Departure Festival And Conference 2025

Recording Artist: Jessie Reyez, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

From Tuesday, May 6, 2025, to Friday, May 9, 2025, I attended Departure Festival and Conference in Toronto, an ambitious reimagining of Canadian Music Week (CMW), which ran until Sunday, May 11, 2025, and which originally launched in 1982 as The Record Music Industry Conference.

The transformation into Departure has been led by Oak View Group (OVG) and other investors, who view the venture as a vibrant, multidisciplinary platform for global talent across music, art, comedy, and technology.

According to the festival and conference, Departure is not simply a name change; it represents a bold pivot toward the future.

The festival is branded as a launchpad for artists and thinkers who are ready to push boundaries and spark new movements.

After my friend and colleague Neil “Logik” Donaldson introduced me to Canadian Music Week in 2008, covering it on behalf of HipHopCanada, and consequently attending it for the first time completely changed my life and career for the better, and I covered it for many years up until 2023.

During my first Canadian Music Week in 2008, among other pivotal moments, I did photo shoots with the likes of M.O.P., KRS-One, and the RZA, I met my now deceased friend and mentor Edward Scott Day, and the idea that I could work with artists and platforms that I admired and respected since childhood started to become a reality, so my expectations for Departure were high to say the least.

Publicist, Journalist, Educator: Dalton Higgins, Visual Artist: Justin Bua, Photographer, Director: Danny Hastings, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

This year, Departure’s various inaugural events took place around the Greater Toronto Area, and primarily within the City of Toronto's downtown core, with the vast majority of its keynotes and panels taking place at Hotel X.

I appreciate Hotel X. Last year, as the art director for Operation Prefrontal Cortex, I attended and documented the third annual Toronto Raptors Youth Summit there alongside our team. Our co-founder, and my friend, colleague, and mentor, Julien Christian Lutz, pka Director X and our producer Franca Abate facilitated guided meditations for groups of hundreds of youth from underresourced communities in the Greater Toronto Area, and it was an excellent event in an ideal environment.

However, for Departure, I found Hotel X to be too isolated a location for a city-wide festival.

This became especially clear when the hotel’s café closed each afternoon, leaving only an off-site Starbucks and the hotel’s restaurant as the remaining options for refreshments and snacks.

Beyond that, the surrounding area offers very little in terms of food, beverages, or entertainment, making it an inconvenient base for conference attendees looking to explore or connect between sessions.

Hotel X was also quite far from many of the venues I attended on behalf of my coverage of Departure, the furthest of which was Comedy Bar Danforth.

In contrast, the Royal York Hotel, longtime host of Canadian Music Week, including the first one I attended, is far more centrally located and accessible, with a wealth of nearby amenities.

Visual Artist: Justin Bua, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

I found that attendance at Hotel X during Departure was noticeably lower than the turnout at the base camps of many Canadian Music Weeks I have attended over the years.

This may be due to a range of factors, including the current socioeconomic climate in 2025, potential gaps in marketing, communications, and funding, or other variables I may not be fully aware of.

That said, the programming, educational offerings, and talent showcased at Departure were truly world-class. I learned a great deal and was able to document an impressive amount throughout the event.

On the morning of Tuesday, May 6th, less than a day after a brief phone conversation with him, I sat front and centre for Mastering Longevity: A Conversation with Justin Bua & Danny Hastings, a keynote moderated by Dalton Higgins featuring two legendary figures in visual art and hip-hop culture.

Both Bua and Hastings are celebrated visual artists and storytellers whose work has helped define the aesthetics of hip-hop for decades.

Bua is renowned for his expressive paintings and iconic depictions of music, hip-hop, and street culture, while Hastings is a pioneering photographer and director behind some of the most influential album covers and music videos in American hip-hop history.

Photographer, Director: Danny Hastings, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

It was an inspiring dialogue between two visionary visual artists and storytellers, especially within the contexts of hip-hop culture and New York City; both men have profoundly influenced me since my childhood and teenage years.

My childhood friend Aaron Mark’s parents own a wildly successful poster company called Imaginus, which became the first Canadian company to license Justin Bua’s artwork.

His posters were sold on most, if not all, university and college campuses across Canada during my time as an undergraduate student; that is how I first encountered his incredible work.

One of the most compelling moments in the conversation came when Justin Bua and Danny Hastings turned their attention to artificial intelligence, particularly generative AI, and its growing influence on the creative industries.

