EP 60: Enneagram, Anti-racism, and Resilience with Jessica Dickson

Uncategorized Sep 02, 2022


We often look at the results of quizzes and personality assessments for language to help describe ourselves to others. And to better understand ourselves. 

These assessments can help us manage how we hire, date, and even want others perceive us. 

The language of these tests can fuel connection and belonging within and with others–to an extent.

But it can also be used to sort, judge, or even shame aspects of another’s personality. These assessments can be used to silo an aspect of how people show up or experience the world, into something that becomes polarizing or seen as “good” or “bad.”

We react to judgments of a trait in someone else instead of being present to someone’s full identity.

Yet, used with self-reflection and curiosity, assessment systems like the Enneagram can further a deeper understanding of ourselves, so we can in turn lead ourselves and others from a place of health.

My guest today is shaking things up around how we experience and use the Enneagram. And I am loving how she integrates the Enneagram into her anti-racism work and writings.

Jessica Denise Dickson (she/her/hers) is a life empowerment coach who believes that when Black women heal, the world heals. She believes that the path to personal and collective healing comes through examining the systemic issues that impact each of us, and unraveling oppressive systems from our personal, internalized, and collective worldviews. She utilizes the inner work of the Enneagram with the context setting of antiracism to create healing environments for her clients in one-on-one work, group work, and with organizations so that every human can live more authentically with self-trust, self-safety, and fully embodied freedom that is collectively sustained and celebrated.


 Listen to the full episode to hear:

  • How shame, fear, and scarcity lay the foundation for the culture of whiteness and how it impacts how white people engage with anti-racism work
  • How systems like the Enneagram give us language to describe and understand our experiences
  • How the Enneagram helps us understand our motivations and reactivity, so that we can approach growth and expansion with more self-awareness
  • Why the goal of Enneagram work is not to overcome your type or exile your reactivity
  • How embodiment builds resilience and connection

Learn more about Jessica Dickson:

Learn more about Rebecca:


Scroll Down for The Full Episode Transcript:

Jessica Dickson: What I really believe the Enneagram gives us access to is self-awareness, and what self-awareness gives us access to is the impact of our type on us and how it shows up and how it means that we live in the world, how we interact with people, how we do our work, how we do relationships. 

[Inspirational Intro Music]

Rebecca Ching: I love a good quiz or personality assessment. I suspect I’m not alone. [Laughs] I remember taking quizzes and silly assessments earlier in my life, often found in the magazines read, helping me find out where I’d landed with the latest assessed pop-culture trends and, of course, all things relationships like who I should date, and what kind of partner I prefer, all of which were [Laughs] (and continue to be) deeply problematic, and yet, y’all, still so enticing, right? Remember those BuzzFeed quizzes that were shared on repeat on Facebook not too long ago? They were fun until they found out how they used our personal data. Yeah, right. Yikes. Big time yikes. 

Now, we often look at the results of quizzes and personality assessments for language to help describe ourselves to others and to better understand ourselves. These assessments can help us manage how we hire and date and even want others to perceive us. I also see how the language of these tests fuel connection and belonging within and with others, to an extent, but I also see how some use them to sort, to judge, even shame aspects of another's personality. Y’all, I’m still weary of sharing my extroversion (hat to Myers-Briggs) or my Enneagram type as I’ve experienced people responding to my, quote, type in ways that shut down conversations and leave me feeling defensive and misunderstood. I suspect you might relate -- or I’ve experienced people who silo one aspect of how someone shows up or experiences the world and something that becomes polarizing or seen as either good or bad.


Now, I confess, I’ve done the same thing to others at times - reacting to an inner judgment of a trait in someone else instead of being present to someone’s full identity. I also see how the language that’s supposed to connect and normalize can do harm when it’s used without self-reflection or curiosity.

I'm Rebecca Ching, and you're listening to The Unburdened Leader, the show that goes deep with leaders whose burdens have inspired their life's work.  Our goal is to learn how they’ve addressed these burdens, how they rise from them and become better and more impactful leaders of themselves and others.

We all have questions about ourselves and others, so it’s no wonder that we seek tools to find some answers. Now, I remember when I first took the Myers-Briggs assessment back in college. During a resident assistant training, I had the opportunity to take this assessment, and it was a powerful and enlightening tool. I still appreciate it. I even took it again years later at another training, and it came out with nearly identical results. You know, this test helped me understand how I recharge and why others recharge differently and why I connect with people the way I do and why I’m drawn to do and learn what I do.

Now, I know lots of folks swear by StrengthFinders. This one left me wanting. Now, Strengths-lovers out there, don't hate on me. [Laughs] My colleagues who love the StrengthFinders assessments say my lukewarm response results from not having a good StrengthFinders consultant to help me understand how my individuation and my woo and input make me, well, me.


Eh, maybe. There are a handful of other assessments that are well-used, especially in the business space, like The DiSC and Hogan, but one that has really challenged, intrigued, and even transformed me is the Enneagram. Now, several years ago, a colleague lent me her copy of Richard Rohr’s book on the Enneagram. She put it in my hand and said, “You have to read this. It is gonna change your life,” and she is far from one for hyperbole, so I listened and read this book. Rohr’s look at The Enneagram was from a faith perspective, and I was really intrigued by the holistic approach to understanding ourselves and others. 

Now, there are many layers of The Enneagram that left me, honestly, a bit overwhelmed initially and not clear on how to integrate all of this information. Then, I took my assessment and subsequently dug in to learn more about my type. Oof, [Laughs] my initial thoughts left me wondering if The Enneagram should be dubbed “how to feel shitty about yourself.” [Laughs] Wise and seasoned Enneagram experts subsequently walked me through the layers of my assessment results and reframed my initial responses to learning about the core motivators of my type, as well indicative of my type. Fitting, right? I value how systems like The Enneagram can further a deeper understanding of ourselves so we can, in turn, lead ourselves and others from a place of health.

