Episode 65 – Ambition and Chill: Lessons in Success and Self-Worth with Jess Ekstrom

Ever wonder how to stay ambitious without tying your worth to your work?

On The Art of Badassery Podcast, host Jenn Cassetta reunites with Jess Ekstrom, founder of Headbands of Hope and Mic Drop Workshop and author of Chasing the Bright Side and Making It Without Losing It, to talk about starting young, trying before you feel ready, and learning through setbacks. 

Jess shares how Headbands of Hope began after seeing kids with cancer want headbands, how a fraudulent manufacturer nearly derailed her, and how later she spent six figures on an app idea before cutting her losses and reframing it as “tuition” for the lesson. They discuss separating output from self-worth, building confidence through evidence, focusing on problems over outcomes, and Jess’s “purpose test” for intrinsic motivation, plus Mic Drop’s mission to help more women land paid speaking opportunities. 

Listen to the episode here

Watch the episode here

https://youtu.be/vDRAbw4I5DE

Welcome to an inspiring exploration of entrepreneurship, resilience, and the art of balancing ambition with self-worth. In a recent episode of The Art of Badassery Podcast, hosted by Jenn Cassetta, Jess Ekstrom shared her remarkable journey of founding Headbands of Hope and Mic Drop Workshop. Jess’s story is a testament to the power of perseverance, curiosity, and redefining personal success.

Meet Jess Ekstrom

Jess Ekstrom is a powerhouse entrepreneur, a bestselling author, and a dedicated advocate for women. Her ventures, Headbands of Hope and Mic Drop Workshop, have not only achieved commercial success but also made a significant impact by empowering women and supporting children with illnesses. From selling toys on eBay at the age of 12 to becoming a Forbes top-rated speaker, Jess’s journey is nothing short of a narrative of ambition intertwined with authenticity.

Jess’s Entrepreneurial Beginnings

Jess Ekstrom’s path to success began with a simple yet profound observation during her college internship at the Make-A-Wish Foundation. Witnessing young girls embrace headbands during chemotherapy sparked the idea for Headbands of Hope. Despite initial setbacks, including a fraudulent manufacturer, Jess’s determination led to millions of headbands being donated worldwide, essentially transforming adversity into accomplishment.

Balancing Ambition with Self-Worth

A central theme in Jess’s narrative is the balance between ambition and self-worth. During her conversation with Jenn, Jess emphasized the importance of distinguishing one’s identity from their achievements. Recognizing that failure is an inherent part of the journey, Jess advocates for embracing mistakes as invaluable lessons rather than setbacks. This mindset shift, outlined in her book Making It Without Losing It, encourages us all to view ambition as an exciting experiment rather than a burdensome goal.

Purpose and Intentional Living

The discussion touched on deeper themes of purpose and intentionality. Jess encourages individuals to evaluate their motivations—who are they trying to impress, and what truly drives their ambitions? Through her “purpose test,” Jess challenges us to consider whether our pursuits would hold the same value if they remained anonymous. This introspection, according to Jess, can align our actions with intrinsic motivations, creating a life driven by genuine purpose.

Key Takeaways:

  1. Failure as a Teacher: Every successful journey involves setbacks. Embrace failures as essential lessons that guide you toward greater achievements.
  2. Separate Self-Worth from Output: Recognize that your worth is not tied to your accomplishments. This perspective allows for healthier ambition and personal growth.
  3. Purpose Over Approval: Focus on what truly matters to you. Evaluate your motivations and ensure they align with your intrinsic values and passions.

Conclusion

Jess Ekstrom’s story is a source of inspiration for anyone striving to balance ambition with self-worth. Her insights resonate not only with entrepreneurs but with anyone seeking fulfillment and purpose in their lives. As we navigate our own journeys, let Jess’s entrepreneurial spirit and wisdom guide us toward authentic and intentional living.

Important Links

About Jess Ekstrom

Jess Ekstrom is an entrepreneur, author, and professional speaker best known as the founder of Headbands of Hope, a company she launched while attending North Carolina State University. Inspired by her experience working with children facing serious illnesses, she created a buy-one, give-one business model that has donated millions of headbands to children around the world. In addition to leading Headbands of Hope, Ekstrom is the founder of Mic Drop Workshop, which helps women develop their voices as speakers and thought leaders. She is also the bestselling author of Chasing the Bright Side, Create Your Bright Ideas, and Making It Without Losing It, and is widely recognized for her work at the intersection of social entrepreneurship, motivation, and leadership. 

