Jessie Berkshires shared their story and experiences with us recently and you can find our conversation below.
Jessie, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What is something outside of work that is bringing you joy lately?
Recently, I started oil painting at a local art school, and it’s been bringing me so much joy. I love the process—learning a new skill, meeting new people, and giving myself permission to be a beginner again. As a creative, it’s always exciting to apply that same creative mindset to something new. I often find myself listening to demos I’ve been working on while I paint, kind of zoning out and letting the two worlds blend together. It’s been such a fun and grounding experience.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Jessie Berkshires, an independent artist and musician. What makes my project special is that everything is created collaboratively at home with my husband—we write, produce, and build the world around the music together. We each bring our own complementary skill sets to the process, and we love inviting friends into that space to collaborate and experiment. It’s a very DIY, community-driven approach that keeps the work honest and evolving. This year, I’m releasing new singles, including a new remix of my 2024 track “Enough,” and continuing to explore darker, more textured sounds.
Great, so let’s dive into your journey a bit more. What part of you has served its purpose and must now be released?
The part of me that has served its purpose—and is ready to be released—is the version of myself that held onto songs just to carry the weight of them. In 2025, while working on my EP Sad Girl Summer, I realized I had accumulated this massive collection of demos, like so many songwriters do—songs that needed to exist, but didn’t need to be carried forever. Releasing them felt like getting things off my chest, emotionally and creatively. Letting that part go has opened up a new perspective and is actively shaping how I approach my creative process moving into 2026—lighter, more intentional, and more present.
What did suffering teach you that success never could?
Suffering has taught me resilience and persistence in a way success never could. Success can feel validating, but suffering is what teaches you how to keep going when no one is watching, when the outcome is uncertain, and when belief has to come from within.
So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. How do you differentiate between fads and real foundational shifts?
For me, it usually comes down to how something feels after I’ve stepped away from the social media doom scroll. I think it’s important to stay curious, take in new ideas, and learn from what’s out there, but not everything needs to be absorbed or acted on. Fads tend to feel exciting in the moment and then kind of hollow once you try to apply them. The things that really matter stick with you and naturally weave their way into your work over time. Staying true to yourself is what keeps the work feeling genuine instead of contrived.
Okay, so let’s keep going with one more question that means a lot to us: When do you feel most at peace?
I feel most at peace when I’m somewhere new. There’s something about a new experience, a new city, or a new country that quiets my mind. It pulls me out of routine and into the present moment, and that sense of discovery feels really grounding for me.
Contact Info:
- Website: https://www.jessieberkshires.com/
- Instagram: https://www.instagram.com/jessieberkshiresmusic
- Youtube: https://youtube.com/@jessieberkshiresmusic?si=vRsVO9zIZVdhpAOd
- Soundcloud: https://soundcloud.com/jessieberkshires
- Other: https://open.spotify.com/artist/0XZ4qfQflc5EIacR9cNyeK?si=99_z7DY-QKW30DT1HgqD1g
Image Credits
Rico Anthony
@ricoisevil
