Turning Frustration Into Inspiration with Jess Ekstrom

2 Feb 2022 · 51 min
The Amberly Lago Show: Stories of True Grit and Grace

2 Feb 2022 · 51 min

0:00

In this episode of the True Grit & Grace podcast, host Amberly Lago interviews Jess Ekstrom, founder and CEO of Headbands of Hope. The conversation weaves through Jess’s personal and professional journey, beginning with her early fascination with entrepreneurship sparked by a Disney internship and a Make‑A‑Wish experience that led to the creation of Headbands of Hope—a company that donates a headband to a child with illness for every headband sold, now approaching one million donations and a ten‑year anniversary. Jess shares how living for two and a half years in an Airstream with her husband (Enneagram 7) deepened their partnership and forced creative problem‑solving. She reveals a hidden family connection to Bernie Madoff, describing how confronting that legacy shaped her optimism and the “inspiration from frustration” mindset that fuels her work. Jess discusses her book Chasing the Bright Side, the role of optimism, and practical tools she teaches: improv’s “yes, and” principle, daily affirmations, and a structured journaling practice via her Bright Pages app (soon to be rebranded as Prompted) that offers “prompt pathways” for issues like imposter syndrome or book writing. She explains her “tree exercise” for mapping book ideas and how to distill those branches into concise speaking talks. The dialogue also covers building a team by hiring for weaknesses, leveraging social media, and advocating for more women on speaking panels. Throughout, both hosts emphasize resilience, gratitude, and actionable steps for listeners to apply optimism, journaling, and purposeful storytelling in their own lives.

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