These conversations are complicated, intense, and trying. Chances are it won't all be deeply connected moments and breakthroughs. So we must also prepare for the challenges that may occur. Below, you'll find some suggestions for what to do in the face of some of the common roadblocks I've heard people are facing.
One of the quickest ways these conversations devolve is because of differing definitions of words. In different political and social circles, different words have different connotations and usage. This can become a challenge when we use words that are loaded with meaning for different groups.
The easiest way to explain this is to think about a word like "interesting." The denotation of interesting according to Merriam-Webster Dictionary is "holding the attention, arousing interest." This is likely what a scientist means when presented a new theory. However, when my grandmother used to say that her neighbor's new furniture was interesting, she meant hideous. And when a doctor says your symptoms are interesting, they mean somewhat inexplicable. Meanwhile, when you say someone is an interesting person, you could either mean they are amazingly fascinating or disconcertingly unusual. Needless to say, language can be complex.
In the context of conversations across party lines and belief systems, this challenge is compounded by the rhetoric of various politicians and pundits. While you may define racism as the exertion of systemic power over people of a different race, your conversational partner may consider it any prejudice or discrimination based on the color of one's skin. While you may define a racist as someone benefitting from systems of racial oppression, your conversational partner may define racist as a member of an organized White supremacist group, like the KKK. You may define White supremacy as the hierarchal system of oppression in our world based on race that defines Whiteness as the norm, but your conversational partner may define it as consciously believing White people are better than Black people. So it's easy to see how the use of these words might halt the progress of a conversation.
For some of you, this won't be the first time you're approaching friends and family members with this conversation. In fact, for many of you this is a conversation you've been trying to have for weeks, months, or even years. This may mean your reputation precedes you, and if the conversations have gone poorly in the past, this may mean you've got a pretty rough reputation, and a pretty steep wall to climb to get back into it.
So how do you break through the eye rolls, the "not agains" and the "you always have to bring it back tos"?
It's no surprise that these conversations often result in insults or screaming matches; that's the legacy of 45's administration and our current news media. Whether you watch liberal or conservative American news, a big part of "news shows" is a group of pundits shouting over each other and insulting each other's intelligence. In the event that your calm approach is met with this kind of behavior, it's best to avoid responding in kind. Additionally, the conversation might cut off abruptly, even if your conversational partner is starting to move your direction, because admitting they might agree with you is scary. This might look like "Well, that's just how it is" responses or dismissal of the whole topic as pointless to talk about.
Sometimes, you might think your family member is ready for this conversation. You might begin it and find it escalates quickly to shouting no matter how you approach it. You may find that the more you talk about it, the more they dig their heels in. You may find it reveals underlying beliefs that are so full of hate, that you're not sure they can be undone.
Not every one of these conversations will be productive. If you're seeing little shifts, even if they feel insignificant, keep the conversation going. If the first conversation with someone is not successful, keep trying. Even if a few conversations with the same person aren't making a ton of progress, it's worth continuing to put in the effort. However, on some occasions, it may be time to give it a rest for a while. If the conversation is going in circles no matter how you approach it, your conversation partner might not be ready to have it. Remember, the lightbulb has to want to change.
As you have these conversations, be mindful of your own battery. If you've spent all the energy you can afford on the conversation, take some time away from it and recharge. Be sure to take care of yourself by taking breaks, doing things that bring you joy, and working out frustration in productive ways. Vent to a friend or journal, laugh at something, get a hug (from someone you're quarantining with), scream or cry, get your heart rate up, or find a way to relax. You'll need it. Once you've taken some time away from a tough conversation, evaluate how it's going, celebrate any progress, and assess your next moves. Often, some time away might give you the clarity and energy to keep chiseling away at it, and sometimes you'll realize it's time to call it.
Make sure you have a support system for this work. White supremacy would have us believe that we are the only one's doing this work and that it's all up to us. Community is integral to social justice work. If you don't have access to people in your social or familial circles to support you, find your community elsewhere. You can look into your local Showing Up for Racial Justice (SURJ) chapter, join an online discussion group, or get on social media and find folks doing similar work. You can do this!