We recently connected with Natalie O’Sullivan Hamilton and have shared our conversation below.

Natalie, thanks for taking the time to share your stories with us today We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.

I think one of the most important risks I’ve taken is quitting my full time job – and I’ve taken that risk several times! Bobcat Goldthwait once said: “You keep quitting until you end up someplace you don’t want to leave and then you’re happy.” I really believe in that philosophy. I’ve left jobs for several reasons, but mostly when I’ve parted ways it’s because there’s a creative opportunity presenting itself to me in such a way that I cannot risk regretting, or never giving myself the chance to try. Here’s the handful of significant times I’ve quit stable jobs: in Chicago, I quit to move to the East Coast because I’d never lived anywhere else outside of college (a change of scenery is a completely valid reason to leave!) Then, I left my job and that city to pursue comedy and acting more seriously in New York City. There, I was encouraged to explore the realms of film and TV production, so I left my full-time position to pursue freelance work as a production assistant and associate producer. Just about two months ago, I finally left my remote associate producer gig to focus my attention on my creative skills.

As a multi-interested artist, I’m happy to have my hands in several projects at the same time. I do not regret leaving any of my day-to-day positions to take the chance to build from and add to my creative well. Of course it can be daunting, and of course there are days when I feel doubt or discouragement, but I have to know at the end of the day the risk is worth it. I really couldn’t do it without the people around me who have my back: my husband Ian, my family, and my friends. They’re my biggest cheerleaders and I’m always so grateful for their support in my endeavors.

Natalie, 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?

I’m an Austin-based actor, writer, and collaborator with a background in comedy performance and sketch writing, something I’ve enjoyed since I was a teenager in Chicago. My acting skills range beyond the stage – I’ve been on screen in short films, online sketches, music videos, and commercials. I’ve lent my voice and writing talents to several podcasts like One and Done TV and Mr. Bunker’s Conspiracy Time Podcast. Plus, I’m a proud member of the Writers Guild of America – East!

I’m a bit of a Jill of all trades with an eye for design – I like performing as much as I enjoy arts and crafts and getting my hands and overalls dirty! Currently, I’m at the beginning stage of starting a home interiors business called Cottontail Nest, one that mixes DIY/upcycling with reorganization and custom wall art. It’s a lot of “zhuzhing” – I’m a zhuzher! I really love that I’m able to balance this gig with my acting goals while helping people make their homes look more like and feel more comfortable and more suited for them.

I’m super excited to share that I’m working on a short film with my husband Ian called Designer Cuts for Men. It’s a piece that has bloomed from a 5-page sketch into a 15-page script. The story is an ambitious comedy about how far a hyper-wealthy couple will take cosmetic surgery to improve their status and legacy. Ian is directing and I’ll be playing the lead female character – I’m thrilled to be back in front of the camera again! We’re currently in the pre-production stages at this time, but we have an incredible team of producers, production designers, and an amazing DP to boot! I cannot wait to share this story with folks from around the world and I hope they get as much of a kick out of it as we all do.

I’m really proud that on any given day, I can work on a home improvement project that helps someone else, a collaborative project with Ian for Lack of Hustle Media (our production company), and I can take some time just for myself – all in the same day! It takes balance, time management, and confidence to juggle my passions. Every day there are lessons learned and mistakes made, but I’m so happy I get to work on cool creative endeavors without being too stressed out, bored, or burnt out.

What’s a lesson you had to unlearn and what’s the backstory?

Somewhere along the road, imposter syndrome hitched a ride with me on my journey. It’s a negative reinforcement that causes you to hold yourself to higher standards while riddling you with self-doubt and unworthiness. Let me tell you, it’s a really awful feeling! Imposter syndrome is a “lesson” I am still unlearning. I don’t know if it ever really goes away, but there’s certainly tactics I’ve started using to combat it – cognitive behavior therapy and challenging irrational thoughts. I believe some of this stems from being multi-interested. Sometimes I think it would just be easier if I could just focus on one thing, but I don’t believe I would be satisfied. I would still be yearning to perform or design or write. Sometimes I feel greedy or guilty for wanting to do all the things I enjoy – but I’m not trying to be the very top tier Olympic gold medalist in all my creative interests. I’m really just trying to enjoy my time doing work I love to do. I have to remind myself that I’m using my skills for good. Even if I’m doing something just for myself – especially if I choose to do something for myself. That’s really good!

Is there something you think non-creatives will struggle to understand about your journey as a creative?

I think the struggle to understand my journey might come from thinking, “Girl, you are all over the place!” when in fact, I am right where I want to be when I want to be there, doing what I want to do while I’m there. There’s strength and character built in that knowingness! I hope “non-creative” folks won’t struggle with understanding that you, too, are allowed to be creative! I’m not sure that all people are open to accessing that gooey visceral part of themselves that houses the creative well, and that’s fine. But I would challenge folks to at least try, even a little bit. Write down some song lyrics, take a photo of something beautiful, get some colored pencils and doodle, try cooking something without a recipe! Follow the feeling and see where it takes you, even if just for a short amount of time. Let yourself be where you want to be when you want to be.

Contact Info:

• Website: http://natalieosullivan.com
• Instagram: https://www.instagram.com/cottontailbandit/
• Linkedin: https://www.linkedin.com/in/osullinat/

Image Credits
Justin Lynk