Now, my guest today is shaking things up around how we experience and use The Enneagram, and I am loving how she integrates The Enneagram into her anti-racism work and writings.


Jessica Denise Dickson is a Life Empowerment Coach who believes that when Black women heal, the world heals. She believes the path to personal and collective healing comes through examining the systemic issues that impact each of us in unraveling oppressive systems from our personal, internalized, and collective worldviews. She utilizes the inner work of The Enneagram within the context setting of anti-racism to create healing environments for her clients in one-on-one work, group work, and with organizations so that every human can live more authentically with self-trust, self-safety, and fully-embodied freedom that is collectively sustained and celebrated. Sounds awesome, right?

Now, pay attention to what Jessica loves most about The Enneagram (hint: it’s what many of us love about it, too), and listen for Jessica unpacking her Enneagram type and her take on how to go about learning about your type and what to caution against, and notice Jessica’s pushback in using The Enneagram as a tool to restrict or exile parts of you that you don't like, especially when doing anti-racism work. 

All right, everyone, now, please welcome Jessica Dickson to The Unburdened Leader podcast.

Jessica, welcome!

Jessica Dickson: Oh, thanks for having me. I’m excited to be here as well. 

Rebecca Ching: We are gonna cover a lot of territory, and I want to start off with just at the time of this recording there’s a lot going on in the world, on top of just a lot going on in our own lives, and the commitment to care and to keep caring is both brave and hard work especially right now. I’d love for you to share about a time -- tell me about a time when your capacity to care was threatened.


What was going through your mind at that time and how did you shift out of that response to protect from the pain of caring?

Jessica Dickson: This question, I love! It feels big in my system. Like, it lands as a big question because I’m not sure that I’ve ever truly had the privilege to check out, and so, when you ask that, I’m like have I ever been able to check out enough to have to pull myself back? I’m not sure that I ever truly have. There have been times when things have felt hopeless and it’s hard to act, but I’m not sure I have an answer to that question.

Rebecca Ching: Yeah, but can you tell me a little bit more about not being able to have the privilege to check out?

Jessica Dickson: So, for those of you who don't know, I identify as a Black woman. My pronouns are She/Her/Hers. I’m descended from the enslaved on both sides of my family, and, historically and presently, the need to always be aware -- if I am not aware and acting for my safety and for the safety of other people like me, who really will?

Rebecca Ching: Mm. 

Jessica Dickson: And so, I have this experience of needing to be aware because I need to know how to protect myself. I need to know what are the threats to my safety, and so, the thought of -- yeah, sometimes capacity to care is low, but it’s never been an option to check out. 

Rebecca Ching: Mm, thank you for that


How do you respond when your capacity to care is low? What’s going on? What’s going on around you? What is draining you when your capacity to care gets to be that low?

Jessica Dickson: Yeah, I think when it’s really low, for me, when it feels like that hopeless place where I’m like does any of this really matter, I think, for me, what’s happening often is a lot of whiteness at play, and when I refer to whiteness, I’m referring to the construct of whiteness as created. So, race as we know it, before the days of slavery, was different, and it changed around that time and whiteness was created as this construct and whiteness controls and dehumanizes. And so, when it feels like there is a lot of dehumanization and when it feels like there is no space to be fully human because of the violence that comes from whiteness, that’s when it’s the hardest for me because I’m like should I even leave my house? Should I even -- how do I move forward even in anti-racism work? What does that look like for me? Do I have, really, the capacity to hold all that needs to be held for the white people that I’m working with to do the work. Sometimes when it feels really hopeless, that gets hard.

Now, when I get with my clients and we’re having these conversations, that falls away. People are doing real, deep work (ancestral work) and reconciling with the violence of their ancestors and healing work and nervous system work and re-embodying their worlds, shifting the culture that they live in, in big ways.


And so, I’ve become present to that. I’ve become present to there are people in the world who care and who are doing the work that is necessary for us to really move forward with more collective healing, and so, I show up, and they show up, and then I remember. I remember why I’m doing it all ‘cause I see how big of a change that can happen in someone’s life through the work. 

Rebecca Ching: And that’s some meaningful work, and when there’s meaning, there’s rejuvenation, there’s clarity, there’s energy there.

Jessica Dickson: Yeah.

Rebecca Ching: Thank you for sharing that. Thank you for sharing that. I do want to just have a quick aside on whiteness, the system of whiteness. If you can just briefly -- ‘cause I’ve been working on identifying that in myself. I bring that up a lot to my clients (this system of whiteness) but, still, for those in white bodies or white-identifying bodies it can feel nebulous and feel like, “What does that mean? I’m white so am I bad?” There’s some defensiveness --

Jessica Dickson: Yeah.

Rebecca Ching: -- or confusion that can come up. So I’m wondering if you could just speak on a high level about the system of whiteness and how it impacts all of us. 

Jessica Dickson: I love this question ‘cause it’s so important because one of the first things, when I’m doing work with white people, that I talk about is  the culture and the system of whiteness, and the specific characteristics that are part of it because it can be really hard to see them when you're in it. It’s, like, the air you breathe, you know?


It’s just the way things are because it’s baked into the systems. It’s baked into our entertainment. It’s baked into how we think of experts and what podcasts we listen to and all of the things that drive our daily lives. It is just a part of it. It’s part of professionalism and those ideals, where we live, where we send our kids to school and why. It is the context of the world that we live in. And so, I’d like to break down what is culture ‘cause I refer to it as a culture of whiteness that was created, and there are specific things that go along with the culture like norms of how to speak, how to relate to family, how to relate to other people, how to relate to authority, shared history about historical events and beliefs about that and assumptions, stereotypes. 

