Managing Career Transitions Part 1: Facing Childhood Demons

Talking about Self-Awareness and Anxiety (with Hello Monday’s Jessi Hempel)

MORRA AARONS-MELE: I’m Morra Aarons-Mele, and this is The Anxious Achiever. Each episode, we look at stories from business leaders who have dealt with anxiety, depression, or other mental health challenges, how they fell down, how they pick themselves up, and how they hope workplaces can change in the future. For the next two episodes, we’re going to focus on managing anxiety through career transitions, whether it means quitting, getting fired, getting promoted, or leaving a job you love because it’s time.

MORRA AARONS-MELE: That means looking at the tough work you should do before the big transition. The hard art of learning to understand your feelings, because doing that will help you manage through whatever transition comes your way. More on taking time off work next week, when we speak to Alyssa Mastromonaco, who was a veteran of the Obama administration. First, this week, we have Jerry Colonna who is a sort of legendary CEO coach, a former venture capitalist, and a very wise person.

JERRY COLONNA: There’s a little voice in our head that says, “We know that this is coming from this shadow place. We know that this is coming from this sort of place of unresolved business,” but we pretend it’s not.

MORRA AARONS-MELE: Jerry argues that a lot of the adult leadership management career problems that we face – anxiety, avoidance, impulsivity, denial, and sometimes things like drinking or drug abuse, anger, and toxic work relationships – spring from our fundamental childhood experiences. That while we might be able to build powerful careers while engaging in these bad actions, and we’ve all known people who’ve done it, understanding how your childhood shaped the adult you became and facing your demons are vital for anyone who truly wants to thrive in the next step of their career.

MORRA AARONS-MELE: He calls it, growing up. A huge theme of your work, Jerry, is how we as leaders reconcile our grown, fancy, accomplished selves with our often-wounded inner children. I’m curious how you discovered this. Although, certainly other professionals have written at length about our inner child and the role of our childhood in our grown-upness. It seems to me you’re the first person I’ve read who has matched our leadership journey so explicitly with your childhood experiences. Why and how did you discover this? Why is this one of the things you emphasize?

JERRY COLONNA: I think the “how” came about looking outward and looking inward at the same time, that is, observing using my prodigious hypervigilant skills that I developed as a child to stay safe, while simultaneously being well guided in a process of my own self-discovery. I don’t see what I’ve done as particularly unique. I actually see it as quite logical.


JERRY COLONNA: It’s that bit that says there is a linkage between the unresolved, unsorted baggage, to use a line from Bruce Springsteen, and the unsorted baggage of our childhood and our leadership challenges. Flip that around and say, “Wait a minute, there’s an opportunity that since being a good leader is so difficult, why not use that to do this work that you need to do anyway, that most of us avoid doing anyway?”

JERRY COLONNA: I happen to, because of the Venn diagram of my odd life, have experience in the realm of organizations and experience in the realm of the heart. The two, in my mind, overlap quite logically obviously in that realm of leadership.

MORRA AARONS-MELE: Was there a moment when you realized in your life, “Oh my God, I’m acting out a lot of trauma from my childhood. I need to look at this more closely.” Was it ever that clear?

JERRY COLONNA: Were there moments?

MORRA AARONS-MELE: Or what was the first moment?

JERRY COLONNA: Oh, I don’t even recall the first moment. I may recall that I’ve spent 30 years in psychoanalysis.

MORRA AARONS-MELE: That’s a lot. That’s a lot of hours.

JERRY COLONNA: Yeah. Can I reframe the question this way?


JERRY COLONNA: Were there moments when my ability to pretend that I was acting out was no longer possible? Yeah.


JERRY COLONNA: Because I suspect this is true for a number of people. There’s a little voice in our head that says, “We know that this is coming from this shadow place. We know that this is coming from this sort of place of unresolved business,” but we pretend it’s not. That’s the interesting moment, when you finally get past the shame and the guilt that prevents you from recognizing that your past is present. When you start to realize that we’re all walking around with the past and dating the present, well, then there’s a relief that can come in. That relief shows up as, “Oh, it’s okay.”

MORRA AARONS-MELE: What are some specific ways that you think trauma or bad models from our childhood imprint on how we lead as adults?

