What it Will Take for Us to Win
- Timh Gabriele
- Aug 23
- 6 min read
Updated: Aug 24

At the most recent DTC meeting, I posed the question to our membership: what do we think it’s going to take for us to win? I think we, as the perennial minority party in North Haven often don’t take this question very seriously. We often think in terms of modest goals or expend far too much energy fighting or campaigning against one another. I’ve been at DTC meetings where the very idea of picking up seats or building towards a long-term goal is laughed away or dismissed.
It's hard to sell yourself as the change party when you yourself believe that your town is locked into a fixed state, and that the way things have always been is the way things will always be. Luckily this kind of determinism is a lie. Historically, things can shift very quickly and very dynamically, as we are currently seeing at the federal level (to cite a negative example). North Haven’s demographics are changing rapidly. It is becoming more diverse, ethnically, religiously, and, one can assume, politically. The median age in town is declining and many of those moving in do not have the same generational connection to North Haven that lifelong residents have. One can only assume that this means that North Haven’s newer residents want different things or are at least open to new ideas.
The town has long had a fairly even split between registered Republicans and registered Democrats, with unaffiliated voters outnumbering each party about 2:1. Because our election results tend to swing Republican, a long-standing assumption is that these independent voters, and even many of the older Democrats, lean more conservative. However, this is not supported by data. Nor is the opposite, to be fair. There simply isn’t any real metric to show where voters land on an issue-by-issue basis.
Likewise, it’s difficult to measure whether North Haven voters are even being exposed to our messaging. The discussion at our DTC meeting on the challenges of winning turned quickly to the death of local media and its replacement with the social media rumor mill. While there are challenges here, there are also opportunities as well. We have to be smarter and savvier in our communications. If we really are interested in winning, we need to think outside of old boxes and old dynamics that aren’t working unless we really are content with being left in the dust or constantly accepting the consolation prize of minority representation.
For my part, I didn’t offer any concrete strategies or tactical maneuvers that would guarantee victory in my part of the discussion. Those are things we’ll have to decide together, and it might be best to keep many of them close to the vest. Instead, I focused on ways that the Democratic Town Committee and our allies can work to be better aligned in our goals.
Pushing ourselves to do a little bit more every week:
I don’t know a single person who isn’t exhausted or spent. Yet, the work that remains to be done grows more and more every day as we lag behind.
How do you even begin to figure out where you can help when faced with such a difficult paradigm? My wife has a saying that she uses a lot : “Yard by yard is really hard. Inch by inch is a cinch.”
In the face of a seemingly insurmountable goal like winning back the electorate or fighting back tyranny, we need to start by thinking small to avoid the trap of paralysis. Start by giving yourself a goal every day or every week or every month. Make a phone call to your senator. Sign up for a DTC committee. Write a letter to the editor. Think of your specific skills and where they might be best utilized. At the DTC, we could absolutely use your talents to help think through our challenges together, but there are also tons of other organizations doing vital work that need your help.
Once you’ve set a goal for yourself, let your friends, your neighbors, and us know what your inch was. Nine times out of ten, it’ll likely be easier and more fun (or at least less dreadful) than you thought it would be. Just today I got a text from a couple who canvassed for the first time. Last year, one of them told me they’d never do something like this, but today they did it, and actually had fun! Others need to hear about these impacts so they can be inspired to inch forward as well. Politics at the local level can have a demystifying effect. From far away, it seems like the people who make change happen are super knowledgeable subject matter experts with decades of first-hand experience under their belt. But in actuality, it’s working people just like you, who make the choice to put themselves out there!

We win by everyone doing what they can together.
We work better collectively than in silos. Without reinforcements, the work becomes lonely. We don’t know if what we’re doing is effective or a waste of time and resources. That’s why groups like the North Haven DTC exist. With a team, we can support one another and help ensure that things don’t fall into the cracks or people don’t get burnt out and quit. It really is true that many hands make light work.
Give one another grace
The establishment is a well-powered political machine with an endless supply of cash, media access, and loyal, well-paid consultants and paid operatives. We have volunteers who are generally working people. That’s our power source. These working people are bound to make mistakes, to forget, and to misstep. They may have things come up at the last minute that take precedence or interfere with our ability to be the most successful we can be. Instead of getting hung up on the shortcomings of others though, we should be offering additional support to them and figuring out where we can step up. When we think of volunteer work, often we think of supporting roles, but in politics we all get the chance to be leaders. Part of leadership is recognizing that everyone comes from different situations and making sure that each and every person is set up to succeed if and when they can step up.
Feedback should be a gift, not a poison pill.
At our DTC meeting, I asked if anyone there had ever been afraid to participate in something because they were afraid they might be criticized. About 75% of the group raised their hands, and I suspect that a few others may not have been raising their hands for fear they might be called on afterwards and thus be put under the microscope. Our political organizing spaces should be safe spaces where no one feels like they’re going to be ripped apart for trying their best. Unless we want our volunteers to go running for the hills or retreating into their bedrooms to play video games and shun participation in the political process forever, we need to ensure our feedback is constructive and not discouraging. Over the years, I’ve seen far too many people drop off because they feel like they were hearing “F you” instead of “thank you” after putting in many hours of hard work. Be gentle in your criticism and focus on creating opportunities to learn and grow rather than laying blame on one another.
Celebrate victories
The go-go engine of politics makes the impulse to immediately pivot to the next thing after each successive action very attractive, but it’s vitally important that we celebrate our successes, even little ones. Not to pat yourself on the back, but to lift one another up and let your peers know how much their efforts mean to you. If you’re in politics for self-aggrandizement or power, you’re likely in it for the wrong reasons (and if you’re doing so as a Democrat, you’re in the wrong party). The rest of us are here to build community and we can’t forget how important it is to be the change we want to see in the world.
Believe that we are the ones who can win
We’re going to tap every network we can and build all the coalitions we can to realize our positive visions for what North Haven can be. That said, no one is coming to save us. As June Jordan once said, “we are the ones we’ve been waiting for”. I believe in us. I’m constantly impressed by what the people on our committee and in our community are capable of and what they’ve achieved in their lives. Elites who feel threatened by new ideas will always try to alienate outsiders from getting involved by using esoteric language, obfuscating procedure, and blocking access to the levers of power, but each and every one of them started somewhere. You are qualified enough to do this work. You are smart enough. Most importantly, you care enough to know how important it is. And if you have read this far, know that you have help! No one needs to face the harsh terrain alone. Your DTC is here to advocate for you, to connect you to resources, to lend an ear, and find you the support you need.
