The Mindful Midlife Crisis

Episode 55--Anti-Racist Conversations with White People with Jesse Ross

April 20, 2022 Billy & Brian Season 5
The Mindful Midlife Crisis
Episode 55--Anti-Racist Conversations with White People with Jesse Ross
Show Notes Transcript

Billy talks to Jesse Ross, a diversity, equity, and inclusion consultant, executive coach, and international speaker who has delivered over 400 speaking engagements at colleges, conferences, corporate and nonprofit companies, with a large number of those being Fortune 500 companies including LinkedIn, General Mills, and the NBA.  

Jesse offers trainings, workshops, evaluations, assessments, and strategy development for schools, businesses, and organizations. Jesse has been engaging his audience with his Morning Minute calls-to-action on his Instagram and LinkedIn page since before our world went into civil unrest. 

He is here today to talk about his diversity and inclusion work as well as the anti-racist conversations he has with white men and white women each week, which you can sign up for here. 

Billy asks Jesse: 

  • His weekly anti-racist conversations with white people
  • How he gets in front of people who would benefit from engaging in anti-racist dialogue in a way that doesn’t activate a fight/flight/fright response from them
  • How he helps people see the nuances when it comes to conversations around race
  • Examples he's seen lately of good-intentioned white people being tone-deaf when it comes to issues within the Black community
  • His experiences navigating white spaces as a person of color

Like what you heard from Jesse Ross?  Contact him using the links above!

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Jesse: I don’t think hope is a strategy, and I think we’ve heard that before, but I have hope in people, and my hope is that there are more people listening to this conversation, there are more people like you and there are more people that I can meet that want to do good and their return doesn’t always have to be monetary, their return doesn’t have to be something that helps them continue to elevate their wealth and their power, but their return is doing something good in the world.


Welcome to The Mindful Midlife Crisis, a podcast for people navigating the complexities and possibilities of life’s second half. Join your hosts, Billy and Brian, a couple of average dudes who will serve as your armchair life coaches as we share our life experiences, both the good and the bad, in an effort to help us all better understand how we can enjoy and make the most of the life we have left to live in a more meaningful way. Take a deep breath, embrace the present, and journey with us through The Mindful Midlife Crisis.


Billy: Welcome to The Mindful Midlife Crisis. I’m your host, Billy. Brian is being presidential right now. His company duties call him to action, but we are blessed today to have as our guest Mr. Jesse Ross. Jesse is a diversity, equity, and inclusion consultant, executive coach, and international speaker who has delivered over 400 speaking engagements at colleges, conferences, corporate and nonprofit companies with a large number of those being Fortune 500 companies, including LinkedIn, General Mills, and the NBA. Jesse offers trainings, workshops, evaluations, assessments, and strategy development for schools, businesses, and organizations. Jesse has been engaging his audience with his Morning Minute Calls to Action on Instagram and LinkedIn since before our world went into civil unrest. He is here today to talk about his diversity and inclusion work as well as the anti-racist conversations he has with white men and white women each Saturday morning and we’ll include a link in our show notes in case you’d like to be part of those conversations as well. Welcome to the show, Jesse Ross.


Jesse: Thank you so much, man. Thank you for having me. I’m grateful to be here.


Billy: Yeah. I’m so happy that you’re here. I know Brian is bummed that he can’t make it. We really enjoy having these conversations because they challenge guys like us and we appreciate that. We know you have a hard stop at five o’clock today so we’re actually going to skip the 10 roles that you play but you can maybe work in some of those roles, I’m sure we’ll get a feel for what kind of roles you fulfill as an everyday human being. We just wanted to start off here and talk about these anti-racist conversations that you have Saturday mornings with white men and white women. Can you talk about what the differences are in those conversations between white men and white women, if there are any?


Jesse: So, differences, I would say the type of things that we talk about, there are no differences particularly. I think the only difference is the gender makeup. Women tend to be more likely to have conversations about personal development, more open to having those types of conversations about race and ethnicity and equity and whatever that looks like. And men like to have them but not as often, not as much, not as deep, and I think we, as guys, tend to be a little more guarded. And so the conversations are pretty much the same. The conversations with the men, there are less number of men who show up. The women, we probably average somewhere between maybe 60 to 70. The men, we probably average somewhere between 10 to 20. And so those are basically the differences but we talk about the same things, have some of the same conversations and I try my best to go deep and not just go deep, not even just to go wide, but really try to figure out how you can create some impact through the conversations.


