerful relaunch story of how she mastered confidence, and transitioned from a 17-year corporate career into entrepreneurship, speaking, and coaching. We dive into the identity crisis that comes with major transitions, the unexpected grief of leaving a successful career, and how to navigate those moments without losing yourself. Henna breaks down the truth about confidence, why the most successful people aren’t less awkward than you, how to master your comeback rate, and how to quickly recover from uncomfortable situations. We explore the psychology behind awkward moments: why we overthink them, what the “spotlight effect” is, and the gap between our perception and reality. Henna also shares practical strategies to handle awkwardness in real time and turn discomfort into connection…

People in this episode

Host: Hilary DeCesare

Guest: Henna Pryor

Topics covered

Keywords

Mentioned in this episode

Books & works: Good Awkward

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