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. Connect with Jess Ekstrom:Instagram - https://www.instagram.com/jess_ekstrom/Website - https://jessekstrom.com/New Book Making It Without Losing It - https://jessekstrom.com/makingit/Send us Fan MailConnect with Jenn on Instagram @jenncassetta or her website www.jennifercassetta.com