Billy: And I’m new to these conversations, I’ve been to two of them, but my plan is to continue attending as many as I possibly can and I think part of the reason I wanted to have you on the show is because I want to encourage our listeners to join these conversations too because one of the things that you talked about in the first call that I attended was how do we get more white men who need to hear these conversations to attend because it feels like most of the people who are attending are kind of already in that headspace so then I believe that part of the conversation was, well, then, how do you use your influence to have those conversations or how do I, excuse me, use my influence, and I’m a big believer in meeting people where they’re at but I don’t imagine you can hold sessions where you say, “Okay, on a scale of 1 to 10, how racist are you? Okay, you should join this group right here because you really need some intervention.” So how do you get in front of people who would benefit from engaging in anti-racist dialogue in a way that doesn’t activate a fight, flight, or fright response from them? Or is that just simply impossible?


Jesse: I don’t think it’s impossible. I think it is very strategic and sometimes very organic. And so part of the ways that I try to get in front of people is really just putting out information on social media, asking current attendees to share some of the information that I’m either speaking about or sharing on social media with some of their circle of influences. And then, ironically, sometimes, I may start a fire here and there and post something that may be a little controversial or a little jab at the group of folks that typically might not show up in effort to get them to engage. We live in a world that is sometimes driven by shock value, sometimes driven by the taboo in the media outlet and so being able to take some of the things that are currently happening in our culture and create a perspective, hopefully, that can offer an alternative and really invite people into the conversation. Anytime, even if it’s a person that I will call like a troll, someone, who, their whole sole purpose on social media is really to just denounce anything that I’m saying, I always invite them into a conversation. Now, 95 percent of the time, they don’t take me up on that offer, which is when I usually hit the block message, but I think our world is so polarized by those news media tabloid headlines and I think if we can get people to have conversations, like the ones that we’re having, but even just inviting someone to a conversation, especially if you disagree or have opposing viewpoints, I genuinely think one of the best things that can come out of that is learning. Now, there’s probably a lot of bad things that can come out of it but I think most of the learning and progress can come out of just hearing somebody out or trying to discover why someone thinks the way that they think.


Billy: That was a big takeaway that Brian and I both had when we talked to Jodi Pfarr about the urgency of awareness and she talks about the triangles and how, for me, all my triangles are facing up. So I’m white, so that’s normalized in society. I’m right handed, that’s normalized in society, and just trying to draw awareness to that and, in our last conversation, you were talking about navigating white spaces and I’m wondering if you could talk about what that experience is like for you that may be something that someone like me takes for granted, doesn’t realize, as we talk about it now, it all of a sudden develops an awareness for me, like, “Oh, I’ll be more cognizant of that.”


Jesse: One of the most helpful things even just starting from that question, which I think is a great question, is I don’t speak for all black people, I don’t speak for all people of color, and so I think there’s a nuance that is always present to individual people and their experiences and I think that that’s important and it’s very complex. I think, from the conversations that I’ve had with people, really going off the last question, providing some type of perspective and point of view to people who have no idea what that experience might be like because of different race, different ethnicity, different genders, different cultural background and where people come from. One of the things that I have found that is almost irrefutable has been someone’s story. We can discuss and debate facts, we can even discuss and debate theory, but when you hear someone’s story and their experience, it’s usually really hard to say, “I don’t believe you.” Now, we know it’s happened before but I think it’s more difficult to dispute someone’s story and so I try to share my experiences, my thought processes, good, bad, indifferent, and just say, “Huh, I wonder if anybody else feels the same way? I wonder if you know exactly what this feeling feels like and what that means and how that shows up?” And 9 times out of 10, my white brothers and sisters don’t and I don’t think that that’s a bad thing. I think it should cause us to pause though and recognize the opportunity to consider another alternative, just like I’ve had to consider as a black man the other alternative for my white brothers and sisters pretty much my entire life. I had a question today, I’m going through a process with the City of Minneapolis to purchase a building, I’m eligible for some funding that’s made to not just people of color but to anybody but there are specifics that they are trying to get to and one of the questions was “Have you ever experienced any type of barrier or opportunity to not progress based on where you live, based on what you look like, or based on where you grew up?” And I just struggled and said, “Absolutely.” And he’s like, “Can you tell me about that?” I was like, “Do you want me to give you the whole 36 years of my life or do you want…” and it was just one of those — it was it was a very blank and basic like aha moment but part of the reason why they have those questions is to make sure that they know that the funding is going to people that are supposed to have it versus people who are just leveraging the system. So I think the stories, that was a long way around just to get to, I think when you share the stories, it’s been helpful and I’ve heard that people who attend these calls end up having greater appreciation for me sharing and being very transparent, and I’m a direct communicator so all I try to do is just be honest about what my experiences are and hope that they will consider that someone else might experience that same thing.


