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Rosalind Wiseman, parenting educator and author, joins the program to discuss how to foster civil dialogue and inspire communities to build strength, courage and purpose. Discover how to create physical and emotional wellbeing by working in close partnership with the experts of various communities–including young people and business leaders.

In this episode you’ll discover:

  • Rosalind’s career journey, including writing New York Times bestselling books (10:30)
  • Common misconceptions in the workplace about young people (19:00)
  • Why many young people are frustrated with the current situation (22:00)
  • Why we need to rethink what it means to be patriotic (24:00)
  • How leaders can be comfortable in not having all the answers (29:00)
  • Why we need to acknowledge generational differences (32:00)
  • The need to have uncomfortable conversations (37:00)
  • Finding more substantive ways to address social issues (53:00)
  • What advocating for equity really looks like (54:00)

Listen in now, or read on for the transcript of our conversation:

JENNIFER: Rosalind, welcome to the Will to Change.

ROSALIND: Thank you so much for having me. I’m so excited to be here.

JENNIFER: Me too. Me too. Just the name of your company, Cultures of Dignity, would have caught my eye, but we also have a dear, dear friend in common whose name is Erin Weed, who has also been on the podcast several times. Did you do a dig with Erin? Is that how you know her?

ROSALIND: I wish Erin was here so she could tell the story because she loves telling the story and she likes to embarrass me. So I’ll tell my version, which is that I had moved to Colorado from Washington D.C to have this whole quality of life thing.

JENNIFER: So to speak.

ROSALIND: Right. So that whole thing where you go and try and not be as maniacally focused on work and your children, have a more balanced life and all that stuff. So I moved to Boulder eight years ago and I joined this coworking space. And I was getting coffee and this wonderful woman, who was Erin Weed, was next to me getting some coffee. And she said, “Rosalind…”

And I had met Erin many years ago, and she had done very similar work. Actually, when I just first started doing my career, I started off doing women’s self-defense, and this was when I was like 21, 22. And Erin had actually gone into that field as well, and so we had crossed paths many years before that.

And so I met her over coffee in my coworking space, which really was probably, in retrospect, the best. It was a great coworking space, but it was truly so wonderful because I got to reconnect with this woman, and then she’s become an incredibly dear friend and she’s a force of nature.

ROSALIND: And I have done the dig. I don’t think I would have had a choice, but I did do the dig. My word Is worth, about a year later. Well, I was always disagreeing with her about [inaudible 00:01:58]… I don’t like being pigeonholed in that way.

I was like, “I want another word,” and she’s like, “Another word?” So I’ve stuck with worth. And actually, she’s right. But yeah, that is how I met Erin, and I have done the dig, and I recommend it to anybody who is listening to this.

JENNIFER: So do I. Yeah. So Erin Weed, everybody. Look her up. The dig is a process where you dig, dig, dig with Erin who holds the space to get deep into that one word, which is the end result of the process. And by the way, mine is power so maybe we can… Ooh. The joining of power and worth. That’s interesting.

ROSALIND: Yeah, wonderful.

JENNIFER: Wonderful, right? You’re right that Erin actually got her start with her company, it’s called Girls Fight Back. And she did, you’re right. She taught self-defense for kids because her best friend was murdered in college and just set her on this path.

So her story is amazing. Please go back and listen to Erin Weed’s episode with us on the Will to Change. And if you want to do some digging into the self, I scarcely know anyone that’s better at this than Erin is so check her out. Big love letter to Erin.

But about you, Rosalind. So the thing most people know about you, and I’m just going to put this out there, is you and your book Queen Bees and Wannabes was behind the Mean Girls world, whether that’s the film, Broadway show, et cetera.

And I guess I’m so interested to know how you understand the arc of the journey we’ve traveled since those days, since you wrote that. And I know we don’t have a lot of time, but we’ve moved through and towards, I think, a better world theoretically since then.

But I’m sure you’re going to tell me that a lot is still alive and well that is causing harm, that is disrespecting… We are disrespecting each other still. And young people, which is your passion, are continuing to be, I think, disrespected, not heard, et cetera, which is the field that now you focus on and you contribute to.

But take us back in time, if you can. Who were you when you were writing it? And what was different about the world? And what would the version of it be today, if you were to diagnose our current state when it comes to bullying and disrespect?

ROSALIND: So Mean Girls is… There’s a lot of positives and there’s a lot of negatives. And you’re asking me about, is it better? And I think as far as girls’ relationships with each other and how they treat each other… And I think it’s always good.

And the reason why I wrote Queen Bees and Wannabes was because I was trying to put words… I was putting words to behavior that it was normal and common, but it didn’t make it right. And meaning, girls were not knowing how to confront each other in ways that honored each other or their own dignity.

So they were surreptitious, they were going behind each other’s backs, they didn’t have the skills to be able to handle themselves competently in their social dynamics, yet their relationships were so incredibly important to them. And of course, to what they were learning about themselves as girls and young women and women.

