Ep. 22 How Brilliant Careers Fail - Dirty Chai with Chio

In this podcast episode, the host discusses the topic of how brilliant careers can fail. The discussion is inspired by a book called "The Right and the Wrong Stuff" by Carter Kost. The book helped the host realize their own mistakes and led to positive changes in their professional life. Kost, a professor and investor, emphasizes the importance of understanding both strengths and weaknesses in order to avoid derailment in one's career. He found that many people struggle to identify their weaknesses and the factors that could hinder their success. Kost identifies five common types of derailment archetypes, with "Captain Fantastic" being one of the most challenging. Captain Fantastic refers to individuals who excel in their own work but struggle with interpersonal skills. They may be seen as arrogant, dismissive, and emotionally volatile. As one progresses in their career, the ability to build relationships and engender trust becomes more important than individual knowledge and competenc Hello, hi, welcome to this week's installment of the Dirty Chai Podcast with me, your host Chio. It's a podcast where we focus on holistic, professional, and personal success by growing and developing the common denominator to all your successes, all your failures, and everything in between, you. It's about the mindset, emotional regulation, and the intentional personal development that underpins holistic success. Today's topic is how brilliant careers fail. How brilliant careers fail. This topic is inspired and informed by a book written by Carter Kost. It's called The Right and the Wrong Stuff, How Brilliant Careers Are Made and Unmade. This book came across my lap three years ago, and it came at a time unbeknownst to me I truly needed to read it. I read it, and I was stunned in a negative way to realize just exactly what I was doing wrong because it was in my blind spot. I wouldn't have known it was there if I had not read the book and if I had not seen myself in what Carter Kost was telling me, and I told everyone who was willing to listen at that time to read this book, read this book, read this book. It was a very uncomfortable revelation, but it was a revelation that has since changed my professional life for the better mostly, and I'll explain to you why. Carter Kost is a clinical professor at Northwestern Kellogg School of Management in the United States. He's also a venture partner at Pritzker, I could be mispronouncing that, Group Venture Capital. He is both a professor of entrepreneurship and an academic, but also a practitioner and an investor. He is one of those people who have the unique ability to see both sides of the coin, and because of that, I think he brings great insight to the topic, and exactly what topic is this. The topic is he teaches business, and he teaches exactly what we talk about here. In teaching, one student after the other, over and over, over many years, he found that a lot of students would come to him and say, what should I do next? Should I join PepsiCo? Should I join a startup? Where can I go next? These are my strengths, and then they would reel them off. These are my strengths. What should I do? He would usually come back with, okay, that's great. Tell me what it is that is most likely to hurt you if you were to go into a career. What is it that's most likely to derail you, because that will tell us where you need to bolster and maybe what you need to avoid, and also maybe even what type of organization you need to be in. To his surprise, almost no one had an answer to that question. One reason why this is so is because the movement to recognize and loud your strengths has been massive and successful, and we all needed it. We needed a little ... You know, the millennials have been through a lot. We needed a little, this is what you're good at, rah, and then get confident, have self-worth, have self-esteem. We needed that, and we did that, except that in doing that, we may have forgotten that it is also a strength to know what you are not good at, to know what you are weak at, to know what needs to be managed about yourself, so that when you are in a space where you need to collaborate and synergize with other people, you can manage yourself when you see a trigger that you know, no, that sort of behavior is going to cause me to do A, B, C, D, and then maybe I shouldn't do this, or this sort of thing is going to make me do this, so maybe I shouldn't do that, or maybe I don't do well in an organization that's overly structured, so I shouldn't be accepting a job there. I should be seeking out instead an entrepreneurial vibe, or a modern vibe, or a we burn incense in the office vibe. That's where I'm going to thrive. This is the power of understanding your weakness. Another reason why this is important, or this was important for Carter Coss to write, was the realization that 50 to 67% of managers derail at least once in their life. So derailment doesn't have to be permanent. Sometimes it is. It doesn't have to be permanent. Think of Carmen Medina. We spoke about her lessons from the CIA on how to survive in the corporate world. It's one of the earlier episodes. Carmen Medina derailed spectacularly, and she worked her way back over almost a decade. To Carter's point, this is not an indictment. Pointing these things out is not an indictment. It's meant for you to work out why you are derailing, or have derailed, or are likely to derail, and then enable you by that knowledge to manage that derailment, to get back to where you should be, to potentially avoid the derailment altogether by being self-aware. This also cross-references quite nicely with last week's episode where we talk about hard-hitting soft skills, and one of those hard-hitting soft skills is self-awareness. It's interesting because a lot of people think that they're self-aware, but research shows that only 10% to 12% of people are actually fully self-aware. That's not many at all. Now, doing his research and working out what causes derailment was also inspired by the fact that he derailed twice in his own career. He derailed twice spectacularly, and spectacularly here is used very much in the negative sense. You will hear me shuffling a lot of paper. This is because this topic requires a lot of notes, right? So the question is, and the question that I would like to provide you with a menu of answers for, is what could possibly derail you? What could possibly be derailing you? What could possibly have derailed you and you are now coming back from it, right? Or it will at least give you a map to come back from it. Okay, so when he did his research into the derailment archetypes, he found that five answers recurred. Most people fell into one of five archetypes, that's what he called them, five derailment archetypes. So let's talk through each one. Number one is Captain Fantastic. Captain Fantastic is one of the more difficult ones because it's an interpersonal weakness. It's an inability or a