“I always wanted to be something. An actor. A singer. I just didn’t know what.”
That’s one of the first things Jaiden Riley tells me — but even if she hadn’t said it, you could probably guess. There’s a certain electricity to her presence: thoughtful, self-aware, and always patient.
She’s got a knack for telling stories that can make you laugh and a voice that will break your heart.
Which is exactly what makes her such a compelling performer.
But what really caught my attention was how she’s building her career behind the scenes — quietly, deliberately, and largely on her own terms.
Everywhere, All at Once
When I first reached out, I was intrigued by what felt like an obvious contradiction.
She doesn’t flood her TikTok or Instagram with updates. She doesn’t really post much at all. But her following is impressive—stronger, in fact, than many other singer-songwriters in the region.
And she’s absolutely everywhere;
- Headlining Bragg Creek Days.
- Placing third in a YYC Songwriting competition hosted by Blue Willow Entertainment.
- Covering Have Yourself a Merry Little Christmas on CJWE-FM, which you can read more about here.
It doesn’t seem to matter whether she’s playing Ranchman’s one night or a library show the next— if there’s a mic and a stage, she’s there.
“I’ve played in the corners of bars where nobody’s listening to me.
Today, I played Marda Loop where maybe 30,000 people will pass through. And then I played at a library for like, five people trickling in and out.
And both of those gigs are valuable for different reasons.”
This summer alone, she booked sixty-six shows in seventy-two days.
“There are also gigs I don’t post. Like a lot of private shows that aren’t on that list…But I’d rather be tired and fulfilled than rested and wishing I was accomplishing more.”
For any emerging artist, that’s not just an impressive lineup. It’s borderline obsessive.
“I can’t do more than four gigs in a day. That’s kind of my max right now. But if I can find a way to fit it in, I will.”
But after speaking with her, it all started to make sense.
The Power of Embracing Your ‘Yes’ Era
By the time we sat down for an interview, Jaiden had already played two Calgary gigs that day — and still managed to squeeze me in right before recording another live session for Turkey and Pistols.
Which she explains is all part of her current “Yes Era” philosophy, inspired by fellow Alberta-based artists like Jennie Harluk and Brett Cassidy.
A season of saying yes to everything: small gigs, new collaborations and last-minute invites. But this isn’t just hustle for the sake of hustle. It’s intentional.
“Right now, I’ll say yes to anything because it always leads to something bigger.”
“I met Rob [from Turkey and Pistols] because I did a gig at the Hut. And then Mackenzie from Blue Willow knew Rob.
So, I said yes. It went amazing. And then I booked Bragg Creek Days. All because I did a gig at the Hut.”
She says it with a hint of surprise, like even she wasn’t expecting things to be going this well.
And it makes sense.
She’s in that rare, early stage of momentum where consistent groundwork — dozens of Stagehand gigs, networking and showing up for every opportunity — is starting to snowball.
The gigs are getting bigger. The crowds are getting larger. And the opportunities are finally starting to come to her.
So, she’s still saying yes — but now, she can afford to be a little more selective.
“If it’s something I really want, I’ll push.
Like when I wanted to play the tent at Ranchman’s during Stampede, I must’ve asked Megan like four times. But I’m also a big fan of what goes around comes around…
Right now, I don’t reach out as much as I used to. People will come to me, I’ll make a new in-person connection, or I’ll do Stagehand.”
Which she admits is definitely a perk.
It’s a sweet spot not every artist reaches: busy enough to feel momentum, grounded enough to know that every show still counts.
And it’s easy to see how she got here.
Every performance, connection and moment onstage has been approached with the focus of someone quietly building a career—not just chasing a dream or filling the gap between school semesters and lesson plans.
But, another part of what makes her current moment so instructive for emerging artists is that the momentum is built on a growing network of artists, mentors, and audience members.
“It’s not like every gig I’ve applied for, I’ve gotten. There are some gigs that I didn’t play again.
Either they went in a different direction. Or I showed up and I wasn’t the right fit for that venue.”
She’s worked hard to earn the kind of community that carries you forward. And it makes a huge difference.