Billy: Here’s the beauty of those conversations that we have is that it’s Monday today but I’ve been thinking about things that we discussed as a group since Saturday. There have been things that have been swirling around in my head, and one of those things, as you were talking about navigating white spaces, it reminded me of just that short time that I spent in Dakar where I was not the normal. And it was interesting to me just maybe the uneasiness that I felt but I think a big part of that uneasiness came from not being able to speak the language and I felt that when I was, particularly in the north of Portugal, when I got to Lisbon and when I got to Lagos, most everybody spoke English but it was kind of 50-50 for me in Portugal, in northern Portugal, and in Dakar, it was just the people at the surf camp not really being able to communicate. So there was that piece where not being able to have conversations that maybe would have alleviated some of the internal bias that I had just because, hey, I was thrown out of this situation where I’m the norm almost everywhere I go and how do I feel about that? I’m a little uneasy. Well, why am I uneasy about that? And it’s like, you know why you’re uneasy. 


Jesse: Right. Yeah. I mean, but it’s funny how that happens, because if you weren’t, let’s just say, you can take someone who had a very similar experience. If they were not aware of those different perspectives, they could go to the same camp, they could go to the same place and location and feel completely different. And that’s the beautiful and frustrating thing at the same time of recognizing how we experience the world. I always talk a lot about our experience and our exposure. Based on our experience and our exposure, where you grew up, what you learned, what the expectations were, what you were exposed to, all these different things, we all can see the same painting, talk to the same person, read the same scripture, whatever, the poem, whatever, and have completely different takes on it based on our experience and our exposure. And, again, it’s beautiful and it’s ridiculously frustrating so I can only imagine.


Billy: I watched the rest of the camp navigate Dakar car much more comfortably than I could just because they could speak the language and I just feel like the great barrier to coming together is a lack of communication or an unwillingness to communicate, which is why I think it really is important, if you are a listener out there, to really think about joining these conversations that you’re having, Jesse, because I’ve only been to two so far and they’ve been two of the most valuable conversations. And I think too, it’s important to stress that they’re conversations, they’re not lectures. They’re conversations. And I think a big thing for particularly white males and white females is the idea that we’re going to walk away from these conversations feeling guilty about our whiteness and that’s not been the case in the two conversations that we had.


Jesse: Yeah, I’m grateful. I think, it sucks to say this, but there are people out there, I know a few of them, who have these conversations and built a business model on shaming white people and having these conversations. And that’s their prerogative, that’s not my goal. My goal is to actually have a conversation with you. You’ve been there and I appreciate you saying that. Just so you know, listeners, I did not pay him to say any of that. Part of my hope, really, is like, yo, can we have a conversation? So I’m naturally a people person, I’m naturally curious and inquisitive, that’s just how the brain works, I’ve studied human behavior and all these different things, so I just naturally have that curiosity. But I also think we need more actual conversations which is going back and forth, exchanging information and viewpoints and perspectives and stories instead of someone just dictating, “Here’s what it is,” and that’s it, and somebody walks away, somebody walks away upset, somebody walks away crying, somebody walks away feeling terrible about themselves. Now, I can’t control any of those emotions. What I can control is how I enter into the conversation and so I always hope and really put my best foot forward to hope that it is a conversation. Now, there are some things that we are more passionate about than others and so, in those conversations, I might get a little riled up, I might get excited, and then some stuff, I’m like I have no idea, but even without going into depth of the conversation that we had this past Saturday, there was a man who hasn’t been on the call very long, a little bit longer than you but not very long, and he shared something that was related but a little unrelated, and my hope is, in the conversation, I can just use this topic as an opportunity to actually build community. Now, he shared something that was pretty vulnerable and it was a chance and I think everyone in the call received it and said, “Hey, thanks for sharing, I really appreciate it.” That took a lot. Now, had we not been talking about anti-racism, we would have never gotten to that and I just imagine that he continues to feel like, “Hey, maybe people are gonna look at me differently for thinking this thing.” But when you get in a room, whether it’s virtual or in real life, with people who can just listen to you and hear you out and not have a judgmental viewpoint on what you said, maybe they don’t agree but they’re not going to judge you for it, it changes things and so that’s my hope with those conversations. And I will say this too. I think we’re talking about it from one perspective of white men and women being changed, but I’ll be honest and I’ll be the first to ever say, I’ve been changed through these conversations. I have shared way more than I probably ever wanted to, historically, but I’ve also built some really great friends, some friendships and some relationships with people I would have never ever, ever met had I not decided to just dive into this. And so it’s very mutual for me and I hope that anyone who participates and anyone who experiences, which is why you even invited me to the podcast which I’m grateful for. I’m always trying to figure out what can I do to serve, how can I help, and that’s just my role, one of the roles that I have, to just do good in the world. So, sorry for the long answer but I just wanted to make sure that listeners heard that and really recognized that it’s not — I’m not just on here dictating, I may come up with some of the topics, I might kind of bring some of the conversation out, but it is a free flowing conversation. I may still have, like, “Hey, let’s talk about this question,” “I want you to walk away with this,” or, “Here’s my thoughts,” but I want people to bring all of what you have to the conversation, which I think makes it very rich.


