Experimenting New Electoral Strategies for Winning 2023

We’re about ten months away from the official start of the 2023 Chicago municipal election, but who’s counting? With our memories of horrid winter 2018–19 canvassing buried away and our hopes on the horizon for a pandemic more under control by next fall (when petitions start), hearing rumblings of challengers hoping to unseat awful alders and imagining the movement getting rid of Lori makes me hopeful during our bleak present-day reality. But what if we take some time to imagine… losing? Stay with me. We have 5–8 solid movement alders whose seats we need to defend, 3–6 opposition alder seats that are contestable, and a mayoral seat (and that’s just the municipal election). The Chicago Left has grown so much stronger since 2019 that the dream of taking all those seats is within the realm of possibility, but so is the potential that we spread ourselves too thin and lose seats we have now.

IMAGINE… LOSING?

I don’t need more 2023-induced horror nightmares either but I do think it is a helpful exercise to think about how we might lose. It’s called a “pre-mortem” (yes, not the best named term) and it is an exercise that agile software teams sometimes use before a feature deploy. In software and organizing communities alike, we often have a debrief after the fact (“post-mortem”) to reflect on what happened in the past and lessons learned to bring with us the next time around. At that point, there aren’t a ton of actionable steps we can immediately benefit from. Instead, if we think through the challenges that could cause everything to go wrong beforehand, collectively with all stakeholders in the room, we have the time to try to get ahead of those risks. At a high-level, you would brainstorm all the things that could go wrong (make it exhaustive, make it specific), narrow that list into two smaller lists: the biggest risks and most likely problems, narrow it further to focus on what we most have control over, and ideate solutions to prevent those from manifesting or minimize their impact. Another framework that could be used is a SWOT analysis, where you outline strategies to maximize opportunities and prevent threats through our strengths and identify potential weaknesses. Ideally exercises like this would be happening with all of us in one room for an extended period of time having a conversation but, in the absence of that, Medium and social media will do. Starting that brainstorm will be the goal of this post and I hope that you engage on social media with your ideas and reactions.

FIRST, LET’S EXAMINE OUR POWER

In Chicago, we have a deep rooted history of Independent Political Organizations (IPOs) that often organize at the hyper-local ward (or neighborhood) level. Since the last municipal elections, we’ve seen the amount of these organizations grow and their collaboration with one another blossom. My own political home, 33rd ward Working Families, was founded after an attempt to unseat the Mell machine in 2015 so it makes sense that after the electrifying wins in 2019 more IPOs were founded and have their eyes on 2023. We’ve also seen great examples of neighboring IPOs rallying together and working together to counter the undemocratic process of filing vacancies and attempting to shed more transparency in recent appointments of the 20th Senate district and 15th House district seats in Illinois.

We also have several organizations practiced in coalition building and solidarity campaigns across larger geographies, from Right to Recovery to the fight for community control of the police, to #NoCopAcademy, to the Collaborative for Community Wellness, and more.

In addition to the coalition campaigns, we also have city/county-wide organizations such as United Working Families (UWF) and Chicago Democratic Socialists of America (CDSA). As a member of both, I’ve seen how they have built empowered memberships across the city. They have different operating structures: UWF is made up of 16 chapters, IPOs, community organizations, and unions as well as individual members, all representing about 100,000 people. CDSA has upwards of 3,000 members across four branches doing work across multiple committees, working groups, and campaigns.

All of this people power translated into tens of thousands of doors knocked, almost $1.5 million donated to the 2019 campaigns of the Chicago Socialist Caucus alone, and a changing face of city council that actively opposes the dominance of neoliberal politics in Chicago.

THE THREATS TO CONSIDER HEADING INTO 2023

There are likely more threats than this but to keep this section focused, I’ll choose three:

OUR ENEMIES ARE EMBOLDENED
Between fascists within and outside of the FOP, remnants of the machine, and Lori’s petty vengeance, they are going to come at us hard and with lots of money. When I think about our most outspoken movement alders, I think about how much defense we will have to play in the upcoming year. We see it already happening in the 33rd ward with a rise of pro-police, tough on crime rhetoric bolstered by machine politicians and Mell followers and I am sure there are similar trends in other wards that I have less visibility into because of proximity.