So there are a lot of things that are part of a culture, and as we think about whiteness as a culture, there are characteristics. So I talk about the foundations of that culture having kind of some emotional roots. Shame - where shame is utilized as a weapon, it is wielded to control. I talk about denial where when bumping up against things that are hard, that defense of denial just pops up, minimizes, and invalidates other people’s experiences. I talk about fear wielded also as part of this system of whiteness where people who don't have power have to fear people in power. The people in power are afraid that those who don't have it are going to ban together and rise against them, that we have to fear each other. So that creates more disconnection.


So those are kind of some of the foundations along with scarcity (that there’s not enough). There’s not enough power to go around. There’s not enough. There’s not enough. You're not enough. I’m not enough, and so, those are kind of the foundational things that I talk about, but then also there are other characteristics like perfectionism where your mistakes are seen as personal failings or inadequacies. They’re not seen as a human thing, as it’s a human thing to make mistakes. No, no, no. We see things like individualism where this is often why white people don't feel like they're part of a culture. Everyone else is, but white people are individuals, and that’s because of this culture of whiteness that values that.

There are other things like an aversion to conflict and defensiveness. So when tense things happen, it usually is put back on the person who brought it up, and so, therefore, it is really hard to have forward motion or talk about some of the hard things and, specifically, maybe that person’s role in perpetuating the hard things or complicity with the hard things because then the person who brought it up is the problem.

Rebecca Ching: Mm.

Jessica Dickson: Because, often, the white-bodied person does not, in your nervous system, have a difference between uncomfortable and unsafe, and challenges have -- the nervous system of the white-bodied person is conditioned to see any kind of challenge as unsafe when, really, it might just be uncomfortable, and maybe the thing that’s being challenged is not your actual safety but your privilege. But sometimes, when people have clung so much to this culture and construct and system of whiteness, they don't know that decentering whiteness is not the same as making themselves smaller, that you actually get to experience more of yourself when you decenter whiteness because whiteness makes all of us smaller.


And so, we have to look at where have I actually taken on whiteness as me, and how can I, then, let that go to actually allow who I really am to arise and be expressed in the world.  

Rebecca Ching: Thank you. So shame, denial, defensiveness, disconnection, scarcity (just to name a few) are really big components of this system, and that can bring up a lot of emotions, physically, in our body and, emotionally, with what we feel. With all this said, when life and work feel so overwhelming and we’re disoriented, right? Discomfort and unsafe -- we have a discomfort problem, particularly those in white bodies for sure. How can we be the best stewards of our emotions without doing harm to ourselves and others?

Jessica Dickson: I like to say to my clients that shame is just an emotion. It’s something to move through, not something to become. Because it’s wielded in white supremacy, people take on shame like it is who they are. Like, they are shameful, they should be ashamed, they should be ashamed for challenging, they should be ashamed for their racism, they should be ashamed for all these things, and my encouragement is that when you start to see shame, not as white supremacy holds it and wields it, but as an emotion to move through, it helps you around your capacity to move through it.


So when you have the capacity to move through it, you don't get stuck in it. You don't get stuck making it about you, and that is something that really opens up a lot of space because when you can say, “Oh, okay, so I’m human, and humans make mistakes, and I’ve been conditioned with these racist ideologies that I didn't even realize were racist, and, okay, I feel shame about that,” that is such a good thing to feel ‘cause it means that you're human. It very much means you're human.

Now, in our society, we do not have the skill to move through shame, and so, my advice is to really hold yourself. So when I’m working with clients, we do a lot around the nervous system, a lot around reactivity in our nervous systems and what does it all mean. I think there’s this idea -- trauma is, like, really having a comeback, right? [Laughs] Everyone’s talking about trauma which is really, really good, but I think that we need to bring a lot more nuance to the conversation. Now, because the white-bodied person, often, is conditioned to have a trauma response when privilege is challenged, and when the white-bodied person starts to do work around the nervous system and say, “Oh, no, no, no. I actually am safe. I look behind me. No tiger’s chasing me. No one’s gonna take away my home for doing anti-racism. The level of safety that I have actually is very secure,” then I can start to look at these things and not internalize that shame.


Rebecca Ching: You have an interesting take on shame, and I think this is an important one where we often don't want to recognize our shame, but it’s a part of the spectrum of human emotions, right? And so, by acknowledging it and recognizing it and starting to build -- like you said, we struggle with how to deal with it as a culture, yes. Shame resilience is not easily accessible for a lot, but I appreciate that piece to say, “Whoa.” This piece that says, “I’m terrible. I’m horrible. Who do you think you are?” Wow, okay, that’s one of these, but if we lead from that or just try and stuff it and deny it, it has so much power over us, but normalizing its presence gives us a chance to respond to it differently and lead it differently. So I really, really appreciate that take. 

How do you navigate your own personal growth and healing and move from, kind of, insight, like, figure out all these things about me, to then taking it to impactful action? 

Jessica Dickson: So one of the things I’m committed to as a coach (I consider myself a healer) is to always be doing my work, and I don't think that we always have to be looking for our work. I think that, often, our work just shows up right in front of us, and we can choose to turn a blind eye to it or we can step into it and move into this next level of our humanity. For me, that’s always happening. That is always happening. 

One of the things that I love about The Enneagram is that it gives us language.