JERRY COLONNA: Yeah. If we can reframe the question just a little bit too, to wounds versus trauma, because trauma is a very, very specific word.


JERRY COLONNA: The truth is we are all wounded even if we haven’t experienced trauma. One expression of that is the notion of a parent or a significant caregiver who has been either absent or disappeared. One of the consequences of that can be what my colleague Khalid Halim often refers to as “early promotion.” What happens within a family structure is that the child assumes responsibility for the emotional, if not physical, wellbeing of the others in the family – either siblings or the remaining caregiver or parent.

JERRY COLONNA: One of the attributes of that can be early lessons in being the caring leader. The one who is responsible for everybody. This is a really important message. These wounds don’t necessarily result in only negative behaviors, like say, conflict avoidance as a result of growing up with violence. They result oftentimes in very, very powerful, positive experiences, such as the ability to step into uncertain situations and to craft a vision and a way to be.

JERRY COLONNA: Well, that was a very useful tool for a child, who say is 10 years old, and has a parent who suddenly dies in a plane crash for example, as one client of mine did, or had. The result was that they had the inner resources to be able to withstand those shocks because they’ve already experienced them.

MORRA AARONS-MELE: Can you talk about “The Greedy CEO? Sorry, The Greedy Salesperson” a little bit?

JERRY COLONNA: Sure. Yeah. Yeah. Yeah. In the book, I tell about how a client came to one of our boot camps. The first night of the boot camp, sometimes people accuse me of being woo-woo. It was a little woo-woo, and I’m reading poetry. I’m no doubt walking around without shoes on. I may or may not have had socks on. It depends on the day. He is getting visibly upset. He is a CEO of a relatively large and fast-growing company. At one point, he bursts out.

JERRY COLONNA: He says, “Why the hell are we reading poetry? This is not why I spent all this money. I came here to be a better CEO. I came here because I have a greedy SOB head of sales, and I don’t know what to do with him.” I said, “You stay, and if at the end of the weekend you don’t know what to do with this greedy SOB, I’ll give you your money back.” He ended up staying, and two days go by, and by that point, we start exploring the union notion of the shadow.

JERRY COLONNA: The parts of ourselves, positive and negative, that for a whole variety of reasons we deny actually exists. We place it, as Carl Jung said, in the shadow behind us. It just starts to act out, and it starts to show up. At one point, I ask him to tell me a story. “Tell me a story about shame,” because shame is a really interesting indicator. If you can create these conditions in which people can open up and speak to the things, the shameful parts of them, there’s gold.

JERRY COLONNA: He tells a story of being a young man, running away from an abusive home situation, and becoming addicted to alcohol and being homeless. Just following an intuition, I asked him, I said something like, “Tell me about the night.” He just starts crying, and he feels a little shaky because he’s been seen. He goes on to tell me about the promise he’s made to himself, that he would never be hungry again.

JERRY COLONNA: What I invited him to see was that that promise he made to himself, when denied, became manifested in a kind of greed. Because what is greed but the wish to have all the toys to feel safe? Right? It’s all-

MORRA AARONS-MELE: Scrooge McDuck on his piles of gold coins.

JERRY COLONNA: Scrooge McDuck is all he’s trying to do, ward off poverty. The problem for him as a CEO was that by denying that that was operating, he had figured out a way to, as I often say, outsource his greed, right? The key point was to ask him, “Well, who hired the guy in the first place?” Well, he did. Did you know that he was greedy? Well, of course. The problem was he wanted that guy to carry all of his negative feelings about that wish while he retained the positive feelings.

MORRA AARONS-MELE: Jerry, are you an anxious person? Do you have anxiety?


MORRA AARONS-MELE: What kind, and how?

JERRY COLONNA: What flavor?


JERRY COLONNA: Part of my continual work in progress is that as a child, the way anger was worked with within my family system was that it was either outwardly expressed with a kind of violence, implicit or explicit, or it was internalized as a kind of safer way of expressing it, either as self-criticism or, more often in my case, just a general anxiety. It was just safer to feel fear, but the thing that will often set me off more than anything is conflict.