Bua made it clear that while technology will continue to evolve, it is unlikely to ever replace the human spirit, nor the singular experiences, sensibilities, and refined taste that artists develop through tens or even hundreds of thousands of hours of dedicated practice.

In his view, true craftspeople, like himself, will become even more valuable as automation becomes increasingly ubiquitous and genuine artistic mastery becomes rarer.

Hastings, by contrast, offered a pragmatic perspective rooted in experience. As both a creative director and art director, he shared how he has embraced generative AI as a tool, using it to enhance his work and generate meaningful financial returns. He urged the audience to adapt to new technologies rather than fear them.

Later, after shooting portraits of both Bua and Hastings, I had the chance to speak with Danny one-on-one.

When I asked him what he learned most from the streets of New York City during the late ’80s and early ’90s, he answered without hesitation: he learned how to hustle, how to monetize creativity in one of the most expensive cities on earth.

His recollections of relentless rejection followed by breakthrough projects deeply resonated with me, as they mirror the trajectory of my journey since launching my career in December 2006.

Soon after, I attended Shaggy Unfiltered: Music, Legacy & Reinvention, a keynote conversation with Shaggy, one of the few international musical superstars to emerge from the small but culturally rich island of Jamaica. I first became aware of Shaggy when I was in the sixth grade, around the time his meteoric rise to global stardom began.

What struck me most during the conversation was how down-to-earth and laid-back Shaggy remained, despite his iconic status.

Recording Artist, Executive: Orville Richard Burrell CD Professionally Known As Shaggy, DJ, Journalist: Robert Lloyd Professionally Known As Spexdaboss, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

I walked away with several valuable insights, including his belief that the most engaging and rewarding collaborators are not always the ones with the most followers or social capital. And what has truly set Shaggy apart from many of his peers in dancehall and reggae, he explained, is his fierce work ethic and discipline; qualities shaped in large part by his time in the U.S. Marine Corps.

He noted that, having been raised in a single-parent household by his mother, the structure and discipline instilled by his military service were instrumental in his long-term success in the music industry.

Shaggy also emphasized that much of his early global success came from personally promoting his music overseas in the late ’90s and early 2000s, long before the age of social media. Travelling across multiple countries and time zones to connect with audiences reinforced the resilience and drive that continue to define his career.

Canada’s self-proclaimed “Reggae Ambassador,” Spexdaboss, who is also one of Shaggy’s longtime friends, moderated the conversation with charisma and depth, and I thought he did an excellent job of guiding the discussion.

On the evening of June 6th, I attended Mustafa the Poet’s concert at Meridian Hall. I sat directly in front of him throughout the performance and found it to be deeply lyrical and evocative; an elegant embodiment of poetry through music.

As I watched him perform live with his live band and a minimalistic stage setting for the second time, and as I documented him for the first time, I was reminded of a critical lesson for any artist: the importance of truly understanding one’s audience.

Recording Artist, Executive: Orville Richard Burrell CD Professionally Known As Shaggy, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

Mustafa frequently paused his set to speak directly to the crowd, often sharing dad jokes tailored to the Muslim community, his core audience both at Meridian Hall and more broadly, across Canada and internationally. I was particularly impressed to learn that he recently bought his parents a home far removed from the harsh realities of his upbringing in Toronto’s Regent Park; realities that his former friend and groupmate MO-G, of the well-known Toronto rap group Halal Gang, described to me in detail during a nearly three-hour phone call about his life, and Project T-Dot, my 19-year-long documentary project on Toronto’s hip-hop culture, community, and history, last year.

While Mustafa’s choice of humour did not personally resonate with me at all, it struck a chord with the packed house, who laughed, cheered, and remained engaged throughout. Mustafa knows his audience intimately, and that connection elevated his performance far beyond music; it became communion.

On May 7th, at Hotel X, I attended a powerful keynote on the mental health crisis in the Canadian music industry titled A Study by Revelios: Soundcheck – Unpacking the Mental Health Crisis in the Music Industry, presented by Unison.

Moderated by esteemed Canadian broadcaster and music journalist Alan Cross, the session shed light on the urgent and often overlooked mental health challenges faced by music professionals across the country.

The keynote centred around findings from the first-ever national feedback survey on mental health in Canada’s music industry; results that paint a sobering picture.

Financial instability, toxic work environments, the relentless pace of industry change, and broader global stressors have all contributed to a widespread crisis affecting artists and industry workers alike.