It gives us language where we may not have had language to understand our own experience, and so, I lead with the Type Eight on The Enneagram, and, you know, that comes with its own stuff. It comes with a hardened heart or feeling like -- not even a hardened heart, but needing a lot of protection around my heart. It comes with a lot of, “Can I trust you to not betray me before I open myself up?” It comes with just so much, so much, so much, so much, so much. [Laughs] 

Rebecca Ching: My system appreciates Eights because there’s no bullshit. It’s just, “Here it is. Let’s do the thing,” and that cultivates safety for me. So I just appreciate that, and I feel like I’ve read that Eights are one of the more rare types, but I also have heard folks kind of give, “Oh, Eight,” like they're scared of Eights. I’m like, no, Eights are my people. I just know where they stand. If we want to go and get something done, I want to be with an Eight. 

You integrate your teachings on The Enneagram with your anti-racism work. I’d love for you to tell me about the time when you started to connect the dots between the two.

Jessica Dickson: Yeah, well, first, I want to say a little bit about The Eight.

Rebecca Ching: Okay.

Jessica Dickson: And some people do say that it’s the rarest type, and there is not real data. There’s no real data for that. So you can maybe -- some people say Four is the rarest, and some people say Eight is the rarest, and it’s like, okay, you know? [Laughs]

Rebecca Ching: Doesn't matter.

Jessica Dickson: Who really knows, and it doesn't really matter. [Laughs] So I learned about The Enneagram in 2013.


I had just been promoted, and I used to work in higher education so that’s my background. I worked in residence life. I worked on college campuses. So I had just been promoted, and I was looking for a new professional development tool, and Google brought me to a PDF about the types, and it was incredible. It was incredible. I was like, whoa, if this doesn't blow smoke up your you-know-what, this is legitimate. This is the stuff. This is it, and I started doing professional development with my staff members, but the thing about that is Enneagram work was always a part of this journey of understanding who we are through our identities and through privilege and through these things, and so, for me, it’s never been disconnected. When I’ve spoken -- when I’ve done Enneagram work, you know, there’s always the conversation of, like, “Well, this is the conditioning that I hear from my mom. I can't tell if that’s me or if that’s her voice in my head,” and then we get to say, “Okay, well, what about --,” and then we say, “Well, the culture that I come from bypasses hard things and goes to joy, so I can’t tell if I’m actually a seven or if that’s just the culture that I’m in and it’s now a pattern that I have in my life.

Rebecca Ching: Before you went too deep on this, I wanted just to backtrack and say Enneagram is a way to understand ourselves through these types of -- how would -- what’s this one or two sentence descriptor of The Enneagram that you offer folks?  

Jessica Dickson: So The Enneagram is a personality-typing system that helps us really understand, beneath all that we do and how we show up in the world, what we are motivated by.


So, there are two main components broken down into smaller ones of our Enneagram type. The first one is our motivations - that’s core fears, core desires, core drives of the type, focus of attention. Then, we have the type’s reactivity, and that is in the form of the passion which is the emotional reactivity. We have the mental reactivity of the fixation, and then we have the defense mechanism of the type. Those are the basic make-ups of the type.

Now, when people are learning about their type, often, they're reading a book or listening to a podcast so they're listening to descriptions. Those can be helpful for us to find our type, but descriptions are not always prescriptive which means that I can listen to someone talk about their experience of being that type, and it’s not necessarily my experience of being that type, and it took me two years to find my way to the Type Eight for that reason because many of the descriptions that I read sounded like these wealthy white men, and I’m like that does -- I did not find my -- I could feel the energy, but I didn't find myself in those descriptions. I’m like this is some white male foolishness that I could never get away with. That’s just not a thing. It’s not a thing for me. So, yeah, that’s kind of the basic overview of it.

So the way that we understand our type is shaped by so many things.

Rebecca Ching: Just pulling back a little bit in general on change -- like, we’re always wanting to change and better ourselves, in your work, what are some common misconceptions that you see on repeat about how we can change or what we need to change to be better leaders and better humans?


Jessica Dickson: Yeah, so I think in The Enneagram world, there is this sense that I have to overcome my Enneagram type, and I don't really believe that. Someone said that they were transcending their type, and I’m like did you die? So our Enneagram type is part of our ego structure, and our ego structure is a very necessary part of our humanity. No one’s walking around without an ego structure. We all have one. It’s a necessary part of who we are. So our type is not necessarily something to transcend or overcome. People are like, “Diagnose me!” I’m like, “What? What are you asking me to do right now? I don't even understand that request. Like, can you please stop?” [Laughs] I think that there’s that idea, but what I really believe the Enneagram gives us access to is self-awareness, and what self-awareness gives us access to is the impact of our type on us and how it shows up and how it means that we live in the world, how we interact with people, how we do our work, how we do relationships. The work is not to obliterate it or destroy the ego; it is to expand. It is to understand this is my default way of showing up in the world, and it’s important for me that I have different ways of showing up, that I can expand beyond this because The Enneagram -- I talked about motivations and reactivity. That reactivity is the protection that our type has for us, and so, when we work through and we look at why don't I feel protected, what are some things that I can do, actually, to sure up my protection by the things that I can do internally but also things that I can ask of the people in my life, boundaries I could set with the people in my life?


And so, when we’re not as protected, we have the opportunity to expand, and I think that we also have the opportunity to say, “Oh, no, no. I need this protection ‘cause I don't live in a world where it’s fully safe to be me all the time. So sometimes, for people of color, when they walk into white Enneagram spaces and everyone’s like, “Just be vulnerable. Let down your armor,” it’s like, [Laughs] “Um, you have not provided any sense of safety,” and then white people often don't like that feedback, and so, then it creates an adversarial kind of experience and ends up usually being harmful for the person of color. So that’s one misconception.

