Learning What It Means To Be Human with Ashley O’Shay

We sat down with filmmaker Ashley O’Shay to discuss the responsibility behind creating a film and how she uses her space to give people of color a voice. Keep an eye out for her documentary, Unapologetic, and follow her on Twitter & Instagram.



Introduce yourself.

My name is Ashley O’Shay. I am 25 years old, a freelance cinematographer and documentary filmmaker.

Let’s start off with getting to know you as a woman, activist, and filmmaker. How would you describe your childhood and beginning in film?

I grew up in central Indianapolis. I was in private education my whole life and I became interested in film when I was 14. I had a tendency to mess around on my family’s computer when I was younger. I was really excited to put things together. My mom could see my passion and dedication to making videos so she found this youth media education program, Youth Video Institute, that basically trains high school age people in different forms of television and media. I really accredit those years for giving me the opportunity to try things and make bad art. It put me in a really great position when I applied to film school. Eventually, it came down to Northwestern and NYU, but I didn’t think I was ready for New York at 18-years-old. I wanted that traditional liberal arts college experience. Toward the end of my undergrad is when I started getting into cinematography. For a while, I was tiptoeing around it because a lot of the sets were run by men, but in retrospect, I realize now that most were in a similar learning position to me. By senior year I was crew-heading more student productions as an intense approach to my last year of college. But if we’re going back to when it all started, it’s been ten years at least.

In a trailer for Unapologetic, you mention that after you finished your undergrad at Northwestern you had a tough time figuring out “what it meant to take up space and finding the courage to not make yourself small.” What was it like when you were going through that journey?

I felt like I had a lot of narratives stocked up in my mind that I wanted to make, but they don’t really make resources readily available for fresh college graduates. I actually bought a one-way ticket to Oakland where my sister lives after I had moved back home, and I thought if I was in a place near the Bay or LA, at least I would be where the industry was happening. Literally the day I got on the flight, I got an email from Kartemquin Films saying I had gotten into their internship program and at the time, the only reason I would move back to Chicago was if I got that internship. If you’re going to work in documentary in the Midwest, that was where you wanted to be. Ultimately I ended up taking it and a lot of things aligned for me. One of my mentors told me that it carried a lot of risks but working for them would set my career in the right direction. That was one of the first interactions I had that was positive. A lot of close family and friends didn’t really understand what Kartemquin was and it was kind of hard to push against that when you’re also freshly graduated. I won’t say my identity is the only one to go through that struggle of trying to enter the media industry, but approaching from a technical standpoint, it was rare at the time to see women of color in positions of power and in technical positions. If you don’t have someone you can talk to about how to access that, it’s a matter of going to seek something smaller that you can take your skills to as you are.

Do you think you would’ve found the same passions for social justice and self-identity if you hadn’t moved back to Chicago?

I think so! Ultimately, I still had a passion to work in documentary. The sequence of events that happened when I moved back to Chicago to a year later were really just beautiful accidents. I think if it had been more planned, it would not have turned out how it has right now. It probably would’ve still happened, but maybe not as quickly.

For a majority of the time filming Unapologetic, you were living in your friend’s living room and working two jobs. Do you think that’s become an expected lifestyle for creatives?

First of all, I used to joke about couchsurfing. When it actually happened to me, I was like, “This is ironic.” I don’t know if it’s expected, but I think it’s more frowned upon than it should be. The friends that I was living with were in media industries as well and the experience was extremely formative because we were all going through that same struggle simultaneously. Knowing I wasn’t getting much from the internship, they gave me the space to get on my feet. Because I had that space, I was able to start Unapologetic. Once I did what I thought was the worst or most difficult thing you could do as an artist, I felt like I could do anything because I’d literally lived in my friend’s living room for eight months. They were all beautiful accidents. I knew I would have to come back to Chicago because otherwise, I would end up in Indiana, and I didn’t really feel like that was a place where I could grow. This approach can definitely have a negative stigma attached to it and I wouldn’t want to do it again, but it put me in a position that I wouldn’t have been in otherwise. It taught me things that I needed to learn.