So the stakes 20 years ago were really important and it was really important to create a language. And the good thing about Mean Girls was because it became such a culturally powerful zeitgeist thing, there was a language for it that lots of people could talk about.

The problem is that when things become, and for many things, about women, when we try and take things seriously about their experiences then we often have a way of superficializing them. [inaudible 00:05:50] work with teenagers a lot.

I am all about laughing as we learn, so having a movie that was a comedy or… All those things are great and it’s really important not to lose the larger lessons. So otherwise things get superficialized like women’s anger or women’s experiences, and that was the opposite of what I wanted and what I was trying to do.

And also by the way, including that with boys’ experiences and young men’s experiences and men’s experiences. I always am trying to look at the things that people are experiencing, but can’t put words to, and then bringing that out so that we could talk about it and we can do better in our relationships. So there’s positives about that.

And then the other thing though is that I was working really hard, and always have, to really have this bedrock of dignity of having people treat each other with worth. And from there, that you learn the skills to have civil discourse and to what does it really look like to treat each other with dignity? And it’s pretty fair to say that recently we, collectively as a nation, have forgotten how to do that.

And that’s where our weaknesses about that, that were always there, have really been exploited so that we don’t listen to each other and we don’t sometimes even listen to ourselves. And so that’s, for me, the bigger… That’s what I’m working on now, it’s what I’ve been working on for a while, which can be a pretty daunting task.

JENNIFER: Yes, tell me about it. It’s like we have been radicalized against each other by forces that we don’t even see, in many cases. And it’s terrifying to think that we’re being guided like puppets to see each other in ways that aren’t fully showing of our full humanity.

Yeah. So we have to fight against that and give each other the dignity. And I love what you just said to ourselves, that’s so beautiful. So there’s a million questions I have for you. You characterize how we treat young people and how they’re experienced in our society and what is happening as they do that, whether it’s climate change or gun violence or Black Lives Matter.

We are in the midst of, I think, a huge moment of realizing their might and yet the diminishment of that continues as I see it from, for example, organizational leaders, politicians. So you talk about a polarity and attention that I think is a huge missed opportunity, because there’s just…

They’re giving us a wake up call and we’re just refusing to listen to it because we’re protecting, I suppose, what has worked for us. We’re fearful of change, all sorts of reasons. But tell us about their voice as you understand it, and why it’s so deeply threatening to so many of us, and what you wish were occurring instead.

ROSALIND: God, what a wonderful, huge question. And I know you work with so many people in the corporate and business world and outside of the direct experience of working with young people, and yet those people are coming into those businesses. And I know because I get a lot of feedback from adults about, “What in the world is happening? This is insane.”

JENNIFER: “You’re mad.”

ROSALIND: “Young people are insane. They’re entitled.”

JENNIFER: “How dare they?”

ROSALIND: Right. “They’re entitled and they’re difficult,” and cancel culture, all this stuff. And so there’s so many things to say that it’s hard for me to choose, but I actually brought it up because a couple of days ago… We have 25 young people from the ages of 14 to maybe 24 who are just constantly in anything. Anything I do. Any book, any article, anything I do, I always have young people inform…

As I’m doing it, inform what I do. And they are very critical of me, and we get into lots of arguments. I’m in an ongoing argument right now with two really smart young women who I work with about cancel culture and also, do you have to agree…? We’re in this huge argument, which I might… I don’t know. I don’t know how this is going to go because we’re having a really interesting discussion [crosstalk 00:10:10]…

JENNIFER: Been there. Totally [crosstalk 00:10:12]. Yeah.

ROSALIND: Oh my gosh. Right. So my head is hurting and I still think that I actually have a point but it’s… Basically, what we’re arguing about is if there’s an article and you’re asked to sign off, that you agree on it and other people sign that letter, do you have to even… Yes, if you’re going to sign, you’re going to agree with the content of the letter. But do you also have to agree with the politics of every single person who signs that letter with you?


ROSALIND: And I am in a very healthy debate with two very smart young women, one who is African-American from New Orleans and one who is white from Colorado, and they both think that I am wrong. And my position is yes, if I see content that I agree with, I’m going to sign it.

And I think it’s even better if I’m signing it with people who have diverse opinions than I do, radically different opinions than I do. They disagree with me. We got into a very, very healthy debate, which actually the feedback that I got from them…

And this is an answer to your question actually, because your listeners might think, “Okay, what Rosalind just said is insane. What those young people just said is an example of young people being insane.” And I get that.

And when that happens, we have an obligation because we are in relationship with young people in various ways to understand where they’re coming from, it doesn’t mean we have to agree. And it means that we come to the conversations being prepared to be changed by what we hear.

Again, it doesn’t mean we have to agree, but what young people in my experience are so frustrated about is that adults, when we even begin to engage in conversations about this, come into the conversation assuming things about them that make it impossible for dialogue and true conversation to occur.

