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

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Connect with the Guest:

🔗 Dessa Instagram

🔗 Dessawander.com

Featured Song:

"Hurricane Party" by Dessa

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🙏 Thank You

This podcast is made possible by the hard work, expertise, and commitment of my team: Max Greene and Joey Biehn. I'm forever grateful. And thank YOU, for listening.

Theme Music: "Thankful" Courtesy of ⁠⁠⁠LUEDVIG⁠⁠⁠