Recording Artist: Mustafa Ahmed Professionally Known As Mustafa The Poet, Location: Meridian Hall, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

The session, which included insights from the study’s author and president of Revelios, Catherine Harrison, and a community activist, was both interactive and deeply engaging, offering practical insights and rallying attendees toward collective action and long-overdue systemic change.

Given my work as a mindfulness consultant and mental health advocate, I found myself wishing the keynote had been longer. I have witnessed far too many tragedies across the Canadian, American, and international music industries that have stemmed from unprocessed trauma, the absence of mental health education, persistent stigma, and a lack of adequate support systems.

In some cases, these unresolved issues have led to hospitalization or death, and the untimely deaths of Prince, Michael Jackson, Kurt Cobain, and many other brilliant musicians impact me to this day. The complexity and urgency of these challenges demand more time, more dialogue, and significantly greater institutional commitment and capital than the industry has historically provided.

Soon after, I had the opportunity to document the red carpet following Jessie Reyez’s receipt of the Allan Slaight Humanitarian Award. It was a pleasure reconnecting with my longtime colleague Tyrone “T-Rex” Edwards, who was one of the first people to help me in regards to Project T-Dot in 2007, and I also captured portraits of several Canadian icons, including Jessie Reyez, Matty Mattheson, and Jully Black.

The energy on the carpet reflected the significance of the moment and the impact of those being celebrated.

The following day, on June 8th, I attended a fascinating session on AI presented by Elevate. Moderated by Amber Mac, President of Amber Mac Media Inc., the conversation featured Sinead Bovell, tech ethicist, futurist, and Founder of WAYE.

Entrepreneur, Broadcaster: Alan Cross, Entrepreneur, Mental Health Advocate: Catherine Harrison, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

Together, they unpacked the sweeping impact of artificial intelligence on the entertainment industry, how it is already reshaping music, film, and digital identity, and the urgent questions it raises about authorship, equity, and the future of cultural leadership.

This was not solely a conversation about technology; it was a bold and hopeful exploration of how Canada can ensure that its cultural future remains human-led and artist-empowering. Bovell’s unique ability to decode the future for next-generation thinkers framed AI not as a threat, but as a call to action for Canadian and global creators, policymakers, and institutions to protect creativity and innovation amid rapid disruption.

Insightful, urgent, and deeply relevant, the session made clear that for artists to not only survive but thrive, the human voice must remain at the center of our cultural evolution.

During the session titled Humans Still Needed: The Future of Entertainment in an AI World, Sinead Bovell highlighted Canada's significant contributions to AI research, mentioning renowned figures such as Geoffrey Hinton, Yoshua Bengio, and Richard Sutton.

She emphasized that Canada possesses the necessary resources for AI researchers to flourish.

However, this perspective may not fully align with the current realities faced by Canadian AI professionals.

Futurist, Educator: Sinead Bovell, Journalist, Speaker: Amber Mac, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

Notably, Bovell participated in the event remotely from New York City, suggesting that her career is, at least in part, reliant on opportunities available in the United States.

Canada has a longstanding challenge in retaining top talent across various sectors, often referred to as a "brain drain."

This phenomenon is characterized by skilled individuals seeking better opportunities abroad, particularly in the U.S., where factors such as higher compensation, greater investment in research and development, and more robust innovation ecosystems are prevalent.

The productivity gap between Canada and the United States further exacerbates this issue. According to Statistics Canada, from 2001 to 2021, Canada's annual labour productivity growth averaged 0.9%, while the U.S. maintained a rate of 2.0% per year.

This divergence is especially pronounced in sectors like information and cultural services, where the U.S. experienced significantly higher productivity growth compared to Canada.

Moreover, the Bank of Canada's senior deputy governor, Carolyn Rogers, has described Canada's poor labour productivity as a national emergency. She noted that, as of 2022, Canadian productivity had declined to approximately 71% of U.S. levels, a drop from 88% four decades prior.

Communications Officer, Media Strategist, Journalist, Manager: Ahmar Khan, Location: Comedy Bar Danforth, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

Given these challenges, it is plausible that leading AI researchers in Canada may be enticed by opportunities in countries that offer more favourable conditions for research and innovation.

Without strategic investments and policy reforms aimed at enhancing productivity and supporting high-tech sectors, Canada risks losing its competitive edge in the global AI landscape.

The evening following Bovell’s keynote and a private retirement party for my colleague and former CEO of my client and partner, Nieuport Aviation, Neil Pakey, I travelled across the city to attend Hassan Phills’ performance at Comedy Bar Danforth. Despite the distance, the show was well worth the effort.

