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What's Your Win?
People are driven by a wide range of motives in their professional lives—some are mission-driven; some are keen for recognition and respect; some find the work its own reward; some just wanna make rent and head home. Working as a touring musician and writer, Dessa has seen performers play for hundreds of thousands of dollars, for media exposure, for food, from a sense of duty, and just for the fun of it. She’s also had the chance to work with an array of talented people well outside her field—neuroscientists, puppeteers, activists, and one dentist. Understanding what really drives potential partners can help create genuinely mutually beneficial collaborations that better serve the goals of all parties. To design an agreement that feels exciting, fair, and tailor-made to the interests of all stakeholders, Dessa suggests starting the conversation with What’s your win?
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Mind Your Metrics
If I love this work so much, how come it feels like an arcade game for social media likes and positive growth reports? Metrics not only measure our performance, but change the way we perform—what we count counts. As a touring musician, Dessa tracks the standard metrics of success: album sales, concert attendance, merchandise profit margins…but also keeps an eye on the number of stage dives per tour, the number of security guards who sneak a peek at the live show. Dessa shares actionable strategies to chart a career path that keep vision and values at the fore, even in turbulent conditions.
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Creativity at Work
Musician and writer Dessa delivers a funny, insightful presentation on building a career that spans genres and disciplines. How do you transform a common experience—like a breakup—into a set of lyrics that fans might get tattooed? How does a rap song get reimagined to be performed in a fancy hall with a full orchestra? How do you self-promote online without sounding like a total dork or ego-monster? Dessa easily tailors her presentation to the experience-level of her listeners, with entertaining stories and an engaging Q&A.
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Pen Sharpening
How do writers really move their readers, towards big feelings or measurable action? With funny stories and actionable ideas, Dessa demonstrates how the written word can inform, inspire, and engage across formats—particularly by harnessing figurative language and mastering the “Show Don’t Tell” maxim. Presentation can be configured to include a reading, Q&A, and workshop component for fiction, non-fiction, lyrics, public presentation, and/or social media.
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SENSELESS LOVE: TORCH SONGS AND BRAIN SCIENCE
Dessa makes her living as a touring musician. She’s earned a reputation as a songwriter who can produce and perform killer torch songs—tracks that run on pining, tragic love. What’s been good for the art, however, wasn’t always good for the artist. Dessa struggled for many years to fall out of love with the same man, and even though she knew it was futile to hope for reconciliation, she just couldn’t seem to put those feelings down.
When traditional interventions had failed—time, distance, whiskey—she tried something drastic. Dessa assembled a team of neuroscientists to try to excise the love from her brain. (Her collaborators include researchers from the University of Minnesota’s Center for Magnetic Resonance Research, led by Dr. Cheryl Olman, and neurofeedback clinician Penijean Gracefire.) The story of her experience is funny, fascinating, suspenseful, and reveals poignant perspectives on our brains, our bodies, and the ties that bind.
See Dessa in action.
A true force of nature both on the stage and on the page
“Language was my first love,” says Dessa, and her work as a musician, writer, and speaker is studded with memorable turns of phrase. Her style is also defined by empathetic curiosity–an interest in finding unlikely connections between seemingly disparate people and ideas. Over the course of her career, she’s partnered with neuroscientists, shadow puppeteers, a dentist, a traveling circus, and musicians of all stripes: subway bucket drummers, flamenco palmas, a Chinese pipa master, and a Zimbabwean mbira player. Her work on stage and on the page is often funny, usually clever, and sometimes melancholy: poignancy tempered by wry wit delivered in a cocktail dress paired with combat boots.
Dessa’s musical career began in earnest when she was asked to join Minneapolis’ Doomtree collective, the hip-hop crew known for bold production, charismatic lyricists, and explosive live shows. She started touring hard as a solo act after her 2010 release A Badly Broken Code. Since then, she’s worked across sounds and styles; her albums include rap bangers; a cappella arrangements; and big, catchy pop hooks. On the invitation of Lin-Manuel Miranda, she contributed a track to gold record The Hamilton Mixtape. She’s also co-composed work for full choirs and cut a live album with the GRAMMY-winning Minnesota Orchestra.
Dessa grew up in the 80s in South Minneapolis as a strong-willed, cerebral, sometimes troubled kid. Both parents were musical—her father played classical guitar and the medieval lute; her mom came up in the Bronx in an apartment where someone (or everyone) was constantly singing. In school, Dessa was studious, with special interest in biological science and creative writing. After earning a philosophy degree, she began competing on the slam poetry circuit where she connected with members of the local hip hop scene. Her songs are the product of this nonconventional trajectory: she remains part academic and part hip hop artist, with moments of playful braggadocio offset by flashes of arresting candor. Dessa’s formative professional years were spent adhering to the DIY model of indie artists: passing flyers hand to hand, touring the world in a grimy van, and learning how to run a business from her backpack. She’s now performed at gritty underground rock clubs in Central Europe; velvet-lined theaters in Australia and China; standing atop a chair in South Africa, and at top-tier festivals like Glastonbury, Lollapalooza, and Riot Fest.
Between tours, and sometimes backstage, Dessa continued to write poems, essays, and short stories. Her written work has been published in the New York Times, National Geographic Traveler, and in literary journals around the country. She’s released three short literary collections, most recently Tits on the Moon, a collection of stage poems published by Rain Taxi and Doomtree Press. Her short fiction has been published in The Iowa Review and her first audio play was produced by 45North in London. In 2018, Dutton Books (Penguin Random House) published Dessa’s memoir, My Own Devices, which tells the story of her life, career, and an ambitious plan to fall out of love. She delivered a TED Talk in Hong Kong titled “Can We Choose to Fall out Love?” that has notched more than 4 million views.
Across formats, Dessa’s work embodies ferocity, intelligence, and tenderness. NPR’s All Songs Considered hailed her as a “a national treasure.” The LA Times says simply she “sounds like no one else.” You can listen to her music—including her 2023 full-length album Bury the Lede—read her writing, and check out the tour schedule at dessawander.com or find her on Instagram as Dessa, and on Facebook and Twitter as dessadarling.
Our speakers get attention.
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How to Resist Like MinneapolisMeet the block, shop the indies, and check on your people.
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Musician Dessa on balancing the needs of body, art and businessDessa is a writer and musician who has chatted with us in the past. She joined “Marketplace’s” Kai Ryssdal to talk about touring, the industry’s changing economics, and doing what…
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Who Am I Without My Voice?I was a singer heading out on tour. Losing my voice was terrifying — but it ended up teaching me everything about myself.
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How Rapper Dessa Brings a New Level of Passion to Her Album ‘Bury the Lede’In an era where the term “multihyphenate” is bandied about with increasing frequency, Dessa stands out as a genuine exemplar of the word’s fullest, most vibrant meaning.
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Rapper Dessa Explores a Literary Pop Wonderland"I don't buy into the idea that pop music can't also feature smart lyrics."
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Indie Rapper Dessa Talks Journey Toward New Album ‘Bury the Lede’: ‘There Were No Steps Skipped’ (Exclusive)Dessa believes that pop music shouldn’t have to be so simplified.