Billy: Well, and you bring up a point here about vulnerability and it’s something that I want to circle back around to because I do think there are not enough safe spaces for men to talk and I have a follow-up that I’ll ask later on in the show but when I asked you the question before about navigating white spaces, I always wanted to make sure that I see what’s your experience or what’s the experience of people that you have talked to because we’ve talked about this before where oftentimes you are asked to answer on behalf of all black America in interviews or in conversations around race and my theory on why people do that is because we’re oftentimes just looking for one solution to a complex issue without having to dissect the nuances or the intersections of human behavior because then we can just cling to an opinion that suits our narrative. And I know that something that’s hard for me is that sometimes I feel like the goalposts are moving when it comes to talking about race because I’ll read how to be an anti-racist by Ibram X. Kendi and I’m like, “Wow, a lot of that really hits home for me,” but then I’ll listen to John McWhorter who’s very critical of Ibram X. Kendi but still doing anti-racist work but doesn’t break it down into the binary that Kendi does. So, how do you help people see these nuances during your sessions and during your conversations so that they understand that, listen, Ibram X. Kendi he doesn’t speak for all black people. John McWhorter doesn’t speak for all black people, I don’t speak for all black people, these are our experiences based on our research and our lived lives.


Jesse: Right. That’s a great question. If I’m honest, I don’t always know. I think — I mean, I’m just going to be honest, I think people have a hard time hearing different points of views. I think people also are looking for that one thing. So we read a book, we go through a course, we listen to a podcast, we watch a movie, whatever the thing is, and we’re looking for that thing to like, basically, defend or to prove you wrong or to prove someone wrong so you can say, “See, look at here,” and I think we just missed the complexities of how human we all are. I think it’s very possible to support one issue and thing and then wrestle with another and that doesn’t make you any less conservative or less progressive, or less right, left, whatever the thing, it makes you human. And so what I try to do is draw from principles that I think can be, again, maybe taboo, maybe a point of interest and hot topic, and then also lay that or underlay that with some foundational good human behavior contexts. And I know that might sound really weird because, yes, we should all be humans listening to this but, for some reason, I think we just forget those complexities. And so I think if we take the emphasis off of, “If I read this book, I’m gonna have an answer,” and if you notice, Ibram Kendi’s book doesn’t really walk you through actually how to become anti-racist. From my perspective. I think he’s a wonderful author. I love his perspective, I love the historical context and how he dives into it, but if you really bring it and boil it down, he’s giving you things that you should be thinking about but it’s not a how-to book, which I think a lot of us are looking for that self-development, “How do I fix this?” and I think that’s strategic. And this is my point of view. He probably said something completely different so just go talk to him about his book. But I think that the goal isn’t always to just fix the thing. I think the goal is can you put yourself in a position to gain greater clarity, to gain more insight, and to gain more perspective, and I think we do that by finding people like Ibram Kendi, like Kennedy, like Robin DiAngelo and Resmaa Menakem, and I’m probably messing his last name up, but it’s M-E-N-A-K-E-M, he’s from the Twin Cities. Like the goal is to gain perspectives from all people, not just those authors as well but from people that you work with, people that you go to school with, people that you live life with, in hopes that we can create a broader worldview of how we see the world, how we engage with the world, and how we can do better by humans. I think that that’s really what I try to do and try to bring in those perspectives. But, of course, you’re going to have to recognize that some people think differently, and I think that’s perfectly fine. So I think that’s one way to engage. And that’s just one way. People that are listening to this podcast, hopefully, you’re getting another perspective. Hopefully, if you are coming from the perspective or the experience of being shamed for being white or for not having a circle of influence that’s very diverse, not just in color or race and ethnicity, but by class, by gender, by education, whatever that is, that you can gain a different perspective from our conversation. But it doesn’t just stop there. What do you do after that? Because if we just get the perspective and the worldview but we do nothing with it, then we’re still left with that, “I gotta do something,” which brings us to the shame, actually. We went around, running around, but, in general, I think that’s the hope is to add diverse perspectives and to be able to say, “Okay, what do we do with this now?” Not how do we fix it, but what do I do with this now.