REDISTRICTING WILL CHANGE OUR LITERAL POLITICAL LANDSCAPE
Right now, the City Council has until December 1 to approve a new map. If 10 alders break away with an alternative map on how to divide our wards, it will go to a referendum that Chicagoans would vote on next June. Most candidates who are going to run in 2023 have already announced or are in the midst of making final decisions now to allow enough time for getting campaigns ready and public launches next year. This is incredibly hard to do if you don’t know which voters you will be canvassing or even if your home will make it into the new ward boundaries. We have an unprecedented opportunity to draw a promising map but between the level of detail in the final product and the ticking deadline, anything could happen. Best case scenario, even if we have a final approved map come December 16, that doesn’t leave a lot of time to make political calculations on where and who to run and get campaigns up and ready by spring/summer public launches particularly for wards who have significant boundary shifts.

WE’RE TIRED AND THE PANDEMIC ISN’T OVER
It’s still a pandemic where too many have died, lost jobs and housing, and generally have been left behind by the state. We’re still grieving. Many of us are out of steam. Our movement sprung into action with mutual aid organizing, the uprisings after the murder of George Floyd, the state withdrawal of support systems as we are forced to “return to normal”, legislative fights that continued around ECPS, education, housing, and budget season, and more. There has been no break for many going full steam since 2019 and in overdrive during the pandemic. Despite large memberships, participation has dropped across the board in our organizations as people face burnout. And beyond that, with elections postponed, election season will feel longer. State and County race petitions start in January for an election day at the end of June, right as most municipal campaigns wrap up public campaign launches and two months before petition collection starts for the 2023 municipal races. Beyond that, there are also LSC seats and the new seats created by ECPS to fill and a brand new congressional district in Illinois which is the size of many wards and will take a tremendous amount of money and people power to contest months before municipal races officially begin.

WHAT ARE OUR OPPORTUNITIES?

I started thinking about this article after the Fair Tax failed and the intense spread of anti-vaxxer and anti-masker propaganda has only made me more strongly believe: our usual tools will not be enough and that we have to think creatively about new experiments to try when it comes to elections. All the organizers I know value the strong foundational building blocks that go into a campaign and we should absolutely rely on those. However, with the new challenges (a handful of which are) outlined above, if we rely on our usual foundational tactics alone, we will inevitably spread ourselves too thin and lose a few vital campaigns. Here are some thoughts and experiments we could try to create more capacity for winning:

IF BOUNDARIES ARE SHIFTING, AVOID BEING AN ISLAND
When it comes to redistricting, we can use geographical continuity to our advantage. One thing that brings me solace is that the 33rd ward isn’t totally an island. We’re surrounded by the 32nd, 35th, 39th, 40th, and 47th wards — all of which have friendly alders and/or active organizing groups. We can use IPO and member geographical spread to inform what races we tackle and in the future advocate for boundaries that work to build power for Poor, Black, and Brown communities.

At an individual level, if you are thinking of moving in the upcoming months, consider ward boundaries as one of the many factors in deciding where to live. I joke about this a lot and have even suggested making a tool to filter down listings by ward but the truth is for me, my continuing engagement in my IPO is largely informed by how local the organizing and community is. Removing distance is one less barrier to meeting new neighbors and engaging new supporters, especially during brutal Chicago winters.

WORK TO OUR STRENGTHS
IPOs and citywide organizations have different strengths and it is important that we play to them, while also being mindful that many folks have overlapping membership when calculating capacity. IPOs have local expertise and connections with neighbors. Citywide organizations have larger memberships to mobilize and money to contribute. That is an overly simple illustration but overall, by working together, we can tackle the work collaboratively rather than reinventing multiple systems for volunteers.

