Alessia Cara on Success, Self-discovery, and Finding Freedom
Ten years is enough time for almost anything to change. Entire industries can reinvent themselves. Technologies can reshape culture. Careers can peak and fade. Audiences can move on.
And yet, speaking with Alessia Cara, one gets the sense that while much around her has changed, the essential qualities that first connected her to millions of listeners remain remarkably intact.
The voice is still there, carrying the same warmth and introspection that made “Here” one of the defining songs of the last decade. The curiosity is still there, too. So is the thoughtful self-awareness that has always separated her from many of her contemporaries. What has changed is something less tangible but perhaps more important: the pressure.
For much of her twenties, Cara occupied a rare and often uncomfortable space in popular culture. She was simultaneously one of Canada’s biggest musical exports and one of its most relatable artists. Her songs captured the awkwardness, uncertainty, loneliness, and self-discovery that define early adulthood. While other artists were building mythology around themselves, Cara was documenting the messy reality of adolescence and discovering her own identity.
The irony, of course, is that she was doing it while becoming famous herself.
When “Here” exploded in 2015, it felt like a disruption. Pop music was still largely dominated by larger-than-life personalities and carefully engineered personas. Then came a teenager from Brampton whose breakthrough hit was essentially a celebration of wanting to leave the party early. Audiences recognized something genuine in that contradiction. The song became a global hit because it articulated a feeling that millions of people shared but rarely heard reflected back to them.
What followed was the kind of ascent most artists spend their lives pursuing. Grammy recognition. Multi-platinum records. Global tours. Collaborations with some of the biggest names in music. A catalogue that would eventually generate billions of streams and position her among the most successful Canadian artists of her generation.
From the outside, it might look like a decade defined by achievement. From Cara’s perspective, it looks more like a decade of evolution.
“I feel like I’m the same exact person,” she says. “My values are all the same.”
She pauses.
“But I do feel completely removed from that version of myself.”
The contradiction is what makes her story interesting. Success narratives are often built around transformation. The assumption is that achievement changes people. What emerges from Cara’s reflections is something more nuanced. The artist she has become is not dramatically different from the young woman who first arrived on the scene. Instead, she seems more comfortable inhabiting that person.
“I don’t feel like I have as much to prove.”
It is a deceptively simple statement. It may also be the most significant milestone of her career.
For young artists, proving yourself is often inseparable from the work itself. Every song becomes a statement. Every project becomes a referendum. Every success creates new expectations. Every failure feels magnified.
Looking back, Cara recognizes that dynamic in herself.
“I was a lot more defiant,” she says. “You always feel like you have something to prove in the beginning.”
A decade later, she has arrived at a different relationship with her craft. It’s not complacency or indifference. It feels more like freedom.
That idea surfaces repeatedly throughout our conversation. It appears when she talks about songwriting, touring, and the recording process behind Love Or Lack Thereof, her latest project and perhaps the clearest artistic expression yet of where she finds herself today.
On the surface, the album is a collection of reimagined songs from across her catalogue, transformed through jazz, soul, and blues arrangements. A straightforward concept, perhaps. Yet the project carries a deeper significance when viewed alongside the broader arc of her career.
For years, jazz existed at the edges of Cara’s work. It informed her phrasing, her influences, and her instincts as a vocalist, but it rarely occupied centre stage. Pop music was the vehicle through which most audiences encountered her. This project finally allows her to explore a musical language she has loved for years.
More importantly, it allows her to approach music differently. Everything was recorded live. Musicians performed together in the room. Imperfections remained. Technical precision became secondary to emotional honesty.
For an artist who describes herself as naturally perfectionistic, the process required a fundamental shift in mindset.
“You have to let go,” she says. “You have to be free.”
The phrase could just as easily describe the larger chapter of life she now finds herself in.
There is a noticeable difference between the way Cara speaks about music today and the way many artists speak about their careers. The conversation rarely drifts toward strategy. She is far more interested in discussing curiosity than outcomes, process than performance.
Part of that perspective comes from experience. Part of it comes from watching the industry transform around her.
The music business that launched Alessia Cara no longer exists in quite the same form. Streaming has reshaped listening habits. Social platforms have rewritten the rules of discovery. Artists are expected to be creators, marketers, personalities, and entrepreneurs simultaneously. Visibility has become a profession unto itself.
“Everything feels different,” she says. “It’s like coming back into your house and all the furniture is moved.”
Yet somewhere amid all that disruption, her own definition of success has become clearer.
When asked what success means to her now, she does not mention awards, chart positions, or streaming milestones. Instead, she offers something unexpectedly personal.
“If I were to die tomorrow, would this be the thing that I want to leave behind?”
It is a striking answer because it reveals the question underneath everything else: Legacy.
Not as a monument, but as reflection. What work would accurately represent who you were? What contribution would feel honest? What remains when the noise disappears?
For Cara, the answer appears increasingly connected to authenticity. Her catalogue has never relied on spectacle. Instead, it has been built around emotional specificity. The details may come from her own life, but the feelings belong to everyone.
“I always try to write in a way that people aren’t thinking about who I wrote about,” she says. “I want them thinking about who made them feel that way.”
Perhaps that is why her audience has remained so remarkably diverse. The teenagers who found themselves in “Here” have grown up alongside her. New listeners continue to discover her work through entirely different chapters of her career. What connects them is not a particular genre or era. It is the feeling that someone is telling the truth.
As Cara leaves her twenties, there is a temptation to frame this moment as a reinvention. The music industry loves reinvention. It provides a convenient narrative structure: Old chapter closes, new chapter begins.
What makes this moment compelling is not that Alessia Cara has become someone new. It is that she seems more fully herself than ever before. Ten years after introducing herself to the world, she is still evolving, still experimenting, still searching. The difference is that the search no longer feels driven by expectation. It feels driven by possibility.
And perhaps that is the real achievement. Not the awards, records, or even the longevity.
After a decade spent growing up in public, Alessia Cara has arrived somewhere many people spend a lifetime trying to reach. She has learned that success is not becoming the person the world expects you to be.
Success, as it turns out, is having the freedom to become yourself.
