We caught up with the brilliant and insightful Rebekah Iliff a few weeks ago and have shared our conversation below.

Rebekah, thanks for taking the time to share your stories with us today To kick things off, we’d love to hear about things you or your brand do that diverge from the industry standard.

I am about one year into building my fourth career business called Free Dreaming Farm (https://freedreamingfarm.com/). My husband and I bought the 15-acre farm roughly 30 miles north of Nashville, TN about a year ago. We live on part of the property while the other part is used to produce film/commercial projects. We have already co-produced campaigns for major brands and hosted several of country music’s biggest stars to shoot promos at the farm. I am also producing client commissioned work and developing my own creative projects under the Free Dreaming, Inc. umbrella.

Currently, I am also working in collaboration with the Tennessee Entertainment Commission to attract more film and television projects to this rural part of the state. Not only does rural Tennessee offer an incredible selection of historic sites and quaint main streets, but small towns are an amazing place to find hidden talent; and they are excited to see new things happen in their local area.

From 25 years of working in the entertainment and tech industries, I have an expansive network of talent and crew, as well as access to filming locations and studio space. This makes our particular area (Robertson County) a unique place to create and watch “Americana” stories come to life. Ultimately, I’m re-imagining what it means to own a production company and work with major brands: you don’t need to be on the coasts to do it, and rural America and small towns are rife with opportunity and nostalgic backdrops. I lived in Hollywood for many years, and then the Bay Area for six years; and I worked in New York and every other major U.S. city before settling in the Nashville area. I am committed to working with good, freedom-loving, creative people who are willing to think outside the mainstream box; and I’m already well on the way to making my dream a reality.

Rebekah, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

As I mentioned before, I’ve been in the entertainment and tech industries my entire career. My first job, at the age of 20, was as a professional ballerina. From there I naturally moved into production, marketing, and public relations, because I loved all aspects of working extremely hard at something, then watching it come to life—and have people appreciate the outcome. In some ways, I suppose there has always been a “performance” element to my work. Not in the gross way we think about performing now, on social media and as a way to attract endless attention, but in terms of the artistic pursuit. I absolutely get a thrill thinking about the best way to craft and tell a story, then figuring out the best way to deliver it. Sometimes that is through a compelling essay; sometimes a piece of music composition; or other times a short film.

In February 2022, I released my first book, Champagne for One, along with a short film to accompany it. Since both releases, the book has picked up four indie awards, and the film has won over 14 awards on the film festival circuit—this was unexpected and a pure rush of joy. I am so proud of the project and all its success, and it is what has launched this next phase of my career as a writer and producer. Now, I’m starting to not only conceptualize and produce creative campaigns for major brands, but I am also working with seasoned creatives on a variety of interesting, thought-provoking projects.

At the end of the day, I really want to be a voice against this trend of creating content and storylines meant to divide and add to the noise. My goal is always to look at something from the perspective of an impartial outsider, then figure out a way to tell that story in a way that inspires an audience; or challenges people to think critically (or think differently) about a topic or product. That’s what keeps me going…the drive for that response.

What do you think is the goal or mission that drives your creative journey?

I want to play a critical role in the decentralization of Hollywood. It’s that simple. Talented people shouldn’t have to escape to the coasts in order to find work; I want to help build the infrastructure so they don’t have to do what I did.

Additionally, I want to create jobs where I live and work, and offer young people (who may not otherwise have it) exposure to creative careers

Can you tell us about a time you’ve had to pivot?

I would replace the word “had” with “chose”, and I chose to pivot my career when my best friend suddenly (and tragically) died in 2017. She left behind a five year old daughter, who barely saw her father and whose mother was her whole world. At the time, I was living a few miles down the road in Nashville, and was a major part of her daughter’s life; so, after my friend died I basically “retired” from the tech company I had co-founded and took a year off to grieve and figure out what was next.

Soon, it was clear that the decisions I was making at this point were from a very different perspective, and I didn’t want my work to be the center of my universe anymore. That being said, while the type of work did shift, what shifted even more was the way in which I chose to work. I took a giant leap of faith, walked away from what I’d known for a decade — and let “Jesus take the wheel” as the song goes.

Contact Info:

• Website: www.rebekahiliff.com
• Instagram: https://www.instagram.com/rebekahiliffweaver/
• Linkedin: https://www.linkedin.com/in/rebekahiliff/

Image Credits
Photo credit: Matthew Simmons Photography