The Challenge of Building Connections
...232 days to go...
“What’s the best way to talk with homeless people?”
I get this question a lot, and it always strikes me as odd. There are at least 10,000 homeless people in our city (above 1% of the population) and some of them are quite visible. You’d think it’d be obvious.
It’s not. Interactions with homeless people on the street can be unpredictable, and many volunteer roles seem oriented to minimize interaction with homeless people or allow only surface-level interaction.
In a city with such a significant homelessness problem, I think it’s critical for all of us to have regular conversations with homeless people. It’s much easier to empathize with people you’ve spent time with, or at least met. You’re more likely to correctly understand their needs. And it’s much harder to reduce them to a political talking point or an adjective when you’ve had coffee or shared a meal with them.
When we stop interacting with people who are different from ourselves, we stop feeling a shared responsibility for our collective well-being. You might have noticed this dynamic playing out in our political environment over the past decade. When conservatives stop talking to liberals (and vice versa), they stop wishing them well. And I think something similar is happening with our homeless neighbors.
The good news here is that a lot of people do ask this question. They understand these interactions would better inform them as they debate political questions, such as whether we should place a tiny home village in a particular location, or how we can best balance taxpayers’ reasonable demands for clean public spaces against the needs of unhoused individuals who have nowhere to go.
The bad news is, it takes a bit of effort.
Over the past few months, I’ve taken on many distinct volunteer roles focused on homelessness. Yet few have involved meaningful interactions with the people we’re trying to help. I categorized the 133 volunteer hours I’ve spent so far into three categories:
No Interaction (50% of my time so far): Sorting food donations, organizing clothing, building tiny homes
Brief Interactions (40% of my time so far): Serving meals, bagging groceries, making sandwiches. These involve maybe 5-60 seconds of interaction per person, enough to be polite, but not enough to understand their situation
Deeper Interactions (10% of my time so far): Direct outreach, mock job interviews, companionship with individuals in permanent supportive housing. These involve real conversations about the challenges faced by these individuals, but they are rare and some require extensive training.
As you can see, the time has been weighted toward opportunities with little direct interaction. This is true even though I’ve specifically sought out opportunities for these deeper interactions to better understand the population I’m trying to help this year.
Obviously, homeless people don’t and shouldn’t have any obligation to educate us about their experiences. They’re dealing with survival, not serving as teaching tools for well-meaning volunteers who want to understand poverty. They certainly don’t owe me any material for my blog posts. Nonetheless, I can’t help but believe we’d find more willing voters, volunteers, and donors if more opportunities existed for one-on-one interactions between these different economic segments of our community.
In the interest of fostering this interaction, I’ll share three ways that I’ve had success connecting with the homeless during this time.
Talking Directly with People on the Street: In my experience, many people on the street are happy to share their stories (in fact, this sometimes works better if you have time on your hands, as they often have a lot to say!). One approach is to ask them after buying them lunch, which at least shows that you’re a friend. There’s a few downsides to this approach. First, it requires a level of comfort with unstructured interactions that not everyone has. And second, it doesn’t provide a full cross-section of our homeless population (for example, you’ll likely miss the sheltered population entirely), so you’ll probably end up with a skewed perspective on who our homeless are.
Attend Open Houses: Occasionally tiny home villages or tent villages will open their gates to building a shared community with their more fortunate neighbors. Typically this happens when a political process is playing out, such as the need for the mayor to extend a lease on community ground, or authorize a new development. Unfortunately, these opportunities are neither regular nor well-publicized, so finding out about them requires some diligence. I’ll try to point them out in the blog when I hear about them though (one such opportunity is TOMORROW, Wednesday 11/19 at noon when WHEEL/Women in Black will be holding a vigil on the steps of City Hall (4th/James) from noon to 1PM to honor 20 homeless neighbors who died unsheltered this year - I’ll be there if you want to join me).
Find Volunteer Opportunities with Deeper Interaction: Seattle Homeless Outreach is one that’s fantastic, but they only go out one Saturday a month (two in winter), so it has to work with your schedule. FareStart’s mock interviews are another, but this requires experience interviewing and is also only once a month. I recently completed training with Plymouth Healing Communities to become a companion for residents in their permanent supportive housing communities. This involves a full-day training session and a minimum one-year commitment. They also only offer this training once or twice per year, making it difficult to access. I’m excited about the opportunity to develop real relationships with people who may have mental health conditions or substance abuse disorders, but it’s probably not a realistic option for someone with limited time to commit.
As I’ve tried to highlight above, each of these opportunities have their own downsides. Most importantly, it’s critical to remain within your own level of comfort and safety. As with any volunteer work involving vulnerable populations, it’s important to follow organizational guidelines (if you’re working with a nonprofit), and trust your instincts about appropriate boundaries. But if you can find a way to try one or more of them, I think it’ll be a worthwhile effort. Not only will it teach the housed about the needs and concerns of homeless people, but done right, it can give the unhoused an all-too-rare opportunity to feel heard.
As a community, I think we could likely be doing more to foster these types of interactions. Unfortunately, the separation between homeless individuals and Seattle’s more fortunate residents seems particularly pronounced in our tech-heavy economy. I know from personal experience. When I worked at Amazon, the demanding nature of the job consumed all my time and mental energy. There was no bandwidth to think about homelessness, let alone volunteer to address it. Only after leaving that environment did I have the space to engage with this issue.
This suggests that creating meaningful interaction opportunities could boost support for homeless services. If we could connect Seattle’s tech workers with homeless individuals in authentic ways, I suspect we’d see increased empathy and engagement. The question is how to structure these interactions so they’re beneficial for everyone involved rather than voyeuristic or exploitative.
So I’m putting this question out to readers, particularly those working in nonprofits: how can we create genuine opportunities for interaction between Seattle’s homeless population and its more privileged residents? How do we build empathy without burdening people who are already struggling?
Building bridges between communities seems like it should be easier than building tiny homes, but in practice, it might be the harder construction project.

