Mistakes Make Momentum: The Art of Failing Forward

Episode #341

Jenni Lewis

Global Inclusion and Diversity Lead

In this episode, you’ll hear the extraordinary journey of Jenni Lewis, a trailblazing leader in diversity, equity and inclusion, who turned every setback into a stepping stone.

From starting her career in the mailroom at J.P. Morgan to becoming the Global Inclusion and Diversity Lead at Block, Jenni has built a career defined by bold moves, reinvention, and an unwavering commitment to authenticity. She shares how she took a leap from finance to marketing, launched a podcast before podcasting was mainstream, and even faced professional consequences for daring to center LGBTQ+ voices. Along the way, she learned that embracing discomfort and failing forward are the true catalysts for growth.

Jenni also opens up about a life-altering wake-up call—a helicopter crashing onto her office building—that forced her to rethink her career, relationships, and purpose. Whether you’re navigating a career pivot, stepping into leadership, or looking for the courage to take that next big risk, this episode will challenge and inspire you to rethink failure and see it as an essential part of success.

Key Takeaways:

  • The Power of Bold Choices: Why trusting yourself and taking risks can unlock career-changing opportunities.
  • Resilience in Action: How to navigate setbacks, pivot with confidence, and turn challenges into career breakthroughs.
  • Leadership Through Inclusion: Why diversity isn’t just a corporate buzzword but a business imperative that drives innovation.
  • The Gift of a Wake-Up Call: How a near-death experience led to radical self-reflection and a purpose-driven career shift.

The future you envision for yourself is often smaller than the one you’re capable of creating.

Jenni Lewis