Reciprocity as a Career Strategy
The second thing you might notice about Jaiden Riley — after the relentless work ethic — is that she rarely talks about herself without talking about someone else first.
There’s Matt Blais, her mentor. Someone she met when he came into the Keg, where she worked at the time after playing a show.
“I think I said something like, ‘Oh, I’m a musician too.’ I wasn’t. I had no idea what that actually meant,” she laughs.
“But he kind of took me under his wing and got me a lot of my first gigs.”
Blais still helps her book shows, but perhaps more importantly, he helped shape her approach.
“He’d say, ‘I got you in. If you want to play there again, that’s on you.’ And I really took that to heart.”
Even in smaller, more casual moments, that instinct to give credit shows up in unexpected ways.
When I mentioned in passing how much I enjoyed her early social media posts — light, funny, and unexpectedly viral — she redirected.
Instead, taking care to emphasize that the original idea wasn’t hers. She’d simply been building on a trend started by another creator and had credited them in the original caption if I was interested.
It’s a small but telling moment.
You often get the sense she’s deeply aware of how she’s perceived and feels responsible for earning every inch of her success.
Maybe this emerges naturally because she’s working in spaces where authenticity and community matter. But also likely, because that’s just the kind of person she is.
Even her approach to interviewing is collaborative.
She never positions herself as an authority; instead, choosing to be generous with her answers—as if she’s inviting you into her thought process in real time.
Which is crucial when you’re building your audience in person.
That emphasis on relationship-building over self-promotion might be part of what makes her feel so accessible — even magnetic — to people meeting her for the first time.
This “word of mouth snowball” is how she builds momentum — and she’s the first to point out how much of that has come from other artists putting her name forward, recommending her for gigs and looping her into their circles.
And now, whether she realizes it or not, she’s stepping into that mentor role herself. Simply by sharing what she’s learning along the way.
Discovering the Music That Was Always There
Despite her fast-rising presence, Riley didn’t always want to be a musician.
“I didn’t do music right away. I went to a performing arts school, so I was kind of raised up to be a performer. But songwriting and playing an instrument are things I taught myself.”
Looking back, music has been a constant thread in her life.
“I grew up going to folk fests and going to a lot of live music, which I think is important for the creation of an artist.”
But even then, there were moments she considered other career paths. “I remember going to high school and feeling like, maybe I was an athlete and being really confused.”
Industry, Grit and Ambition
Currently, Riley balances music with teaching. But when asked if she’d like to do it full-time, she doesn’t hesitate: because, surprisingly, even small library gigs pay well.
And places like the local library or platforms like Stagehand are extremely invested in supporting the local music scene and paying their artists fairly.
She’s blunt about the money part. Maybe a little sheepish or worried that might “sound bad”. And likely aware that the “ideal” portrayal of an artist is someone who simply loves the craft, so much success magically follows.
But for Jaiden, there is a very real, clear ambition underneath it all.
It doesn’t sound bad, of course. It sounds wise. By acknowledging pay and thinking in terms of career viability, Jaiden shows a clear-eyed understanding of music as a business— and what it actually takes to make that dream an everyday reality.
That’s real grit talking.
Her pragmatism also extends to advice for other artists. “For young artists asking if they should enter a songwriting competition. I think I’d ask, how thick is your skin? Because it’s not for everybody, and it’s definitely not necessary to be successful.”
That perspective comes from experience.
Jaiden is candid that the YYC Songwriting Competition didn’t define her career, but it did toughen her resolve and strengthen her confidence in her own music — lessons she still finds valuable.
She even mentions, almost in passing, that she’s considering entering another, less intensive competition down the line.
Going Viral, Then Walking Away
While Jaiden considers her real debut as an artist to be 2023, her first experience with internet fame came earlier — through a series of viral TikTok covers she now views with mixed feelings.
It started lightheartedly enough: a reimagining of Dolly Parton’s “Jolene”.
“I saw that version. Wanted to sing it to [my mom]. And the response to that was just crazy. So, I ended up doing a series of covers.”
One video even reached nearly two million views. But the high didn’t last.
Visibility, especially online, often comes with the pressure to keep performing. And when you’re working inside the logic of an algorithm, even overwhelmingly positive attention can become toxic.