Billy: Well, you talked about the role of being a good people so what I want to do here is I want to take a quick break because when we come back, I want to talk about how good intentions can go awry sometimes when we are talking about anti-racist work. Thank you for listening to The Mindful Midlife Crisis.



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Billy: Welcome back to The Mindful Midlife Crisis. Brian is off being presidential at his company but I am joined here today by Mr. Jesse Ross, diversity, equity and inclusion consultant. You can follow him on Instagram at @mrjross. You can also go to Those will be linked in the show notes. We’re trying to encourage you to join his Saturday morning anti-racism conversations here by having a conversation very similar to what we would have on those Saturday mornings. So, Jesse, one thing that you talked about in those conversations and you also send out calls to action a couple days a week via email that people can sign up for, and a couple of weeks ago, you brought up an example of good-intentioned white people being tone deaf when it comes to issues within the black community. So, can you give some examples there of what you have seen lately and maybe talk about the example that you shared with us?


Jesse: Man, you’re going to forgive me — you’re going to have to forgive me, Billy, I put so many call to actions, I don’t remember exactly which one it was.


Billy: It’s the one about the Minneapolis school teacher who was doing the Kendrick Lamar rap.


Jesse: Yes, okay, thank you. I just had to make sure. And, listeners, just so you know, here’s where I run into trouble when you not even just put out so much content but when so much is happening, and I mean that in the most sincere way, when so much is happening, it’s almost like wait, what fire was that? What call to action was that? What problem? What happened? And so that is part of what that was. Okay. So, man, I almost forgot about that. Basically, the setting of the scene was here in Minneapolis, Minnesota, the Minneapolis Public School District was on a strike, the educators were on a strike for about three weeks. Most of the strike was centered around support staff and teachers not being paid and not receiving raises and all these different things. And everyone is basically underpaid in the district except superintendent, who also happened to take what I believe was a 5 percent raise this past year. So, they’re on strike for multiple reasons, but within the strike, the Minneapolis Public School District is about 80 percent made up of white educators. Now, there is about 2, we’re about like 1.5 percent across the country of African American educators. 1.5 percent across the country. Here in Minnesota, it’s right at like 0.9 percent, I think it might be like right over 1 percent or something like that. So we’re par for the course across the country. Most of the people who were on strike and we’re demonstrating and protesting were mostly white individuals. There were some people of color there were also in there but when you dig into the data, and I think that’s really important, most of the people who are underpaid are folks who identify as people of color. So that’s just the setting. I’m also, again, from Minneapolis so when you think about the events with George Floyd’s murder, Daunte Wright being killed here in the Twin Cities, there’s just a lot of pain, a lot of people remember what protests like in the world and the world remembers that too. There were problems from the white community when people were protesting about George Floyd and when people were protesting about Daunte Wright, when people were protesting about Ahmaud Arbery, Breonna Taylor, black and brown individuals being killed either by the hands of the police or whatever, just injustices. People were bothered by protests. But here you are, you have hundreds, hundreds of educators in the city of Minneapolis who are predominantly white who are protesting and nobody has a problem. That was the first kind of call-out and I just said, “Hey, does anybody recognize the differences?” I mean, they were organized. I’m talking about T-shirts, hats, scarves, being escorted, all these different things. So that was the first layer. The second layer was while I was driving to my kids’ school, I passed, and this is in a pretty, for lack of a better term, a wealthy neighborhood, one of the protest locations were playing music the entire time. Now, cultural appropriation, if you don’t know what that is, you should look it up, is a real thing, and this was one of those moments where it just caught me off guard. It wasn’t like I was looking for it. I definitely wasn’t. I was just driving to my kids’ school. And I happened to notice that they were listening to Kendrick Lamar, which is an African American hip hop artist, and the song was called “We’re Gonna Be Alright” and I was like, wow, okay, songs playing, got it, and there’s a white guy on the microphone singing the songs and it was just so — it wasn’t like I was disgusted. That’s not the feeling. I was so perplexed at the nuances of this experience, because “We’re Gonna Be Alright” was written by Kendrick Lamar in response to the protests, in response to the killing, in response to injustices, basically saying, “Hey, I know that things are bad but we come, as an African American people, come from a lineage of kings and queens, come from a lineage of overcomers and we’re gonna be able to get through this and let’s celebrate while we are also still going through it,” and then here you have this white guy singing the song and he doesn’t know why he’s going through it at all and I just was like, wow, and I just pulled over and was just like this is it. This is at the heart of why I want to have these conversations. I didn’t say anything that he did or said was wrong. Now, I want to make sure that our listeners are hearing that. I didn’t say anything that he said or did was wrong, but him singing the song had a whole different perspective, experience, or even exposure than when I hear Kendrick Lamar singing it or when I heard tons of people singing it after Jamar Clark was killed at the protests at the Minneapolis Police Department. It’s just a different context. And, for 18 days, I believe, these educators protested at multiple locations and most of them were going to be alright, pun intended from the song, but there are so many people who were not able to be there because they were still fighting for a livable wage. They also were not part of the majority. They also were dealing with the repercussions of the civil unrest. And here we have just this nuance of a white man singing Kendrick Lamar’s song. And so that’s one of the call to actions that he’s referring to but I also think there’s so many of these things that happened, we just saw, and I won’t really go into this because it still is taboo, but we just experienced the Oscars and Will Smith and Chris Rock and Jada Pinkett Smith and, again, I didn’t say what was right or wrong, but I wanted to provide the perspective of I saw a lot of people on social media quick to make a judgement statement that came from a predominantly white perspective. The Oscars was predominately white and I just offered, “Hey, maybe this is one of those times where my white brothers and sisters can hear, experience, or be exposed to a different perspective coming from the black community, being that the situation happened with three African American individuals,” and, boy, did we have some great conversations.


