The Privilege to Experiment and Fail

‘What would you do if you knew you couldn’t fail?’ is one of those questions that I’ve usually heard as an icebreaker or as part of personal development workshops — never as the kind of framing for iterative discussion and planning in the nonprofit setting — until I came to Common Future. We are a Black-led, multi-racial, majority woman, mission-driven racial justice organization that is eliminating the racial wealth gap through creating a more equitable economy.

Doing this kind of racial justice work and solving problems that don’t have readily available solutions requires us to experiment — that is, to push boundaries, try what hasn’t been tried before, and try what has been tried before in new ways or in communities that have historically been excluded. Beyond experimenting, this work requires us to trust those who are often overlooked in providing solutions precisely because they are closest to the challenges.

With that experimentation, we can generally expect two outcomes: supporting or refuting a particular hypothesis. Refuting a hypothesis is an opportunity to learn, gain new insights, or pivot in a different direction. But sometimes, it’s also known as plain old “failure.”

As a Black-led organization, we are taking calculated risks as if we could not fail, but we are also granting ourselves permission to fail — truly an empowering act in spaces that by all accounts do not grant such a privilege to organizations like ours. The idea of failure is usually one that must be avoided at all costs, as the risks and narratives that result and that are rooted in white supremacist notions are often too great to bear. Failure can be the difference between funder relationships and multi-year general operating dollars that give Black-led organizations the breathing room and resources needed to truly tackle deeply entrenched and enduring societal issues, often inextricably linked with race.

As a starting matter, Echoing Green and Bridgespan note that the “revenues of the Black-led organizations are 24 percent smaller than the revenues of their white-led counterparts, and the unrestricted net assets of the Black-led organizations are 76 percent smaller than their white-led counterparts.” They further note that persistent challenges for Black-led organizations, even when controlling for issue area and education levels include: 1) inequitable access to social networks that foster ties to philanthropy, 2) interpersonal bias that can manifest as mistrust and microaggressions, 3) the over-reliance of philanthropy on evaluation and methods already familiar to them, and 4) arduous grant processes reflecting mistrust, all inevitably leading to a racial funding gap that widens over time. Further, the Building Movement Project notes how BIPOC groups are seen as risky investments and pitted against one another for resources while larger and white-led organizations are the ones that typically receive substantial funds.

An emerging lesson is the level of mistrust, sometimes couched as risk — intentional or not — that is apparent when it comes to supporting and funding Black-led organizations. As a result this limits organizations’ ability to engage in the mission-critical work needed to fully address challenges from a systems and root cause approach rather than symptoms-based approach.

As a Black-led organization, we have had to grapple with these same considerations at various points in our lifecycle as we apply solutions to enduring challenges around the racial wealth-gap and an inequitable economy. At times, we have not been as well-resourced as white-led peer organizations, not trusted to lead and offer viable solutions, and not supported in the critical work to address racist systems, even with our collective knowledge, insights, education, and lived experiences that shape our ideas about what might work. We have been on the brink of not making payroll and not having the funding needed to cover critical operational and programmatic expenses. When deficit is the basis from which an organization is operating, it’s near impossible to apply your talent, time, treasure, and ties toward innovative solutions. Instead, the focus is spent on seeking and securing resources and maintaining funding relationships, even those that are toxic and detrimental to mission, at all costs.

So why then, would an organization knowingly risk any of its hard fought and won resources to experiment, possibly fail, and invite even more scrutiny, mistrust, and threats to critical resources by coloring outside the lines and thinking outside of the boxes? For us, we are choosing to take such risks because we know our ability to shift capital and power to BIPOC communities and to create sustainable equitable economies, comes precisely from us taking calculated risks experimenting, and possibly failing.

To experiment in an environment where our resources, credibility, and connections can be threatened at any moment requires boldness, audacity, and stepping into a level of privilege typically not available to organizations like ours. In so doing, we are removing the buttons of respectability, the hood of appeasement, and the cloak of perfectionism.

We are choosing to not simply accept the status quo of burn out, systemic racism, underfunding, and other pitfalls as we seek to carry out and live out our vision and mission.

We are deliberately choosing a different path because we know this is the key to us achieving our mission on our terms — terms which reflect decisions by staff and board with lived experience in the challenges we seek to address. We are experimenting externally through our Character Based Lending pilot, designed to make capital accessible to BIPOC entrepreneurs typically excluded from the capital needed to execute their vision. We are also experimenting internally through our 4 Day Work Week pilot, designed to prioritize our people, create more space for rest and joy, facilitate true work-life balance, and challenge the usual norms about how work is done, particularly for a multi-racial and majority women organization.

In conducting these and other experiments, we do our due diligence and develop hypotheses about the outcomes, but we don’t know for sure if we will see success or failure. However, a failure in the wake of experimenting should not be the sole barometer by which we are judged for our ability to make sustainable impact and likewise secure or maintain resources. We know that in the wake of the COVID-19 pandemic and in the aftermath of the murder of George Floyd many philanthropic institutions moved to provide flexible support to Black-led organizations and we know that this flexibility is a must to sustain thriving organizations. In fact, we have been the recipient of such giving that recognizes and further enables us to experiment, iterate, fail, and try again. But as old habits die hard, we know it would be too easy to return to past norms that leave Black-led organizations mistrusted, underfunded, and restricted in solutions they can advance. This kind of crisis funding that is responsive to immediate stimuli is not a long-term solution to the long-term challenges Black-led organizations are trying to address.

So I ask you, do we and other Black-led organizations deserve to have our funding, relationships, and credibility be threatened when we fail?

Or instead, can we be treated as partners who can offer up our lessons so that other organizations may learn from them and possibly carry them forward with some adjustments? Can we instead use our time to pivot toward other solutions rather than continuing to try to prove merits and outcomes to funders when we have learned through our failure that something different may work better when we have the opportunity to experiment and iterate? Can we take both the successes and the failures as part of the tapestry we are weaving to advance justice? Answering these questions in the affirmative best positions us to create a thriving, equitable, and empowered organization and society.