Jessye DeSilva: “To teach is to be constantly learning”

I used to think that being a singer-songwriter was all about me. About my talent. About the music I make. And I could just go into a room… an open mic or something… and just blow them all away if I was good enough. But music — especially the music I’m drawn to, which is rooted in […]

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I used to think that being a singer-songwriter was all about me. About my talent. About the music I make. And I could just go into a room… an open mic or something… and just blow them all away if I was good enough. But music — especially the music I’m drawn to, which is rooted in the folk and Americana traditions — is really about being part of a community. It’s not enough to just show up to a gig and expect to be hired again. You’ve got to live the music and be part of the community/s you’re making music for.

As part of my series about leaders helping to make the entertainment industry more diverse and representative, I had the distinct pleasure of interviewing Jessye DeSilva.

Jessye’s (they/them/theirs) brand of indie folk music centers around a philosophy of radical openness and specificity in storytelling. They believe in the idea that empathy is an artist’s greatest tool in nurturing a sense of community with their listeners. Armed with a piano and a voice which is both fierce and fragile, Jessye “… evokes a chest-ripping emotion that hovers inches above the ground, pouring forth the kind of wellspring folk music rarely witnesses” (Jason Scott, B-Sides and Badlands). Their upcoming EP Hover deals with the dilemma of remaining emotionally present through mental health struggles, grief, and political unrest all while showcasing Jessye’s trademark confessional lyrics and a sound which is both ethereal and firmly rooted in Americana.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

As a little kid who never really felt at home with the gender I was assigned at birth, I was always looking for safe places to “play” where I could really live my truth and be who I wanted to be. When I was really young, I used to run around the backyard with a blanket wrapped around me like a cape, pretending to be a witch. At 15, I discovered the music and magic of Stevie Nicks, and my father took me to see her live during her “Enchanted” Tour. From way back in the “cheap seats,” I witnessed this incredible woman, rocking out with “the boys,” while simultaneously twirling and weaving her graceful spell, and I said, “I need to do this.”

Can you share the most interesting story that happened to you since you began your career?

Haha… well this is QUITE random, but since I don’t consider myself all that interesting, here goes. When I was in college, studying opera, I sang as a countertenor (which means someone who isn’t female who sings soprano or alto — quite high in falsetto). I once sang a public performance after which an elderly lady came up to me and shyly asked if I “still had all my bits and pieces.” In retrospect it was a pretty invasive and inappropriate question… but at the time I identified as male and understood how jarring it could be for some folks to hear those sounds coming from my body.

Oof. I can’t believe I just shared that…

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

This is a silly little thing, but I’ve learned about the importance of being prepared and not relying on performance venues to handle everything for me. I’ve twice forgotten to bring an extension cord and as a result, have ended up performing cramped in a corner just to plug my equipment in! I came from a classical background, where microphones and electronic equipment were rarely used and I’d just show up and sing and go home… I’m not the most technically minded person, but I’ve learned how to operate my own equipment and to be more appreciative of sound and light folks when they’re there for me!

Ok thank you for all that. Let’s now jump to the main focus of our discussion. Can you describe how you are helping to make popular culture more representative of the US population?

Well first, I no longer underestimate the power of just living one’s truth. In today’s society more than ever, just BEING a nonbinary queer person and making art is an act of resistance. But beyond that, I’m also a voice teacher for students who study Musical Theatre at the Boston Conservatory at Berklee. Broadway

and the Musical Theatre industry are like so many subsets of our culture, still benefiting from white supremacy and cisnormative depictions of gender. My students know when they enter my studio that I’m an ally and advocate for them. Although I and my students are often disillusioned by the theatre and music industries, we know that we’re the ones with the power to change it from within.

Wow! Can you tell us a story about a particular individual who was impacted by the work you are doing?

I’m not sure I have one particular story I feel I can take credit for, but occasionally I’m lucky enough to either hear from a former student or perhaps a fan/listener of my music about how something I said or sang or wrote helped them to feel seen and less alone. That’s really all I can hope for. It might sound like a cliche, but I’m not in it for the accolades or hero worship.

As an insider, this might be obvious to you, but I think it’s instructive to articulate this for the public who might not have the same inside knowledge. Can you share three reasons with our readers about why it’s really important to have diversity represented in Entertainment and its potential effects on our culture?