Billy: I think the one thing that I struggled with in that was I heard people in the black community saying that, as a white person, you need to stay out of this, you shouldn’t have an opinion on this, and I was like, huh, I don’t know how I feel about that. Now, I do think that before we have an opinion on it, I think before anybody has an opinion on it, they need to look at the intersectionality and the multitude of layers that go into it but maybe it didn’t sit well with me when there were people saying — one person I’m thinking about is Adam Grant, who is a known psychologist and people were coming at him for his commentary on it and he was like, “Listen, studying human behavior is my job so I do have a response to this,” and during the anti-racist conversation, someone talked about how happy they were that someone put Glennon Doyle in their place and so I looked at what she said, I’m like, well, she came out really quick with it but at the same time too, she’s an advocate for women so I understand why she came out with that statement. It might have been better for her to take a pause, kind of like what Brené Brown and Mel Robbins did after the whole Joe Rogan Spotify thing came out where those two, they didn’t take their podcast off of Spotify, they said, “We’re gonna take a pause for a week and we’re not gonna release a new episode until we have a conversation with Spotify and then we’ll move forward as necessary.” And I think, from my point of view, that might have been the better response for people to take but I wasn’t a fan of the stay in your lane and you don’t have an opinion on this, and kind of curious your thoughts on that.


Jesse: I think both perspectives, statements actually meant the same thing but were received in — or were said differently, and were received differently. I think there is a thing called tact and I’ve been working on it my whole life and so I think part of it is just how will we say things. I mean, there’s books on that, psychology of how we receive things, how to give feedback, all those different things. I genuinely think both meant the same. They meant the same but were received differently. I also think that it is okay because we are complex individuals. I think it is okay for there not to be just one right answer. I think there are complex ways of approaching it and I think that I feel in Adam, I follow Adam, I actually follow Glennon Doyle, Brené Brown, all the people that our society have deemed to be some great insight and thought leaders, I think that what they offer is such a wonderful, diverse perspective, even very similar minded, but I also think, because they are white, there’s still a limit to their perspective, regardless of how much education, regardless of how much experience and exposure, and where I think we are now, it’s not about just who says it, it’s not even just about how someone says it but what is being said. I think the other perspective that I would like to add is what’s not being said. And so we’re hearing from people who happen to, because of social media, now have the opportunity to share their perspective and if you happen to share it and then I happen to share it and someone else happens to share it and Shaun King who follows me happens to share it, then it’s like, boom, this thing just blew up. And most of the time, you, I, Shaun King or, and I’m just naming a random person that has way more followers than I do, when the person who’s posting what they’re posting, I just like to believe that most of the time, they are offering their perspective, right, wrong, or indifferent, and I think that that’s the complexity of humans, the complexities of the time that we’re in. And so because of your experience and exposure, you may prefer one way or the other. Because of my experience or exposure, I may prefer one or the other. I don’t think one is wrong or one is right, it’s just a different take on it. And I think that if we could live in that space more and have more people providing diverse perspectives instead of focusing on what is right, again, I think that we would have a greater worldview or perspective of these situations. Now, do some things just need to be solved? I do believe. Not interested in solving anybody else’s problems other than my own.