Thanks to Hassan’s manager, Ahmar Khan, I was able to meet and document Hassan in the green room before the performance. He was joined by fellow comedian Marlon Palmer, whom I have documented for years through Project T-Dot. Meeting them in this setting felt like a full-circle moment, especially with Marlon having been part of the culture I have documented for nearly two decades.

Ahmar had already struck me as a competent manager through our e-mail exchanges leading up to the event, but meeting him in person reinforced that impression.

Even as he recovers from a car accident and recent back surgeries, he remains focused, calm, and deeply committed to his client’s success, which is a testament to his resilience and professionalism.

Comedian, Actor: Hassan Phills, Location: Comedy Bar Danforth, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

Hassan and Marlon had just come from filming the new, critically acclaimed and funny TV series Office Movers and were visibly exhausted, particularly Hassan.

Still, Hassan demonstrated an impressive level of professionalism. It was clear that, like me, he takes his commitments seriously and delivers his best no matter how drained he may feel. His ability to engage and energize the crowd under those circumstances spoke volumes about his work ethic and dedication.

It is no surprise that Hassan is featured on Drake’s recent album with PARTYNEXTDOOR, $ome $exy $ongs 4 U. His sets typically blend sharp cultural commentary with personal anecdotes, offering a hilarious yet thought-provoking experience that resonates with diverse audiences. Hassan is a strong voice representing Toronto’s multiculturalism; Hassan is of Jamaican and Djiboutian descent with an Islamic faith, and he draws from his rich cultural background to reflect the diversity, wit, and authenticity that define the city’s creative identity.

He also represents a new generation of Toronto’s hip-hop-adjacent talent, and he is one of the newest figures I have begun documenting for Project T-Dot.

The performance was packed with memorable moments and plenty of laughter.

After the show, a long line of fans formed to meet him and take photos; a clear sign of his growing influence and magnetic presence in Toronto’s comedy and cultural scenes.

On May 9th, I attended T-Minus in Conversation with Brian "B.Dot" Miller.

T-Minus, born Tyler Williams, is a renowned Canadian producer celebrated for crafting some of hip-hop and R&B's most iconic tracks. His impressive portfolio includes hits like Kendrick Lamar's "Swimming Pools (Drank)," Drake's "The Motto" and "HYFR," and Nicki Minaj's "Moment 4 Life,” and he is one of my favourite hip-hop music producers.

The conversation was guided by Brian "B.Dot" Miller, a distinguished New York City-based journalist and Delaware State University alumnus.

B.Dot is best known as the co-host of the acclaimed Rap Radar Podcast, which has been discontinued, and where he and Elliott Wilson conducted in-depth interviews with prominent figures in hip-hop.

His extensive experience includes serving as MTV News' Lead Music Correspondent and hosting the web series Complex Brackets. Recognized as one of hip-hop music journalism's trusted voices, B.Dot has been featured on platforms like CNN, MSNBC, and Fox News.

During the session, T-Minus expressed deep admiration for my longtime supporter, Matthew “Boi-1da” Samuels, who is like a Canadian Dr. Dre in many ways (in my opinion), highlighting the mutual respect and camaraderie that exists among Toronto’s top music producers.

Producer: Tyler Mathew Carl Williams Professionally Known As T-Minus, Journalist: Brian Miller Professionally Known As B.Dot, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

What resonated with me most was T-Minus’ emphasis on the value of social and emotional stability outside of work. He spoke candidly about how being grounded in his personal life, particularly as a dedicated family man, has allowed him to maintain clarity and focus in the studio. It reinforced for me how vital a well-balanced life is to sustaining creativity and long-term success.

The next keynote I attended was presented by SOCAN and featured Murda Beatz, born Shane Lee Lindstrom, who is one of Canada’s most successful and globally recognized music producers. His journey from humble beginnings in Fort Erie, Ontario, to producing chart-topping hits for artists like Drake, Travis Scott, and Nicki Minaj was deeply inspiring.

What stood out most was his emphasis on the power of initiative. Much like Danny Hastings had reminded me days earlier, Murda reinforced the importance of my commitment to sales and marketing.

He spoke openly about how his career took off not only because of his production skills, but because he relentlessly sent e-mails, direct messages, and made cold calls that most producers would be too intimidated to pursue. This kind of proactive self-promotion played a critical role in establishing his reputation.

Murda also highlighted the importance of personal branding and public visibility.

Once he reached a certain level of notoriety, he made a point of showing up at events, in the media, in the music videos featuring recording artists he worked with, and across social platforms, to strengthen his brand.

