Sincerely Michelle and Having Difficult Conversations on Race

As a personal finance enthusiast, I love Michelle Singletary’s Color of Money column. I referenced her 10-part series “Sincerely, Michelle” in a post a few years ago. In it, she described the Black experience in the US, especially as it relates to personal finance and legacies of discrimination. 

I was challenged as I read the “Sincerely, Michelle” article on microaggressions. I remember complimenting a young Black father in a Washington DC hotel who was feeding his baby while engaged in an in-depth conversation with his 12-year-old daughter. After reflecting on Mrs. Singletary’s article, I now realize I was complimenting the father because I did not expect him to be so involved with his family. I don’t think I would have complimented a white father in a similar fashion.  

The “Sincerely, Michelle” series really has me thinking about some tough racial topics, and I hope your students will benefit from discussing the series too. It can be hard to have courageous conversations about race, and the guidelines below may help.

Managing Difficult Classroom Discussions suggests:

  • Establish discussion guidelines like listening respectfully without interrupting
  • Be real about the challenges present in the discussion
  • Actively manage the conversation reminding students of the guidelines as necessary
  • Beware of sharing your own views as doing so may curtail discussion
  • Synthesize the conversation at its end 

(Source: Indiana University)

My LINCS colleague Dr. Carmine Stewart adds the following to the list above:

  • We have inherited these legacies, and “It is not our mess but we can help clean it up”
  • “If we never talk about [challenging topics], nothing will change.”
  • Create the classroom climate where people get to know each other’s character first. When we know others’ character, we are much less likely to criticize their characteristics
  • Unpack people’s discomfort by asking “What makes you uncomfortable about this discussion?” 

(Source: Interview, Dr. Carmine Stewart 2/5/24)

What thoughts do you have on managing difficult conversations?

Thanks for your thoughts,

Steve Schmidt, Moderator

LICNS Reading and Writing Group 



Thank you for this post.  I appreciate you sharing your experience with the father in the hotel.  I think you asked a key question in: "Would I have said that to a father who looks like me?"  I always challenge people to pause for reflection when they are confronted with a cross-cultural interaction, whether this is thinking something, saying something, or doing something.  This is actually a 3-part process.  Your question is the first thing to ask: "Would I have asked this of someone from my same social identity group?"  The second part is examining the narrative in your mind that led you to make that assumption.  "What stereotypes, biases, of assumptions do I hold that informed my actions?"  Last , is action.  What action should I take now that I am aware of my bias?"  If you have that a-ha moment quickly, it might be an apology.  It could also be creating a new narritive to supplant your original belief (Black men are good fathers- I know ____ Black men who are great fathers."  That could also include sharing it with others as you have done.  That helps others learn from your experience and process.