“Going viral on TikTok really does a lot to your psyche… you don’t know what it’s going to do to you until you’re in that position…and it ended up being really unhealthy.
I had tied my entire self-worth to the amount of likes I was getting… [which] wasn’t sustainable for me.”
The shift since then has been noticeable.
Today, her digital presence is minimal but intentional: fewer posts, fewer reels — more high-quality live recordings and simple announcements.
“[Now], I’m making music for me and if people are connecting with that, then that’s really good.”
In a scene where emerging artists lean hard on social media as their primary lifeline, this shift — toward creating for yourself, and showing up in person — feels almost radical.
But the real surprise might be that promoting yourself the old-fashioned way still works.
People see her live and follow along after the show — not because she asked them to, but because something about it stuck with them.
The same way seeing Mary Gauthier perform “Mercy Now,” at the Canmore Folk Festival in 2003 stuck with a then two-year-old Jaiden Riley.
And it makes sense.
The idea that you have to be constantly online to stay relevant flies in the face of anyone who’s ever fallen in love with a local band playing a DIY show in someone’s barn.
Discovered their favourite musician through a weird little indie play in a Kamloops theatre.
Or watched a singer perform at a free Stampede tent and carried that memory for years.
We don’t connect with content. We connect with moments. And Jaiden Riley is in the business of making emotional memories.
On the Sound
“There’s a lot that goes into a brand and the way you project yourself. So, it’s important to get that right.”
When I asked Jaiden if people ever get confused about where to place her sonically, she gave me a surprisingly thoughtful and nuanced take on what folk music is all about.
“For a really long time, I would say I was writing for and as a folk singer. And [like] I say in my artist bio, I’m still really connected to [those] traditions.
But if you go to a folk festival, there are so many different sounds that you’re going to hear.”
She doesn’t just speak about it like a keyword or a category for a spotify playlist.
“I think that folk is a really good way sometimes to describe the outcasts, the outlaws, the people that are not subscribed to a specific genre.
I do country. And, “I Drink” is a folk song. But the album it’s on, Mercy Now has a lot of country elements, grit and twang. But it’s folk cause it’s Mary Gauthier.”
She’s clearly extremely knowledgeable and deeply articulate about the differences between sounds, styles and genre expectations.
“I think the throughline for me is my voice and the person I show up as on stage. But…what comes first for me before sound and genre is storytelling.
When I’m promoting myself it’s country, folk, comma bluegrass. But it’s all of them at once. I can’t pick just one.”
While she admits that genre can be important, she’s also never precious about it. To her, it’s a living, breathing thing, a vessel with emotional weight.
“I definitely ebb and flow between vibes in a single set when I’m up on stage.
Sometimes I’m singing chickens and I still crack up when I’m singing it. Other times I even give myself goosebumps.”
And that fluidity extends to her on-stage presence as well.
She’s not afraid to be funny or “get a little weird” with something like her debut single Chickens in a Trailer Park. But she also never undercuts the emotional depth when it matters.
Instead, she uses comic relief with purpose: she knows when the feeling is getting too raw, and punctures it with absurdity.
But she’s never just talking about style or craft — she’s also talking about a belief in the responsibility of letting music speak for itself.
“I would rather be so loud from the outside that people can’t ignore me and they go, ‘Who is this girl? We need to have her [play]’, as opposed to, ‘Why does this girl keep sending us a message?’”
That compass — one grounded in grit, honesty, and storytelling — seems rooted in home, too.
Identity, Storytelling And Honouring Your Roots
Identity for Métis and Indigenous artists can often be complex, with some choosing to frame their experiences through genealogy, community, art or ceremony.
For Jaiden, she roots her identity in both lived experience and family lineage.
On her Kokum’s side, her family carries records tracing their roots back to Chief Kahkewistahaw, a Plains Cree leader who guided his people through the turbulence of the late 19th century.
On her father’s side, they connect to Peter Hourie, a Métis trader and community leader whose family name is still recognized across Treaty 6 territory.
Not every artist has ties that can be documented this way — which makes these connections feel especially significant for her. It creates a thread of continuity she can hold alongside her lived experience.