One of my dreams is that the Chicago Left gets together to have a de-siloed conversation about our collective vision for the future and think strategically about who is best equipped to tackle different parts of that work and what gaps exist that we can work collaboratively to bridge. It’s hard not to be reactive during these times, but much like neoliberal budgets’ lack of investment in safety nets, if we don’t proactively define clear strategic goals for the futures, we will always be in reactive mode.

At the individual level, it is important to recognize when silos are being built where instead collaboration can take its place and to reduce redundancy in process and deliverables where instead capacity can be redirected. We make up organizations and it is important to speak up early and often (even if you have the tiniest platform like I do).

SHARE THE LOVE
Let’s take a look at an average aldermanic race: it will probably cost $250k-$500k, require at least six core staffers (Campaign Manager, Field Director, Communications Director, Volunteer Coordinator, Policy Director, Fundraising Coordinator), and 3,000 petition signatures (hundreds of volunteer shifts to gather) to securely get on the ballot and win. Multiply that by 5–15 races happening at the same time, right after a handful of state, county, and likely congressional races. In order to make that seem less daunting, one new thing we could try is build a shared staffing model. This is what it could look like:

• Build apprenticeships/shadowing into staffing plans. Have folks that fill those core staffing positions on municipal campaigns work as apprentices or at least shadow state/county races, especially if it is their first time in the role, to learn and get practice. Even if that specific opportunity doesn’t arise, making a plan to build skills for each role during the municipals will be vital to success and gearing us up for success in fast follow campaigns (like committeeman races, LSC seats, etc).
• Build a network across campaigns so that each of these roles has multiple other folks doing this work they can lean on. Imagine if you were a volunteer coordinator and had even five other volunteer coordinators from other ward races that you were in regular communication. You could compare sign up platforms or brainstorm how to deal with attrition or bulk buy hand warmers, and other examples of reducing the load and sharing knowledge. In addition to that, creating community with others doing the same work at the same time can help create a pressure valve for stress or normalize sharing mistakes and learning from them in time to course correct.
• Create a forum this spring for veteran campaigns to share best practices with new campaigns. There’s a lot that happened in 2019 that was probably not visible or well documented but helped build victories. One example from the 33rd ward was our precinct captain program. As someone that participated in that, there are a lot of benefits and lessons learned on how to improve it in the future. Having a forum to share those lessons widely could be effective as new campaigns get in formation for the first time.
• Create a data sharing policy and set your info sec practices. The importance of strengthening our digital security during a time of emboldened fascists and where doxing is commonplace deserves its own article but suffice it to say that convenience often wins out and leaves us vulnerable especially during a crunch time like an election. There is ample opportunity for skill building here. A related area to think about: figuring out how to best share canvassing data in an ethical way for overlapping geographies with back-to-back elections to maximize volunteer shifts. Where possible, we must always model the world we want to build and when it comes to making sure our data stays safe and isn’t abused or shared widely, being explicit about our data policies and prioritizing consentful tech is paramount.
• Create a rapid response notary network to reduce the bottleneck that happens when the proportion of volunteers collecting petition signatures isn’t aligned with the amount of notaries you have on your campaign. Imagine one of our larger citywide organizations building a notary sign up drive, maybe even sponsoring a few applications (it ends up costing less than a dollar a month to become a notary for four years! …*steps off soapbox*), and creating a lightweight system that any campaign can request a notary and have someone show up within an hour. Beyond electoral campaigns, this can be used for ballot referenda, as a way to reduce the burden of legal paperwork for working families, etc.
• Create a language justice team to help get our message out in as many languages spoken in Chicago as possible. During the last Bernie campaign, I volunteered on the language justice team in part because I remember during AOC’s campaign, seeing her literature in Albanian (background: her district has a large Albanian population and I’m Albanian) resonated with something deeper inside me than just our values alignment. We still live in a world where translations are seen as burdensome and even when we prioritize it, we often scramble to make it available. Instead of each campaign having to recruit the same language speakers to translate their campaigns, what if we had a team that worked across campaigns to write and proof translations, to build a library of common phrases like “Tax the Rich”, to live tweet debates or build captions/transcripts for videos, and more? It would make recruitment easier, reduce the need to reinvent this process for each campaign, help the communications team, and most importantly reach populations that feel neglected by the status quo.
• Really prioritize accessibility. Similar to the language justice team but create an explicit team or role or responsibility for someone to make sure campaigns are accessible at every point. It breaks my heart when websites provide an awful experience on mobile devices or with assistive devices, especially in 2021. In this day, especially as we’ve learned during the pandemic, our websites and digital spaces are just as important in welcoming everyone as our physical spaces. As someone that works with software teams on this everyday, I know it takes work and expertise to do this right. So let’s build skills in this area (and/or a budget to pay people to do this work). As with the previous ideas, having a shared team spreads the load of this work a little bit.

