On finding greatness
Prelude
Grammy-nominated singer-songwriter, producer, and multi-instrumentalist Charlotte Day Wilson has made a name for herself through her fusion of contemporary R&B, jazz, and deeply expressive vocals. Recently honored with the 2025 Innovator Award at Billboard Canada’s Women in Music event–the first time the accolade has been presented in Canada–Wilson is entering a new creative chapter with Patchwork, her latest project.
Conversation
On finding greatness
Musician Charlotte Day Wilson discusses avoiding the rat race, knowing your voice, and not listening to outside opinions.
As told to Sarah John, 1564 words.
Tags: Music, Inspiration, Success, Beginnings, Process, Identity, Mental health.
You said in an interview that your advice to young musicians would be to study the greats. I’m curious, how do you define greatness?
In terms of music, I would say just music that stands the test of time. When it came out, it was good. Five years later, it’s still good.
How do you define greatness outside of music, like in your personal life or outside of the work sphere?
Greatness, how do I define greatness outside of work? I don’t know if I would use the word greatness, but I think I personally aspire to just live a balanced life and have healthy relationships. If you can achieve that, it is actually a very big feat. It’s really hard to have all of the baskets in your life filled all at the same time.
So when you say balance, are you talking about work-life balance? What are some of those baskets that you want to keep full?
Yeah. I think having a healthy, romantic relationship, one that is very fulfilling. Based on my experience, that’s probably something that a lot of folks resonate with.
Then, just having a healthy community, a strong community, being involved in the community that you live in. Knowing and helping your neighbors and being a supportive friend, being someone that people can actually rely on.
Something that happens with musicians a lot of the time—or go-getters, high achievers, or people who are in the public—is they kind of start to seem unreachable to their community.
That’s something that I’ve always tried to reject. I try to make sure that people know, “If I’m your neighbor, I will go over to your house and help you with whatever it is you need. If you’re my best friend and you need me to go shovel off your car, I will be there.” You know what I mean? I might not always be in town, but you should always feel comfortable to try me.
You kind of got your start from an internship at the music label, Arts & Crafts. At the time, you were also working shifts as a janitor on the side to earn cash. So I’m curious, what kept you motivated and believing in yourself during that time period?
What kept me motivated in terms of working as a janitor was literally just the paycheck, but–
[Laughs] I meant more so the music, but yes.
In terms of working at the label, my motivation was literally just to figure out how to be an adult. It wasn’t like, “Oh, I’m going to use this as a way to become a successful artist.” It was just, I know I need to have a job. I don’t think that the janitor thing is a good one for long term. If I can get my foot in the door at a label, I can work on the industry side–like marketing, advertising, or managing. Or I make music, so maybe I can do that. It was literally just trying to figure out life and just take steps into new positive directions.
It seems like you weren’t necessarily fixated on any one outcome. You were just open to whatever opportunities came your way.
Exactly. I know how precarious and difficult it is to make a living as an artist in music. Of course, it was probably ultimately my underlying goal and my dream and my desire, but I just think I knew how precarious and difficult it was to make it in that world. So I just left my options open.
I know you said in an interview it can be tough to separate your own voice versus what the industry is telling you. How do you make sure you’re chasing your own goals and not someone else’s?
That actually took quite a bit of time to figure out. The truth is that it does take some trial and error. I didn’t know myself very well in the first few years of my career. I just didn’t have a sense of very sturdy values. I didn’t necessarily know exactly what my goals were. I allowed a lot of people to project onto me what they thought my goals should be, because mine just weren’t necessarily sturdy enough.
I wasn’t sure. I think over those years, I was very impressionable to other people’s opinions on what I should do. I guess just with some trial and error, I realized not necessarily always what I wanted to do, but what I didn’t want to do. Through that process of elimination, I’ve figured out the sweet spot of knowing what my goals are, knowing how to navigate the industry.
The industry can be a choose-your-own-adventure thing. You make it up as you go. You define how it is you want to be an artist in the industry. Or, you pursue the ever-changing, ever-evolving goal pump that you can just never fully reach. There’s a lot of people who get stuck in that rat race of wanting more and more and more, whatever’s next. Once you reach one goal, the goal post just changes. That rat race is something that I just did not want to participate in.
Yeah, that makes total sense. Okay. Next question. What’s your strategy like for dealing with rejection?
Oh, that’s interesting. Rejection. What kind of rejection are we talking here?
When I wrote the question, I was thinking specifically in the context of being an artist. It could be a disappointment of some sort, a sense of something that feels like a failure. It could be something like a project not turning out the way you want, or it could be a more concrete business aspect of not hitting a certain number in some sense.
But I was curious in general, because I do think that in the arts, people are evaluated more frequently than in other fields. So I’m always curious how people with a platform deal with rejection, because I do think this career magnifies those experiences.
Yeah. It’s funny. I think maybe my instinct and how I want to answer this question is probably a testament to how I have grown in my own self-confidence because my instinct is to say I don’t really deal with rejection. I’m sure there are tons of rejections every day. I’m sure people hate my music. I’m sure people who I might respect might not respect me, but I’m not really tapped into that. I think what is meant for us is what will ultimately be around us. I don’t look too far past that. You know what I mean?
Yeah.
I’m not going to let ideas of things impact me more than the reality of my surroundings. The reality of my surroundings are that I’m so deeply blessed to be living the life that I live. I guess maybe I’m just not super aware of the rejections. Maybe people are hiding them from me, but I just don’t see them really.
Oh, that’s really beautiful. I mean, constructing a life where you are grateful for your everyday so that you’re not worried about the hypothetical and abstract validation of others. That makes total sense. Okay. Last question. What are some of the biggest emotional obstacles or fears you faced on the journey to becoming a musician, and how did you deal with them?
I think the biggest challenge that I’ve dealt with is imposter syndrome, and it’s something that I do continue to feel every once in a while, but I think I’ve functionally eliminated it. I don’t think it necessarily finds its way into my everyday in my practice anymore. The imposter syndrome is so specific, but like I don’t think I’m good enough at instruments.
I think my limitations have kind of in some ways proven to be blessings in disguise. But in my darker moments throughout my journey, I’ve thought like, “Oh, I couldn’t possibly be successful at this because I’m not good enough at playing bass.”
I do deal with stage fright. That is something that I’m like, it’s kind of still a process for me. I would say also, I went to the Grammy’s last year and I was like, “Oh my God, it’s amazing. I’ve made it to the Grammy’s.” You get there and you’re like, but I’m at the bottom of the barrel at the Grammy’s, you know?
Yeah.
And that’s kind of the rat race thing that I tried to avoid as much as possible, those types of inner narratives. Everyone around me is so proud of me. Then I get there and I’m like, “But I’m like a nobody here.” It’s like, that’s insane. I need to step outside of comparing myself constantly to others. Because once you narrow your vision too closely into what other people are doing you lose perspective. I’d say those are some of the challenges that I’ve dealt with.
Charlotte Day Wilson recommends:
Going to bed early & waking up early, preferably with the sunrise.
Letting out a big cathartic exhale/ yell into your towel after you shower. Lots of energy gets stored in the throat, let it out.
Exercising every day.
Paying your blessings forward.
Having a dog.
- Name
- Charlotte Day Wilson
- Vocation
- Singer-songwriter, producer, multi-instrumentalist
