Ep. 75: Making Art, Making Choices, and Making It Work with Dessa

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 didLessons from Doomtree on collaboration, community, and persistenceHow Dessa decides which projects are worth her timeThe financial realities of making art — and the unavoidable tradeoffs, from touring and merch to sustainability and personal valuesThe moral gray areas of brand partnerships and choosing who to align withWhy curiosity, experimentation, and adaptability are the keys to longevityThis 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.Episode Links and Mentions🌐 Doomtree🌐 Ryan Smith🌐 Andy Thompson🌐 Lazerbeak🌐 Deeply Human Podcast🌐 29:11 International Exchange🌐 Curtis SittenfeldConnect with the Guest:🔗 Dessa Instagram🔗 Dessawander.comFeatured Song:"Hurricane Party" by Dessa🎧 Listen on Spotify👀 Watch on YouTubeGet new episodes by email: Join the Secrets From The Scene newsletter.Secrets From The Scene is made by Helvig Productions, a Twin Cities recording studio for artists and bands.