JERRY COLONNA: If two people that I love are in conflict, then at one level, the fear is that they’re going to hurt each other, but at another level the fear is they’re going to hurt me. Right? Because “it’s always going to end up in a fight,” as my father used to say. It always ends up in a fight. Now, I will say to you, you asked, am I anxious? Of course, I’m anxious. I’m human. Just like, do I get to experience anger? Of course, I do. I’m human.

JERRY COLONNA: What is different for me now than has ever been before in my life is that my skills with working with those feelings are so much higher than they were before. I can experience anxiety knowing that the anxiety will end.

MORRA AARONS-MELE: I want to talk about hypervigilance. I think that this is something that people who are achievers may share in common but talk about too little. I was extremely hypervigilant in my childhood. I still am. It seems like from what I’ve read in your writing, that you are hypervigilant. You cherish those gifts, but it’s your superpower, I think you even say, but you also know that it can distract you. It can make you extremely anxious. Can you talk about your journey with your hypervigilance a little bit?

JERRY COLONNA: Sure. I think you’re wisely making a connection between perfectionism and hypervigilance.

MORRA AARONS-MELE: That’s right.

JERRY COLONNA: I define hypervigilance as the capacity to, or the tendency to, be hyper aware of every shift, especially in the emotional subplot of whatever organization and grouping of people we have. For me, my hypervigilance really was established in response to my parents. My dad was an alcoholic, and my mom was mentally ill and taking on … as children will often do, I had this sort of magical thinking belief system that my responsibility was to get everything right.

JERRY COLONNA: To make sure that Dad would not be drunk, and that Mom would not have a delusionary outburst, which was one of the ways her mental illness manifested. She might go off into the corner and rant to a dead politician like Bobby Kennedy. She’d have a conversation with him. We’d all be sitting there terrified because Bobby Kennedy is not in the room. I do describe that as a kind of superpower, because the way … My first job as an adult was as a reporter.

JERRY COLONNA: It actually served me really, really well because I would often hear things that the person that I was interviewing themselves weren’t even hearing. I could play that back in a question. It’s a superpower because all of a sudden, I could step into an empathetic stance. Instead of me being the interviewee and you being the interviewer, we get to have an emotionally intimate conversation. We get to be human beings together because I notice.

JERRY COLONNA: The negative side of it is that I will drive life and business partners crazy because I will say, “Well, wait a minute, you said the word ‘red,’ when really you meant burnt orange, didn’t you?” It’s like, it can turn into a hyper-factualism when it’s at its worst expression. Especially when anger is denied, then it becomes a prosecutorial vigilance.

MORRA AARONS-MELE: Is micromanaging hypervigilance? Is it another word?

JERRY COLONNA: I think it is probably hypervigilance, but it’s probably hypervigilance married to the thing that you said before, this perfectionism, which is, if the thing is marginally out of alignment, if things are just marginally off, then chaos is going to ensue. Micromanagement as a coach, when I work in an organization, if I see micromanagement as a predominant cultural attribute, chances are there’s a tremendous amount of fear.

JERRY COLONNA: I think that the most hypervigilant micromanaging perfectionist people make themselves feel awful. Oftentimes, a threat is a misreading of the situation – a filter through the lens of the past.

MORRA AARONS-MELE: Whether that lens of the past is conscious or unconscious, right?

JERRY COLONNA: That’s right.

MORRA AARONS-MELE: It could be an Excel spreadsheet with numbers for the quarter but-

JERRY COLONNA: That’s right.

MORRA AARONS-MELE: How is that informed by the past?

JERRY COLONNA: Well, there’s a Buddhist story, and I’ll mangle the story, of a man who spends his entire evening sleepless because he’s convinced that there’s a coil in the corner of the room that’s a snake, only to wake up and realize in the morning that it’s a rope, right? Now, there’s wisdom in pointing out that, because I think many, many times we live like that. Many businesspeople will live in that experience. What is often lost in looking at the wisdom of that is a very, very important lesson from childhood, which is, it’s better to be safe than sorry.

JERRY COLONNA: What I like to do, what I like to recommend as a coach, is to work with someone and to help them appreciate the wonderful survival strategy that was hypervigilance and fear and the strive for achieving. Then to really ask oneself, does one really need to worry about whether or not you’re safe than sorry? Is the threat that you once experienced as a child still present?

