I'm facilitating a session on financial sustainability for a gathering of commissions training programs later today, and spent most of the evening last night thinking through a tool that would support conversations about getting money from non-foundation sources. And I have to admit, I'm a little unsure of how to broker one specific way forward – asking for money from wealthy people.

I know that the folks I'm talking with in this session will generally be more amenable to charging for a fundraising event or even engaging in fee-for-service with some of their training materials than this one simple thing, which just happens to be the thing that we talk about all the time when we talk about economic inequality: Wealthy people have the money. We need it. How do we get it?

And I have a problem with it too. The thought of approaching one of my wealthy young neighbors in my heavily gentrified San Francisco neighborhood and asking for financial support for any of the organizations I work with kind of makes my toes curl. When I talk about my new neighbors, it's generally to complain that they don’t say hello on the street, don't respect the older residents who have been here for 20, 30, or even 40 years before them, that they don't know how to park to make the most of our limited street-parking spaces. After basically bashing them for ten years, it's hard to imagine a productive conversation in which they pledge 10% of their income to ending oppression. I mean, they can't even park right.

And yet, the gap between the rich and the poor is wider than ever. The gap between the well-off and the scraping-by is pretty huge too, and boy can we feel that here in San Francisco. I can teach my first-gen college students about wealth distribution every day in the classroom setting, but when it comes to engaging with better-off people (include well-paid young adults!) to move their money into supporting liberation for those who have much less (or nothing), I feel ...

And there stands the ellipses, the ellipses I need to solve in order to make this sustainability training work today. When it comes to asking wealthy people for money, not only do I feel … but I hesitate to even broker this conversation with my colleagues because I know that many of them feel that same profound, unnameable discomfort with the conversation as well, whether they come, like me, from a worse-off economic class or from a well-off class.

That ellipses is about the less-discussed stigma of socioeconomic class identity. Racial identity most often speaks quite loudly when we walk into a room or engage in a conversation with folks of different races. Over time we've at least built a vocabulary for talking about differences, and even a few "rules" that function kind of like mathematical order of operations (Parentheses, Exponents, Multiplication and Division, and Addition and Subtraction!). Sure, lots of people still refuse to use racial PEMDAS, but those of us who have been at it for a while know that until they confront their own personal privilege, take a look inside their invisible knapsack, and consider white fragility, they sure aren't going to be dismantling any white supremacy with us.

Class identity, however, can be slippery, and it's harder to engage in cross-class conversation because we don't really have an established PEMDAS for it, though of course the order of operations would be similar. Until people who grew up with and benefit from wealth examine their own class privilege, take a look inside their Salvatore Ferragamo Firenze leather weekender duffle, and stop hoarding money (for example), they sure aren't going to be dismantling capitalism with us. (Or making it better or whatever.)

But while I can be flippant (and hopefully funny) about owning-class folks in a blog post, the truth is that I still wrangle every day with trying to navigate others' class privilege and my own conditioning to distrust, dislike, and avoid well-off people. And many of my colleagues feel the same and were conditioned similarly. And some of my colleagues grew up well off, and they too are trying to overcome their own kind of imposter syndrome as they navigate relationships in the nonprofit world. And it would probably help if we talked about it more. But we don't.

A few months ago, when I was tasked to develop today's financial sustainability workshop, I signed up for emails from Resource Generation, whose mission is to "organize young people with wealth and class privilege in the U.S. to become transformative leaders working towards the equitable distribution of wealth, land and power." Though my agriculture-class inner-teen had a kneejerk reaction to the word "leaders" here, I do appreciate the Resource Generation model, and I encourage you to check it out. They describe themselves as a multi-racial constituency of young adults with inherited, earned, or future wealth, and who, along with their cross-class allies who participate as board members, trainers, and organizational partners, are committed to "working for a just world." Like other leadership programs, RG draws on best practices like group identity formation, peer-learning, and collective action.

This morning, as I was finalizing the details for my economic sustainability workshop, a post by RG Portland chapter member Emily Bookstein arrived in my inbox and caught my eye. Bookstein's honesty about her own upbringing really struck me. Often, when upper-class folks talk about their class privilege within the context of racial justice, they do so in a self-degrading, self-dismissive way. I've read that dismissiveness as shame, and I'll bet I'm reading it right, but what's not typical in these self-disclosures is the next-step level of interpersonal awareness that Bookstein provides, and that serves as an important bridge between her own desires and mine:

"Even after college, despite being financially clueless, I wanted badly to be self-reliant. This, along with the deeply-rooted Jewish fear of the worst, translated into perpetual anxiety about spending money and wasting what I’d been given. It was hard to see myself as part of any extended community or interdependent network. So I’ve come to understand that for me, personal liberation means letting go of perfectionism. It means connecting instead of isolating, sharing resources instead of keeping them close, and believing in my self-worth as well as the worth of others. Atoms may seem lonely and alone, but really they are affected by, even bonded with, the atoms around them. My liberation, likewise, is part of the liberation of all people."

Our liberation is bound together. And this realization makes it much simpler to imagine that someone like Bookstein would want to hear about the amazing work that our folks are doing – that they'd want to hear, for instance, about how the commissions training programs are effectively supporting self-determination for low-income communities of color. Our work is so worth supporting, and when we imagine the well-off person we are talking with as a whole person, an actualized person, a person working toward collective and self liberation also, then the conversation seems much easier because it's genuine, built on common ground.

Still, it's easier to host a pool-toss or a gala, I suppose. But if we think structurally, if we really think about our work as mapped to structural disparity, inequity, and oppression, then solutions such as building bridges between those who are currently holding the wealth and those who are burdened by that wealth-holding are the only ones that, ultimately, are worth pursuing. I'd like to see us getting better at it.

Laurie Jones Neighbors is an independent consultant and educator who specializes in developing, implementing, and assessing programs and educational experiences in support of equitable political representation and local, regional, and national decision making by low-income communities and communities of color.