We caught up with the brilliant and insightful Jessa Sky a few weeks ago and have shared our conversation below.
Alright, Jessa thanks for taking the time to share your stories and insights with us today. Do you wish you had waited to pursue your creative career or do you wish you had started sooner?
I often used to think of this narrative for a long time. I even find myself if I am not in a “good” mental space criticizing myself and being “too hard on myself”, that “if only I started young.” Or “I wish I didn’t allow the bullies in junior high influence me to delete my YouTube channel. This trap of “what ifs” and “should haves” can be a deadly trap that leaves me feeling not good enough, hopeless, and quite frankly very debilitating. I am pretty good at reframing my negative self talk and catching it before it has me spiral. I have to remember WHY I started pursuing a full time career as a singer/musican/artist in the first place, and that is with the 100% intention and passion to turn my pain, my story, my experiences into something creative that can hopefully help another human get through their worst day. I do not get the luxury to play “God” and I do not get to “know all the answers”. I choose to have faith and find purpose in that everything is happening exactly how it is supposed to, in this exact moment.

Jessa , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
Well.. Tansi/hello!! My name is Jessa Sky. I am a Metis Cree Indigenous Artist. Basically I write, sing and create music in hopes to help connect to others who listen. I use music to process my pain, life experiences, feelings, thoughts, and get through anything I experience that I cannot put into “words”. Those “feelings” that seem to bottle up and need a release, I write a song about it. I started my professional career in music in 2019. I went through a lot of rebirths ands awakenings since then and my music has evolved from a little studio in a friends basement, to being heard on Sirius XM, the Indigenous Music Countdown, CBC, and various listens across Canada. My dream is to tour across Canada, US, and eventually worldwide, Since 2019 I have released 7 singles, 3 music videos, and am currently working on my debut album, which is set to release late August 2023. I truly feel what sets me apart is my authenticity in my music, my social media, and the fact I choose to share the most vulnerable experiences in my life on my platforms. I do this for the purpose to show others that it does not matter what has happened to you, what you have done, what adversities you have experienced, or what losses you have faced in life. I want to show little humans, teenagers, adults that there is hope and a silver lining in everything. I remember being a little girl, having no one who “looked like me” on t.v or in magazines that had experienced such darkness and come out the other side and used it for good. Nobody connects to perfection, they connect to quite the opposite. I choose to share my darkest moments with such a large audience, because I can almost guarantee someone is or has experienced what I have, and to help someone see they are not alone, that is what I am most proud of. To try and help somebody else, it’s really not about me. It’s how can I help someone else? Through my experiences, my music, my story? That is my purpose.

What do you find most rewarding about being a creative?
The most rewarding, and it may seem simple to some, but it is receiving the messages from people who can heard my music and it has touched them in some way. I remember one specifically that really spoke to me. When I released “On My Own” in 2021 I had 100’s of messages from fellow Indigenous women, sisters, allies. who were struggling with the intergenerational trauma they face due to the dark history of Residential Schools here in Canada. Summary of the messages I received was that the lyrics in that song and the video gave them hope for our people and helped them navigate the emotions and losses they were feeling. They felt hopeless, but the song spoke to them and have them a little bit of hope. The fact that a song I wrote had the ability to do that, blows my mind. Still to this day, and it keeps me motivated to continue writing, continue sharing my experiences through music, because the only purpose I can find in dark moments, is to help somebody else. It’s beautiful and it makes me very emotional. Another time was when I went through the hardest moment of my life, losing my daughter (pregnancy loss). I really had no idea how I was going to overcome that. I laid in bed for 2 months straight completely defeated, broken, and hopeless. No one can prepare you for the grief and loss that comes with that. After literally just surviving day to day, I knew I needed to get in the studio and write about it, because that is the only way I know how to deal with that type of insurmountable pain. The single “Never Be Replaced” was released and I reached a whole new avenue of women. I would never with loss of a child on anybody, however it brought me some healing, and hope being able to touch other women who have lossed a child through that song. The first lyric spoke to some women who reached out to me. It goes “More than one heart stopped today, never got to see your face, didn’t hold you in my arms, but I know just where you are”. The fact I could connect with another women experiencing the same loss as me, there really is no greater honour.

Is there mission driving your creative journey?
Really the whole goal, mission, and motivation driving my music career journey is to break glass ceilings, societal norms and stereotypes. I want the future generations to see that you can come from become whoever or whatever you want. We need more people in the public eye who share what they have been through behind closed doors and have overcome so the little humans on this planet can see they can become anything they desire to be. In order for me to pursue this everyday, I needed to get real with myself and heal the broken parts of me. The only thing you have in this world I believe, is your word. I choose to show up, do what I say I am going to, and do it with integrity. You can go through all the things, all the pain, and come out the other side. This idea that “I need to be x to become z” needs to be smashed. You can do ANYTHING you set your mind to, with the correct thinking, drive, and belief in yourself. You need to have 100% believe in yourself or how can you expect anyone else to believe in you?
Contact Info:
- Website: https://jessaskymusic.com
- Instagram: https://www.instagram.com/jessaskyy/?hl=en
- Facebook: https://www.facebook.com/people/Jessa-Sky-Music/100066691154653/
- Twitter: https://twitter.com/jessaskyy?lang=en
- Youtube: https://www.youtube.com/channel/UCPv2fs4o21SXLdaqflxPZxg
- Other: Tik Tok: https://www.tiktok.com/@jessaskyy?lang=en Spotify: https://open.spotify.com/artist/2s3owRsjkaanegjOOxmCC8 Apple Music: https://music.apple.com/ca/artist/jessa-sky/1571992446
Image Credits
@madgirlproductions @sarahthowsenproductions @chelseawiesinger @Johnbfilms

