Freedom Dreaming: A New Collaborative Invites Philanthropy to Reimagine Itself


In his 2002 book “Freedom Dreams: The Black Radical Imagination,” historian Robin D.G. Kelley wrote, “Recovering the poetry of social movements… particularly the poetry that dreams of a new world, is not such an easy task.”

“For obvious reasons,” he went on, “what we are against tends to take precedence over what we are for, which is always a more complicated and ambiguous matter. It is a testament to the legacies of oppression that opposition is so frequently contained, or that efforts to find ‘free spaces’ for articulating or even realizing our dreams are so rare or marginalized.”

Kelley wasn’t referring specifically to philanthropy, but it’s easy to see how an enterprise like nonprofit grantmaking — often so very hierarchal, top-down and plutocrat-driven — maps onto his commentary. Philanthropy likes to refer to itself as a space for risk-taking, innovation and experimentation beyond the constraints of government and business. But all too often, the dreams of people working in philanthropy end up subsumed by the familiar drive for measurable, incremental change, settling for reactive measures to immediate problems.

Freedom Dreams in Philanthropy, which describes itself as a collaborative and is actually something quite distinctive in the philanthrosphere, seeks to offer social sector folks a chance to envision what the field could and should be through the lens of their own dreams and imaginings.

The collaborative will not itself engage in funding or regranting. Rather, according to Dr. Chera Reid, co-executive director of the Center for Evaluation Innovation (CEI) and one of three people on the Freedom Dreams team, it’s about engaging in a process and way of seeing things with longstanding roots in the Black radical tradition in the U.S., but applicable to the social sector more broadly. 

“We are not making an institution, an organization or an initiative here,” Reid told me. “We are inviting people into a body of work. We are inviting people to join us if this resonates, if this is part of their way into the work of philanthropy.”

“Really practicing our freedom”

What, exactly, is freedom dreaming? It’s much more than some flashy slogan accompanying a new sector initiative. Reid emphasized the long lineage of freedom dreaming as an established practice within social justice movements, and characterized Freedom Dreams in Philanthropy as part of that larger current. 

“Freedom dreaming is a verb, a process,” Reid said. “It is the work of imagining possibility beyond what we have today, imagining into our collective liberation, imagining into what a just and multiracial democracy or society could be. And then identifying where there are places where we can experiment.”

The collaborative’s approach draws strongly on Kelley’s work, as well as that of other intellectuals and movement leaders of color. It also draws upon Reid’s own experience as a former program officer at the Kresge Foundation, and as Kresge’s inaugural director of strategic learning, research and evaluation. 

Despite her successes in those roles, she said, she found herself grappling with larger questions. "Why do I work in philanthropy? Why am I stationed here? Why work on race equity in a big philanthropic organization? There are other things one could do.”

That led her back to Kelley’s book, which in turn helped her realize that “this work is about creating new visions for where we’re trying to go.… This work is about freeing ourselves, and really practicing our freedom.”

The collaborative began in earnest as Reid — along with the other two team members: Efraín Gutiérrez, a senior fellow with CEI, and Trinel Torian, a sociologist — went about asking other philanthropic leaders of color about their own freedom dreams. “Not about their dreams for their organization,” Reid said, “[But] about their freedom dreams, their visions for our society. What does that sound like? Would they be willing to go there? And again, not talk about their organizational mission statement so much as their own?”

Proving the concept

Those initial conversations, conducted over the course of about a year from June 2021 to August 2022, called on over 25 foundation CEOs and executive directors of color (anonymous for the time being) to share their freedom dreams and offer their candid thoughts on topics like philanthropy’s role in societal transformation, how philanthropy can ease the path to an inclusive, multiracial democracy, and what it might take to truly “acknowledge and redress” historic and contemporary harms.

Their answers, some of which Freedom Dreams shared in a press release, affirmed that there’s an appetite for what the collaborative’s offering. At the same time, they point to deep tensions around where philanthropy stands in the minds of these leaders of color.

For instance, while leaders’ dreams for society centered things like love for humankind — the old, expansive definition of the word philanthropy —  as well as meeting basic needs and an emphasis on collective good, the leaders were also strikingly downbeat on philanthropy as it exists today. “I don't see philanthropy as being compatible with a high-functioning, multiracial democracy,” one remarked. “Because it just gives unnecessary power and voice to those who already have power and voice.”

That initial research effort, which Reid said was enthusiastically received by the leaders interviewed, was “proof of concept” for what would become Freedom Dreams in Philanthropy. The aim going forward, Gutiérrez said, is to continue "inviting people in philanthropy and philanthropic institutions to move beyond what they need right now and what they can have right now, into what they desire, and what they — what we — deserve as a community.” 

Although this work originated at the Center for Evaluation Innovation, it’s a broader offering extending beyond people involved in learning and evaluative work to the wider population of philanthropy professionals. In addition, it could eventually encompass people working outside formal philanthropic institutions in community-based roles. 

For the time being, Freedom Dreams in Philanthropy counts five institutional funders among its supporters. They include California Healthcare Foundation and The California Endowment, which had existing relationships with CEI, as well as the Teagle Foundation, which Reid said is a new funder of CEI. There’s also the California Wellness Foundation and the Levi Strauss Foundation, which expressed direct interest in backing Freedom Dreams.

Love of humankind

The path this work will take going forward is still taking shape. Additional conversations and outreach to leaders may well be part of it, as well as artistic engagement and work in specific communities. Notably, there will also be a virtual event series, set to start in June, in which the team will further lay out their research findings and invite engagement. The team intentionally chose this unorthodox and more interactive way to present their research as a counterpoint to the more typical approach of writing up a report that’ll end up doing little more than “sitting on a shelf,” as Reid put it. 

That sort of thing — finding space to let go of ingrained sector norms and experiment with other ways of working, is a big part of what Freedom Dreams is all about. “We all know a lot of people are frustrated with philanthropy and the way that we conduct ourselves. And I think freedom dreaming in this work is an opportunity for people to just be human,” Gutiérrez said.

That, as well, seems to lie at the core of Freedom Dreams’ ethos — a return to that original definition of philanthropy as love of humankind, and here, in particular, seeing people in the sector as valuable beyond their role as cogs in a social impact machine. 

Perhaps that’s why Reid ended on a positive note. “For people who believe that philanthropy is just broken and shouldn't have a role, Freedom Dreams in Philanthropy… may not be for them. We believe that philanthropy has outsized power and influence relative to the actual dollars. And we believe that people are actually the biggest asset.”