When I asked her whether she describes herself as a Métis artist because of cultural practices she consciously draws from — or because she’s simply steeped in them and that likely comes through in some small way — she doesn’t offer a clean answer.
Instead, she gives me a story.
“I was really lucky that I grew up doing ceremony. My Kokum is a Cree woman and a residential school survivor…but she’s not my blood relative.
She was someone my mom met before I was born and we were ceremonially adopted into her family.”
And it’s the little nuances of those experiences that seem to matter most.
“My experience as a Métis person is different and kind of intersectional because I was raised doing Cree ceremony.” She explains.
“I powwow danced, I didn’t jig. I danced jingle dance and fancy shawl and I’ve been to many Sun Dances. I sweat…I’m also learning Michif and speak some Cree.
Métis people have a very specific culture that’s not that. So culturally I think I’m kind of a mutt.” She concludes.
She uses the word “mutt” as shorthand for complexity. Something many culturally mixed or diasporic readers may identify with instinctively.
And it’s that complexity that shapes how she sees storytelling itself.
“Growing up my Kokum told me so many stories. And my grandfather, John Hourie had the ‘gift of the gab’.
He loved to tell stories but he had a major stroke before I was born and he lost his ability to speak. So, I didn’t get that side of him.
But I do think some of that is just inherent.”
At some point in the interview she describes this inherent need again, this time as “the need to pass stories on from me to you, from my mouth to your ears.”
Which underlines how much emphasis she places on in-person connection.
Not in an aggressively extroverted way. But, in a meaning-making way.
“I love to just talk. I don’t even need to always be singing to accomplish that.”
For Jaiden, story is the thread that connects everything: her family, her music, even her presence on stage.
“What comes first for me is storytelling.
Some stories can be really fun and uplifting. Some stories can be kind of weird. And some stories are worth being approached with reverence and honesty.”
She’s cautious here too, with how she represents her identity out of care — conscious never to speak for anyone else’s experience when she’s really just speaking from her own.
Jaiden Riley is a lot of things. A performer by training. A storyteller by inheritance. And an artist shaped as much by her environment as her own will to succeed.
But what comes through most isn’t someone trying to define herself — but someone trying to speak as truthfully as possible in a world that always wants a cleaner answer.
She’s carrying stories: her own, her mother’s, her friends who raised chickens in a trailer park — and probably a few that haven’t been written yet.
And she’s doing it with a kind of deep, deliberate vulnerability that both reflects oral storytelling traditions — and extends them.
For Jaiden Riley, the reverent lives alongside the playful.
On Her Debut Single “Chickens in the Trailer Park”
Jaiden’s debut single is quirky, upbeat, and full of personality — a sharp contrast to the emotional depth and reverence she often brings to cover songs like “I Drink”.
And clear evidence of range in a performer.
It’s also a weirdly specific song that left me wondering where it even came from and (secretly) hoping it was based on something real.
“I grew up with two best friends, they’re twins. And they lived in a little trailer park in a place called Greenwood Village.
[A couple months] before the competition, I found out their neighbours had pet chickens, and I said to myself. ‘This needs to be a song’… I went home and wrote that song in 10 minutes.
Then thought, oh, this could use some harmonica. Oh, this could use some yodelling.”
It’s risky to make your debut single something offbeat.
But the reception has been very positive.
“They say you get told what kind of songs people want in other ways. So I didn’t even have a choice. It was just something I had to make.”
Conclusion
Against the backdrop of an industry obsessed with “content strategy”, Jaiden Riley is proof that authentic presence and hard work still matter.
Her story is threaded with resilience—through competitions, TikTok fame and creative burnout.
She’s weathered it all with grace. And now, she’s choosing her own gigs, building her brand and sharing her sources.
And always carrying with her a world of stories—some her own, some from the people who helped shape her, and probably a few that haven’t even been written yet.
If you’re interested in supporting her, you can find Jaiden Riley’s debut single, “Chickens in the Trailer Park,” on all major platforms.
Follow her on Instagram, TikTok, and YouTube: @jaidenrileymusic
Or check out her live schedule for updates and more at jaidenrileymusic.com.
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