Another misconception I’ll talk about in anti-racism work is that everything has to happen now. Part of the culture of white supremacy that I didn't talk about is urgency. I call it white urgency because this form of urgency is very specific, and it often makes things that maybe need to be dealt with into emergencies, and this has to do with being disembodied often, you know, not really being connected with our own. So it’s like I’m not connected with the reactivity that’s happening in my body. I’m having a flee response or I’m having a fight response, and instead of actually tending to that, I’m gonna go into doing or I’m gonna go into shutting down a conversation.


You know, white men tend to do this a little bit differently because their most important thing about men -- they’ve been conditioned to believe the most important thing about them is their intellect.

So, for them, it turns into having a healthy debate even though it’s not usually healthy, but debating turns into them shutting down conversation because, “You're not answering the question that I asked.” It’s like, “You just asked a hypothetical question. You didn't ask a real question. Like, ask a real question, then we’ll have a real conversation.” There’s a need for white people to be embodied to understand, “Oh, I’m having a trauma response right now. What’s happening with me? Why am I having it? Why is it fueling this sense of urgency?” Then, to slow down because change is something that happens over time. Change happens more naturally as we embody our Enneagram work, as we embody our anti-racism work, and so, it’s important to slow down. 

Rebecca Ching: You got it, Jessica. Yeah, I have a lens -- I don't know if you've heard of Internal Family Systems, and there’s a big overlap with the language that you're talking about that resonates with me, and we can't think through this stuff. We have to feel through it, and that is a scary invitation but an essential one. 

How do you move from exiling the parts of you that you don't like and the world doesn't like to befriending them because I think that is so key, and I’m curious how you navigate that. When there’s a part of you that comes up and you know because of your type or you know your system, and you're like urgh, how do you move through the default to want to exile it, transcend it, whatever the language may be --

Jessica Dickson: Right. [Laughs]

Rebecca Ching: -- or when you feel the world’s rejecting something of you, what’s your practice around befriending these parts that are so easily rejected and hated by self and others?


Jessica Dickson: Well, I’m very much a we celebrate our reactivity. So hear me out [Laughs] when I say this. We’re not necessarily celebrating the reactivity, but we’re celebrating that we’re present enough to ourselves to notice the reactivity. Some things that are just part of our humanity have been demonized. One of my clients was kind of upset that they were kind of moving into emotion and moving out, and they were moving into an emotion and moving out. I’m like I know that you want to stay in it, but that’s actually healthy for your system. Your system is saying it’s too much, and it’s giving you the space to take a step in and to take a step back so that you can do that in a way that’s safe and does not overwhelm your nervous system. This is really, really a beautiful thing. So, for me, what I encourage and what I do myself is to really look at, all right, what is the -- usually, for me, it’s a shame response around not being strong enough. I didn't prove that I was strong enough or I showed some kind of vulnerability, and I would rather be invulnerable to everyone in the world including myself, and so, when a shame response comes up, what I do is I like to look at what is this thing and what is it protecting and how can I thank it. How can I be grateful for it? How can I say, “You know what, shame, you came up because you thought that that would make me unsafe. You thought me being vulnerable in this way was actually making it so that I would not be able to protect myself, and so you wanted to shut that down, and so, then, I had this reaction.” For me, it’s a lot of dialogue, a lot of holding myself (holding my body, literally) and having that dialogue and reminding these parts of myself, “No, no, no. I’m not unsafe.”


Rebecca Ching: Oof. 

Jessica Dickson: “I want to thank you. I want to thank you so much, so much for your concern because you were really worried about me, but I want you to know that we’re safe, that I’m safe and we are safe right now, and that it’s a little bit uncomfortable right now.” And so, for me, I lead with gratitude. I don't do IFS work, but I do talk about it in terms of these parts of ourselves so that we can just maybe relax a little bit, you know?

Rebecca Ching: That’s beautiful.

Jessica Dickson: “Thank you for doing such a great job. You have been so amazing at protecting me, and I’m actually safe.”

So, then, the next question is what are the things that I need to integrate so that I can have the feeling of safety?

Rebecca Ching: Mm. 

Jessica Dickson: We can know, intellectually, that we’re safe, but if there’s also still a sense in our body that we’re not, it’s gonna be hard to move forward. So it’s safe to honor this part so we can move forward. It’s safe to own it. It’s safe to love this part. It’s safe to do whatever, and so, what then do I need? Do I need to go to the ocean and put my feet in the sand? Do I need someone to come over and hug me for a few minutes and just hold me? What is it that will help me embody the safety that I know is present but my body, my embodied experience, hasn’t quite caught up with. Our minds work a lot faster than our nervous systems.


Rebecca Ching: Lightning fast. I love that, and, you know, this really comes down to we need to -- well, the answer is not going in and just working harder.

Jessica Dickson: Yeah. 

Rebecca Ching: The answer isn't numbing out whether it’s, you know, the common go-to drugs, alcohol, comforting with food, sex, gossip, spending. This is not something to work through. It’s about saying, “I need something, and it’s okay to need. I need connection. I need to get away from my workspace.” You and I live in San Diego, so we’re fortunate to be able to say, “Go in the ocean,” and, “Get to the ocean.”

Jessica Dickson: Yeah. [Laughs]

Rebecca Ching: You know, but whatever that might just be, and that’s not the cure, it’s the moment.

Jessica Dickson: Right.

Rebecca Ching: It’s the moment, and it’s the practices of needing, and that individualism that you touched on. I’m really focusing on this lately and realizing this is probably my biggest growth edge and my default is that it’s almost a flaw to not push through and suck it up, chip up, boost straps in, and recognizing -- I’m from Minnesota, so, I mean, we brag about shoveling snow in below-zero weather. I mean, that’s like a badge of honor. Walking to school -- I mean, I have the stories for real, you know? Walking to school in the snow.

