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Tactful Tough Love: Effective Conversations about Privilege (plus resources)

This is a subjective, evolving list of ways that I have personally had effective conversations about privilege, identity, and anti-racism. The Maddie Way is a platform centered around empowerment, thus these tactics have empowered me to engage myself and and others in courageous conversations, a necessary step in actively advocating for social justice.

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How do you channel grief, anger, and frustration with injustice into dialogue?


During Covid-19 and after a weekend of protests against the killings of black people by white supremacists and police, educating myself and other white people is not optional. These learnings come from DEI trainings I’ve participated in, recounting times I’ve been called out, and when I’ve had transformative conversations with others.


Why have these conversations? As Audre Lorde said thirty years ago, “Black and Third World people are expected to educate white people as to our humanity. [. . .] The oppressors maintain their position and evade their responsibility for their own actions. There is a constant drain of energy which might be better used in redefining ourselves and devising realistic scenarios for altering the present and constructing the future.”


Living in a white body, it is crucial that I channel grief, anger, and frustration into dialogue with other white people. I call these “Tactful Tough Love” conversations.


Tact is an awareness of what you say in order to keep whomever you’re speaking with engaged. Winston Churchill first got the word in my vocabulary when I read his definition: “Tact is the ability to tell someone to go to hell in such a way that they look forward to the trip.” If someone is saying something ignorant or inflammatory, you may want to tell them to go to hell. But tact is a way of calling someone in so the conversation doesn’t crash upon arrival. The second part, “Tough Love,” is just that; these are tough conversations that are spoken to generate more love through justice.


This in no way means these aren’t candid conversations. These are uncomfortable and often emotional and that’s okay. The stakes are too high to sugar-coat real violence and oppression. I’m still learning everyday how to engage with myself and others in a way that uproots harmful actions or beliefs. So far, these are some ways I’ve been able to internally challenge my own beliefs and have these courageous conversations with others effectively.


  1. Acknowledge areas of ignorance

  2. Remember your Aha moments

  3. Listen to Understand, Speak to be Understood

  4. Speak from “I,” not “You”

  5. Rinse and repeat


Art by @madelinekate_illustrates



Acknowledge Areas of Ignorance


I try to process the news, history, and my emotions frequently and either alone or in thoughtful company. If an airplane is crashing down, it’s protocol to put the mask on yourself first. With Tactful Tough Love conversations, how can I expect to speak to others about something I don’t know about?


There’s so many amazing resources, from books to Instagram accounts to blogs to podcasts. A list of the most eye-opening ones for me have been:


  • 13th by Ava Duvernay (documentary)

  • Blindspotting by Carlos López Estrada (movie)

  • Just Mercy by Destin Daniel Cretton (movie)

  • Lemonade by Beyoncé Knowles Carter and Kahlil Joseph (music film)

  • When They See Us by Ava Duvernay (miniseries)


  • A Girl's Guide to Joining the Resistance: A Feminist Handbook on Fighting for Good, Emma Gray (book)

  • Americanah, Chimamanda Ngozi Adiche (book)

  • Bad Feminist, Roxane Gay (book)

  • Beloved, Toni Morrison (audiobook)

  • Becoming, Michelle Obama (audiobook)

  • Black Looks: Race and Representation, bell hooks (book)

  • Between the World and Me, Ta Nehisi Coates (book)

  • Feminism Is for Everybody: Passionate Politics, bell hooks (book)

  • Freedom Is a Constant Struggle: Ferguson, Palestine, and the Foundations of a Movement, Dr. Angela Y. Davis (Book) (Currently reading this one)

  • The Color of Law: A Forgotten History of How Our Government Segregated America, Richard Rothstein (Book)

  • Their Eyes Were Watching God, Zora Neale Hurston (book)

  • The Fire Next Time, James Baldwin (book)

  • When They Call You a Terrorist: A Black Lives Matter Memoir, Patrisse Khan-Cullors and asha bandele (book)


  • Still Processing (podcast) Fanti (podcast)

  • Fresh Air with Terry Gross (podcast)

  • Code Switch (podcast)


  • The writing of Jenna Wortham (NYT, mostly)

  • The writing of Fariha Rosin (Bon Appetit magazine, mostly)

  • Say it Loud from PBS (YouTube channel)

  • Chescaleigh's videos for MTV Decoded (YouTube channel)


  • @cleowade (Instagram)

  • @rachel.cargle (Instagram)

  • @veggiemijas (Instagram)

  • @wellreadblackgirl (Instagram)


I implore you to Google “anti racist resources” to find other lists, too. This one by Sarah Sophie Flicker and Alyssa Klein is a good place to start. So is this whole website, Teaching Tolerance.


