From Frustration to Legacy: Ambition, Speaking for Pay & Making It Without Losing It with Jess Ekstrom

What happens when frustration becomes a lifelong operating system? In this episode of Roar, Danielle Davies sits down with Jess Ekstrom, an entrepreneur, bestselling author, and founder ofboth Headbands of Hope and Mic Drop Workshop , for a conversation that is equal parts practical, personal, and unexpectedly profound. What begins with a childhood camping trip and a tangled Walkman cord quickly expands into a wide-ranging discussion about advocacy, economic empowerment, ambition, legacy, and what it really means to build something without losing yourself in the process.What You'll Hear in This Episode•      Why Jess's dad's response to a frustrated middle-schooler became the foundation for everything she's built•      How Jess ended up being the first woman to speak at a conference that had been running for 15 years, and why that's not a compliment•      The moment she asked an event organizer why they booked her, and what his honest answer revealed about the speaking industry•      Why women second-guess their place on stage while men confidently ask for $50,000, and what's actually behind that gap•      Danielle's own experience taking Jess's free course and landing a $2,500 paid speaking gig almost immediately after•       Jess's philosophy on over-delivering vs. gatekeeping, and why she pushed back on advice to hold more back•      The Bernie Madoff connection in Jess's family, and how that trauma quietly turbocharged her hustle•      What happened when Jess accidentally signed up for a death-and-dying silent retreat in Asheville, and how it reframed her entire relationship with ambition•      The shift from checklists to legacy: how Jess thinks about building things that outlive her goals•      Practical speaking tips: the 'spotlight to lighthouse' mindset shift, the 'start button' technique, and why being relatable is your competitive edge in the age of AI•      The 'contribution vss. completion' framework from her upcoming book, and why most of us are exhausted because we keep chasing 'done'•      Her upcoming book Making It Without Losing It (available TODAY!)Links & Resources: 📖 Jess's new book, Making It Without Losing It, available TODAY! https://shorturl.at/DC2bi🌐 Jess’s website: www.JessEkstrom.com🆓 The FREEBIE Class that Danielle took that TOTALLY WORKED: https://micdropworkshop.com/home-free-webinar🎤 Mic Drop Workshop: https://www.micdropworkshop.com📚 Headbands of Hope: https://www.headbandsofhope.comRelated Episodes:Our convo with NYT Bestselling author Katherine Center: https://open.spotify.com/episode/0mBOic9PTXjWbtLwSuYLdV?si=2c46bd9a10934a1aA chat with visibility dynamo Cheldin Barlatt Rumer: https://open.spotify.com/episode/5H8J8d2zKXqpptZG53k2wr?si=b9fd9904efd74f60Follow & Subscribe to Roar:🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-roar-podcast/id1791584834🎧 Spotify: https://open.spotify.com/show/5A3yVooECAKII1a3HV3bcf▶️ YouTube: https://www.youtube.com/@roarpod📩 Newsletter: https://substack.com/@roarwithdanielledavies🙋 Be a guest: https://www.danielledavies.com/be-a-guestConnect with Danielle:Instagram: https://www.instagram.com/roarwithdanielledaviesLinkedIn: https://www.linkedin.com/in/danielledaviesmedia/Website: https://www.danielledavies.com/#RoarPodcast #JessEkstrom#MicDropWorkshop #WomenWhoSpeak #SpeakingForPay #MakingItWithoutLosingIt#WomenInBusiness #WomenInLeadership #DanielleDavies #PublicSpeaking#WomenEmpowerment #HeadbandsOfHopeWhat You'll Hear in This Episode