Billy: You brought up something right there that gave me a little pause. You talked about how you’ve had to develop tact and I wonder how much of that is so that you’re not perceived a certain way, if you get —


Jesse: 100 percent of it. 100 percent of it is, and I don’t know the actual percentage but I would say, going back to one of my earlier comments, I think that there — I know people, unfortunately, that have built their business around diversity, equity inclusion centered on shaming white people. I know people who’ve also built their business shaming people of color. And it just doesn’t feel good. That’s not true to me. I am a people person and so my mom used to always say this thing when I was younger: people are important to God so they should be important to you. And that sat with me for a really long time. The basis of it was like, “Hey, listen, I don’t care how you feel about someone, they are important to someone and because they’re important to someone and somebody, they should be important to you but that doesn’t mean that’s always gonna be true but you should treat them well.” And so I think tact has been less of a, “Let me not be the angry black man,” and more of me learning my fascination with communicating with people. I have a very cynical mind around wanting to — it has nothing to do with wanting to be liked but it has everything to do with my studies around human behavior and really believing that I can win someone over. We don’t have to be best friends but I think if you offer care and support and serve people, even if we don’t agree, we can at least be cordial and be polite and that’s kind of just the value that I try to live by. And I think the worst case scenario is we don’t fight. We gain some respect. We have a good time and crack a joke and laugh at something that we never thought we would. But best case scenario is we grow. We expand. We feel like, “Man, I’ve connected with somebody and I don’t even know where they live but I hope I see ’em on the call again,” “Hey, you’re interested in this. Let me introduce you to somebody else,” and, “Hey, could you share this?” and, “Oh, man, this was really great,” I think those are best case scenarios. But, yes, I would say 100 percent of everything that I do has been making sure that I take care of people and unintentional outcome of that is making sure that I’m not being the angry black guy. I will say this though, and just kind of the side note or the asterisk that I want to put by, I’ve done a lot of self-development and personal development, I genuinely do not care what people think about me. Now, that sounds very not tactful, I just want to make sure that that’s out there. What that means for me is I don’t thrive from social admiration. I get my value from purpose, doing things that are important to me, that create good in the world. And if you don’t like it, man, that sucks. I really hope you do but I’m not going to stop doing it because you don’t care about it or you don’t like it or you think I’m doing it wrong. And a lot of people do get their value based off perception and admiration. So I say that in a sense. Now, do I want to be liked? Of course, everybody wants to be liked, but I learned a long time ago, my mom told me that not everybody’s going to like you and that started early. My wife likes me, that’s all that really matters.


Billy: Well, and it hits home a little bit for me because when I was a dean of students, you’re always the bad guy. Nobody likes the dean of students. And a lot of times, you’re doing crowd control in a group of teenagers and I’ve always said that one on one, teenage boys are generally pretty nice, but you get them around a group of their friends and their IQ drops by about 50 points and I would lose my damn mind around these teenage boys when they’re in a group but then if I could get them one on one and we could have a conversation, I’m like, “For the most part, we can get along, like we can see eye to eye when it’s you and me and we can have this conversation,” so that resonates with me a bit. You talked about purpose and, for me, starting this podcast, a big component of it was prioritizing conversations around mental health and normalizing conversations around mental health and thinking more about how I can create safe spaces for guys to talk and I feel like you have done a great job with that, not necessarily around mental health, but I think just having conversations is important and one thing that you’ve talked about is if you’re unsure about how something might impact a community, maybe ask a few people from that community to get a better understanding so you don’t do some damage. And I guess my last question for you here, and like I said, we started off this podcast to normalize conversations about mental health and through our research, the data from the American Foundation of Suicide Prevention shows that it’s middle-aged white men who have the highest rate of suicide and white males accounted for 70 percent of all suicides, I don’t know that that’s necessarily talked out loud often, and we want to be mental health advocates and focus on this demographic because Brian and I are members of this demographic, but I’m going to guess it’s not going to go over well if we chant, “Middle-aged white male lives matter,” and I even hesitate to put that on a recording so somebody can clip that right there and say, “Oh, that’s what he believes right there.” I guess how would you suggest we package that messaging because I feel like that’s our demographic right there but then, at the same time too, you’re a man of color and you need a safe space to have a conversation, you can be part of our group too, so that’s kind of the thing that I’m wrestling with a bit, so I’m just curious to get your take on that.