Jessica Dickson: I’m from Michigan, so… [Laughs]

Rebecca Ching: So you get it! You get it.

Jessica Dickson: [Laughs]

Rebecca Ching: And so, I can hear some people listening to you like, “I need to reach out to a friend, I need to go get outside, get near the water, in the water.” Like, oh, Rebecca, no, because along with urgency is (it’s the BFF of) efficiency. It doesn't feel efficient. “I want to just get this done. That feels too slow or that’s needy. I’m uncomfortable with needing. I got this. I don't need,” but, eventually, our bodies are the wisest parts of us. They shut us down, and so, I just really appreciate -- ‘cause this message needs to be heard, again, from many different directions that this is resilience.


It’s connection to ourselves, connection to others. It’s to be embodied. It’s connecting that just through our intellect or to the world around us.

Jessica Dickson: Yeah.

Rebecca Ching: So thank you. 

Jessica Dickson: Well, one thing you said is it’s not a cure, and nothing is ‘cause there’s nothing wrong with us being human. You know, some people come to The Enneagram 'cause they want to fix themselves. Some people come to anti-racism because they want to fix, and when we go into fixing, it often can be something that creates more harm. You know, when we do our Enneagram work from a place where I have to fix myself, when we see ourselves as broken, then, that’s when we feel like we have to transcend or we have to, you know -- no, no, no. There is an embracing. There is an expansion that comes from anti-racism work. The expansion that says, oh, that whiteness has been the default context, that white people have privilege because of this default context, and we want to actually just expand -- there are some things that we’re gonna have to dismantle, but we want to expand so that there’s equity for more people, you know, so that more people have opportunities. It’s not a collapse; it’s an expansion. It’s not a collapse. It’s not an implosion; it's that everyone gets to take up more space and experience abundance. 

Rebecca Ching: Yes or what I would say is enough-ness. [Laughs] It’s just enough-ness.

Jessica Dickson: Yeah. 

Rebecca Ching: That expansion piece instead of fixing, right? That really is about expanding. I’m curious. How has befriending these parts of you that aren’t pleasant or the world doesn't experience pleasant -- how has befriending these parts helped you become a better leader of yourself and others?


Jessica Dickson: Yeah, well, it helps me be able to hold other people when their parts that are similar come up, ‘cause it’s like, oh, no, no, no. I know that! I know that when it’s saying that to me it’s a whole liar. [Laughs] So I know that when it’s coming up for you, it is lying too. I don't mean that in the real way. I mean, I really do think that these parts come up because they are trying to protect us, but they don't have all of the context, so they’re not intentionally lying. They're deceptive because they don't have everything that they need.

Rebecca Ching: They don't have all the information. 

Jessica Dickson: But we have the opportunity to give ourselves that information. So I really find my leadership style to be helping people see themselves with more clarity so that they can actually step up into their own leadership, and so, I’m really about holding this space for people and their becoming and their unbecoming.

Rebecca Ching: And their unbecoming, oh, my gosh, yes. For those of you listening, I was, like, fist-pumping the air, jumping up out of my seat just now because you said something I think that is ground zero, that if we’re befriending the parts that we don't like about ourselves or the world’s rejected in us, if we don’t be friend that, we can’t sit with others when they're in that, and there’s no vulnerability. There’s no connection. There’s no trust built, then, but if we can sit with the ish in us, then we can sit with the ish in others, and there’s where relationships happen, and where there are relationships, that’s where change can happen.

Jessica Dickson: After George Floyd was murdered, God told me to put on this Disrupt The Narrative program (my first program), and I didn't really want to, but I listened. So [Laughs] I listened, and I’m really grateful that I did.


One of the things that I really, really got clear about is that we cannot move forward if people are disembodied, and you cannot truly say, “Black Lives Matter,” if you hate your body, if you're self-loathing, if you're always in comparison with other people, if you don't have -- maybe you're not part of the body positivity or body love, but if you don't have some kind of body loyalty, body respect, body honor -- and so, it is especially important for white people to be able to do that because whiteness would have you rather be disembodied. Because if you're disembodied, then you can be disconnected from the harm that comes to other bodies, but when you're actually in your body and you see someone else being harmed, oh, it connects you in a very different way because when you're in your body, you are much more present to how you are connected to every other body.

Rebecca Ching: And that’s painful.

Jessica Dickson: Yeah, and that’s what we’re meant to be. We’re meant to be in that delicious, painful, heart-breaking but also healing connection with one another. That’s what we’re made for, and so, embodiment is so crucial. It is so crucial.

Rebecca Ching: If we’re not embodied, we’re not safe to self and others, right?

Jessica Dickson: Correct. Yeah.

Rebecca Ching: That’s what I’m taking away from this kind of connection with this conversation -- which I’m givingly language to that. So on that note, how can we -- and I guess, specifically, I know you work a lot with those in white bodies -- how can we be more effective (the “we” meaning the white bodies, just to be clear) in cultivating safety in the spaces where we work and where we lead?


Jessica Dickson: Mm, I love this question. I created a workshop series because I’m like we need to be having these conversations a little bit more. So I think that we need to -- there needs to be a bigger conversation around defining what safety actually is. I think that white people need to have an understanding of -- you know, if you're really gonna consider yourself a leader, you need to have an idea of what systemic oppression is and how it actually impacts people and the ways that it lives, not just in the experiences of people of color, people with marginalized identities, people who have disabilities, or trans folks, but it lives in the systems. It lives in redlining. It lives in laws. It lives. It has real roots in the society, and so, white leaders need to understand that and not just see it as an interpersonal thing ‘cause, often, it can get caught up there. People are like, “Well, slavery was a long time ago so --,” well, you know, the systems that come along from that time are still functioning in all their glory in 2022. And so, if there’s not an understanding of that, what it’s going to do is not make you a safe person to be able to talk about all my stuff with because if you're not gonna be able to see, you're gonna think that my issue is something having to do with me like a mindset issue or a simple issue with my Enneagram type or whatever you utilize in your leadership, but it’s not always.


