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Rising Music Star Naomi Sky On The Five Things You Need To Shine In The Music Industry

An Interview With Edward Sylvan

As a part of our series about rising music stars, I had the distinct pleasure of interviewing Naomi Sky.

Naomi Sky is a singer-songwriter, dancer, and model that is originally from Arlington, Virginia but grew up in Philadelphia, Pennsylvania. Naomi Sky is a recent graduate of the University of Miami, where she attended the Frost School Of Music. She is known for her honest and introspective lyrics. Her music explores all the facets of herself. As Naomi Sky puts it: “We all play many different roles in life, and every unique role that we play, every part of us, makes up the whole. Life is a combination of logic and magic.” Naomi Sky’s music is deeply rooted in love, faith, loyalty, curiosity, self-exploration, and embracing the unknown. Her songs have been featured in various media outlets. Naomi Sky is currently working on her debut album that is slated to be released in 2022. As she ascends in the music industry, Naomi Sky hopes to further serve as a beacon of inspiration to individuals struggling to accept, celebrate, and release their emotions and be unapologetically themselves.

Thank you so much for joining us in this interview series! Can you tell us the story of how you grew up?

I grew up near Philadelphia, Pennsylvania, and I always felt a pull towards music, even as a little girl. I started taking piano lessons when I was 5, and I would run around the house singing and dancing. I loved art, especially drawing, and I also played a lot of different sports. My younger sister and I put on choreographed shows for our parents in the basement. I was shy when I was younger, so I think music gave me a place where I could just be myself. When I was 11, I started writing my own songs. Singing was always my favorite passion. My elementary school music teacher recommended I wait to start voice lessons until my voice matures, so I started voice lessons when I was 13. I also started modeling in middle school, competed in a couple of pageants and modeling competitions in high school, and performed in talent shows and showcases. Being onstage gave me a place I could explore all the different facets of my personality.

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

I credit part of my interest in music to my parents. There was always this natural pull towards music, like singing to the radio on car rides. A person who really inspired me to start creating music is my dad. He plays the piano, and I remember thinking it was so cool that he could improvise. After listening to him play one day, I begged him to let me take piano lessons. That’s how I started my music career with the interest of learning to play like my dad. Then, when I heard a song on the radio that I liked, I would ask my dad to print out the lyrics, so I could learn them. Eventually, I incorporated pop music into my piano lessons. Now, I consider myself to be primarily a singer-songwriter, but my understanding of music stems from the piano.

Can you tell us the most interesting story that happened to you since you began your career?

I think the most interesting part of my career was when I completely switched majors in college. I started out as a music major at the Frost School of Music at the University of Miami because I love singing and songwriting, but I was accepted as a classical vocalist. Pop music has always been my favorite to sing, so I knew I wanted classes that focused on that genre. I took extra coaching lessons and after my freshman year, I auditioned for the pop/contemporary program. I was so excited to be accepted! Then, during my sophomore year, I almost lost my love for singing. I thought I wanted to completely switch careers. I ended up turning my music major into a minor, and I became a communication studies major. My classes during my junior and senior years were almost all communication classes and elective credits, but I continued writing music in my free time. Songwriting has always been my way of getting in touch with my feelings because I write in a flow state. It’s a way for me to reflect. I also knew that I wanted to continue recording music, so I worked with a couple of producer friends in my free time, too. At the beginning of my senior year, I had a concept for an album, and halfway through the school year, I had written almost every song for it. At some point during my senior year, I realized that there are challenges in every career path, and I decided that I want to focus on doing something I love. So in the end, changing my major turned out to be better than I could have ever imagined because it led me to feel more confident in my intuition and following my heart.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One of the first times that I ever performed as a solo singer, I completely mixed up the verses of the pop song. I was performing a cover, and I sang the second verse as the first verse and vice versa. When I left the stage, I felt so embarrassed! I told my parents what happened afterward, and they said they didn’t even notice. I’m human and I made a mistake. Instead of beating myself up for it, I ended up laughing it off because I thought if no one noticed, then I must have been doing my job as a performer. There may be times when something goofy or unexpected happens. This experience taught me the importance of giving myself grace when I make a mistake and being confident or gracefully moving forward.

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

Right now, I’m working on an album called “Vulnerable,” and it explores the challenges that come with opening up to everyone I love. It used to be easy for me to keep the hardships in life to myself. Music has helped me to embrace all the different emotions I feel as a woman, and it’s been the key to helping me let people in. On this album, I sing about falling in love, anxiety, intimacy, passion, vulnerability, heartbreak, finding a purpose, and growth. I’ve learned a lot of life lessons and a lot about vulnerability in the past couple of years. I’ve realized vulnerability is truly a strength. It adds to my life because it helps me connect to my family and friends. My favorite part about this project is the way it allows me to explore all these different sides of myself. We all play so many roles in life (a friend, sister, daughter, and girlfriend to name a few), and I believe all those unique parts of ourselves make up the whole. I hope people feel inspired to explore their emotions and the different parts of themselves when they listen to this album.

We are 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?