So for example, young people think that adults believe that young people get all of their news from TikTok and Instagram, and so that all of the news they’re getting is from a social media feed that is not legitimate. So therefore, anything that a young person says about politics, they don’t know what they’re talking about or they’re not realistic.

And in my experience with young people is actually they’re more media literate than older people. They look for primary sources way more than we do. And we can’t say that because we go to CNN and Fox… Even though those two diametrically opposed media sources, if those are your places that you’re going, and that’s where you go, I would argue that young people have actually a point, which is why are you trusting those two sources just as you are 100% where you’re getting information from?

And so they’re very frustrated about that. They’re very frustrated about that. I just had a 21-year old say to me, “My mom and my family says we do not talk about money, religion, and politics,” which is what we all grew up…

JENNIFER: That’s [crosstalk 00:13:21] talk about.

ROSALIND: Well, I didn’t but many, many people did. And so I think that felt like it worked for awhile, but it doesn’t work anymore because… And it didn’t work then, by the way, because what that allowed is even more reinforcement of the inequities and the discrimination and the real painful structures in our society that we’re seeing the consequences of now, and we just can’t avoid it.

We can get really reactive about it and we can dismiss it, demean it instead of moving forward and saying, “I got to figure this out. I got to figure this out for myself. I have to figure this out for my community. I have to figure this out for my country.”

Patriotism should be moving forward into having difficult conversations. So that is what civics education, frankly, should be and does not often teach young people, which is why, frankly, [inaudible 00:14:08] civic education in this country has been so poor for so many generations.

It is one of the reasons why adults are so unskilled at having these conversations, and then they go back to, “Let’s not talk about money, religion, and politics.” And the thing that young people have said to me is, “Adults are afraid to talk about these things. We are not afraid to talk about these things.”

And one of the specific things that they point to is the difference between the definitions or even the existence of privacy and the difference between adult adults and the adults and young people that are coming up now because young adults and children…

Again, people who have grown up with social media and smartphones have a very different, expanded view of privacy because they’re sharing everything through technology, which means that their politics and everything… They think about things as part of that larger context of what they’re sharing.

And so for them it’s like, “I’m sharing my politics because I share what I ate yesterday. I shared a picture of my food yesterday, so why am I not going to talk about politics? What are you talking about?” And that’s another reason why young people are just befuddled, angry with adults about why they won’t talk about these things. And then because for young people, and rightfully so, they see the issues in front of them and say, “We have to clean up this mess.”

JENNIFER: Yeah, rightfully so.

ROSALIND: And they’re right. They’re right.

JENNIFER: Yeah. Oh gosh. You’re reminding me of a question I get a lot. So I work a lot with executive leaders and on inclusion and diversity and what they need to do as leaders to create psychological safety, to do their own learning, to be different kinds of leaders that would resonate with the incoming generation.

I use an iceberg model and we talk a lot about lowering our waterline, meaning sharing our vulnerabilities as a way of going first because the leader has power and doing that in an organizational context to say, “Not only is this okay, but this is the way that we build trust with each other, it’s the way that we build cultures of belonging, where we can all feel more seen and heard in a way that we weren’t traditionally.” And the question I get so often is what about people’s privacy? And you’re making me think that is such a generational question to ask. Right?

ROSALIND: Oh, for sure.

JENNIFER: I love that you just said that because it just clicked into place. And I’ve never had a good answer for that because I’m Gen X, and I understand we even… And you might be too, we looked at it as work and home and personal and it just doesn’t… Never the [inaudible 00:16:42] shall meet.

And that’s what literally is being redefined underneath us… Has been redefined and certainly this year has done that. So they say, “I don’t want to intrude on people’s privacy.” And then with social justice and being black in the workplace, for example, we did not want to name a lot of things traditionally.

I wasn’t even allowed to say the word white when I was… Before this year, there was a tremendous fear around language and naming things and certain words and we just weren’t ready to talk about… And we’re still not really ready to talk about, but we have to talk about it now, which is good.

But even just asking someone about their experience and relating to their identity is also… It feels like a privacy violation for people of a certain generation where we were told this is not something that… HR tells you almost, “Do not know your people.” You are not allowed to inquire about this. And this year has been super confusing, I think, for a lot of us that were raised, A, not to see color. Remember that one, not to see color?

ROSALIND: I hate that.

JENNIFER: Oh, yeah.

ROSALIND: I hate that.

JENNIFER: Yeah, I know. I know.

ROSALIND: I think it’s so disrespectful to people of color.

JENNIFER: Exactly.

ROSALIND: I hate that.

JENNIFER: Exactly. So I’m just trying to like unwind all of these generational things that we thought were the right things to do that actually are exactly the wrong things to do now. It’s really interesting. So the privacy thing, I really appreciate you saying that.

What’s your view? If I have a manager who’s like, “I don’t want to run afoul of somebody’s privacy and what is private and what is… What they want to show to me. And I don’t want to push on that and I don’t want to make them feel tokenized or under a microscope.”