Jesse: Yeah, I’m going to enter it in an example story form that I think applies. So, listeners, if it doesn’t, just scratch it, just fast forward it and just forget that 30-second part. I’m in the process of purchasing a commercial real estate building in effort to change the wealth dynamics within my own community, and for the last year and a half, I’ve been very focused on studying and learning about wealth redistribution. Basically, there’s a group of people who happen to be more likely to attain wealth or that have wealth and they don’t look like me. They are part of the group that is, ironically, the 70 percent part of the National Suicide survey so I appreciate you mentioning that. And what I’ve learned in some of my research, there are basically three groups of people. Now, there’s not a study that shows this, these are Jesse Ross’s words, but there’s tons of data to back what I’m saying, I just try to make it very digestible. There are three groups of people that typically are out in the world. There are people, one, who give and want to give money away. Sometimes they feel guilty, sometimes they’re like, “It doesn’t matter, I just wanna support the thing, whatever it takes,” have you, that’s group one. Group two, typically, they will give but they would like a return. They have the means but it’d be nice to get something back so that they can keep it going. And then group three are typically what we will call investors. They’re people who will just, they really want to return, that’s their business model, that’s their whole purpose. They’re in it for the game. And the way that I’ve processed that question is recognizing I’m going to run into all three groups of people but group two intrigues me the most because there’s some knowledge, there is some education, there’s some awareness right there based on them saying, “I’d like a return. I got it, it’d be great to get something back, it’d be great to see increases,” but I genuinely believe that group number two, if you talk to them, if you convince them, if you craft the pitch right, if you build a relationship, if you get to purpose, whatever the thing is, they would give, they just naturally are leaning towards wanting a return. And so I say that in that context because I think there should be, of course, there should be support groups for all people, everybody needs some like-minded individuals that they can be safe with, they can create community with and all that, but I think for folks like you, Billy, I think it is important, call it what it is. “Hey, I’m part of the majority, I recognize that whether you look at my bank account or not, I have some type of power, and instead of acting like I don’t have it, let me acknowledge that I do have it even though I don’t even want it, even though I didn’t even do anything to earn it. I’ll recognize it, I’ll acknowledge it, and I’m going to do everything in my power to either give it away or to make good on that return.” I don’t think that group two is like group three. Group three really wants the return, that’s what they’re in it for. Group two is like, “It’d be great if I could do something with this but if I do something that is good, I don’t have to get anything back, I just want to put good out in the world.” I don’t think hope is a strategy, I think we’ve heard that before, but I have hope in people and my hope is that there are more people who listen to this conversation, there are more people like you and there are more people that I can meet that want to do good and their return doesn’t always have to be monetary. Their return doesn’t have to be something that helps them continue to elevate their wealth and their power but their return is doing something good in the world. And maybe it’s a Saturday morning call. Maybe it’s not. Maybe it’s volunteering. Maybe it’s becoming a better parent. Because I have this acknowledgement and this awareness, now, the good that I’m going to get on the return is going to be hopefully tenfold but you might not be able to count it in my bank account. You might not be able to see it but you can feel it. And so that’s kind of how to answer that question and I just genuinely believe there’s so many more people that land in group two and I’m really excited to meet them, I’m really excited to engage with them, and I’m grateful that you invited me to this conversation. 


Billy: Yeah, that hit for me. That stuck. And so I appreciate that because I think that’s what I grapple with is the, “Well, how am I gonna make money on this?” that sort of thing, because I got to eat, but, man, it feels good to help other people. 


Jesse: Exactly. 


Billy: So, good will is not going to put a roof over my head but maybe it will, you know what I mean? So I appreciate you framing it like that and that really helps me move forward with some bigger ideas that I have that are intrinsic in nature that it would be great if there was a paycheck tied to those things but maybe that’s what comes on down the road. Maybe that’s the karma that gets paid on down the road or one good deed returns another, something along those lines. So, I like that answer a lot. I appreciate that. And, Jesse, I want you to continue putting good out into the world and I want to invite all of our listeners to join these conversations. You can sign up for these. If you go to Jesse’s Instagram, it’s @mrjross, and then there’s a link right there that you can join these conversations, he’ll send you an email and you’ll get information about when to join those conversations, you’ll get the calls to action. You can also go to Again, we’ll link that in the show notes if you want more information about Jesse and what he has to offer. Maybe you want him to come and do a training or a workshop or an evaluation or an assessment or a strategy development. Jesse’s your man. I strongly recommend it. I strongly recommend joining those conversations. Jesse, I know you got to get going but I want to thank you for your time.


Jesse: Thank you so much. I’m grateful and I hope everyone, man, finds themselves in one of those buckets. So, thank you so much for inviting me.


Billy: Absolutely. So, for Jesse, for Brian, this is Billy, thank you for listening to The Mindful Midlife Crisis, and may you feel happy, healthy, and loved. Take care, friends.


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