Episode 341: Mistakes Make Momentum: The Art of Failing Forward

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.

Visit our website where you will find show notes and links to all the resources in this episode, including the best way to get in touch with our special guest.

The key moments in this episode are:

[00:00] Introduction to Beyond Barriers Podcast [01:00] Introducing Jenni Lewis: Breaking Barriers [03:49] Jenni's Journey: From Mailroom to Marketing [08:59] Embracing Failure and Finding Gratitude [16:03] The Role of Inclusion and Diversity in Leadership [20:03] Why Jenni Chose Block [24:11] Introduction to Momentum Metric Quiz [24:39] Navigational Skills Gap in First-Generation Professionals [25:01] Generational Differences in Workforce Integration [26:04] Strategic Career Advancement for Women and People of Color [27:15] Challenges in Networking and Soft Skills Development [31:16] Imposter Syndrome and Leadership Journey [34:31] Aha Moments and Personal Transformation [38:18] Reflection and Grounding Moments [40:32] Lightning Round and Final Thoughts