But then at the same time, in the same breath, I’m saying this generation wants to be seen and heard and named. They want to be named, and all their identities to be named, and they want us to be comfortable speaking about it instead of being afraid and silent, which is what they encounter when they come into the workplace.

ROSALIND: Yeah. You’re making me feel really… I felt this way anyway, but you’re making me feel really grateful that I work with teenagers and don’t edit themselves.


ROSALIND: Because I’m like, “Euw, gross.” [inaudible 00:18:53]

JENNIFER: Yeah, it’s gross. It is actually, now that I think about it. Yeah.

ROSALIND: I’m like, “Oh, that sounds fun.” And then you get that whole thing where white people can’t say the word black and they get all twisted up. I had an experience recently with that, with a professional person that was asking me to do something.

You just feel so badly for them because you see them [inaudible 00:19:13]… And this was on a Zoom call so I could see [inaudible 00:19:16] twisted up and this discomfort of saying the word black. I’m like, “What are you talking about? You want me to talk?”

Oh my goodness. Yeah, look. The answer to, at least for me… I always, for my entire career, which I like is I’ve always dealt with things that are uncomfortable. And the only thing that I know how to do in uncomfortable things, and especially in [inaudible 00:19:39] in a position of authority, and maybe you don’t know…

One of the things we constantly make a mistake about with authority figures is that they’re supposed to know everything and that they’re supposed to have all answers to everything. And one of the most powerful, I think, leadership moments is for a leader to say, “Well, I don’t know the answer to that question.”

Or, “I’m uncomfortable with something that just happened here, but I’m going to go figure out the answer to that, and I’d love your help figuring it out. I’m going to figure it out with you and I’m going to take some time on my own too. Then we’re going to come back to it because it’s clearly a really important issue,” whatever it is.

So I think in those situations, when a leader says something like, “I have a really…” Well, actually what I would do around the table is I would have everybody write down how they define privacy, and I would maybe even do it anonymously.

One of the tricks that we do and… Because remember, I work with high school people and high school people, for very good reason, they are as cynical as people in corporations often about doing HR things on sexual harassment and DEI work.

They’re like, “Oh gosh, I know I [inaudible 00:20:52] to say the right thing and I can get out of this meeting.” Oh my God. So remember, I’m dealing somewhat with a similar demographic, which is a group of people who don’t want to be there.

And also, for good reason, have had bad experiences where they can’t say what… It’s understandable, confusing things of, “Okay, I don’t get this. And I want to be able to actually say it, but I don’t want to get… People give me the look,” and whatever.

So a trick that we do in my work is that we just say… If we get to a really stuck place, I just would say to everybody, “All right, everybody spread out.” And because they’re teenagers, I’m like, “Don’t sit next to your friends and don’t look at people while you’re… And having telepathic communication while you’re doing this. And so write down the answer to the question, what is privacy to you?”

And we actually asked that in our classes that we do at Cultures of Dignity. We have from fifth grade on. We ask them like, “What does privacy… What does it define for you? And you have to actually keep going and checking in with yourself about what that means.”

But as adults sitting around a corporate table, I’d say, “So what does that mean to you?” Because a 22-year old or the 25-year old who, by the way, grew up with a smartphone when they were in middle school… So remember that, people who are listening to that, if you’re working with people who got…

Because smartphones came out 2007. So you’re now working with people who went to middle school with smartphones, it was the first generation to do that. And so you think about that. And so somebody who’s my age, people in their 40s and 50s are going to have a very different response to what privacy is.

So [inaudible 00:22:32], you get it out there. And then as the leader, you say, “Okay, so I have a really different definition of privacy. It’s not right or wrong. I just need to understand this.” You can’t crinkle up your nose in that weird way or get like, “I don’t understand…”

JENNIFER: Or roll of the eyes, yeah.

ROSALIND: Roll the eyes like, “I don’t understand why you need to post everything about yourself.” As soon as you do that, you have you have dismissed the other person. Really, you have to actually really check yourself about that, and then say, “Look, I might bumble along the way. I might make mistakes along the way. I am going to make mistakes along the way. This is a high learning curve for me about what privacy means and how much you want to share and what you want to share, and we’re going to do this together. And the most important thing is that if I make a mistake, then here’s how I want you to come to me about it, which is don’t wait until you’re sitting on it and seething on it, and then you get so upset that you blow up and it gets much, much bigger.”

I think those are the kinds of things that you create. You create the relationship and the road that they can hopefully choose. And if they can see that you really treat them with dignity, meaning you see their inherent worth, that you would knowledge their…

That you don’t have to know all of their experiences, but you would acknowledge that they have different experiences than you and you’re curious about knowing what those experiences are, people are going to feel comfortable taking the risk of… Small at first, of being able to say, “Well, this is what this means to me,” or, “This is what I want to share.”

