Redefining Leadership: Courage, Confidence, and Taking the Leap with Reagan Cannon

Badass Women in Business

Send us a text

Reagan Cannon shares her transition from leading Fortune 15 companies like Amazon to starting her own business as a leadership speaker and coach. She opens up about the challenges of leaving corporate security, how relational courage helps women break through barriers, and why taking calculated risks is essential for growth. Reagan offers powerful insights into redefining identity, building confidence through action, and creating leadership cultures that inspire innovation and success. This episode is packed with practical advice for women ready to take bold steps in their careers or entrepreneurial journeys.

Show Notes:

Introduction: Reagan Cannon, leadership expert, coach, and former Amazon executive, shares her inspiring journey and actionable lessons for women in business.

Corporate Career:

• Insights from Reagan’s 20+ years leading teams of 10,000+ at major corporations.
• The pivotal moments that kept her in corporate and eventually gave her the courage to step out on her own.

Relational Courage:

• The importance of relational courage in breaking societal barriers for women in leadership.
• Research findings on how women can shift from compliance to strategic influence.

Confidence vs. Courage:

• Why confidence is overrated and courage is the actionable step needed to grow.
• How repeated acts of courage lead to real confidence over time.

Calculated Risk:

• Reagan’s approach to smart experimentation and managing risks while launching her business.
• Why failure is a stepping stone and how to measure risk using the “Monster Audit” framework.

Leadership Lessons:

• Moving from control to building team capabilities and fostering innovation.
• The importance of delegating effectively and focusing on driving strategy as a leader.

Identity Shift:

• Redefining her personal and professional identity after leaving a corporate role.
• The challenges and surprises of introducing herself as an entrepreneur.

Practical Advice:

• How to overcome fear, embrace change, and take ownership of your career path.
• Why waiting for the “perfect time” is a myth and how to make bold moves with intention.

Connect with Reagan Cannon:

• Website
• LinkedIn
• Instagram

Call to Action:
Dive deeper into Reagan’s journey and lessons with her blog, The Eight Things I Learned About Entrepreneurship, at her website. If you enjoyed this episode, subscribe and leave a review to help others discover Badass Women in Business. Stay tuned for more stories of courage and success!

Keep up with more content from Aggie and Cristy here:

• Facebook: Empowered Women Leaders
• Instagram: @badass_women_in_business
• LinkedIn: ProveHer - Badass Women in Business
• Website: Badasswomeninbusinesspodcast.com
• Athena: athenaac.com