Chelsey Bennett is Fighting to Fulfill Her Dreams – Forever


“Fight to fulfill your dreams.” – JD


Chelsey Bennett.

What do you do & what inspires you to do it:  

I create and perform Jazz Soul music. I was lucky to have found an outlet that made me feel really good at a young age and just followed that feeling. It can only be described as a place where nothing else matters; whether I’m creating or performing. And often I have to fight for that feeling. But it’s always, always worth it when I do.

How do you define success:  

In terms of my career – success is reaching the goals I’ve set for myself. This has been things like: getting more comfortable in my writing voice, finding other creatives to collaborate and perform with, and just continue to find ways to be inspired. In general – success for me is finding ways to not work constantly and enjoy the time I have to be alive!

What would you say to motivate a younger you to be successful in life:

There will be a lot of opinions about what you should do and you shouldn’t always listen to them. Be critical of the advice you’re given and follow your instincts. Write more original material and stop worrying about what it sounds like. Jam and play all the time!

Are you doing now what you’ve always wanted to do or did you have other aspirations previously:  

I always sang, in choir or at home with family. When I was quite young, I wanted to be a dancer. But from the time I was about 13, singing became the only thing that really mattered. And still is.

What’s the best business or personal advice you’ve ever received:

The creative industry causes you to live in a world where the highs are higher, and the lows are lower. But as you get experience in both, the gap gets smaller and you get stronger. So persevere the lows and trust the highs will always come around again.

What’s something people would be surprised to know about you:

I am very tall, and I don’t lie about it. I love being tall! I tell people I’m just under 6 feet and they always insist I’m taller. But I wear heels a lot and it throws people off because I often look like I’m 6’3”.


Do you believe in a higher power:

Ya, I believe we’re all connected by something we can’t see. Something that’s greater than all of us individually. The power of our connectedness is what I feel when I create or when I perform. It’s an energy I think I will spend my life exploring.

What’s something you can’t live without:

My cheeky answer would be wine :p. But I really appreciate a cozy place to call home and time alone.

Where do you see yourself in three years:

Spending more time in another city. Hopefully NYC or LA and being the opening act on the tour of a bigger artist.

Single or taken:

Taken. My partner is an incredibly important piece of the puzzle in my life, as he is the one who sees the day-in, day-out nitty gritty details of my artist life. He provides a calm and impartial voice of reason to things that I sometimes freak out about. And I probably say some crazy shit!

How many tattoos do you have:

Only one (for now). It’s a painting by an artist I used to fan out about, Drue Kataoka. It’s called “Around the World in a Single Stroke” and I actually looked up her description for this again because it’s worded so perfectly. The painting is of the ancient Zen symbol that represents openness, creativity, elegance, the void, the universe and the harmony of body and mind. All things I’ve been striving to explore since I got it done 5 years ago.

Name a Song you like and Artist:

I’m going to choose 1 of each that are different because they are on my mind right now!

Song I can’t get enough of right now is “Lake by the Ocean” by Maxwell and Artist is probably PJ Morton.

Name a movie you like:  

Just watched Roxanne Roxanne – it was incredible!

What do you like to do for fun: 

Swim and spend time at the beach, amongst many things. But that’s what I wish I was doing right now.

Where can we find you online:

What’s next for you:

I’m writing a song-a-day at the moment and I’m going to focus on recording more so that I can get more up-to-date material online.

I perform a monthly residency at Poetry Jazz Cafe in Toronto and that’s my baby. My heart and soul gets poured into that show and I look forward to it every month. Next one is July 21st. I post it on all of my platforms!


Photos courtesy of Chelsey Bennett | © 2018 DRTY ONES