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 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

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Featured Song
"Hurricane Party" by Dessa
👀    • Dessa - Hurricane Party - Official Music V...  

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