There’s no checklist for self-education. Rather, the point here is to open my worldview and expand my toolbox to have courageous conversations. It’s disheartening to get out of “the dream,” as Ta Nehasi Coates so aptly puts it, but so essential for channeling privileged rage into understanding.




Remember Your "Aha" Moments


I am so grateful for the people in my life who have been gracious and candid when I’ve been naive. I remember once in a WOC-centered organization, I inappropriately said “I understand” to a woman of color in the group who was very vulnerably sharing how the org changed her life. Though my intention was to relate, my impact was erasing of her experience, which was very different from mine.


A white woman who was older than I took me aside as I got emotional. She gave me the time I needed to let out the ugly tears that come from guilt and feeling misunderstood in a way that hurt someone else. (I cringe as I write this, but it’s true!) Then, she told me about a time when she had done something similar and what she learned from that experience. Finally, she was brutally honest about why what I said was harmful.


She absorbed the emotional labor, gave me empathy, and kept it real without explaining the woman’s experience on her behalf. She didn’t coddle me; she provided tactical tough love. Pro white fragility work, let me tell you!


I use moments where someone said something to change my understanding in tactful tough love conversations. I’ll even text someone a meme if it helped a light bulb go off in my brain.


If you have been called out, feel the sting, read this, and then use one of the many resources linked on this page and others to learn.



Art by @ohhappydani


Listen to Understand. Speak to be Understood.


In order to engage and not preach, I’ve found that giving people the space to air it all out is crucial for an effective conversation. With white people who may not have had the same access to these conversations as I’ve had, sometimes listening can feel exhausting. But when it turns into a rant and I just want to shake their shoulders and yell “ever heard of Google??” I try to think how good it is that they’re letting it out here with me. We all have limited energy, but because of my positionality, I have more energy to invest in these conversations.


Hearing someone rant about something I deeply disbelieve in or is offensive feels like nails against a chalkboard, but that discomfort is part of the work. In regards to anti-racism conversations, this is important so that white people can process their emotions with me, a fellow white person, rather than putting the weight on black people to do that unpacking work.


Listening, then asking follow up questions, allows me to know where I can be most effective. This helps me reach them where they’re at, rather than assume. Asking questions has been a good way for people I’ve talked to not feel like they’re being preached to. It's all about tact.


“I’m hearing you say ___” is a good way to start. Maybe they can find the break in their logic.


Some other questions I’ve used are:

  • Why did you call __ the/ a __?

  • Where did you hear that from?

  • What makes you say that?

  • How so?

  • Can you tell me more about why you think that?


Like with any active listening, listen to understand, then speak to be understood. This may mean dropping off jargon from my sociology class. I try to remember my audience to be understood better, such as using stats if they are data-driven or stories if they’re a storyteller. Having those stats and stories on deck is why #1 is so important.


Speak from I


I've noticed that using your relationship with this person is a powerful way to make the dialogue more impactful. Even if I’ve wanted to say, “What you think is hypocritical,” I’ve found this to stop a dialogue in its tracks. Rather, I’ve swapped it out for “I know you, so I know you value ___” as a way to show a parallel between something they believe in and the topic at hand. I’ve also found this phrase to be helpful, too: “I think you intended to ___, but when you said ___, I found it ___.”


I also will bring up my own experience with the topic, often in a self-deprecating way. I’ll think back to my aha moments with the topic at hand, then share that story. It may sound something like this: “Totally, I thought __, too, since that’s what I learned in my history class. But when I found out about the history of __, I realized __.”


Stats paired with stories are potent. The point here is to engage in order to uproot harmful beliefs or actions.


Rise and Repeat


I try to remember that these are repeated conversations. Talking through layers of white supremacy, overt and covert, takes time. I reflect on where in the conversation I didn’t have the information or vocabulary to have an impactful dialogue, then read and listen to what I need to. Again, there are so many resources, that I’ve even googled the exact thing I was trying to respond to such as these anti-racism responses from KatyKatiKate or this video by Franchesca Leigh on comebacks for transphobic relatives. Get granular!



If you’ve ever felt lost trying to educate your people, I hope this is useful. I’m very open to other suggestions and constructive feedback, as knowing better and doing better is essential.


For further reading on this topic I suggest BoldConversations.org for conversations with adults and RaceConscious.org for conversations with kids.



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