Finding Fearless

Good Awkward: Growing Through Discomfort with Henna Pryor

Madeline Reeves Season 6 Episode 13

In this inspiring episode of Finding Fearless, I sit down with Henna Pryor, a workplace performance expert, award-winning author, and keynote speaker whose journey from corporate conformity to entrepreneurial authenticity challenges everything we think we know about professional success.

Key themes we explored:

  • Henna's bold leap from Big Four accounting to founding her own venture
  • Why traditional definitions of success are failing us
  • The revolutionary power of embracing professional awkwardness
  • How personal experiences shape our willingness to take career risks
  • Strategies for practicing effective vulnerability in professional settings
  • Building a sustainable, energizing career that aligns with your values

00:00 Introduction to Finding Fearless

00:38 Guest Introduction: Henna Pryor

01:51 Henna's Career Journey

05:35 The Call to Entrepreneurship

11:34 Defining Success and Mindset Shifts

18:07 Embracing Awkwardness: Henna's Book

28:34 Understanding Burnout and Energizers

28:52 Identifying What Energizes You

29:24 The Clock-Watching Test

30:21 Adjusting Your Workload

32:04 Balancing Multiple Passions

33:01 The Importance of Charging Your Worth

33:49 Trial and Error in Business

35:07 Diversifying Your Business

36:31 The Reality of Hustle Culture

38:25 The Myth of Overnight Success

39:20 Authenticity and Vulnerability in Business

41:01 The Power of Vulnerability

46:02 The Value of Lifelong Learning

52:28 Redefining Success on Your Own Terms

54:44 Conclusion and Final Thoughts


Connect with Henna's Work:

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Finding Fearless is an exploration of human-centric leadership and a celebration of ambition, releasing every other week on Wednesdays, 6AM PST. If you liked the show, please rate, review, and share! You can also visit our website to learn more about how to become a sponsor of Finding Fearless!


Finding Fearless is produced by Fearless Foundry, a creative consultancy focused on advancing ambitious humans from around the globe to amplify their impact through branding, marketing, and business development. You can contact us at hello@fearlessfoundry.com if you are interested in our services and can follow us on all social media @fearlessfoundry.


Season 4 music is by Premium Beats. All audio is recorded and owned by Fearless Foundry.

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