Learn more about Jess Ekstrom at https://jessekstrom.com/

Episode 64 – Being 40: The Decade of Letting Go with Stacey Lindsay

Have you ever wondered if turning 40 could actually be the beginning of your most authentic chapter yet?

For generations, women have been handed a script: get married, have children, build a career, stay youthful, and somehow do it all on a prescribed timeline. But what happens when you decide to write your own story instead?

In this episode of The Art of Badassery, I sit down with multimedia journalist and author Stacy Lindsay to discuss her book, Being 40: The Decade of Letting Go and Embracing Who We Are. We explore why so many women are finding greater freedom, confidence, and clarity in their 40s by releasing expectations around aging, success, relationships, and identity.

Stacy shares her own journey through a challenging period while writing the book, along with insights on unlearning shame, embracing change, and navigating the realities of perimenopause and hormonal shifts. This conversation is a powerful reminder that getting older isn’t about becoming less—it’s about becoming more of who you truly are.

Listen to the episode here

Watch the episode here

Welcome to The Art of Badassery podcast, where Jenn Cassetta, your Chief Badassery Officer, dives deep into the decade of the 40s with a special guest, Stacey Lindsay. As they explore this transformative period in life, they uncover the nuances of societal expectations, personal growth, and the power of women standing in their truth. Let’s explore the key takeaways and insights shared during this enriching conversation.

Introduction

Jenn Cassetta opens the podcast with a heartfelt welcome to her listeners, introducing Stacey Lindsay, a multimedia journalist and the author of “Being 40: The Decade of Letting Go and Embracing Who We Are.” Known for her empathetic approach, Stacey has interviewed countless influential figures and shared her work across global media platforms. Together, they embark on a dialogue about embracing the 40s, a decade often misunderstood and underestimated.

The Beauty of the 40s

Stacey Lindsay shares her insights on how the 40s serve as a radical declaration period for women. Contrary to societal narratives that view this age as a time of decline, Stacey reveals it as an empowering phase where women let go of societal timelines and embrace their true selves. Through candid conversations with women of various generations, she highlights the newfound clarity and courage that arise in this decade.

Setting Intentions

Jenn and Stacey discuss the importance of setting intentions, not only for this episode but for one’s life. They encourage listeners, regardless of their age, to embrace their journey and empower themselves through self-awareness and acceptance. By sharing personal stories and insights, they aim to create a space for women to declare their desires and needs unapologetically.

Conversations on Motherhood and Perimenopause

A significant part of the discussion revolves around the themes of motherhood and perimenopause. Both Stacey and Jenn share their personal experiences and the societal pressures that often accompany these topics. They delve into the complexities and emotional landscapes that women navigate, emphasizing the need for open dialogue and support networks.

Radical Self-Declaration

At the heart of the episode is the notion of radical self-declaration. Jenn and Stacey emphasize the importance of asking oneself, “What do I want?” and allowing that question to guide choices and actions. They discuss how this self-awareness can lead to profound personal transformation and empowerment, encouraging women to carve out lives that reflect their true desires.

Key Takeaways

  1. Embrace the 40s as a Time of Empowerment: The 40s are not a time of decline but a powerful decade for self-discovery and embracing who you truly are.
  2. Set Intentions and Declare Your Desires: Be intentional about what you want in life, and don’t be afraid to declare it. This clarity can lead to transformative change.
  3. Open Conversations on Motherhood and Perimenopause: Engage in honest discussions about the challenges and joys of motherhood and the hormonal shifts during perimenopause, acknowledging the varied experiences of women.

Important Links

About Stacey Lindsay

Stacey Lindsay is a multimedia journalist, writer, and editor who lives in the Pacific Northwest. She is the author of BEING 40: The Decade of Letting Go—and Embracing Who We Are.

Known for her warm, empathetic approach, she has interviewed hundreds of public figures and civilians on topics like spirituality, health, civics, politics, identity, art, sexuality, women’s equality, and work.

Learn more about Stacey Lindsay at https://www.staceylindsay.com/