Producer, DJ: Shane Lee Lindstrom Professionally Known Murda Beatz, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

He explained that as he began working with high-profile artists, he strategically leveraged those collaborations to build relationships with other major public figures.

His approach reminded me that consistent outreach, paired with excellence in execution, can open doors to opportunities that might otherwise seem out of reach.

The final keynote I attended was a conversation between Brian "B.Dot" Miller and Kardinal Offishall, who I have been documenting for Project T-Dot since 2007, and whose music I have been a fan of since the seventh grade. It was powerful to witness Kardinal reflect on his multi-decade journey as both an artist and executive, one that has helped shape Toronto and Canada’s cultural identity and hip-hop landscape.

One of the most fascinating moments was hearing Kardinal speak about his longstanding friendship with Def Jam CEO Tunji Balogun and how that relationship helped pave the way for him to become an A&R at what is arguably the most iconic record label in hip-hop history. His role at Def Jam symbolizes a major shift, not just for Kardinal personally, but for Canadian artists and tastemakers being acknowledged and embraced at the highest levels of the U.S. music industry.

It was equally inspiring to hear him recount the grind of the mid to late 1990s, when he and his crew, The Circle, would often pile into a rental van with very little capital and drive to different cities across the U.S. to break records, perform, and appear on local radio shows. That kind of relentless hustle, doing whatever it took to break into the American market and put Toronto on the map, was a recurring theme in his story.

Kardinal also spoke with humility and clarity about the importance of reinvention, faith, and self-awareness. He described moments of doubt, frustration, and sacrifice, but underscored how resilience, cultural pride, and a clear sense of purpose kept him moving forward. His journey was not solely about personal success; it was about carving out space for others and redefining what global recognition could look like for Canadian hip-hop.

He also reflected on a deeper truth that resonated with me: many people in the music industry, including artists with massive audiences, end up crashing out, harming themselves and others through maladaptive behaviours, because they lack grounding in a higher purpose.

He emphasized that those who approach their careers and the music industry in a purely superficial or transactional way, or through overcompensation, often lose themselves in the process.

In contrast, Kardinal’s longevity and clarity come from his alignment with something bigger than fame or accolades, his cultural roots, his community, the wisdom of his mother, and a higher sense of mission.

That perspective, especially coming from someone who has navigated multiple eras of the industry, was both sobering and profoundly motivating.

That said, Departure Festival and Conference is an ambitious and commendable attempt to reimagine what Canadian Music Week could be in a new cultural and technological era.

It is multi-disciplinary programming, world-class speakers, and a commitment to elevating Canadian talent alongside global voices that mark a bold step forward. Yet, for all its innovation, Departure is still finding its rhythm.

Recording Artist, Producer, DJ, A&R, Entrepreneur, Social Activist: Jason Drew Harrow, Professionally Known As Kardinal Offishall, Journalist: Brian Miller Professionally Known As B.Dot, Location: Hotel X, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

One element I missed deeply, something that characterized the earliest Canadian Music Weeks I attended at the Royal York Hotel, was the spontaneous, word-of-mouth hotel room parties that sprang up in the afternoons.

These gatherings, often featuring a DJ and an eclectic mix of artists and industry professionals, were not listed in any schedule or app. They offered organic opportunities to connect, decompress, and celebrate, often leading to lasting friendships and collaborations.

Departure, for all its programming strengths, lacked that sense of serendipity and unstructured community.

Moreover, while the inclusion of iconic figures such as my favourite comedian, Dave Chappelle, Shaggy, Kardinal Offishall, and Murda Beatz gave the festival weight, Departure still needs more of these legends. Not only to draw larger crowds, but to create landmark moments that define an era. The talent is there; the infrastructure, the vision, but a higher volume of such voices is necessary to compete with international festivals of similar ambition.

In many ways, Departure’s value proposition is closer to South by Southwest (SXSW) than to North by Northeast (NXNE), which is based in Canada, ironically. But to earn the global reputation that SXSW commands, Departure will need significantly more capital devoted to marketing, communications, and diverse, immersive programming.

The foundation is solid, but future iterations must go beyond safe, siloed panels and fixed programming. They need to capture the electricity of chance encounters, the energy of unexpected performances, and the intimacy of after-hours conversations that can only happen when a city truly opens up to its creative community.

Departure is a strong step in the right direction, and I sincerely hope it continues to evolve. Canada deserves a festival that does not solely showcase culture, but one that generates it.

Departure Festival And Conference 2025

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