Mindset stuff with people of color - maybe it’s mindset, maybe it’s systemic oppression, and so, if white leaders aren’t really present to that, if they don't understand how that functions, then they aren’t going to be able to speak to that which leads, often, to really kind of a lot of gaslighting where what happens is I’m talking about something, I’m hoping to get support about something, and you're saying that it’s about me. When it really might be that there was some systemic racism -- there were microaggressions that were happening, you know? It wasn't actually just me, and so, we need people who are gonna be able to speak to that and to be able to hold it when we speak to it. You know, I’ve had people -- 

Rebecca Ching: Ah. 

Jessica Dickson: That’s been my experience, you know? I’ll speak to it, and then if the leader can’t hold it, then I’m left feeling alone. I’m left feeling invisible, and I think that most people who are committed to their leadership don't want to leave people feeling that way. 

Rebecca Ching: No. 

Jessica Dickson: But it takes work, it takes learning, and it takes your own embodiment to be able to do that, and it is worthy work. It is worthy work. 

Rebecca Ching: One hundred percent. So, as we grow in how we lead ourselves and others, how can understanding what drives us be a true tool for not just internal change but also systemic change?

Jessica Dickson: Yeah, so I like to think of those things that drive us -- I like to think of them as strengths that we have for ourselves but also gifts that we can give to other people. You know, I have a close Type Three friend, and the Type Three is the achiever, the star, and what she brings to me is an insight about how to talk about this thing that, to me, just seems very normal and very kind of mundane about maybe an aspect of my work, and, for her, because that’s her focus of attention, she’s able to pick out, edit, and help me expand the way that I’m even able to speak to some of my stuff.


As an Eight, there’s a focus that Eights have on power. You know, where’s the power in the room? Who’s holding it? Are they wielding it well? Is there a systemic power that is harming? There is this focus of attention, but one of the gifts that The Eight has is empowering others to arise in their own power, and so, I think that as we move forward, that becomes what we offer to the world in our personal life, in our anti-racism journeys. People who are committed to anti-racist practice, they're gonna bring all of those beautiful strengths that come with the type, and they're gonna be able to set the world on fire in a beautiful way by dismantling whiteness and allowing the true beauty and the true depth of their soul to come and be present and run in the world.

Rebecca Ching: To me, this is hope. It’s a hope, and how what makes the best of us is not just for us to hold onto, but it is even our mandate to give back to the world, not just for us to naval-gaze and to understand and strategize, but it’s like, okay, I get to know myself better, befriend, and lead myself better, and then I am in a position to share that with the world, and the excitement and the joy that you just shared that with just echoes in my system because that’s for the collective, right? That’s for the collective, and if we’re all showing up.

Jessica Dickson: Yeah


Rebecca Ching: So shifting back to safety, and even on this topic, then, tell me about a time when you felt safe to truly be yourself. What was happening that supported your system to show up authentically?

Jessica Dickson: I would say this happens the most with my friendships. There are people in my life who have made it through all of my [Laughs] I’m-gonna-put-a-toe-in-and-then-take-my-toe-out, all of the me testing the waters to see if they're gonna be able to hold me. It’s something that happens very automatically, but the people who have made it through, I have such a deep love and appreciation and gratitude for them because I would not be able to -- I wouldn't be who I am if it were not for the love that they give me when they see me, fully, when they see me in my humanity which, I will have to be honest, sometimes I’m like, “Who wants to be human? Can I go back to being some, like, robot who just gets things done and is killin’ it? Why do I have to feel these things?” They see me even in that, and they see the tenderness of my heart and in those places when I can just ball my eyes out and know that it doesn't change anyone’s feelings about me, you know? I feel like I’m always dodging people’s perceptions of me ‘cause I’m the strong one and what happens when I’m not? Do I get to not be? With them, I don't always have to be, and that is a complete gift to my soul. It’s an affirmation of my soul.


Rebecca Ching: I feel that.

Jessica Dickson: It’s not just a validation of my type but deep affirmation of who I truly am.

Rebecca Ching: So people who are there for the haul to let you take your time to warm up to trusting the relationship and then to be really seen and witnessed and still held.

Jessica Dickson: Yeah, it’s a beautiful thing.

Rebecca Ching: I love it. I’m curious, Jessica, is this work that you're doing right now what you thought you’d be doing today? 

Jessica Dickson: No, not at all. This isn't what I expected, but it has been beyond, beyond a gift to me. Even when I started my business -- I started my business, really, with the belief that when Black women heal, the world heals, and I believe that in the depths of me. I always knew diversity would be a part of the conversions that I’d have about The Enneagram ‘cause it always was. To me, it’s like what you talk about when you talk about The Enneagram. You’re not a disembodied type, so you would never just talk about your type. Yeah, it has been a gift. [Laughs]

Rebecca Ching: That’s beautiful. So I’d love to shift into some quick-fire questions as we wrap up.

Jessica Dickson: Oh, rock on.

Rebecca Ching: This has been a delight. Okay, so, Jessica, what are you reading right now?

Jessica Dickson: Hmm, am I reading anything right now? I would say the closest thing that would come to mind is All About Love by bell hooks ‘cause I’m running that book club soon.