Funds are usually an issue for filmmakers. Over time, you were able to raise enough money to get through the first stages of the film, but at times it seems as though there just isn’t enough to go around. When resources are stretched thin, how do you stay motivated?

It’s really hard. Unapologetic went through a momentum from late 2016 to early 2017 where we were hitting the grant and fellowship circuit and going to feedback events and getting funds, and it felt like it was building to one big thing that would take the film all the way to the end. I even pulled back on my job hours because I was able to start paying myself and work full-time on the film. But by the end of 2017, it didn’t happen. We had the money we raised, but we weren’t getting receiving any more grants. Motivation during that time was very fleeting. I think a big source of motivation for me is my main characters because I’ve documented so many parts of their lives. I want to finish the film so they can see their journeys as I was seeing it through my eyes. We usually don’t reflect on social movements until they’ve already happened so the lessons can feel much further away. Leaning on those core pieces of the film that I know the audience will see, and having a good internal team is important. There is accountability for those who support and have large investments in the project. It’s sort of what carries you through.

Do you feel pressure as the project’s director?

I feel pressure all the time. I’m tired all the time! Documentary filmmaking, especially for first-time filmmakers, can be extremely isolating, regardless of who’s around you. I have probably the best support anyone can have as a first-time filmmaker. I have guides I can look to in Chicago and New York and California, but at the same time, they’re not here on November 15th, when I’m in my apartment having to fill out another grant application. There were moments where I knew that if I didn’t move, nothing else would. That’s a lot of pressure to have when sometimes you just don’t feel like it or when you have that calling to move on with your life. I started Unapologetic as a cinematographer, and it didn’t really make sense for me to pass it on to someone else when I was so close to it. But cinematography is my real passion, and only being able to grow that in bits and pieces until the project is done is heartbreaking sometimes. I’m working to get better at asking for help because it’s my natural instinct to do things myself. But at this point, we have a five-person team and there are people around me to help and I’m trying to be better at doing that. Sometimes there’s a ton of muck to dig through that it’s hard to remember what my vision is and my direction for the film. I’m trying to implement journaling and free-writing to help me stay close to that. A lot of things take twice the time than I would’ve thought they would. It’s all about trusting the process.

When people think of filmmakers, they usually think of characteristics like quirky, indie, or independent. When they think of movies, they think of entertainment. However, there are so many genres, such as documentaries, that require more attention. What truths do you want film watchers to know about this industry?

Remembering that filmmakers are humans. Filmmaking can be such a nontransactional space. Coming out of school I saw a lot of people going into finance, business, and law, spaces where you’re often giving something and getting something in return and that wasn’t really my experience. I was thinking, “Why am I a filmmaker? What about the process makes me want to do this for the rest of my life?” The process of making a film is the process of learning what it means to be human on every level of your life. That takes a lot of work and internal reflection and in turn, creates very vulnerable work. Regardless, people can start to see it as another transactional thing. I want to move away from that in my own documentary practice and not make it seem like I have this absolute power over the subjects I’m filming. Last year at a film summit, filmmaker Rodrigo Dorfman shared that documentaries are really just documenting the space of interaction between two human beings. That holds a lot of weight for filmmakers and it’s not something you can easily translate on screen but if it’s happening behind the scenes, you’ll feel it in the work. Also, people should understand that filmmakers are probably working five other jobs at one time and that freelancing ain’t free! Especially when you have a funding gap.

Many marginalized groups spend an entire lifetime oblivious to the oppression that has been set against them because it is so ingrained in American politics. Based on your experience with the film, how would you define activism for those who aren’t trained to identify these forms of institutional racism?