For each of these ideas, there is ample room for collaboration between ward level IPOs/campaigns and citywide organizations. Some of this work may already exist in trainings that organizations hold but if we want to win bigger in 2023, we’ll have to scale our resources and reach significantly. Sharing some of the work is one strategy.

At the individual level, I’m not sure what this looks like but let me know if any of these ideas are interesting to you to collaborate on?

IF OUR ENEMIES ARE EMBOLDENED, DOUBLE DOWN ON OUR MESSAGE AND UNITE
Another strategy is to run on a slate and use this to take the shared network idea from the section above to the next level: collective decision making.

In my opinion, given that the amount of media coverage of the mayoral race dwarfed aldermanic races in 2019 and the number of times people on the door asked who the alder was supporting for mayor, a slate is most beneficial from a communications standpoint if there is a Leftist running for mayor. If we want voters to hear our message multiple times, having someone at the top of the ticket in addition to the ward level helps amplify that message and makes it easier to canvass voters. Even if the mayoral seat is a longshot, this benefit is worth it. Of course, every ward has its own particulars so the platform a slate shares doesn’t have to be a fully overlapping Venn diagram. There will inevitably be ward-level issues that the rest of the slate won’t touch on. But it is an opportunity to double down on countering the neoliberal rhetoric we’ll see and for uplifting topics that aren’t yet clear issues for voters (ex. making municipal broadband a bigger platform item!).

Even without a mayoral candidate helping on the messaging front, there is value in a slate when it comes to coordination and even decision making. At a minimum what this could look like is a daily stand. (Daily stand is an agile software concept where the team meets everyday for a short meeting (usually 15–30 min) to share what they did yesterday, their plan for today, and any blockers they need help with.) How would this be helpful? Well in the heat of a campaign, it is easy for the rest of the world to fall away as you focus on your race. On a campaign your goal is to recruit as many volunteers as possible to maximize voter outreach and raise as much money to get your message across, your volunteers resourced, and your staffers paid.

Here’s an example (perhaps idealistic a tad bit): Imagine being in a daily stand with the slate talking about canvasses this upcoming weekend. Campaign A has 50 volunteers, more than enough, for Saturday’s canvass and Campaign B is far from their canvass goal and has had trouble recruiting. The idea of telling volunteers “we don’t need you this week; please go to campaign B Saturday” is difficult because 1) it’s natural to make decisions on emotions, like fear of losing, that lead to wanting to maximize your resources and 2) it’s hard to know which campaigns need more resources at a given time as reality can change rapidly. During that stand, campaign A or a citywide org on the call could maybe say something like “we’ll ask our volunteers if they can redirect their plans to campaign B this Saturday.” It’s hard to have that level of tactile solidarity without regular communication and coordination. It’s also important to make a commitment to building mutual expectations like that before the need arises so we aren’t in reactive panic mode.