JENNIFER: You’re so right. That’s exactly the teaching point I make when I share my pronouns, and you can imagine how that goes over with senior executive leadership.

ROSALIND: Oh, man. [inaudible 00:24:15]


ROSALIND: Oh my gosh. Oh my gosh.

JENNIFER: Oh my goodness.


JENNIFER: When I used to be in the room, the physical room, and there was thousands of people, you would… A silence would fall over the room and everyone would lean forward and say, “Is she going to explain this whole pronouns thing to us?” You feel like you’re an alien from another planet thing from the future, basically saying, “I’m trying to save you people from obsolescence here.”

And I think that’s why speakers like you and me, there is such an eagerness because people… At least some people are like, “Oh my goodness, I so do not get this. And there’s so much I have to revisit. There’s so much I have to change in my language, in my frameworks, in my mindset.”

It’s a lot at once, and this year has been a lot at once, particularly when we have literally… I think I see in myself, I don’t have the resilience that I need to challenge myself around racial justice because white people don’t develop that.

And so there’s an emotional fragility to, I think, be overwhelmed by your [inaudible 00:25:17], that that’s real. I don’t excuse it, but I think it’s real, and if we can just name it… But I’m obsessed these days about the emotions of coping with this year, particularly when you’re not in one of the, I’d say, most affected groups and you’re on this other side saying, “I want to be a good ally.”

So we’ve got a lot of people waking up and a lot of emotional hijacking going on. And I know you love that topic as much as I do, which is we’ve got to not just develop new skills to pivot through this, but we’ve got to also deepen our self-knowledge about how we respond to challenge and discomfort. So you just role modeled what it sounds like but meanwhile, that leader is shaking.

ROSALIND: I know. They’re so worried. I know. I have friends who are in these [inaudible 00:26:04] positions who are just terrified.

JENNIFER: They’re terrified.

ROSALIND: They’re terrified. They’re super terrified. Yeah, it is painful. And if we don’t address them with competence, they’re… First of all, we’re going to go through life being so scared, walking on eggshells. That’s so boring.


ROSALIND: And then the other part is that, if you really… We really have to sit back and I hope that we can sit back as a country, all of us. I’m all about, how do we repair these villages? No matter how small or big, from our families to our neighborhoods, our towns, to our cities, to our country, how do we repair? Because I work in corporate America some and everybody’s so polite, is so polite and… So I bounce back between corporate America and teenagers.

JENNIFER: That sounds refreshing actually.

ROSALIND: [inaudible 00:26:59] Right. Yeah, it’s funny. I’ve never lost the adolescent like, “Ooh, what can I say right now that’s going to…?” But more importantly, and really more importantly, is can we all just take a step back and say, “I don’t exactly know how or where it’s coming at me, but it is a fact that no matter what your politics are…” Because if you use technology and social media, you have been manipulated by those social media platforms to believe at least something of what you are believing right now.


ROSALIND: And so we don’t need to blame it on certain politicians, we actually can just say it is a fact that the things that we use every day are manipulating the way we think about the world, from the things obviously that we’re purchasing, but to the way we are thinking about things.

And so we have to acknowledge that for ourselves and acknowledge it about other people in the world. And that means the only way through this is to be able to be more competent about having strong relationships with other people, the people we actually know.

And that is very true for our children as well, who are desperately, desperately trying to find meaningful relationships in their lives. And I just had that Zoom meeting with these kids from 14 to 24. And you would think the last thing that they’d want to do is get on another Zoom call.

But all of them, when we are asking them like, “Are you okay to do this?” and they were talking about what they thought about civics education in the country, all of them said, “I need meaningful relationship, and this is the only way to get it right now.”

JENNIFER: [inaudible 00:28:44]

ROSALIND: We are desperate, desperate for meaningful… And having uncomfortable conversations. The more you practice them and the more skilled you get at them, the better they get. They actually get to a place of like, “Oh, I didn’t think of it like that. Oh, never occurred to me.”

This whole thing, if you’re a white woman like I am and you make the mistake… It is a mistake of saying, “I don’t see color.” That might come from a good place, like somebody said that to you when you were growing up because your parents wanted you to think people are equal and those kinds of things… Okay, we really got to stop that. If I could stop one thing, I’d stop [crosstalk 00:29:22]…


ROSALIND: It is a top three of white women saying…

JENNIFER: That is the top three…

ROSALIND: [inaudible 00:29:28]. That is in my top three of, “Do not have that out your mouth.” And if it does come out of your mouth, then apologize and say, “Oh, wow,” because… And I’ll just say it. I know you know this better than I do.

But when we say we don’t see color, that is the most white privilege thing to say because when a black person walks down the street, the whole world interprets and interacts with them on the basis of their color.

And so when we don’t recognize that, we are endangering people of color because we will not recognize the life experience that they’ve had historically in this country and right now to this day. It is so outrageous to me. That’s what privilege is.

