We’re excited to introduce you to the always interesting and insightful Kailee Shedeed. We hope you’ll enjoy our conversation with Kailee below.

Hi Kailee, thanks for joining us today. Can you recount a story of an unexpected problem you’ve faced along the way?

I had just finished film school at UCLA Extension – a short two year program in directing – when the pandemic hit. I had to move home from LA, and basically for a whole year had to live with people online saying how dead the industry was. How movie theaters were never coming back, how businesses had to close, how films going straight to streaming would be the new norm. I was at my lowest that year, as I watched and read about how everything I worked for was essentially gone. There didn’t seem to be a way to come back from this, and the future was so uncertain, for everyone and every thing.

I began reconsidering my future, and was looking into college programs for Funeral Science, but my dad sat down with me one day and told me that doing anything else with my life was not an option. Film is my one passion that I’ve carried since I was young, and my dad really championed me into not giving up on all my schooling that I had just completed.

The funny thing is, every year since then people have said the Industry is dead. It’s a really common refrain. Every year it has felt like catastrophe has hit Hollywood, and yet I’ve kind of given myself no other options except to keep going.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I am a writer and director currently living and working in Los Angeles. Since 2021 I’ve been working on short films — I hate when people ask “what kind” because I think genre can be really limiting–but for the most part my films are dramas. I have a production company called Office Cowboy Productions, and I’ve been lucky enough to make most of my shorts with the same core team for the last four years. They were my friends first, but when I found out about their individual creative gifts I was able to pull everyone together to make a short called “Ersatz” in 2022. After that experience we really learned how to work with each other, and we made another film last year called “I’d Rather Die,” and now we are in preproduction for my next short called “I’m Your Man!”

My previous films have done well with festivals, but with this next one I hope that my career as a filmmaker can really start to gain momentum. I feel I’ve just been in learning stages for the last couple years, but I’ve gained a lot of confidence in myself and my abilities, and feel like I’m ready to move beyond making short films and hopefully get the chance to make features. I think this is something that sets me apart from my peers: short films aren’t a stepping stone, but a practice arena. Its the venue for crafting your style and your voice, and while a lot of people tell me I’m too hard on myself, the truth is that I can see the caliber of filmmaker I want to be, and I know that I have some distance until I get there. I believe that this next short will give me a real chance to show that.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I think something I’ve been unlearning is the idea of an auteur. I think directors helm the ship, and I do think that many directors are auteurs in the sense of their creative instincts and sense of style. But there’s something about giving the director total credit for the production of a film that just doesn’t ring true for me anymore, now that I’ve made films of my own. A film is so completely reliant on the collective effort of every cast member and every crew member. It would have been impossible for me to make any of my films alone. The ideas and energy that my friends have brought to every film has been the thing that kept me going. Because I doubt myself a lot! And their determination to continue on, even when I felt like it was impossible, has been the most important gift I could have ever received.

Have you ever had to pivot?

“Pivoting” is basically what filmmaking is. Things rarely go exactly the way that you plan for them to! I’ve had to pivot so many times on so many projects.

On my last film, I had a “producer” who told me that he had raised two thousand dollars for my short. He didn’t have any proof of this money, but he reassured me for months that it was real, contributed from people who had read the script and wanted to support him. Meanwhile I was still crowdfunding on my own, and had managed to raise only half of the budget that I wanted. So when I finally got my DP and crew locked, ready to move forward with actual production, that producer ghosted me! He wouldn’t respond to texts or calls or emails. He completely disappeared. Whether the money he promised was actually real or not, I don’t know. So I was two thousand dollars short in my budget that I thought I needed to make the film, but then I changed my plans. I rewrote the script to be cheaper, changing locations to my production designer’s apartment and a soundstage. We found another producer to help us out, but when we presented them with our plan, they told me I had basically done all the work already and didn’t need much help! It was a huge compliment to me, and probably the most unexpected thing that I enjoy about being a filmmaker is having to problem solve in this way. At first it might feel like the world is ending, but movies are so malleable that no curveball can really be the death of a film.

Contact Info:

• Instagram: officecowboyy
• Other: Vimeo: https://vimeo.com/user60004665

Image Credits

Set photos by Andrew C. Phan