Cupcakes, Crisis, and the Cost of Compliance

Notes from a Long Arc offers a candid, narrative-driven look at the unseen mechanics, inherited myths, and emerging possibilities within philanthropy and wealth work. Through stories, analysis, and movement-grounded observations, Sadé Dozan examines how resources flow—or fail to flow—through our social change ecosystems, and what that reveals about power, belonging, and democracy.

It was late in the evening. An hour when retail stores are deserted and exposed, and the fluorescent lights hum louder, a time when tired people try to finish one last shopping errand before going home. My friend Monica and I were done. We gathered our bags and headed toward the exit to hop into a cab when, suddenly, we heard voices rise behind us—sharp enough to cut through the end of the day haze. We paused, then doubled back to look.

An older woman was attempting to buy food and formula, holding cupcakes in her hand, but the checkout clerk wouldn’t let her process an EBT payment and use her SNAP benefits. The store policy required the physical EBT card to complete the purchase—a fraud-prevention mechanism—yet it also allowed customers to type in their EBT cards to order and pay in advance. The rule wasn’t unclear, it was inconsistent and disconnected from the realities of the customers it served.

We heard her frantically explain—for what felt like not the first time—that they could simply type in the numbers. The cupcakes were for her granddaughter’s birthday, which was that weekend. She just wanted to do this for her grandbaby and go home. She repeatedly explained to the cashier that she had her ID along with her EBT card number, and that this had worked before. Still, the cashier refused to help her, called the manager, who then called security.

At what point does following the rules become a moral failure, and who gets to decide?

We are at an inflection point where we must ensure that judgment and decision-making power lie where they belong: not in arbitrary systems but in the hands of the people—because systems fail arbitrarily, and at times, by design.

By the time Monica and I walked closer, a guard was hovering nearby, loudly telling the grandmother that she could either pay cash or leave. There was no conversation or acknowledgement of her circumstances. Her anger—justified, human, but measured—was treated as a threat to be managed.

I saw the look in her eye. How quickly the grandmother’s confusion turned into a sad, defeated anger. Not loud. Not violent. Not chaotic. But a composed, compounding frustration as simple truths cascaded out of her mouth. She asked questions, named the inconsistency. She understandably pushed back on being told no without explanation.

“Why?” she asked, over and over.

The cashier rolled her eyes, disinterested. The manager avoided the whole situation, staring towards the floor, moving closer to security. The guard stepped even closer to the grandmother—crossed arms, squinting as he continued to hover over her.

The grandmother conceded and began to put back items from the conveyor belt to the cart. First came the cupcakes. Then the formula and, slowly, the rest.

The Systems We Sustain

What unfolded didn’t look chaotic; it looked procedural. Each staff member did their job exactly as designed. The cashier followed protocol. The manager escalated in response to a situation they could not manage rather than trust the woman at her word. Security arrived to contain, not to understand.

Every action made sense inside the system they were operating within—and that precisely was the problem. What Monica and I witnessed was not a breakdown but a transfer of responsibility from human judgment to flawed policy. No one involved considered whether the EBT card was needed to confirm identity, and the woman had both a photo of the card and a hard copy of her ID, why could they not enter the numbers? If this had worked before, why not try?

As the grandmother’s voice rose, while returning the items to the shopping cart, Monica and I intervened to help.

Monica approached her, made space for her words and emotions. She spoke with the cashier, gently reminding them that this customer was a person. I deliberately—though not exactly dramatically, at 5’2”—placed myself between the security guard and the grandmother, creating a physical barrier while asking the manager to understand her perspective. We stepped in not because we thought we were better people, but because we could see what the system was converting confusion into threat and a demand for dignity into disruption.

These weren’t just our instincts. It was practice. It was proximity. It was years of understanding how systems fail and how quickly people are punished for naming that failure or challenging it. Monica, who was executive director of the nonprofit SisterSong, had access to a rapid-response community impact fund designed for moments like this. She didn’t need to ask permission or justify whether cupcakes “counted” under the rules. She had discretion and the authority to use it.

She purchased all the items on the grandmother’s behalf.

As our democracy swells, fractures, and rebuilds all at once, our moral obligation to challenge long-standing practices and systems takes on new urgency.