JERRY COLONNA: Chances are the programming is still present, but the threats are different. The quickest way to understand that the threat has changed is that the amount of power that we have as adults is vastly different than the power we had as children.

MORRA AARONS-MELE: Imagine that I’m that person, and I’ve done so well. I’m such a good worker, and I’m going to get promoted. My fear of finally being revealed for the person who probably won’t catch the mistake next time or is really just a big ball of shame that I worked so hard to hide, is actually holding me back from taking that leap. What do I tell myself?

JERRY COLONNA: Well, there’s a bunch of questions that might occur to me as a coach. I might ask that person to consider, “What would it feel like in their body to no longer worry about being found out as a fraud?” We often will feel something in our body before our conscious mind is able to discern it. “How would it feel in my body?” enables me to envision having a different relationship with that emotional thought, with that feeling.

JERRY COLONNA: When I realized that being anxious kept me safe from being angry, I got to say thank you to that little jujitsu move that I used to do, because, oh, it kept me safe. Yay.

MORRA AARONS-MELE: I feel like I want to have an Oprah moment and repeat what you just said. Being anxious kept you from being angry.

JERRY COLONNA: Yeah. Or it kept me safe from being angry.

MORRA AARONS-MELE: Safe from being angry. Are you angry now when you need to be?

JERRY COLONNA: Yeah. One of the moves that I’ve made – I often make references to superpowers, Marvel comics, and DC comics – I fixate on the Hulk as a beautiful expression of that anger. In one of the early Avengers movies, Mark Ruffalo, playing Bruce Banner, envisions being locked in a subway car, crowded with people. “Don’t put me in.” He’s like, “That’s not a good thing.” I like thinking about the Hulk. I think that the move that I’ve tried to make is not to shut Hulk up behind a cloud of anxiety but to actually turn Hulk into Thor. Hulk-

MORRA AARONS-MELE: My son would love that.

JERRY COLONNA: Well, Hulk into Thor. What’s the difference? The two of them … The reason that mythologically they put them into battle in the comic books is that they’re actually two sides of the same coin. Thor has purpose, and his purpose is social justice. When I can connect to the purpose, to justice, I can feel really, really solid and comfortable in my anger, because the anger is no longer threatening to be out of control the way Hulk is.

JERRY COLONNA: It makes me angry to think of how often business leaders, and those who hold power, misuse that power – abuse the power and do harm and violence to the world around them. Physical world, the planet, the communities. It makes me angry. Now, I can get up on a soapbox and yell and scream and maybe even punch something, or I can become Thor and double down and work my tail off to make the world safe for human beings. I’d much rather be that other person.

MORRA AARONS-MELE: Jerry, can you be an anxious warrior? Because I relate to that, but part of me is like, “I would be an anxious warrior.”

JERRY COLONNA: Are you asking, can you be an anxious warrior? Or are you asking, is a warrior unafraid?

MORRA AARONS-MELE: Oh, right. Or what does a warrior do with her fear?

JERRY COLONNA: Yeah. See. See, warriors are not unafraid. A warrior acknowledges there’s wisdom in the fear. Fear is the wish to keep you safe. It’s reckless and foolhardy to deny fear. The strength comes when we choose to act in the face of fear. Here’s a true threat at work. Companies may fail. That’s a true threat. You may be fired. That’s a true threat. Remember the story? In the book, I tell about Chad Dickerson.

MORRA AARONS-MELE: I was just going to ask you actually to tell that. Yes.

JERRY COLONNA: Yeah. Yeah. Yeah. I tell the story of one of my former clients, Chad Dickerson, who is formerly CEO at Etsy. I tell the story of he and me, sitting on the rooftop of Etsy’s building the night before he’s announcing that he’s been fired. The powerful moment was the realization that there was a man who could have chosen to slink away, could have chosen to basically hide behind the, “I’m going to resign because I’m going to spend more time with my family.”

JERRY COLONNA: Instead, he made a very fearful declaration. “I have been fired.” In doing so, he owned it and snatched from that moment his own grace and dignity. Now, that’s not to say it wasn’t painful. It was incredibly painful. It’s not to say it didn’t cause all sorts of self-doubt. Of course, it caused all sorts of self-doubt. To our point, he was afraid, “What am I going to do? How are people going to view me?” The fear was based on an existential threat, “How would I be perceived?” It was fear of shame.

