Sheronna Osbourne: 5 Things I Wish Someone Told Me When I First Became A Filmmaker

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Stop overthinking: Still something I struggle with, but I’m learning that things don’t need to be perfect before you execute the idea, it will refine and take shape in time

As a part of our series called “5 Things I Wish Someone Told Me When I First Became A Filmmaker”, I had the distinct pleasure of interviewing Sheronna Osbourne.

Sheronna Osbourne is an award-winning Canadian actress and filmmaker based in Toronto. As co-president and owner of Crossfield House productions (A Black owned and 80% women led company) Osbourne has written, directed, and starred in both theater and film productions which have been selected for festivals throughout North America. Her most recent short film Out of Order that she co-directed, co-wrote and played the lead role in was recently awarded best actress, best short film and best editor at the 2022 Hamilton Black Film Festival.

Earlier this year Osbourne directed a short film Boxed In starring Renée Neuville (of the 90’s R&B group Zhane) which is currently making the festival rounds. Osbourne was one of the hundred selected to take part in the 2022 Banff Spark Accelerator for Women in Business of Media and has also produced content for major brands such as Sony Music, Wray & Nephew, and TD Bank. With a background in fashion business, Osbourne is also a Costume Buyer for the IATSE film union, where her work can be seen on the OWN Network’s The Kings of Napa, the Netflix Original series Locke & Key and Lifetime’s Salt-N-Pepa. Currently Osbourne is on tour for her latest co-written and directed play Ninety Four in which she also serves as costume designer and co-star.

Recognizing the importance of nurturing and supporting young talent, Osbourne has worked directly with youth through the Ada Slaight Youth Arts Mentorship Program and the Forgiveness Project to give opportunities to young adults who wish to develop their skills in front and behind the camera as she continues to hone in on her own skill sets.

Thank you so much for joining us in this interview series! Our readers would love to get to know you a bit better. Can you tell us a bit of the ‘backstory’ of how you grew up?

Hey, happy to be here! Growing up, artistic expression was always a part of my life. I’m an only child so I grew up making up one woman shows , singing and dancing for an audience at every family gathering. Travel was introduced to my life at an early age as well which I think is what sparked a curiosity for human behavior and self expression.

Can you share a story with us about what brought you to this specific career path?

I remember the first time I saw a musical on Broadway, it was “Mamma Mia” I remember watching in such awe, thinking “I want to make people feel the way this show is is making me feel right now.” By the time I got to high school I traded in my gym shoes and headed straight to the school play audition line. As I got older the desire to tell stories only intensified, seeing Black women like Issa Rae produce content for her and her friends from YouTube to HBO put a battery in my back and it’s been charged ever since.

Can you share the funniest or most interesting story that occurred to you in the course of your filmmaking career?

So a few summers ago I was directing a music video. There I am in a room full of hot girls and guys setting up the next scene. Everyone is looking at me as I sit on the top ledge of a couch in order to be seen and heard by everyone. All of a sudden, I felt the couch tilt back, the next thing I know I’m lying flat on my back legs in the air …EMBARRASSING!! I let my co-director take the lead for the rest of the night lol.

Who are some of the most interesting people you have interacted with? What was that like? Do you have any stories?

I recently met Janelle Monet at a TIFF party. She was super easy going and down to earth. She’s been one of my fashion icons since she stepped on the scene so when she told me she loved my outfit ..honey!! I was on cloud 9 for the rest of the night… mama I made it!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Definitely my core tribe. My family, my best friend’s and my CHP team. My mom has been my biggest cheerleader from day one and never lets me forget that I am worthy of the dreams I’m believing for. Me and my girls have a weekly routine where we leave voice notes for each other about what we are grateful for and which miracles we are expecting for each other. Having a tribe that truly BELIEVES with you, is the biggest help I could ask for.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“A man’ gifts make room for him and bring him before great men” — Proverbs 18:16 This game is all about timing, patience and preparation. It’s easy to get caught up in doubt and comparison as you wait your turn. This quote is a reminder that I am talented, qualified and worthy enough for the dreams I have for myself. There is only one me and what I bring to the table is unique to who I am.

I am very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in film and television? How can that potentially affect our culture?

We need to see and hear from people who look like us, there have been too many examples in films where non BIPOC people get cast in roles that were not intended for them.

There is a wide spectrum of diverse stories to be told. It often feels like the industry is mostly interested in trauma stories coming from BIPOC communities, when in actuality we can be superheroes, royalty and baristas too.

We are all here to learn, and teach, diversity on screen is a peephole into culture and information.

What are some of the most interesting or exciting projects you are working on now?

Ninety Four is taking all my brain cells these days lol. But with every rehearsal I am discovering new ways to perform, direct and produce so to me it never gets boring.

Which aspect of your work makes you most proud? Can you explain or give a story?

Providing opportunities for fellow artists makes me the most proud. From casting new actors, to hiring my girls as stagehands on tour, it’s been a blessing to give so many people their first “yes”. I know what it feels like to just need someone to take a chance on you.

Ok super. Here is the main question of our interview. What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

  1. Stop overthinking: Still something I struggle with, but I’m learning that things don’t need to be perfect before you execute the idea, it will refine and take shape in time
  2. Become comfortable with being alone: In the earlier days of my artistic career the thought of walking in a room or sitting at a table by myself terrified me. Did I know enough? Was my resume long enough? But I’ve come to learn that some relationships are for a time and season, people will shift away but I have to keep my eyes on the prize and walk this thing out.
  3. No just means not yet: As an actor I’ve heard “no” 1000000 times, but I recently saw a video that changed my perspective on hearing no. The speaker said “If I told you that you were 25 no’s away from that billion dollar business how happy would you be to hear no?” I was shook! And I was reminded that I’m only getting closer to my dreams so long as I don’t quit.
  4. Don’t feel guilty about taking breaks: Today’s Sheronna is a self-care queen, but in the earlier days I felt like I had to grind non-stop in order to achieve my goals; A common mentality of an artist but… the lie detector determined …that was a lie.
  5. Have fun/don’t take yourself too seriously: I’ve chosen a career that really just gives me permission to play all day so I’m trying to have more fun with it.

When you create a film, which stakeholders have the greatest impact on the artistic and cinematic choices you make? Is it the viewers, the critics, the financiers, or your own personal artistic vision? Can you share a story with us or give an example about what you mean?

While I understand the business I’m in, I am an artist first so for me I think I’m always going to push for the story first. What is this world? Who do these lives belong to and why are we here, today? I remember hearing Issa Rae speak about advocating for herself to play the lead in Insecure. When she wasn’t a household name, and did not have an extensive resume she stayed true to the vision and told the story she wanted to tell. #GOALS

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I have a heart to protect children. I want them to feel safe, loved and heard. Maybe it’s providing access to children’s therapy or programming for them to explore their gifts and interests. Growing up in a Caribbean family I’ve heard too many stories of older siblings having to take on the responsibilities of parents, or kids being exposed to adult things too early. My wish is that kids will be given an opportunity to just be kids.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

Issa Rae call me girl!. Like so many women in the industry, Issa has shown me the importance of trusting your voice and timing as an artist. She’s found a way to incorporate her love for storytelling, music and friends into a fruitful and growing empire all at her own pace. That is what I see for myself too.

How can our readers further follow you online?

You can follow me on Instagram at @yoursheronna

This was very meaningful, thank you so much! We wish you continued success!

Sheronna Osbourne: 5 Things I Wish Someone Told Me When I First Became A Filmmaker was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.