The energy in the space shifted. Security moved back. The cashier relaxed. The manager wandered away. The grandmother’s posture changed. We walked her out with her food, her formula, her cupcakes—and her dignity intact.

All totaled, it was a $50 intervention.

This is not an argument to issue mini funds to be utilized at grocery store checkout lines. It is to spark curiosity to better understand the systems that we participate in every day—including those within the social sector that we create and sustain.

What happened in that store wasn’t about cupcakes, baby formula, or an EBT card. It was about whether anyone in the room was authorized—and supported—to exercise judgment when the rules stopped making sense.

That kind of discernment is already happening across our sector, often quietly, often off the books, and often at personal cost to the people exercising it. For those of us in the social change sector, this is a call to collectively ask ourselves:

• Where in our work do we follow procedures even after they stop making sense, simply because they are familiar, sanctioned, or safer than deciding otherwise?
• When a system produces harm, do we recognize that harm as a failure of design—or do we allow it to become “no one’s fault” because everyone was just doing their job?
• What judgment are we quietly surrendering to process and procedures, and what would it mean to take responsibility for it again?

The Shifts We Must Make

In the social sector—and in philanthropy in particular—we have grown quite adept at navigating broken systems without challenging them. We tend to reward calm navigation of these systems, upholding a culture that tells leaders: Be a pioneer but don’t travel too far into the future. Be bold but not too explosive. We call this risk management, but, in practice, what we’re doing is labeling human judgment as a “risk” and abandoning it to inflexible processes that are detached from the realities of life.

As we eye futures rooted in justice and democracy, we must normalize making shifts to exercise judgment rooted in community care and thus undo our inclination towards compliance and rigidity.

Community-rooted movement leaders like Monica follow in a lineage of those who understand that direct service and systems change are interdependent, which is how democracy functions in practice. From the Highlander Folk School to the Student Nonviolent Coordinating Committee, community organizers throughout our history have understood that bail funds, food, transportation, leadership development, and political education are mutually reinforcing forms of protection and power-building. There was no separation between meeting immediate needs and advancing systemic change. Judgment was not centralized, nor systematized; it was distributed and backed for the long term.

So, what does it mean to courageously carry this legacy forward?

For nonprofit and grassroots organizers, this requires explaining directly to funders how their teams’ own clear-eyed judgment is already at work behind the scenes, speaking explicitly about the tough choices attached to proximity, and being honest about the support this work requires. Being explicit about what compliance in this work costs us—time, trust, safety, strategic clarity—is a necessary act of transparency; it is what justice requires.

For funders, this requires dismantling design systems and processes that quietly undermine trust or reinforce control. It means asking not only about outcomes, but whether leaders were resourced to navigate complexity with integrity. And it will mean funding our most proximate leaders—people like Monica, who are not simply service providers or advocates but bridges; people capable of holding direct service and systems change as water in the same river, flowing upstream and downstream at once.

We are now living with the consequences of what happens when judgment is systematically stripped from everyday decision-making—when discretion is replaced by obedience to procedure, and responsibility is diluted until no one feels accountable for what follows.

This did not happen without warning.

For years, movement leaders have been naming the limits of defending democracy the way it was sporadically funded. They told us that civic engagement could not be reduced to voter education and turnout alone. That democracy requires durable infrastructure between elections—not just bursts of attention every two or four years. They named how episodic investment was not only insufficient but destabilizing, severing long-term organizing from the resources it needed to hold ground when the spotlight moved on.

Trans leaders warned that the attacks on their communities were not isolated culture wars but early signals of a broader strategy that was testing how fear could be mobilized, how bodies could be legislated against, how the state could rehearse control. Black leaders repeatedly named that racial equity investments without generational commitment would function more like pressure valves than transformation. Reproductive rights leaders pointed to the necessity of state-based coalitions, not just during elections but in the long stretches between them where policy was shaped, narratives hardened, and power quietly reorganized itself.

And yet, despite the alarm bells, our processes in philanthropy remained narrow and slow-footed.

Many funders translated the scaffolding movement leaders needs downward—reshaped to fit one- to three-year grant cycles, trimmed to what could be funded, and softened to what would not fully disrupt the system meant to support it. In this way, obedience became a professional skill. We learned how to stay legible, fundable, and contained within the rules of our systems.

