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Have Tough Conversations

The holidays can be both magical and fraught with interpersonal tension. And, with the compounded impact of all things 2021, these relationships may be even more strained. If you’re heading into the holidays expecting some tough conversations, here are some resources to help you through. Remember, all of these are only suggestions; relationships are unique and complex, and these best practices might not be best for you. Share your thoughts on today’s conversation in our digital community.


Consider how to build the capacity to hold a conversation this holiday season.

Make your plan beforehand if you can, using the resources in the last section of the newsletter.

Reflect: How has someone called you into a tough conversation recently? What did you learn from it? What did you appreciate about it?

Call in, not call out.

Often, confrontation isn’t as effective as a nuanced conversation about a tricky topic. Consider leading a generative conversation by leading with your feelings, using “I” statements, and being vulnerable about your own journey with the topic(s) at hand. Please note: if calling someone out is a more direct and straightforward way to start the conversation and feels more generative to you, please do so.

Don’t wait for something to react to.

Most of the work regarding dismantling white supremacy happens as a reaction to a single incident. But for this work to be sustainable, we – especially those with privilege – need to get comfortable with the discomfort of this work proactively, not just as a reaction. Bring it up directly, perhaps by naming how a recent interaction made you feel.

There is no such thing as the “best” time.

Many people are hesitant to get into tough conversations during the holidays, a time that can feel precious and “distanced” from the tension of everyday life. But there’s rarely a “best” time for difficult conversations. Consider instead: how can I host this conversation in the most generative way at this moment? How can I start this conversation now to create more space for it in the future?

Center whiteness, not Blackness (or other marginalized identities). 

When discussing race specifically (and in the lens of whiteness), many try to defend or validate marginalized communities. But it’s more critical to acknowledge the harm of whiteness itself. When the focus is deconstructing the harm of dominant culture, it gives those who identify tangible ways to analyze and change their actions. This is a critical act in itself; no community needs to be validated by another to “deserve” respect. We all deserve respect, and we need to adjust our actions and recognize our shortcomings to provide it.

Set consequences.

Hold your loved ones accountable. Ensure that you’re no longer tolerating their statements. Note how their continued racism will affect your relationship, and be prepared to stand firm. Remember that accountability is a practice of love, and so is setting boundaries for you and yours.

Lead by example.

Demonstrate the actions you’ve taken to dismantle white supremacy in your own life. Use examples of what you’ve learned and unlearned in your own education. Be vulnerable about where you’re still growing – because we all have space to improve! And note how else you’re moving forward.

Invite them to join in.

If you feel resourced, you can use this time to invite this person to join in – perhaps by reading a book together, having further discussions, etc. If that’s not available to you at the moment, you can offer to check in with them later to see how they’re progressing.

Resource yourself.

Tough conversations with loved ones are not easy. If you have the opportunity, make a self-care plan for before, during, and after. Beforehand, practice some deep breathing and grounding exercises. Remember to check in with your breath and body during the conversation. And, plan for some time to decompress afterward, whether that’s scheduling time to decompress with a friend or therapist, taking a long walk later, journaling, etc. It might also be helpful to write some talking points and goals beforehand to help you feel more comfortable.

5760 3840 Nicole Cardoza

Nicole Cardoza

Nicole is an entrepreneur, author, investor, speaker and magician passionate about reclaiming our right to be well.

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