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

Katie , appreciate you joining us today. How did you learn to do what you do? Knowing what you know now, what could you have done to speed up your learning process? What skills do you think were most essential? What obstacles stood in the way of learning more?

I was 29 years old when I realized I wanted to work in film. To set the scene, I had been working corporate jobs for most of my career, and had never imagined that I could make a living as a creative. I’ve always loved writers and writing, but something about sitting in a room alone day in and day out felt misaligned for me. It wasn’t until I started doing The Artist’s Way that I began to figure out I really wanted to write for film, because film is the exact opposite of a solo endeavor. And not only did I want to write for film, but I wanted to direct.

This idea – that I could be a director and a screenwriter – felt WILD to me, and candidly I would experience crippling overwhelm anytime I started to think how I could make the shift from a Business Marketing job to filmmaking. I began to take one step at a time: I started reading books like Save the Cat, watching masterclasses led by Aaron Sorkin, and scheduling countless phone calls with anyone I was remotely connected to who touched the film industry. Everyone I spoke with said the same thing: there is no better way to learn than by doing.

I swallowed my pride, knowing the first thing I would make would fall short of my expectations for myself, and decided I would do it anyway – I would write and direct a short film. I quit my job and poured (quite literally) every dollar of my savings into the short film. (A very important note: this is not a necessary step for everyone, but it was a necessary step for me. My personality type needs something at stake to force me into action – “jump and the net will appear” was my motto during this phase of life.)

Through this process of creating my first film, I listened to an interview with Greta Gerwig on Sam Jones’ podcast religiously, where she talks about the beauty of the beginner phase; when you aren’t yet aware of the limitations, you can’t be hindered by them.

So for example, I wrote a 16 page script, with 8 pages of it happening as a one-shot walk-n-talk through a New York City public park…and I figured we could shoot it in two days. For reference – there are about 1000 limitations and challenges that will come up with a plan like that, and those limitations double when you factor in a first-time director and a minuscule budget.

I learned more in those two days shooting than I could have learned reading 100 books on how to make a film. Any time I felt ashamed of not knowing the “right” way to do something, I tried to remember Greta’s advice to embrace the beauty of beginning.

Someone asked me not too long ago what the happiest moment of my life has been so far. I reflected for a second, but quickly knew it was the moment that we had this first short in the can. I had done it – I had charged into the darkness, daring to not do things perfectly. I had leaned on a much more experienced crew and actors to usher me along the way. I had been humbled, I had been inspired, and I had made a story I wanted to tell. It felt electric.

Since then, I’ve directed two more short films, written a feature, and produced countless commercials, brand activations and events to pay the bills as a freelance creative. I’m currently attached to a feature in development as a producer, and I’m editing the first thing I directed that I did not write myself. Every single thing I do right now, I learn from. It’s not always easy and it’s not always fun, but it informs the way I write, the way I direct, and it allows me to learn from people who have been doing this much longer than I have.

So, my advice is to simply…. start. So many of us are scared to make the first thing because we believe it won’t be as good as we want it to be. Let me go ahead and tell you: it won’t be. But it will make the next one better, and move you one step further towards the life that you are envisioning. And you just might get the best moment of your life from it.

Katie , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

My name is Katie Cunningham and I’m a director, producer, writer, and consultant living in Los Angeles. I love the diversity of work that my career brings: from writing and directing narrative films for brands, to consulting for powerhouse women on their latest ventures, I combine my passion for people, my love for writing and producing, and my background in marketing to bring unique projects to life over and over again.

I’m a lover of movement (yoga, dance, and any workout Deuce gym makes me do), Armchair Expert, a long catch up with a friend, every frame in a Nancy Meyers’ film, and the ambiance of chatter and steaming milk exclusively found at a coffee shop. I’m a gemini, cancer rising and sag moon, a 6/2 human design, and an enneagram 2. (Do with that what you will.)

Professionally, I’m most proud of the narrative piece I created with an outrageously talented group of people for Marly Garden. (It is currently up for Short of the Year on ShortFilmsMatter.com. Please vote us up!) Personally, I’m most proud of the relationships I have in my life and my commitment to earning my 200 hour certification in yoga this year.

I spent my first 18 years of life in Southern Pines, North Carolina before earning my bachelor’s degree at UNC-Chapel Hill. By way of Texas and New York, I now live in LA with my boyfriend and my dog, Petey, who has earned the nickname The Mayor, treating every person who walks by the house as his constituent. He “found” me, thanks to fate and a coffee shop, on my 34th birthday.

I write at katiemaysay.substack.com and you can check out some of my other work at katiemaysay.com.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

I’ve always been fascinated by the idea of “freedom.” As a freelancer and creative, I once thought the ultimate freedom was the ability to work for myself, make my own schedule, and do what I love. But the biggest lesson I’ve had to unlearn is that true freedom doesn’t come from avoiding structure—it comes from embracing it.

In my opinion, being your own company requires more structure and discipline than a traditional 9-to-5 job. I know I’m an entrepreneurial broken record right now, but it really IS about setting boundaries, establishing routines, and creating systems. (I know I know, I just eye-rolled myself, too.) Candidly, I am still figuring out how to do this, but one practical change that’s been transformative is I’ve started physically writing out my weekly schedule every Sunday. There’s something grounding about physically time-blocking out my calendar every week, (but I still use pencil instead of pen because I’m a realist…) When you write something down, it reinforces your commitment to make it happen.

There are so many other hacks around creating structure to give yourself true freedom. Jenna Kutcher shares a lot about her routines and her tech stack for organization and is a great resource if you’re on this journey to structure as well.

Have any books or other resources had a big impact on you?

There are countless books, podcasts and videos that have shaped the way I approach my business, my art and my life. These are the ones that I either return to again and again, or changed my life on the first read:

The Tools by Phil Stutz
Stolen Focus: Why You Can’t Pay Attention by Johann Hari
Heart Talk: Poetic Wisdom for a Better Life by Cleo Wade
Mind Magic: The Neuroscience of Manifestation by James R Doty
Letters to a Young Poet by Rainer Maria Rilke
You are a Badass by Jen Sincero
Little Weirds by Jenny Slate
Atomic Habits by James Clear (his newsletter is great and his conversation with Brene Brown on her podcast truly rewired my brain)
The Power of Now by Eckhart Tolle
The Artist’s Way by Julia Cameron
Untamed by Glennon Doyle
The Body Keeps the Score by Dr. Bessel van der Kolk
Everybody’s Free to Wear Sunscreen by Baz Luhrman
Jason Segel on Armchair Expert
Greta Gerwig on Off Camera with Sam Jones

Contact Info:

• Website: https://www.katiemaysay.com/
• Instagram: https://www.instagram.com/katiemaysay/
• Other: https://katiemaysay.substack.com/

Image Credits

1. Tyee Tilghman
2. Ill Gander
3. Still from Didn’t Hurt at All
4. Still from Grow
5. Katie Cunningham
6. Kaseberga
7. Behind the Scenes of Didn’t Hurt at All
8. Sean Brennan