One of the most important reasons that diversity needs to be represented in film and television is because it helps us all to better understand each other. We only know what it’s like to experience life from our own perspective and our own circumstances. Seeing various cultures in film and tv helps us to imagine what life looks like for people of various backgrounds. It expands our empathy skills, broadens our thinking, and it can help us to be more compassionate humans.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

Five things I wish someone told me when I first started are:

  1. I wish someone told me that I didn’t have to be perfect. I put all this pressure on myself in high school because I didn’t want to be viewed as a bad musician, but music is all about the raw emotion and the imperfect parts of being a human, and there is always so much to learn. We all start somewhere, and there are people willing to help you or teach you every step of the way.
  2. There’s no right way to be an artist. Authenticity is one of the biggest keys to success as an artist! I love being at a concert where the artist’s performance feels so free. I think part of that freedom comes from having the space to express themselves and fully be themselves onstage. One of my performance goals is to exude that “free” feeling.
  3. Try different things! When I was forming my artist identity, I tried out different vocal techniques (growling in a song and singing in whisper tones). I tried wearing different types of clothing (girly, baggy, or edgy). I experimented in every area! By trying out different approaches, I learned what made me feel like my most authentic self.
  4. Get introspective! Think about why something feels authentic. Understanding the reasoning for my feeling of authenticity helped me to figure out how to incorporate that element in my artistry. For example, I love wearing soft colors, like baby pink and light blue, because I feel those colors showcase my sensitive side. And I love wearing a bold pink eyeshadow look or a red lipstick look because I feel like those two makeup styles showcase my fierce side.
  5. You are your biggest competition. The music industry can feel extremely competitive, and that competition has made me feel lonely at times. At the end of the day, though, if I’m growing as an artist and musician, I believe that is a success. I think it’s important to celebrate the accomplishments and growth, and I cherish feeling gratitude and excited in the moment.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I recommend reflecting and figuring out “why” you’re doing what you’re doing. Whether it’s purely for fun, because you want to follow your heart, to make a difference, or you have a specific purpose and intention for your music, knowing that “why” makes the challenging days a little easier. You can remind yourself of the reason that you started working in the music industry, and do whatever it is that lights you up inside!

You are a person of enormous influence. If you could inspire 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. :-)

If I could inspire a movement, I would love to be an advocate for mental health and help create a space for more honest conversations about the ups and downs of being a twenty-something-year-old in today’s world. Introspection, honesty, and compassion are my key ingredients to creating a healthy relationship with myself. Over the past couple of years, reflecting on my actions and choices has helped me to learn about who I am and how I can improve. It can be a slippery slope because while I crave growth, I don’t want to criticize myself. I aim to create a balance by making lists of the change I crave to see, like more time for self-care or spending more time outside. Mental health plays such a huge role in our daily lives and our levels of happiness, and I would love to see the mental health of people around the world improve across the board (at all ages).

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?

I am extremely grateful to my voice teacher, Cassandra Claude. I started taking voice lessons with her in 2017, and at that point, I felt like quitting music. Singing was not making me happy, and I felt like I didn’t have a purpose as an artist. I was confused. One day, during my lesson, Cassandra told me that she wasn’t there to tell me what to do or how to sing. She said she was there to coach me on how to create a healthy sound that allows me to sing and perform for my whole life. That was the first time that someone in my life gave me permission to be free and just be me! A lightbulb went off in my head! All of my blocks in that lesson seemed to dissipate. There were no boundaries or rules I had to follow. I could experiment with different vocal tones as long as I produced the sound in a healthy way. I credit that moment and Cassandra’s perspective for being one of the many reasons I stuck with music. That was the year I started to experience the most growth in my singing voice, too. Cassandra, if you’re reading this, thank you infinitely! xxoxoxoo

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

“Life is a combination of logic and magic” — me, Naomi Sky! I love philosophizing and having deep conversations with my friends and family about life, and I wholeheartedly believe in balance. It’s important to be rational and think things through, but it’s also equally important to follow our hearts and take risks. We don’t always know how something might work out or manifest in our lives. If we keep working towards our goals and stay true to our values, I believe life works in mysterious ways to gift us opportunities and help us achieve our dreams.

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 just see this, especially if we tag them. :-)

I am such a big Ariana Grande fan! I love how authentic and honest she is in her songwriting, she has an amazing voice, and I love her whole vibe. She’s accomplished so much in the past few years; she’s one of my biggest musical inspirations. If I could have a private breakfast or lunch with Ariana Grande, that would be a dream come true!

How can our readers follow you online?

You can follow me on Instagram @officiallynaomisky, on Tiktok @naomiskyhigh, on Twitter @naomiskyhighh, and on Facebook @officiallynaomisky! I’m also on Spotify, Apple Music, Soundcloud, and all streaming platforms as Naomi Sky! If you want to stay updated on my music, follow me on your favorite platform! I also have a website: The links are below!







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

About The Interviewer: Growing up in Canada, Edward Sylvan was an unlikely candidate to make a mark on the high-powered film industry based in Hollywood. But as CEO of Sycamore Entertainment Group Inc, (SEGI) Sylvan is among a select group of less than ten Black executives who have founded, own and control a publicly traded company. Now, deeply involved in the movie business, he is providing opportunities for people of color.

In 2020, he was appointed president of the Monaco International Film Festival, and was encouraged to take the festival in a new digital direction.

Raised in Toronto, he attended York University where he studied Economics and Political Science, then went to work in finance on Bay Street, (the city’s equivalent of Wall Street). After years of handling equities trading, film tax credits, options trading and mergers and acquisitions for the film, mining and technology industries, in 2008 he decided to reorient his career fully towards the entertainment business.

With the aim of helping Los Angeles filmmakers of color who were struggling to understand how to raise capital, Sylvan wanted to provide them with ways to finance their creative endeavors.



In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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Edward Sylvan, CEO of Sycamore Entertainment Group

Specializing in acquiring, producing and distributing films about equality, diversity and other thought provoking subjects