We’re excited to introduce you to the always interesting and insightful Jenna Cipolloni. We hope you’ll enjoy our conversation with Jenna below.
Hi Jenna, thank you so much for opening up with us about some important, but sometimes personal topics. One that really matters to us is overcoming Imposter Syndrome because we’ve seen how so many people are held back in life because of this and so we’d really appreciate hearing about how you overcame Imposter Syndrome.
The short answer is: I didn’t. Rather, to me it doesn’t feel as though imposter syndrome is a physical beast to slay, but a state of mind that I can drift in and out of depending on my current mentality.
It seems like it’s entirely up to myself. I’ve had nothing but constant support from mentors, friends, and coworkers, but it’s my own voice in my head that consistently tells me I’m doing a bad job. I think part of this is that I’m still young and relatively new to the art that I’m making, or maybe because I’m not necessarily where I’d like to be in my career. But realistically, I know that no matter my number of accomplishments and how far along I progress both professionally and personally, I will always be prone to hearing a voice that says I don’t know what I’m doing and that everyone will find out.
I think half of feeling this way is comparing myself to others. I look at my peers who are up to all kinds of respectable things and it’s hard not to think I’m lagging behind them. But the reality is that I’m ALSO doing those things and just not giving myself any credit, or that some of those items aren’t part of my goals, or that I have different successes that I throw out the window when compared to someone else. My imposter syndrome gets better when I write my accomplishments on paper, because I can see a consistent track record of things I’ve done without feeling in-the-moment like my current position is a fluke. It’s easy to forget your entire history and sum of your parts when you see a single success attributed to another person, and it’s frankly uncool to do that. Others deserve success and fulfillment as much as you, and insecurity can quickly turn to bitterness if left unchecked.
Supervisees have told me things improved under my management. Colleagues have said they’d be lost without my guidance. Teachers have said my assignments were some of the best they’ve seen. My film and writing have received nothing but positive feedback. But none of it swayed my opinion of myself whatsoever, at least not long-term. At a certain point, it gets ridiculous how much you tune out in the name of insisting to yourself that you’re a fraud. But that’s what imposter syndrome is. It’s a stubborn, insidious delusion that’s determined to undermine your value through detachment of reality. But I like to think it’s at your mercy, rather than you’re at its.
An old boss of mine, a photographer who I admire very much, says he doesn’t feel imposter syndrome anymore only because he’s had decades to make mistakes and learn from them. To him, imposter syndrome simply becomes obsolete with time and ability. Like, the more mistakes you make, the more things you do, the more problems you solve, it all contributes to chipping away at this self-doubt until you find yourself finally feeling confident in your capability just due to the fact that you’ve done it before. And I think that applies to me. Some days I go about my business and I realize I haven’t felt self-doubt that day. It’s never a eureka moment of, “I’m not a fraud anymore!” But rather a passive realization of, “I haven’t felt like a fraud in a while.” It’s fluid, it’s irrational, and I think it’s completely normal, especially in a creative field.
Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?
I’m a Maryland-based writer and filmmaker. My short film “Concealer” has been shown in various film festivals across the Mid-Atlantic and won several audience awards, including Best Direction and Best Experimental Film. Poems from my self-published zine “School Nights” have won community competitions such as the Des Moines Poetry Slam. In 2023, my poem “Names” was featured in the debut exhibition of Havre de Grace’s Gallery 220. I served on the screening committee for the 2024 Maryland Film Festival and the selection committee to nominate the state’s next poet laureate. You can usually find me at local open mics or arts events.
I’m currently working on a feature-length horror anthology as a production coordinator and segment writer/director, of which I aim to shoot by this summer. The movie and the company behind it, Potential Strangers LLC, is a joint endeavor between me and several colleagues, and we hope to see the film released by 2025.
There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
I want to preface that these are things that have been helpful to me, and may not apply to everyone. I’m also still young and building my career. But these are thoughts I’ve had and advice I’ve gotten that I’ve had to grapple with in my effort to take my work more seriously.
1. Self-reflect strongly, but fall into yourself
This is essentially “be yourself” but taking it a step deeper. If you’re a filmmaker, you’d normally receive the advice to watch everything to be worldly and develop your style, which is good advice. But I’d also add a layer of introspection to ask yourself what types of films you like and what types of films you want to make, and go and seek out a broad expanse of those niches specifically. My favorite art is usually very identifiable and attributable to the artist, and to make unique art it helps to have a level of self-introspection. What are your interests? What’s your story? But also a level more personal: What do you care about? Who do you love?
