Announcing “Dream Big Darling” by Jade Jackson

Q: The story of you writing the “Dream Big Darling” song in the car on the way to the retreat is truly magical. Can you take us back to that moment? What was going through your mind?

A: I’d wanted to write Amanda a song for her non-profit for years, and when she invited me to perform at the retreat, the timing just felt right. On the drive over, the song just poured out and finished itself. I wasn’t sure I’d be brave enough to play it, but my sister told me to “vibe it out”—basically, just go for it if you’re feeling it. So I did, and it ended up being one of the most meaningful moments I’ve shared on stage as a songwriter.

Q: The lyrics perfectly capture the mission of “moving one stone at a time.” What specifically about the Dream Big Darling community or your own journey inspired this powerful metaphor?

A: My sister Audrey painted the label for One Stone wine, which Amanda started alongside Dream Big Darling. Years ago, I asked Audrey what inspired her artwork, and she explained Amanda’s vision: if one person picks up a stone, it doesn’t feel like much. But when you picture a whole group of people, all with the same mission, moving stones together, it suddenly becomes possible to move something much bigger. That metaphor really stuck with me, and it shaped the song.

Q: Music is often deeply personal. What does this song mean to you, now that it’s become the official anthem for Dream Big Darling?

A: It feels like something bigger than me now. I love when a song starts personal and ends up belonging to everyone.

Q: You’ve been connected to the Dream Big Darling community for many years. How did those previous experiences and the energy of the retreat influence your songwriting for this specific piece?

A: The retreat created an atmosphere of “try new things,” which gave me the courage to share the song even though it wasn’t polished. That supportive energy made all the difference.

Q: What was it like to share this song for the very first time with the Dream Big Darling community, having just written it?

A: With new songs, you never know how they’ll land. I asked myself if I’d still stand behind it no matter what, and when the answer was yes, I played it.

Q: The music video is a beautiful and personal narrative. How did it feel to tell your own story and showcase your relationship with your sister, Audrey, in such a public way?

A: It all came together naturally. Amanda encouraged me to include pieces of my own story, which made it more meaningful.

Q: The video incorporates so many meaningful elements: the chapel, the horses, the beach. How did you feel about these concepts being woven into your story, and what did you hope to convey through them?

A: Capturing all those epic locations in one day felt like a love letter to my hometown, the Central Coast. No matter where I tour, there’s no place like home. 

Q: You mentioned the experience of riding a horse on the beach was a “bucket list” item for you. What was it like to fulfill that dream and have it captured on film?

A: It was pure joy—like living a dream and getting to keep it forever on camera.

Q: The video shows a powerful transition from a long, flowing dress on a hilltop to authentic cowgirl wear. What did this visual transformation represent to you personally?

A: It shows how multifaceted we are. Some days I feel like wearing a ball gown, some days jeans and boots. There’s no need to box yourself in when you’re creating. Go where the flow takes you. 

Q: The video is a collaboration with so many people who love and support you. What was it like to have your friends and family, including Amanda and her daughter, become a part of this creative project?

A: It was the best part. It reminded me of filming my music video “Finish Line,” which felt like a glorified home video with people I love. I can dress my art up and make it cinematic, but at its core, it’s still about real relationships. Having friends and family there made it easier to translate those emotions.

Q: Amanda’s essay about the song and video mentions how this project came at a time when you were able to “call your own shots” and direct your own future. How has this experience, both creatively and professionally, impacted your journey as a musician?

A: It gave me confidence to continue to create without waiting for permission or validation.

Q: What message do you hope people take away after watching the “Dream Big Darling” music video?

A: That small steps matter. You don’t have to do everything at once—just keep moving forward and you’ll get to where you need to be. 

Q: Now that you’ve had this incredibly personal and collaborative experience, what’s next for you? Are there other projects or creative endeavors on the horizon that you’re excited about?

A: Yes. I’ve spent the last year writing and recording a new record. Before I begin to release the full record, I have two other special songs up my sleeve that I plan to share in the upcoming months. 

Q: How has your relationship with the Dream Big Darling community evolved since you first became connected, and what does it mean to be a part of it?

A: At first it was inspiration, now it’s family. This community proves that when people lift each other up, incredible things can happen.