And I know people are very active about the word privilege, basically get over it. We really have to get to a place because this is… It’s more about how are we going to show up in life? Are we going to get reactive and all annoying and superficially react to things and not have engaging conversations? Or are we going to actually have interesting conversations with people where we listen to their experience, and then it makes it much easier for them to listen to ours?

JENNIFER: Oh, I love that. And the part of the equation that leaders don’t understand amidst all the fear and hesitation and feeling threatened and denial and, “I’m a good person,” and, “I don’t see color,” we forget and they don’t even know about the potential transformation that they could have.

ROSALIND: [crosstalk 00:30:52]

JENNIFER: And the fact that you just said you can get better at this. This is something you can learn through practice and something that won’t always feel this uncomfortable. It won’t.

ROSALIND: Yeah. And I make mistakes all the time, all the time, all the time with this.

JENNIFER: Oh, [inaudible 00:31:08]. Oh, yeah.

ROSALIND: People are so worried because what is going to happen? I think this actually goes back to a larger issue of just our… We’ve not been raised to know how to treat ourselves and others with dignity in practice. We don’t often know what the definition of that is. We often conflate it with respect, which… They’re really, really different words and they mean very different things.

But I think really this comes down to that we have lost, and we are losing… For lots of different reasons, we are losing the skills to be able to be in relationship with each other, which was always really hard. And we don’t know how to define what’s happening to us, it just feels like being overwhelmed, or it feels like being really stressed.

And so you say, “I’m so stressed, I’m so stressed,” but actually what does that really mean? Because the more you can define what that really means, then the more emotionally intelligent you’re going to be about describing your state, which means to understand it better.

And the more you have self-agency and the more self-agency you have, the more you can change your situation, and that’s regardless of your age. So we just say these words, “I’m so stressed, I’m so stressed,” don’t know what to do with it so it just sits with us.

And so it’s really important that we understand that emotions are not permanent. They’re real, but they’re not permanent and they can change. And so I think in the corporate world, when you’re dealing with somebody who’s so angry at you or so upset, and you feel like, “Oh gosh, I’ve said something wrong,” or something’s running off the rails, it feels like it’s always going to be that way.

And if you can actually think, “Oh, wait a minute. If I get the skills and I walk through this with somebody, this can change, this can transform,” then you feel like there’s a road in front of you that you can walk and you can walk it with this person, which is awesome.

JENNIFER: Which is awesome. What a gift that you aren’t alone. You really aren’t alone. But the isolation, I think, is part of the fear. And then the lack of competence like, “Oh, I’m never going to get it. This is never…”

ROSALIND: [inaudible 00:33:11]

JENNIFER: And then we do, we shy away from the discomfort. And yet as humans, in order to grow, growth means there has to be discomfort. We’ve got to break some things in order to get past them, to get through them. I love that saying, the only way around is through.

ROSALIND: Oh, yeah.

JENNIFER: We’ve got to go through this with each other.

ROSALIND: I do, in deference though… Not deference, but out of respect, meaning the work that people do in corporate America, I do have to say though, because I’m checking myself as I’m saying this and I’m thinking to myself, “Okay.”

The feeling of you can’t make a mistake, I feel like when I work in corporate America… I’m usually speaking in public or in a very public forum. And I remember the first time I was working with a big financial services company… Lovely people. Lovely people.

And when I first started working with them, they gave me the template that they wanted for their slide decks, where I would put my slides into their slide deck. And my fear about not doing it correctly in their template was so high. I was paralyzed.

And I’m usually pretty like, “Oh, it’s fine. Things will work out,” whatever. I was so terrified that it wasn’t going to be according to the stupid template and that I would get fired. Really the thing is I’m like, “All right, how honest is this?”

Because the fear is high of, “I can’t make a mistake.” [inaudible 00:34:32] I need to acknowledge that it really can feel like you can’t get the template wrong and you’ll get in trouble, and that is really hard to make mistakes. It’s hard. I don’t want to make light of how hard it can be in these kinds of cultures.

JENNIFER: Yeah, for sure. And that point, I think, to the larger issue of workplace cultures needing to change to give the room to learn, and part of the learning process is failing. And so how do we normalize? Or like I prefer to say, usualize the failing for purposes of learning, for purposes of growth. We’re not getting it right.

And then I also think you brought up calling in and calling out earlier. There needs to be the holding of space for all that are involved, the learner and the one who’s giving the feedback or doing the teaching, or registering the complaint, giving the constructive feedback or whatever it is, that if we could not call out along the way…

The calling out, I think, is the… While sometimes necessary and certainly for big causes… MeToo, for example, was a huge call-out, and it was public and embarrassing and damaging in all the right ways. It was needed. But in the organizational context, I think we can…

And this is an interesting thing. I’ll be interested to see how young people figure out how they can give their truths in a way that brings others along and balancing the harshness of it as it will be perceived as harsh, even though it shouldn’t be, but it is. And doesn’t lose the learner in the process, doesn’t lose that person on the other end. And I don’t know if they… They’re young. I don’t know if they know how to do that, something you’ve learned over time-

ROSALIND: Well, that’s the argument. That’s the argument I’m having with the young people in my life right now.