This also makes it easier for voters, volunteers, and supporters to have a reliable source of truth when deciding where to spend their time, efforts, and money. Right now, you have tens of thousands of people individually making those decisions based on a variety of factors, most of which are based on their gut reactions rather than an informed sense of real-time reality. If I knew that the five campaigns I cared most about had this level of coordination, I would feel like I’d have somewhere to check where to direct myself if I had an extra evening free to canvass.

If doubling down on our message and creating a louder and wider platform to spread it in a more coordinated way sounds promising, then what is in our way? Well, besides the work and communication to make that happen there is also another elephant in the room. The Left has a long memory. I am guilty of this as well. I forgive easily but don’t forget and can let missteps or disagreements sit too long in my subconscious, judging people/orgs rather than remembering the larger picture. I think our visions for a future filled with accountability and transformative judgement are beautiful but they will remain visions rather than become reality if we don’t get better at practicing it in our one-on-one relationships and normalizing those practices in our organizations. I was part of the UWF accountability taskforce after last year’s budget vote so I know this work is happening across the city and sometimes isn’t very visible. However, as recent examples have proven (including the disagreements over this year’s budget) we have a lot more room to go in practicing this regularly and more widely. So at the individual level it means not scoffing when someone you disagreed with or fought with asks for turnout next year or not skipping a donation to someone who you agree with the majority of the time or not publishing that tweet in your drafts. Another harder example: if we have a mayoral candidate who is a progressive but moveable and that is the best we get, then not making it easy for Arne Duncan (or whoever else fits that mold) to step all over them. The Fair Tax loss last year and Trumpism today are lessons that the truth doesn’t matter as much as rhetoric and repeated messages do. The least we can do is not be each other’s enemies because we know that our actual enemies will use our public critiques against each other. As tough as it might be, it’ll be vital to remember every time we are in a public forum going forward.

LET’S LEAD WITH ACCESSIBILITY AND CULTURES OF CARE
One thing I’ve noticed throughout the pandemic has been how much more accessible meetings, events, and general organizing have been for those with childcare responsibilities, those with non 9–5 working hours, those who speak non-English languages primarily, the physically disabled, and likely others as well. Engagement increased when meetings were on Zoom, events were recorded, and Slack communities grew. People also became more mindful of access needs and better equipped at how to provide them. At the beginning of the pandemic I attended the Allied Media Conference where framing access needs as something everyone has was normalized at session after session and have since carried with me. During the pandemic, I saw our organizing community start to normalize prioritizing access rather than treating it as an accommodation that needed to be asked about. I also saw spaces where accessible documentation became a new focus (swoon). These are all elements of building cultures of care.

So too are talking about burnout and building a culture where it is ok, encouraged, and celebrated to step back and take care of yourself and loved ones. This one is still a work in progress but will be crucial to keep working on and modeling loudly and authentically.

I also saw people prioritizing neighbor’s needs first (ex. Food pantries) and perhaps because of that then saw those neighbors come back later to engage in the political work. We listened to their stories and shared resources first. We can replicate that and should because there are so many COVID stories that need to be shared. Deep canvassing is one way to gather these while building trust. It can help bring to life the story of how our movement electeds have provided valuable services and responded to thousands of requests all while pushing bold policy. It’ll make electoral work feel more connected and less transactional.

Overall, my hope is that we make this work on accessibility and building cultures of care an explicit priority. How we win is as important as if we win. Centering disability justice means that no one is left behind or seen as disposable and sometimes that means countering the reactive urgency that feels needed. Moving slowly is anti-capitalist and an important practice for our movement, one we can all practice every day.

BEFORE YOU CLOSE THIS TAB

First, thanks for making it to the end. This Medium account was part of a pandemic goal of elaborating on my political musings and practicing long-form writing so it is engagement like this that make that goal feel successful. (For tweet sized takes, you can follow me here.) I’d love to hear your reactions to these ideas and hear your thoughts on other experiments or new approaches we could consider for the upcoming electoral races (and non-electoral campaigns too)!