Sure. In my opinion, all forms of performing arts — whether it be music, film, theatre, television — teach us empathy. Not just the people like me who are creating and performing, but also (maybe especially?) the people who are consuming it. For me, music is how I learned to take in the stories, heartaches, and joys of others — artists who I never knew personally, but whose music kept me company and helped me feel

like my own feelings were valid. Even so, most of these artists were straight, cis women and men. As a kid, whenever I saw a queer singer songwriter making music and living their truth loudly, that feeling of connection was amplified one-hundred-fold. Folks who aren’t straight, white, and cisgender know from a really early age that they are being “othered” by society. They learn quickly of a world that wasn’t “made for them,” but to see their faces, their spirits, and their stories reflected in the Art and Entertainment World is huge and empowering. Art is supposed to reflect life and humanity — all of it. Not just a small, “normalized” population.

Can you recommend three things the community/society/the industry can do to help address the root of the diversity issues in the entertainment business?

SEEK OUT, CONSUME, and SHARE art which is being made by gender diverse artists and artists of color. The first one is REALLY important, because so many folks will say, “Well, there’s just so little out there in the mainstream… I just haven’t been exposed to it.” You’ve got to seek it out, because trust me. It’s there.

How do you define “Leadership”? Can you explain what you mean or give an example?

Leadership is a tricky one for me. I don’t feel like I’ve ever sought out leadership roles or necessarily considered myself a LEADER. But I think for me, the most important quality of a leader is to listen first and listen often. I think society tells us a leader is someone with all the answers. Someone who just bulldozes through situations and takes control. To me a true leader is someone very different. A leader is someone who listens to their community and not only LISTENS, but AMPLIFIES the voices of their community members and other communities who have less societal privilege. A leader is also someone who isn’t afraid to admit when they’re wrong.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

1. I wish someone really told me how important it is to work at your craft. That it isn’t just about “talent,” but about constantly seeking to learn and evolve and be better.

2. Related, but on a different note, I wish someone had also told me how important my own voice and story is in the music I’m trying to make. I think, especially when you study music, so much emphasis is placed on the product or the art itself… can you sing well enough? Can you play well enough? Can you write a decent hook or capture the sound of the moment? But at the end of the day, you can do all those things but if you’ve got nothing to SAY with it, it’s really meaningless.

3. When I first went to college for music performance (I was originally a voice and opera major), I wish career development courses were mandatory. Again, you get so much great training in your craft, but often no one tells you how to navigate the business — or even how important it can be in today’s music industry to find some sort of correlating career… NOT a fallback, but just something else you enjoy that you can support yourself with.

4. I think when I first started teaching, I felt this immense pressure to know the answer, or at the very least to come up with something and sound really confident that I was right. I think, much like I mentioned earlier with leadership, an important part of teaching is NOT knowing. If you define a student immediately and put them in a box, OR if you think you know definitively and without doubt how to do what it is your teaching, you should probably stop. To teach is to be constantly learning.

5. I used to think that being a singer-songwriter was all about me. About my talent. About the music I make. And I could just go into a room… an open mic or something… and just blow them all away if I was good enough. But music — especially the music I’m drawn to, which is rooted in the folk and Americana traditions — is really about being part of a community. It’s not enough to just show up to a gig and expect to be hired again. You’ve got to live the music and be part of the community/s you’re making music for.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Honestly, if I could inspire a movement of empathy — just to get folks to care about and fight for communities of which they aren’t already a part… issues that don’t affect them directly — that would be enough for me.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I’m not great at remembering quotes, so you’ll have to forgive me. I remember hearing or reading a while back something which really stuck with me in terms of what music means to me and what I hope to contribute myself. Unfortunately I don’t remember who said it… I just know I didn’t come up with it myself! It was something to the effect of: “We don’t feel connected to famous artists [entertainers… musicians… actors] because we think we KNOW them. It’s because they help us to know OURSELVES.”

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

Aside from Stevie Nicks… I’d love to chat with Brandi Carlile. I’m really inspired not only by her music, but by the way she uses her platform to amplify social justice issues and the voices of other marginalized folks.

How can our readers follow you on social media?

You can follow me @JessyeDMusic on both Twitter and Instagram, and @JessyeDeSilvaMusic on Facebook. If you’ve got Spotify, follow me at

This was very meaningful, thank you so much!

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