This pattern was not confined to funding institutions alone.

The Architecture of Obedience

Obligatory compliance has been the drumbeat of obedience. It has lived in rooms filled with leaders, program officers, and board members—people who cared deeply, who believed in the world’s ability to change, and yet who nonetheless learned, over time, to stay in their lanes. Staff translated movement warnings into fundable language, trimming urgency into something that could pass internal review. Board members emphasized fiduciary caution, governance norms, and reputational risk, synonymously naming restraint and responsibility. Fundraisers learned to read the temperature of funders before speaking plainly, calibrating their truth to what might be tolerated rather than what was required.

Movement leaders were not immune to the impact of obedience. Many navigated the delicate dance of compliance, not because they lacked clarity on what movements needed but because survival demanded it. Feeding people, paying staff, keeping the doors open often meant choosing partial alignment over principal rupture. Menial funding felt preferable to total withdrawal. Obedience, in this context, was not surrender but a form of movement triage. Many of us told ourselves that this is what we needed to do for our movements to survive.

I have learned that this is not a failure of values but a failure of a system that steadily reallocates judgment away from people and into process—until no one feels authorized to intervene, even when harm is plainly unfolding.

We are at an inflection point where we must ensure that judgment and decision-making power lie where they belong: not in arbitrary systems but in the hands of the people—because systems fail arbitrarily, and at times, by design.

This is not a call to dismantle every rule that governs our sector, nor am I calling for chaos in the name of urgency. It is simply an invitation to ask harder questions about which rules protect people—and which merely protect systems from discomfort.

The pattern of obligatory compliance and chosen inactivity has consequences far beyond our sector. Across the country, we are watching obedience—preemptive and explicit—harden into infrastructure. When people are trained not to decide and are disempowered from using their judgment, the abuse of power does not disappear but rather consolidates. When judgment is deferred upward, enforcement fills the void.

This is how bureaucratic procedure turns into militarized presence. How silence becomes permission. How authoritarian regimes are built not only through force but through familiarity—through people doing what they only feel sanctioned to do. To do what feels professional, survivable, across our sector and beyond.

As our democracy swells, fractures, and rebuilds all at once, our moral obligation to challenge long-standing practices and systems takes on a new urgency. If we keep our heads down and follow only the rules we’ve inherited—often those self-imposed by our predecessors—our civil society will continue to hollow out. And most days it will not feel like a loud scream; justice will move further away from us, quietly, procedurally, and with everyone “just doing their job.”

The cost of compliance is not theoretical. It is paid in delayed action, in muted warnings, in the slow normalization of harm that feels professional because it is familiar. Our most pressing civic imperative today is not to strategically plan for impact or perfect processes. It is to dismantle systems that mistake obedience for safety and to deliberately resource judgment—to continue to hand over power to those closest to harm with the lived expertise to move swiftly. Because sometimes justice does not arrive as a policy shift or a strategic framework.

Sometimes it looks like a grandmother leaving the market with groceries, baby formula, and cupcakes for her granddaughter’s birthday—and a community still capable of deciding that those things matter.

Sometimes justice looks like a board willing to risk discomfort—or even an endowment—in service of the futures they claim to steward, or a nonprofit leader naming what they actually see, despite what they were told to report on the template.

Sometimes it looks like moving resources between election cycles, between headlines, between moments of urgency—because democracy cannot wait to be funded. Sometimes it means disrupting a system even when doing so feels unsafe—because the truth is, people’s lives are already on the line.

The real question the long arc is asking of us now is this: how much more are we willing to lose by pretending we didn’t have the authority to choose differently?

SisterSong Women of Color Reproductive Justice Collective is a national organization dedicated to advancing reproductive justice by centering the leadership, expertise, and lived experiences of women of color. Monica Raye Simpson, its executive director, has long been a leading voice in building community-rooted infrastructure that bridges direct support, advocacy, and long-term movement strategy. The moment described here reflects not an exception but the kind of judgment and care SisterSong invests in every day. Monica is also an amazing singer, hilarious human being, and my sister-friend.

Support their work directly here: https://www.sistersong.net/donatesistersong