Announcing “Dream Big Darling” by Jade Jackson
official release of our Anthem
When Jade Jackson agreed to perform at a Dream Big Darling retreat, she quietly carried a hope: to give back to a community that had always held her. On the drive to Parkfield, CA in June 2025, as she marveled at the vineyard and hills passing by, inspiration for a song struck—one that would become the official anthem for Dream Big Darling. What began as music notes handwritten in the car, has become a much-loved piece that shares the story of women lifting each other up.
In the interview below, she opens up about inspiration, creative risk, and what it means to let a song become communal.
Show your support AND download the song!
Watch the official music video here
“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.”
Click to read our interview with Jade Jackson and get a behind-the-scenes look at the creative songwriting process.
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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.
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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.
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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.
Our Song, our story
A note from Amanda Wittstrom-Higgins
I believe music is magic. It has the power to evoke deep emotion, to transport you, and to remind you of who you are and what you stand for. For as long as I can remember, I've wanted a song for Dream Big Darling. I’m not a great singer myself, but I’ve always been drawn to how a simple melody can become the soundtrack to a community and a movement. For years, I had conversations with my dear friend and Central Coast musician, Jade Jackson, about this dream. But life, contracts, and other obligations meant the timing wasn't right. The universe, however, has a way of knowing what’s best for us, even when we don't.
This year, the stars aligned. After our annual retreat in the hills outside of Paso Robles—an incredible weekend of nature, adventure, and community—Jade gave us a gift more special than we could have ever imagined. She was driving to the retreat with her sister, Audrey—the same Audrey who created the beautiful artwork for our One Stone Wine project—when inspiration struck. That night, as the final song of her set, Jade played a brand-new song she had just written. “I haven’t even played this all the way through yet,” she said. The song was for us, for Dream Big Darling, a tribute to our mission of moving one stone at a time to build a mountain. The lyrics captured the very heart of our organization. It was an anthem.
I knew in that moment we had to record it. The world needs more joy and more powerful, heartfelt messages, and this song was a beacon of both. Jade recorded the track in Nashville, and as she was returning home to California, my mind raced with ideas for a music video. At first, I thought it would be a personal tribute to my grandmother, who always called me "darling," and to the next generation, including my own daughter. But I quickly realized the most compelling story was right in front of us: Jade's story.
She is a young woman who has overcome so much. She is still moving one stone at a time, pursuing her passion in an industry that is incredibly tough. So the video became a tribute to her journey, to the beautiful, unconditional love between her and her sister, Audrey, who quietly and powerfully shows up for her every day. It’s a story about the simple, profound gift of presence and truly loving someone for who they are.
The video also became an adventure for us. I knew I wanted to incorporate horses—a true love of mine—and a bucket-list item for Jade was riding a horse on the beach. Before the shoot, she came over for three days, and we spent hours riding and talking. The moment she touches the horse in the video, she is transported into a dream world where anything is possible. We found the perfect place to symbolize this journey: the Clark family’s beautiful, steep-hillside chapel in Shandon. For Jade, it represented a climb toward a deeper connection with God, and for all of us, it’s a powerful symbol of spiritual health and our ability to climb any mountain. Seeing her in that long, flowing dress at the top of the hill was absolutely magical.
And of course, we had to get her into authentic cowgirl gear, with the fringe vintage lambskin jacket and turquoise jewelry, thanks to our friends at All Good Supply Co. My cousin Tami even helped with her makeup. Seeing the "little cowgirl" in the video, we're reminded that the next generation is always watching us. They're watching how we handle failure, how we succeed, and most importantly, whether we get back up when we fall down.
This entire project was a dream come true, and a testament to the power of community. It was a true gift to work with Jade, Audrey, and all of our friends to bring this vision to life. This song is our story, a reminder that we can build mountains, one stone at a time, and that the greatest gift is the love and support of those who quietly cherish us along the way. I hope you enjoy our song, "Dream Big Darling."
