By Melissa Vincent
In a story for The Walrus, “The Death of the Middle-Class Musician,” Luc Rinaldi issued a clarifying edict on the connective tissue of our industry: “When musicians can afford to pay rent, put food on the table, make music, and play shows, everyone benefits. When they can’t, the entire economy suffers. Venues close, artists abandon their craft, and Canada’s cultural fabric tears.”
For Maddy Oliver, this reality extends beyond artists to those building careers across the industry. Recently appointed Interim Executive Director of the Canadian Live Music Association (CLMA), she’s a fierce advocate for reimagining what sustainable careers in the music business could look. Through centering the everyday lived realities of the next generation of professionals, she’s focused on the holistic solutions for the music sector as a whole.
Everything that’s happening on a societal level is making a mark on the music industry,” she says. “The economic reality is affecting all of us. There is a degradation of the middle class of workers, and that impacts the whole ecology of music in this country.”
In response to these challenges, she founded Young Music Professionals (YMP), a network designed to support emerging professionals as they enter and navigate the industry, and work toward the next stage of their careers. The organization reflects a growing need for clearer pathways, stronger networks, and careers that avoid burnout for those coming into the sector at all ages. Through initiatives like Young People Doing Cool Shit, a YMP project highlighting innovative work of young people across the music industry, the organization has also helped spotlight emerging talent within established institutions. CMRRA was featured during its 50th anniversary, spotlighting team members 35 and under making an impact across the organization.
“A core philosophy of mine is balance. There are very polarizing ideas on what it means to be a worker in 2026. Hustle culture never sleeps, or, on the other end of the scale, it’s come in at 9:01, leave at 4:59, never go beyond the call of duty. I think it’s really important for us to know our boundaries, but still be a good team player.”
That perspective is something Oliver has lived first hand. YMP launched in 2024 while she was working full-time at the Canadian Live Music Association, and, like many other young professionals eager to make waves, Oliver quickly realized she wasn’t the only one. “I was learning about what all these young people were doing ‘off the side of their desk’ or at their organization. I thought, ‘my goodness, the leadership needs to hear about this.’”
“All we had was anecdotal data, so I had no idea what to project in terms of number of members.” What she did notice was a clear need for opportunities to meet peers and build relationships that could lead to leadership positions. Today, YMP supports just over 700 members across a wide range of roles and career stages. “It felt like everyone was waiting for something like this to exist,” she reflects. “Both the young people that make up the membership, and the industry leaders who are looking for succession planning solutions and looking to meet the next wave of leaders, so there was this enormous hunger.”
For Oliver, that drive can be traced back to her early years. Growing up, she split her time between piano lessons at the Royal Conservatory of Music and sports. “I will sing from the mountaintops that team sports are so important. Learning how to work with people are lessons that you carry forward.” An early appreciation for the storytelling potential in soundtracks led her to discover the work of music supervisors like Alexandra Pastavas, helping her see how music could become a viable career path.
After completing a postgraduate program in Music Business at Humber College, Oliver moved from an internship at the City of Toronto Music Office to a role with the CLMA. “Career advancement in music can be difficult because it’s so non-linear. There are so many opportunities that are often pieced together to make a full-time equivalent,” she says. “People have so many different skills across the industry. It’s very easy to move diagonally. A little up, a little out. It’s not always easy to move straight up.”
She cites projects like Black Canadian Women in Music and the South Asian Music Accelerator as the tip of the iceberg of the ways young people are disrupting the status quo.
She identifies mentorship as a significant pillar of YMP, since it has played a defining role in her own journey. Oliver credits individuals like Mike Tanner, Music Sector Development Officer at the City of Toronto, and Erin Benjamin, the former President & CEO of the Canadian Live Music Association, for offering guidance and sharing frameworks for success.
“[Tanner’s] outlook is the epitome of what YMP tries to exemplify: invest in the next generation, understand that they are forward-thinking and are the future of this industry, then work really hard to connect them with the right people and the right opportunities.” He was the one who introduced Oliver not only to most of Toronto’s music infrastructure, but also to Erin Benjamin, the other mentor whose advocacy and passion remain an ongoing inspiration.
When she reflects on what insights she would impart to her younger self, a crucial part of the equation is getting to know yourself well enough to be industrious about your career, but always go on your own terms. “I have a finite social battery. I am passionate about my work, but I don’t want it to be my whole life. Finding the matrix in there somewhere, as all of those factors overlap, is where your sweet spot is going to be.”