JENNIFER: I’m sure.

ROSALIND: Because I’ve said to a couple of them, “I don’t really see…” Over the generations, shame does not work to bring people in. Shame doesn’t work to have people be in a situation where they can learn. Shame just shuts people down and makes them hate you.

JENNIFER: And how could we do anything from there?

ROSALIND: Yeah, it just doesn’t work. Again, I’m very sensitized about the words like call out and call in. When someone says, “I’m calling you in,” my BS thing starts going way up like, “Okay, where are we going with this?” I would rather…

Again, these are the conversations I’m having with young people is that, “Well, what do you mean by that? What are the parameters?” This is actually the conversation I’m having right now and the argument I’m having with the young people I work with right now is, “Define what it means to call someone out. Define what it means to call someone in. Define what it means to cancel them.”

Just so you know from a business point of view, what was interesting that I’ve just been talking about with this group of young people this week was that there was a focus on canceling being very aligned with not supporting that person or the products that they are aligned with.

But that was what was defined as canceling someone. And my job is to push their thinking is, “Well, then where do we then lead into canceling someone because they make a mistake?” Or, “Where’s the definition, or where’s the line between you disagree with them, therefore you cannot tolerate them?” So there were a lot of different ways they were defining canceling that I’m going to do a lot more work on because I think the waters are pretty muddy.

JENNIFER: Oh, [inaudible 00:38:22].

ROSALIND: And we’ve got to get very clear about what this means because we can’t be so fast and loose with this stuff because these are people.


ROSALIND: We are actually people.

JENNIFER: Yes, these are jobs, these are lives.


JENNIFER: I simultaneously admire the purity of that voice that wants to cancel. There’s a lesson in it that’s really important to hear, which is that it’s making me question, “So who do I associate with? What do I say yes to?” Where I know this has happened with me with almost all white panels, for example, that I haven’t put together, but which I’ve been invited to speak on. The risk of doing that, from a canceling perspective, is high.


JENNIFER: And I’ve seen it happen where even just through association, which is I think what you’re saying, if there’s a… If you choose to share any voice or platform with someone who is more problematic, you get swept up. You get swept up in it and you are accountable in a way that I think is really new.


JENNIFER: So I’ve learned a lot from that. Whether I agree with it or not, it’s an interesting… I try to be just objective about it and unemotional. And I say, “Look, I’ve learned.” And now every single thing I’m a part of, I actually write to the organizers and I say, “I want to know how everybody identifies that you’re inviting before I say yes. And then I have some wonderful people to recommend so I can make sure that this is a truly representative conversation.”

And if those things are not addressed, then I say, “I’ll have to step down.” But I learned that the hard way through getting caught up in a whole Twitter storm about an event that it was not organized by me and that I just randomly said yes to that I didn’t really dig in.

And that’s the other thing I learned is I get to influence. I have power. I think I’m simultaneously the ally accomplice, but I’m also the person with a foot in marginalized identities and as an LGBTQ person and a woman.

So I can say, “I’m not comfortable,” and then I can also represent and make sure that other voices that I want to be in solidarity with are representing there too. And I can actually better, I can better the way somebody else plans these things in the future. That is a piece we can influence.

So it’s just one of the many ways I think about… Hold people accountable. But by the way, I don’t do this on Twitter, I don’t call anybody out publicly. I try to get on their calendar and have a conversation with them so they can learn and say, “Oh my goodness. Thank you so much, Jennifer, for telling us. That hadn’t occurred to us. What do you recommend?”

And then I can just take a moment and educate. And they will never be the same again after that conversation. Usually people pick it up and they say, “Thank you so much. We are learning so much. We are going to do what you advocate.” You would never have to have that conversation with them again.

And I’ve done that so many times. I guess when you’re young I’m not sure you understand that there is that give and take that you can work with. You can actually join hands and say, “I don’t need to call you out, I can call you in, and we can have a conversation where you can learn what you need to learn without being shamed in the public square,” which I think causes a lot of collateral damage.

Sometimes it’s needed when nobody’s listening. But most of the time, I think if we can get really creative and by the way, compassionate as well because so many people just don’t know what they don’t know. If we take that moment to think about our strategy, I want young people to understand they have choices. There’s many ways you can tackle something, and they all have different consequences. So as long as we know that.

ROSALIND: Yeah. Look, I think we can totally confront young people or anybody about… Well, let me back up and say I also made those same mistakes, being asked too… I want to own that. I also made those same mistakes when I was asked to co-present on things and I’ve looked back on stuff…

It started about two years ago and I was really… I had a moment, many moments [inaudible 00:42:40] of just, “Wow. Wow, that’s my privilege blinding me to being more equitable.” I definitely have had that experience.