MORRA AARONS-MELE: Okay. I think that’s amazing, and the Etsy office in Dumbo is the coolest office I’ve ever been to. I will say that. It’s amazing. You have a great quote in the book, which I can actually hear my father saying. I think it’s, “The higher up the pole the monkey climbs the more his ass shows.” I can imagine listeners saying, “Okay. Fine. That’s one thing for the CEO of Etsy. That’s a cool company. He was the CEO and he was a big deal. He was going to be fine. If I did something like that, I would be exposed, and my life would be over as I know it.”

JERRY COLONNA: Right. I want to acknowledge something, that as a white cisgendered male, it may even be easier for me than it might be for someone who identifies in other social locations.


JERRY COLONNA: That is a truth. There’s nothing I can do about that. What I can say is there are altruisms about the degree to which we let the world change our internal sense of self. The greatest strength, the greatest dignity comes from the internal knowing of our own self-worth. That is the greatest source of risk. It’s the thing that gets attacked. It’s the place from which the warrior springs. It’s, I know I have failed to live up to the aspirations that I hold to myself every day.

JERRY COLONNA: I fail every day, but I will get up tomorrow, and I will try again, regardless of what the external world thinks of me. It took me a long time to grow up in that way. I think that that’s the opportunity that leadership presents for us. Can we grow to that point?

MORRA AARONS-MELE: I am not my job, and I am not what other people-


MORRA AARONS-MELE: I want you to talk to the listener, and I include myself, who is obsessed with creating enough money for themselves because of a childhood experience or who knows. The anxiety around money I think keeps many of us trapped. One of the things that you talk about in the book is how to deal with our anxiety and our historical anxiety around money. I’m curious either if you have an aha moment about how your childhood fear of being poor was holding you back, or if there’s a story of someone you’ve worked with who realized that their money anxiety was affecting them or limiting them in a certain way.

JERRY COLONNA: Sure. In the book, I tell the story of my grandparents’ home, my mother’s parents’ home, Dominic and Nicoletta Guido in Brooklyn. Dominic Guido was an iceman. He was one of the first entrepreneurs I ever met. Self-taught, sixth grade education. Dominic and Nicoletta Guido’s home always felt to me like a bastion of calm in a very chaotic childhood. My younger brother, John, and I would often spend nights with my grandparents, especially when mom was in psychiatric hospitals.

JERRY COLONNA: The kids would be parceled out. We’d spent a lot of time there. Grandpa liked lemon drops. In the pantry of their house, there was always a tin canister of lemon drops. I always associated having enough lemon drops with having enough money to feel safe and calm. The realization for me came about that there was this relationship with the pursuit of money, which was really a pursuit of lemon drops, which was really a pursuit for safety.

JERRY COLONNA: The realization came to me after some particularly challenging times in my 30s when I was financially successful and still not feeling safe, where the inner part of me was not matching the outer part of me and where I was finding myself pursuing a life as a venture capitalist. The moment came when the infamous Dr. Sayers, my analyst, in a bit of our own frustration, said, “How much is enough Jerry?” I found myself exasperated and saying, “Bill Gates.”

JERRY COLONNA: She said, “What are you talking about?” I said, “I need to have as much as Bill Gates.” When I heard myself say that out loud, I began to realize that I was chasing a fantastic Zorak ghost that has nothing to do with the reality of whether or not I in fact had enough already. No amount of financial accumulation was going to make me feel safe until I understood what it was that I was truly looking for.

JERRY COLONNA: What I was truly looking for was the feeling of going into the pantry, reaching into the tin canister, and always knowing that there were lemon drops in there.

MORRA AARONS-MELE: That’s it for this week’s show. If you like what you’ve heard, be sure to subscribe and submit a review in Apple Podcasts or wherever you get your shows. If you have an idea for the show or you want to tell us your story, drop me a note at, or you can tweet me @morraam. That’s M-O-R-R-A-A-M. Special thanks to the team at Harvard Business Review, my producer Mary Dooe, the team at Podcast Garage, and all of our guests who are telling us their stories from the heart. From the HBR Presents network, I’m Morra Aarons-Mele, and this is The Anxious Achiever.

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