Jessica's Main Street Conference Experience

Richmond’s Main Street America conference delivered reminders of the power of volunteers organized around one central mission, openness to collaboration, and strategic “scrappy” solutions for the universal woes that impact historic downtowns. To connect with like-minded leaders was refreshing, and to wear the Great American Main Street title among peers was charming. 

I respect Main Street America’s community, from their acclaimed, exiting President and CEO Patrice Frey to the volunteers who pour beer and collect trash for the chili cook-offs, parades, and festivals. I believe the work is essential. It supports a quality of life for the populace, giving a safe place to connect, experience, and engage in conversation. 

I respect Main Street America's community, from their acclaimed, exiting President and CEO Patrice Frey to the volunteers who pour beer and collect trash for the chili cook-offs, parades, and festivals. I believe the work is essential. It supports a quality of life for the populace, giving a safe place to connect, experience, and engage in conversation. 

The urban landscape of Richmond offered bold reminders of the troubling issues our communities are facing in the wake of the pandemic, but more importantly, as a result of a dark history of inequality, bigotry, and ruthless pursuit of status by way of wealth. Frankly, I found it challenging to focus on the Four Points of Main Street, having seen the reminders of a bigger picture. 

In collecting my thoughts on what I took home from Virginia, many of my experiences from past conferences returned.

  • In 2015, I attended my first Main Street America conference in Atlanta. While exploring Grant Park, a predominantly white-collar and white neighborhood near the city center, I met a woman in her early thirties. She shared she was on disability, dealing with chronic illness, and providing for her extended family solely on the income made driving Uber–the only job she could hold with her circumstances. 

  • In 2016, Wyoming’s Main Streeters ogled the award-winning Milwaukee Public Market in the heart of the city’s Historic Third Ward. The revitalized warehouse district, previously called “The Bloody Third” for its rowdy reputation, was developed on the backs of immigrant labor. It now homes Milwaukee’s most affluent and educated in spacious lofts, modern offices, and luxury food, art, and retail experiences.

  • In 2019, a deceased homeless man sat upright on a public bench around the corner from the high-end conference venue in Seattle’s Business District. Throngs of corporate city walkers passed by the familiar-to-them scene without a flinch. In 2020, over 11,700 individuals experienced homelessness on a single night in Seattle’s King County. The average home price is $854,748.

Along with the learning experience, each conference has presented eye-opening invitations to dig further into the unpolished stories behind pretty places. Within each award-winning community project is another lesser told story that isn’t emboldened by glossy marketing materials. The tour buses don’t often pause between inspired details to present the ugly truths of what came before or exists despite the accolades. 

Virginia’s conference presenters delved into discussions of Equity and Inclusion, housing development, and impactful data collection. Then, attendees were released to explore the city to find blocks of boarded-up businesses and restaurants bursting at the seams–their understaffed dining rooms still in recovery from the impacts of COVID-19. Polished neighborhoods sprawled around luxury hotels, tucked just blocks away from areas stricken by poverty, homelessness, unemployment, and health crisis. On the same street that I purchased a $10 green juice and gluten-free, vegan scone, I watched a man offer a cold Coke to the homeless man crouched with his belongings on the curb.

I’m proud of the work, but, I don’t want to work this hard to support the people of privilege anymore.

I took notes on fundraising strategy, data collecting, and advocating for the program's needs, yet, I haven’t considered them since I returned home. Instead, I’ve repeatedly played a conversation I had with my partner.

“I’m proud of the work,” I said. “But, I don’t want to work this hard to support the people of privilege anymore.”

In ruminating, I’ve arrived at:

1. Work on Main Street is fluid.

Hearing the widespread conversation around the power of shared narrative at the conference allowed me to see the value in the storytelling work I’ve done for Main Street over the years and presented an opportunity for pivoting. As a staff member and committee volunteer, I have, up until now, gathered the stories, told the stories, and created experiences to have conversations around the stories. Now, as an Executive Board member, I believe it’s time for me to step back from that work and, instead, challenge the stories.

Why are there gaps in diversity?

Why are there repeated challenges?

Where can we identify missteps? 

Where are the opportunities to engage in tough conversation?

What are we hearing and not acting on? 


The value of this internal shift is not exclusive to me. No different than the infamous “seven-year itch” of lovers, the relationship between Main Street and its people is susceptible to stagnant work and unfulfilling tasks. Assessing the history of a volunteer’s position within the organization and strategically setting challenging and novel goals ahead not only supports the retention of volunteers but also better assures the organization and the individual are mutually reaping the benefit of the relationship. 

2. The efficacy of the work requires focus and rest. 

Main Street’s success depends on volunteer labor, and dividing that load is the only way to conquer it. Currently, too many individuals are managing too many responsibilities for the organization. This predicament invites us to set individual, self-honoring boundaries and shed commitments, but additionally, it begs conversation on volunteer workload policies and capacity. The organization has been lucky to move forward despite volunteer shortages without significant issues. However, relying on a small collection of individuals for an extensive calendar of events and campaigns leaves us vulnerable to catastrophe in the event of unexpectedly losing a key volunteer. I’m reluctant to expect “luck” to carry the organization as it continues to expand, and this needs to be approached with less conversation and more action.

3. The work was done with privilege for the privileged.

When I came to Main Street, downtown beautification projects and collaborative street events were enough to inspire the work. A rehabbed Christmas wreath brought me to Main Street’s office for the first time. However, the degree to which these projects sustain my work has faded as my understanding of the power of place has grown.

No different than Atlanta, Milwaukee, Seattle, and beyond, Laramie is home to significant populations burdened by the inaccessibility of security and safety in work, healthcare, homes, and support. No different than these conference destinations, Laramie is prone to shift the collective gaze away from these realities. Instead, we must turn toward them.

We had the honor of being celebrated for our work to bolster a lively community–the result of a board and volunteer base that is predominantly white, non-disabled, and of a career and lifestyle that allows for a non-profit’s mid-day meetings, volunteer tasks, and email chains. Now, on the tail of recognizing our capabilities as a team, I believe it’s time to explore actionable solutions that allow Downtown Laramie to be a thriving community for the humans who do not look like or experience the world like us. 

Richmond offered a long-overdue reminder of why it’s important to step away from the community that is our familiar home and inquire, “Now what?” as we use our GAMSA as a page break, not a bookend, in doing whatever important work is next.

Travel presents novel experiences and reframed snapshots of what it means to be a human in a community. So often, as Main Streeters, we’re unable to see the forest for the trees as we bury ourselves in Laramie’s properties, events, and fundraising goals. Richmond offered a long-overdue reminder of why it’s important to step away from the community that is our familiar home and inquire, “Now what?” as we use our GAMSA as a page break, not a bookend, in doing whatever important work is next.