In my personal life, I truly believe that I need to be unabashedly myself in order to attract people who have similar ideals and behaviors. This has caused like-minded people to gravitate into my life and created very strong, long-lasting relationships. I don’t treat my art any differently. I believe that if I make art that is utterly myself, it will attract an audience that connects with me and vice versa. I think a common pitfall of beginner filmmakers is that they create films they think they SHOULD make, or films that SHOULD be popular, rather than films that come from their own heart. If you have a favorite artist, it’s also worth evaluating why/how their art comes from their own heart, and it helps to consume THEIR favorite media to see what inspires them. Ask yourself why you like their art and what it means to you. At the same time, critique your own work and figure out what ways you can improve. Understand yourself, your darkness, your truth–or don’t, do something with that too! This sort of leads to the next point.
2. Have understanding and empathy for the human condition
I genuinely care about other people, and experiencing new things is a passion of mine. I love meeting people of all facets and getting to know their subsets. In short: I like knowing what’s up. That doesn’t mean I get along with everyone or even should, but it’s valuable to me to see how people act firsthand. This causes me to have a greater understanding of the world and people around me, what others care about, what parts of our own worlds are alien to each other. Understanding others helps me understand myself. It helps me write believable characters and find the heart in the world, as well as my place in the grand scheme of things. Media created by well-informed individuals has a sense of reality behind it. It makes antagonists have realistic motivations, it prevents stereotyping, it creates better representation, it tells more original stories, and it’s just more engaging overall.
3. We’re all wearing fur coats with nothing underneath
This is actually some advice my film professor gave me, which I’ll never forget. It relates to imposter syndrome and remarks that we’re ALL imposters, but it also means that there’s no secret barrier where illegitimate things become legitimate. There’s not some network of insider professionals who have superpowers that you don’t.
Using film as an example, it’s easy to think that professional sets are, like, ontologically separate than movies you made in the backyard as a kid. And while there are obvious differences, especially when dealing with unions and finances, there’s no corporeal threshold where you suddenly evolve from an amateur to a “real” filmmaker. Sure, there are industry standards and procedures and much more expensive equipment, but there’s also usage of everyday items like clothespins (they’re called “C-47s” to make it sound technical). This idea helps to legitimize yourself in all knowledge levels. And when you get behind the scenes of people much more experienced than you, you see they’re still just human beings and they still do–to be frank–the same stupid bullshit you do as well. I think this is true for a lot of fields. I’ve seen my seniors break rules, make mistakes, and feel insecure, because the only difference between you and them is your level of experience. And that’s completely within your grasp.
Okay, so before we go, is there anyone you’d like to shoutout for the role they’ve played in helping you develop the essential skills or overcome challenges along the way?
I can’t attribute it to any one person, since I’ve been so fortunate to be supported by so many people throughout my life. I had two English teachers in high school who made me feel very confident in my writing ability, and to this day I aim to make them proud with my work. My parents put me through school and have given me the opportunities needed to thrive. My friends have been my greatest cheerleaders and source of improvement, and our constant intellectual conversations about art have shaped my entire worldview and urged me to really live into myself. My college professors always encouraged me to take risks and strive to do what I want to do.
But I want to give a particular thanks to my fellow colleagues at Potential Strangers LLC, J.B. Yaskovich and Brooks Vernon, without whom my art would be theoretical. They taught me that I could make really good work at the level I’m at now, and that I don’t need to wait for some hypothetical opportunity where the stars align to finally grant me the ability to make art–it’s something tangible that I can do right here, right now. I think the three of us are on the precipice of something good, and I’m excited to see what comes next for us.
Contact Info:
- Website: https://jennacipolloni.com/
- Instagram: https://www.instagram.com/jennacipolloni
- Linkedin: https://www.linkedin.com/in/jenna-cipolloni-a9368112a/
- Youtube: https://www.youtube.com/channel/UCQFSnlouJCQSvNtjbGCy47A
- Other: https://www.potentialstrangers.com/

Image Credits
Lyndsay Nissen Isabella Otterbein Liz Robley J.B. Yaskovich