Rebecca Ching: That book is a game-changer.

Jessica Dickson: It’s so good.

Rebecca Ching: I know anyone who reads it is shook permanently. What song are you playing on repeat?

Jessica Dickson: Ooh, I like this question. Do I even have a song right now? Really, right now, what’s on repeat is Hamilton. So you can almost pick any song, but “My Shot,” that’s my go-to Hamilton song. [Laughs]


Rebecca Ching: When I saw Hamilton, I literally had to hold my body in the chair ‘cause I wanted to stand up the whole time and just -- yes.

Jessica Dickson: Right? I cried so hard the first time I saw that musical. It’s powerful.

Rebecca Ching: Best TV show or movie you’ve seen recently?

Jessica Dickson: Everything Everywhere All at Once. It’s a movie about the multiverse. Just so everyone knows, I’m a crier. It’s a thing, and OMG. A third of the way into the movie or maybe two-thirds of the way into the movie, I’m just crying the whole rest of the movie. It is powerful. It is powerful in ways that I had no idea when I went in the first time, but it is excellent. 

Rebecca Ching: I keep hearing about this movie. I haven't seen it yet but I’ll get my Kleenex ready for when I do. [Laughs]

Jessica Dickson: Yeah.

Rebecca Ching: I can't wait. What is your favorite ‘80s movie or ‘80s piece of pop culture?

Jessica Dickson: I mean, can I say myself since I was born in 1985? Um… [Laughs]

Rebecca Ching: [Laughs] Fair enough. Fair enough. I’ll take it. I’ll take it.

Jessica Dickson: [Laughs]

Rebecca Ching: That’s a first, and I love it. I love it, Jessica. [Laughs]

Jessica Dickson: [Laughs]

Rebecca Ching: Oh, my gosh, we need a moment for this one. [Laughs]

Jessica Dickson: Oh, thank you for indulging me in that. [Laughs]

Rebecca Ching: What is your mantra right now, Jessica?

Jessica Dickson: The better it gets, the better it gets, the better it gets, the better it gets, the better it gets.


Rebecca Ching: Mm. What’s an unpopular opinion you hold?

Jessica Dickson: That white feminism is harmful.

Rebecca Ching: Mm. Who or what inspires you to be a better leader and human?

Jessica Dickson: The first thing that came to mind is the participants in my fitness classes. So I run my own business and I teach two different group fitness classes, and they come and they show up and they just inspire me every single time.

Rebecca Ching: Ah, I love it. Jessica, where can people find you?

Jessica Dickson: The best place is probably my Instagram. So that’s @jessicaddicksoncoaching or if you want my personal one where things are just a little bit more wild -- I mean, I’m pretty wild on my business one, but just a little bit more wild and more personal, it’s just @jessicaddickson. [Laughs] 

Rebecca Ching: Awesome. Jessica, this has really been a pleasure. I’m gonna be thinking about this conversation for a while, and I know anyone who listens to it will be doing the same, so I’m very grateful for your time today. I’m just grateful for how you show up in the world, and I appreciated getting to know you today. So thank you so much.

Jessica Dickson: Thank you so much. Thanks for having me! This has been just a really good conversation for me, and I’m just very grateful. 

Rebecca Ching: The next time you take a quiz or dive into a system like the Enneagram, I hope you see these assessments as tools as opposed to something to use to globally diagnose or perpetuate dogma. The seductive default to silo or other is a slippery slope from the important data you can glean about yourself and others when exploring personality assessments. Jessica reminded us today the power of nuance and seeing systems within systems as we explore better understanding ourselves and those around us with assessments like The Enneagram.


She also walked us through how The Enneagram can be a powerful tool to dismantle and unlearn as we take a long hard look within and better understand why we do what we do, especially when integrated with an anti-racist lens.

So I’m curious. How do you engage with assessments like The Enneagram? What are ways you can go back and dig deeper into the results and learn more about your motivations and responses to those around you? What practices can you put into place so you can use assessments for deepening understanding versus judging and demeaning? Now, while we enjoy assessments like The Enneagram, let’s make sure not to weaponize them or fall into reductive traps. Stay curious and connected to your inner system and to others, and remember the multitudes that make up you and those around you. This is the work of an Unburdened Leader.

[Inspirational Music]

Leading is hard, and leading is also, often, controversial as you navigate staying aligned to your values, your mission, your boundaries. Navigating the inevitable controversy can challenge your confidence and clarity and calm. Now, I know you don’t mind making the hard decisions, but sometimes the stakes seem higher and can bring up echoes of old doubts and insecurities during times when you need to feel rock solid on your plan and action. 

Finding a coach who gets the nuances of your business and leading in our complex and polarized world can help you identify the blocks that keep you playing at safe and small. Leading today is not a fancy title or fluffy bragging rights, it is brave and bold work to stay the course when the future is so unknown and the doubts and pains from the past keep showing up to shake things up. Internal emotional practices and systemic strategies are needed to keep the protector of cynicism at bay and foster a hope that is actionable and aligned. 

When the stakes are high and you don't want to lose focus, when you want to navigate inevitable conflict between your ears and with those you lead, when time is of the essence and you want to make hard decisions with confidence and clarity, then Unburdened Leader Coaching is for you and where you deepen the capacity to tolerate the vulnerability of change, innovation, and doing things differently than the status quo.

To start your Unburdened Leader Coaching process with me go to www.rebeccaching.com and book a free connection call. I can’t wait to hear from you!

Thank you so much for joining me on this episode of The Unburdened Leader. You can find this episode, sign up for the free Unburdened weekly email, find the show notes and other Unburdened Leader resources, along with ways to work with me, at www.rebeccaching.com.


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