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If you’ve ever struggled to balance multiple passions, questioned whether to “pick a focus,” or wondered how to actually make a creative career work long-term, this episode is for you. This week on Secrets From the Scene, I sit down with Dessa — a writer, rapper, singer, podcaster, and speaker who’s built one of the most multifaceted careers in the Twin Cities and beyond. From Doomtree to the Minnesota Orchestra, The Hamilton Mixtape to her BBC podcast Deeply Human, Dessa has carved a path that defies easy labels. We talk about what it really takes to sustain a creative career over the long haul — the tough decisions, unexpected opportunities, and constant balancing acts that come with living a multidisciplinary life. In this conversation, you’ll hear us dive into: The pressures artists face to “pick a lane” — and why Dessa never did Lessons from Doomtree on collaboration, community, and persistence How Dessa decides which projects are worth her time The financial realities of making art — and the unavoidable tradeoffs, from touring and merch to sustainability and personal values The moral gray areas of brand partnerships and choosing who to align with Why curiosity, experimentation, and adaptability are the keys to longevity This conversation left me thinking a lot about what it really means to build a creative life that lasts and how there’s no single “right” way to do it. It’s about making your own lane and finding ways to keep going. Whether you’re balancing multiple passions, trying to make your art sustainable, or just figuring out your next move, I think you’ll walk away from this one with a few new ideas — and maybe a little reassurance that you’re not alone in the process. Full transcript and show notes: https://secretsfromthescene.com/75 01:51 Dessa's Multifaceted Career Overview 03:55 Early Career and Multidisciplinary Path 06:51 Balancing Multiple Creative Pursuits 10:04 The Role of Curiosity in Creativity 13:18 Impact of Minneapolis on Dessa's Career 14:15 DIY Ethic and Collaboration 17:14 Navigating the Music Industry 21:45 Building Healthy Partnerships 25:38 Deciding on New Projects 29:28 Financial Realities of a Creative Career 31:03 Reflections on Brand Partnerships 32:25 Navigating Moral Ambiguity in Creative Work 34:13 Balancing Environmental Impact and Career 36:09 The Influence of Peter Singer's Philosophy 37:12 Exploring Human Behavior and Collaboration 39:45 Lessons from Cross-Cultural Collaborations 43:33 Reflections on Success and Career Goals 46:17 The Role of Social Media in Modern Life 51:19 The Future of AI in Art and Music Interested in working with us on your next song? 🧰 https://helvigproductions.com/letscon... Connect with the Guest 🔗 / dessa Featured Song "Hurricane Party" by Dessa 👀 • Dessa - Hurricane Party - Official Music V... Connect with me! ✉️ Subscribe to the newsletter: https://secretsfromthescene.com 📷 Connect on Instagram: @secretsfromthescene 🕺 Connect on TikTok: @secretsfromthescene 📺 Subscribe on YouTube Let me know how I'm doing! 📬 Send me a message: [email protected] 💬 Suggest a guest or topic: [email protected] 🧡 Like and Subscribe ✍️ Leave a comment 🎙️ Brought to you by: https://helvigproductions.com Production, videography, and coaching to help you sound your best, tell your story, and promote your music. Think of us like your extra bandmate, 100% focused on helping you create something special that you and your fans will enjoy for a lifetime.