And I think, and I say this to young people a lot, is that posting something on Twitter that you’re angry about for five seconds and you move on to something that you’re angry about five seconds later, that is not a courageous political statement, nor does it make anything better. No, I call BS on that completely.

Say you’re in student council, say you’re… Because most student councils, frankly, this is the thing that we don’t talk about school it’s a lot is that student councils, let me say it in a positive way, are ripe for opportunity for more racial and all different kinds of the equity in student councils.

And it’s a very frustrating thing to work in schools on that issue, but it’s really important. So it’s really important to say to young people, “Yeah, I don’t really care about your Twitter feed, I actually care about you and the positions of leadership that you have, or the voice that you have doing something to bring more voices to the table.”

ROSALIND: That’s a much more interesting, much more substantive way to address the issues that you say are really important to you, rather than having a little temper tantrum on… And I do use these words and I will use it… I don’t care. We all have temper tantrums on social media so this is irrespective of age, is that I don’t care. I don’t care about your Twitter rant. I really don’t. It doesn’t make things better.

It might make you feel better in the moment, but doesn’t make it better. So if you want to actually do the things that you say you want to do, then do it. Do it where you go to your faculty sponsor of your… Whatever. Of your student leadership group and say, “We need to make this group more racially equitable.”

I noticed because I’m in an AP… This is for high school people I noticed because I’m in an AP class. And I noticed in my AP classes that they’re vastly majority… They’re tracked. They’ve been probably tracked since [inaudible 00:44:48] school and they’re really pretty white. What’s going on with that? For example, even in my Spanish AP class where 40% of the kids who go to this school are Hispanic, Latinx, and yet in my class 95% of the kids are white. What’s going on with that?

JENNIFER: What’s going on with that?

ROSALIND: That is what advocating for equity actually is about. It’s not about Twitter.

JENNIFER: Yeah. Oh, thank you so much for that. I really appreciate… It is the measure… It’s not the glamorous thing, it’s not the easy thing, it’s not the quick thing, it’s the hard work in the trenches. And it is, you’re right.

It’s like, “Okay, so if you have an issue with it, then join it and try to make it better from the inside.” And that’s what’s going to create lasting change. I know [inaudible 00:45:34] you go, Rosalind, I hate it. But this has been so awesome. You have a new book out. I want to give you a chance to talk about that, and then there’s other books too you might want to mention for people that want to learn more about your body of work.

ROSALIND: Oh, sure. For the parents out there, I published about eight weeks ago, a book. I co-authored a book called The Distance Learning Playbook for Parents because over the summer I thought, “It’s possible that we might need skills on this.”

JENNIFER: I don’t know. It’s just a wild guess.

ROSALIND: I don’t know, [inaudible 00:46:05] a wild guess. So yeah, so that book is available. It’s [inaudible 00:46:12], and it just talks about some of the things that we’ve talked about today about social, emotional… How to manage emotions.

Because if really there was ever a time that it was clear that we needed to know how to manage our emotions and how that impacts our work life, and our ability to work, and our ability for our children to go to school, I think this is a pretty good example.


ROSALIND: So it goes into that. And then the other thing that we have that I think is really, really good for managing, you talk about emotional hijacking, and what does that mean? We have these things called tiny guides that are these little…

They’re PDFs that you can have on your phone and they just walk you through. There’s 18 of them. And it just walks you through just all the different components of what emotional regulation is, and how to manage anger, and metacognition, and how your brain works, and how your brain responds to emotions.

Frankly, one of the things I’ve learned this year is less is more. I’m definitely somebody who was more is more, until this year. And less is more. Less is more. People have such limited bandwidth. And so these tiny guides, I would strongly suggest…

Let me say it to you this way. When I’m having a hard moment of which I have a 17-year old who just got diagnosed with COVID on Tuesday, so we’re right in the middle of… We’re on day eight. So far, so good. But these tiny guides are the things that I am actually going to, to remind myself of how to manage myself. And I do this for a living. So that’s a resource for people that I would strongly suggest that you check out.

JENNIFER: Thank you so much. I’m intrigued by the tiny guides. The bite-sized learning is everything, and I think that’s not going away with our busy lives. But also, I think it’s very manageable as learners. I think it’s an idea whose time has come.

ROSALIND: Mm-hmm (affirmative).

JENNIFER: So wonderful. I just loved this, Rosalind. And thank you for the voice you’re giving young people and the way that you’re contextualizing what they’re bringing, who they want to be, the world they want to grow up in, the workplaces they want to inhabit and thrive in. You’re really connecting a lot of important dots, and I think you’re holding space and respecting and giving dignity to so many pieces of the equation, which I think is the really hard but wonderful work that we do. So I just appreciate you, and thanks for joining me.

ROSALIND: Oh, my pleasure. Absolutely my pleasure.


Cultures of Dignity