I would definitely differentiate between activism and organizing. Organizing is every day, boots-on-the-ground, strategizing to improve the lives of people that experience oppression on different identity levels. I think activism is being an advocate and putting your support behind an issue in as best a way you can. There’s more at risk when you’re organizing. That wasn’t a risk that I felt fully invested in. Activism for me is making media that’s advocating for a lot of the work of organizers and folks in the community. I think it helps lower a barrier of access toward a lot of these issues that people may not come to otherwise. If they see it in a film versus having to travel to a meeting across town, they may come to it more easily and not in the way of feeling that they have the education or career experience to come into the issue. Activism is getting those people in the room so they can help organize or advocate for themselves.

I think we can both agree that accurate representation of any diverse group is crucial. Why is it especially critical for women to take part in these movements?

Because women are lit. I frame a lot of the conversation of the film around my experience as a Black woman. Women are able to see things from every side of the issue and women of color, in particular, are able to see things on an even deeper level because of their intersectional experience. It’s this idea where freeing those furthest in the margins automatically frees everybody else; so many organizations here employ this mindset in their work. Because of our involvement in that experience, it creates a stronger movement because you’re thinking of things in the deepest level instead of the way it immediately affects you.

What is the most rewarding part of being a director?

You literally see everything from every side of every issue. The fact that I, with other people, have been able to create something that did not exist before is a pretty dope experience. It’s been amazing to travel with the project in progress-form and connect with other documentary filmmakers. Often times I’m the youngest person in a space. Although I definitely feel like I have a lot to contribute, I’m also learning so much that I’ll carry with me in my career and future projects. I wouldn’t have been able to access that unless I was directing the film. I think I’ve grown in my power a lot. I didn’t even realize that it was abnormal for me at my age to be directing a film on this level until people started telling me, which initially did freak out a bit. But because of that, I try to make sure to own my power in a space. I never want my age to be a reason why people don’t give me the space to talk. But all of the filmmakers that I’ve met have been extremely giving spirits and have become some of my best mentors.

You commented on a panel for The Road to Sustainability Midwest Summit that within the filmmaking community, many are left out because they don’t have the privileges to put their skin in the game. How would you like to help those who are overlooked?

Creating an open line of communication. I don’t ever want it to feel like an “I have the power because I’ve been in the game longer and they have to listen to everything I say” type of thing. I always try to make myself available for any questions. For example, people may come to an idea without any clue of how to fund it. I’m getting a lot of knowledge around that so I’m always randomly texting people about different grant opportunities. I’ve made it a rule for myself that I’ll try to do my absolute best when I’m contacted through a youth media organization, like the one I was in from Indiana, to make myself readily available for any sort of teaching opportunities or mentorship sessions. I really think that if it wasn’t for the Youth Video Institute and my formative high school years, I don’t think I would’ve ended up here as quickly. You really need those years to fuck up and have time to not make good things. I want to stay in those spaces. But maybe one day when I’m dripping in funds I could start a media fund for up and coming filmmakers of color. Who knows!

What can we expect from you in the future?

I’m continuing to build my cinematography reel. I got a chance to work on the new R. Kelly documentary that’s coming out on Lifetime and I’ve also been doing work with the mayoral campaign for Amara Enyia and the partnership with Chance the Rapper. I’ve also been putting the beginning steps into creating a vlog with fun stuff to engage with the community. It forces me to continue growing my knowledge in cinematography. There’s a very long growing list of people to thank: Rubin Daniels, Morgan Johnson, Ethan Senser, Amber Love, Natalie Frazier, and the list is far longer than that. We’re still in the process of raising funds for the film and are running a campaign on Giving Tuesday, November the 27th, but you can definitely expect Unapologetic soon.

If you like what you read, here’s an overview of Ashley’s Unapologetic Documentary. Donate to the film here.

After two Black Chicagoans are murdered by the police, young Black citizens begin challenging the city’s corrupt policies while redefining the meaning of community organizing. Unapologetic goes behind the veil with two young, Black queer women, providing an intimate peek into the personal lives that sustain a movement.

Written by: Andrea Carrillo