We caught up with the brilliant and insightful Jessica Moss a few weeks ago and have shared our conversation below.

Jessica, thanks for joining us, excited to have you contributing your stories and insights. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.

Throughout a career rooted in community-centered artistic practice, one persistent caution has remained clear: trust no one. “Don’t invest here,” critics have said, “you won’t see a return.” This skepticism reached its peak with The Garfield PGH Project—a long-term solution to the short-term housing needs of Black visiting artists in Pittsburgh’s Hill District. Questions arose about the decision to beautify a space in a community already suffering from disinvestment and displacement.

In response to these critiques, the core of this work has remained grounded in a different understanding of risk—not as a matter of financial return, but as a belief in the restorative power of community, culture and collective care. The real opportunity lies not in perpetuating the status quo, but in reshaping how we view, engage with, and invest in the communities most often overlooked by traditional systems of power. These efforts should not be seen as risky at all; rather, they are an essential investment in dismantling the transactional, profit-driven models that have historically shaped development and institutional funding. By prioritizing trust, empowerment and resource-sharing, Jessica Gaynelle Moss’ work and projects demonstrate that the real risk lies in failing to see and invest in ourselves—our culture, our communities and our future.

A focus on creating dignified, autonomous spaces has always been central. These projects, environments and initiatives must reflect the richness and resilience of Black, queer, trans, Indigenous, and m/other artists. This commitment manifests through initiatives like Moss’ the Aboveground Railroad Grant Program and The SEED Money Fund, which dismantle traditional models of grantmaking by offering unrestricted support to emerging Black arts leaders. Traditional grantmaking bodies often perpetuate institutionalized bias, creating resistance to initiatives that challenge the status quo. Starting a program that supports a historical excluded group, specifically emerging Black artists, carries what many might consider “inherent risks”, particularly in terms of financial sustainability and ideological pushback. Moreover, offering unrestricted funding, as seen in the SEED Money Fund, disrupts traditional models that favor strict oversight, questioning the value of trust and autonomy for recipients. Critics have viewed this work as “niche” or “political,” failing to recognize the broader cultural value. These programs are essential for addressing historical underfunding and exclusion, but convincing others of their worth is a challenge.

The Roll Up CLT artist residency program, launched in 2016, was a direct challenge to the norm of institutionalized gatekeeping in the art world. It centers Black and queer artists, offering a platform for collaboration and personal growth, free from the constraints of conventional funding systems and residency models. Despite skepticism about the sustainability of such an approach, the residency has raised over $500,000, demonstrating that when the focus is on authenticity and establishing trust, everyone thrives—not merely as beneficiaries of resources, but as active contributors to a reimagined arts ecosystem.

Similarly, the Clarissa Mural Project in Pittsburgh’s Hill District reclaimed a space in a historically Black neighborhood ravaged by systemic disinvestment and gentrification. Critics questioned the choice to invest in beautification when so many surrounding material needs remained unmet. Yet, this project was not about ignoring those needs; it was about affirming the cultural identity of the community and investing in its aesthetic, emotional and cultural value. By creating a space of beauty and pride, the mural challenges the narratives of neglect and erasure imposed on Black neighborhoods, asserting that these communities deserve more than survival.

The core of these projects lies in a radical reimagining of public art and community engagement, where safety, authenticity and care are not secondary considerations but foundational principles. There is no risk in trusting these communities, in rejecting the limitations of conventional wisdom; this action is not a gamble but a strategic commitment to transformative, inclusive change.

Jessica, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

Jessica Gaynelle Moss is an artist who supports other artists through her curatorial work, consultancy and custodianship.

In addition to her role as the founding director of The Roll Up CLT, a neighborhood embedded artist residency program she launched in 2016, Jessica has collaborated with notable artists, contributing to social practice, public art and community engaged projects that center the interaction as art, like Mel Chin’s Fundred Dollar Bill Project, Theaster Gates’ Black Artists Retreat and the Stony Island Arts Bank, and Alisha B Wormsley’s Sibyls Shrine, an artist residency and network of 100+ Black artists who have m/othering practices, where she currently serves as the collective’s managing director and curator.

Jessica received a bachelors in Fine Art from Carnegie Mellon University in 2009; a masters in Arts Administration, Policy and Management from the School of the Art Institute of Chicago in 2015; and graduated from the University of Pittsburgh School of Law in 2018.

What do you think is the goal or mission that drives your creative journey?

At the core of Jessica Gaynelle Moss’s creative journey is a commitment to transforming both the spaces where art is created and the systems that govern access to it. Her mission is driven by a vision of collective liberation that prioritizes historically excluded communities, particularly Black, queer, trans, Indigenous, and m/other artists. Moss’s work aims to cultivate environments in which these artists not only have the opportunity to create but also to thrive, within ecosystems that are both equitable and sustainable.

Rather than integrating these artists into existing frameworks, her focus is on dismantling those structures and replacing them with models grounded in collaboration, care and shared resources. Through initiatives such as The Roll Up CLT, the Aboveground Railroad Grant Program and The Garfield PGH, Moss challenges the transactional, profit-driven frameworks that dominate the art world, advocating instead for practices that center community, trust and mutual support.

Ultimately, Moss seeks to create spaces where artists can rest, research and build enduring legacies—spaces where the arts function as tools for both societal change and the revitalization of communities.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

Several key texts have shaped my philosophy and approach to leadership in the arts.
Curatorial Activism: Towards an Ethics of Curating by Maura Reilly has significantly helped guided my practice and principles, advocating for an activist framework centered on ethics and equity, beyond simply representation.
Black Futures by Jenna Wortham and Kimberly Drew has helped deepen my commitment to uplifting living Black artists and reimagining autonomous spaces.
Rest Is Resistance by Tricia Hersey and Let This Radicalize You by Kelly E. Hayes and Mariame Kaba have informed my practice through their messaging of prioritizing rest, emphasizing collective care and uplifting the need to trust each other.
Revolutionary Mothering, edited by Alexis Pauline Gumbs, China Martens, and Mai’a Williams, further underscores the role of care in radical transformation, grounding my work in creating nurturing, equitable space and practices.

Contact Info:

• Website: https://www.jesseplane.com
• Instagram: @jesseplane
• Linkedin: https://www.linkedin.com/in/jessmoss/

Image Credits

All images courtesy of the artist.