weakness in dealing with other people. So Captain Fantastic is also challenging because he presents or she presents with the exact same traits that are lauded early on in the career. You know, that hunger, that I want to do this, that I will get this done no matter what. And often they are not at all hesitant to push people out of the way, to talk past feelings, to be completely insensitive to emotional things in getting the work done. I was listening to an interview yesterday or a conversation on YouTube. It was a remarkable conversation between Cody Sanchez and Tom Bilyeu, if I'm pronouncing it correctly, and Cody, in describing her type of personality, actually describes herself as Captain Fantastic to the T. She was focused. She was ambitious. She knew what she was there for. This is when she was still in corporate. She wanted something and she wanted it badly. So if it meant that she had to work late, she wasn't interested in social things, she wasn't interested in hanging out with other people, this is how she describes it. She was, I wasn't there to hug people and make friends. I was there to do the job. And she did it and she did it really well. So what was interesting is then when she got 360 degree feedback later in the year, what HR gently tried to tell her was, we think generally no one likes you and we think that you would leave bodies behind you to get to where you need to get. That was the description that they used. And she thought, how very interesting. How she received it was particularly important. How she received it was, okay, maybe this is not the right place for me because this is what I am like and this is what I'm trying to achieve, right? So she went on, she learned what she needed to learn there and she went on to move on to another job and ultimately started her own business. Having started her own business, she didn't lose sight of that feedback. She did not change into somebody else, but she has hired people who closed those gaps for her. People who are touchy feely. She addresses her weakness upfront and she explains to people that this is why she's driven da da da da, it's not personal, et cetera, et cetera. And that provides some level of connectivity so that people are able to work with her. Now Captain Fantastic, this personality is described as a wrecking ball, right? They're insensitive, tend to come across as arrogant and dismissive. They also tend to be emotionally volatile. This archetype gets more people into trouble than any other and it presents as trouble or problematic later in your career, early in your career. It is exactly what these organizations want. They want your hunger, they want your drive, they want your results and you get them, right? It's just that those characteristics work well in a silo where you are in complete control or even in a team that you're in charge of, but you are in complete control. But the higher you go up the management structure, the more you need to rely on interpersonal skills, on synergizing and Captain Fantastic does not have that ability. They are like step aside, let me do it, often described as me, I, myself, right? Stuart Kaplan, the Director of Leadership Recruiting at Google says, as you progress in your career, your relationship with others is more important than your knowledge and relationship with data. This need kicks in as you move into middle and upper management. It's a mindset change. You have to suppress your ego, let go of having the answer and embrace the relational world. It becomes less about having competencies and more about engendering trust. Captain Fantastic fails there because Captain Fantastic wishes to remain me, myself and I. Now, pay attention to how you have been behaving, right? And ask yourself if you fall into this category. What Carter Kast found in his research was when he does assessments, etc., etc., people will bend over backwards to avoid falling into this category, even if they actually do. They do not want to face that they might possibly fall into this category. And because of that, a lot of people don't then address these weaknesses. And it is very, very important that a person be willing and self-aware enough to say, this really sucks, but this could really be me. And also, it's very interesting to note that one of the key characteristics of Captain Fantastic is defensiveness. And you will find where things fail or things fall apart, Captain Fantastic always assigns blame elsewhere. They struggle with composure. They tend to say, it wasn't me, it was over there. And because they are not able to synergize, we all make mistakes and we all come to something that we're not good at. We all come to a point where we make a mistake in our career. A lot of us need grace at some point in our career in order to move to the next stage or to get past a mistake. Captain Fantastic's behavior is such that in the moments when they need grace or a sponsor, no one steps up to the plate because they have not bothered to invest in any of the relationships that would feed the need in another person to step up and speak for them. That is the danger of being Captain Fantastic. So Captain Fantastic does not derail immediately. Captain Fantastic progresses and then derails later. Number two is the solo flyer. The solo flyer works independently, does not need feedback or collaboration. They kick ass and take names. They are so good at what they do. I had a little chuckle because they describe the solo flyer as that person who not only brings the bacon, they kill the pig, they smoke the meat, and they bring the bacon all in one. They are able to do all of the things themselves. They work so well independently that they progress. And at about the point that they become responsible for other people, they start to derail because they still want to do those things themselves. My current CEO describes this as being a technocrat. And you'll find technocrats are exceptionally good at the technical aspects of their job. They are not very good at delegating, at saying to somebody else, you do this. They want to create, to keep the doing. They want to be the ones who continue to do. So they are typified by over-managing, hiring poorly because they are blind to their blind spots. They tend to hire people who are exactly like them. So you'll find they build a department of people who are exactly like them. They don't communicate well to the team because they say, give me, let me do it. They often also don't resolve conflicts and they don't develop their subordinates, which are key aspects of managing and leadership. Also, they don't secure resources for their team because if I could do it with just this, you can do it with just this too. And that is the solo flyer, right? The solo flyer eventually loses the support of their teams because their teams feel like reporting to them is a dead end, which is very sad. They feel like they can't go anywhere if they report to a solo flyer. So I'm looking for a quote, you know, I'm thinking here. So yes, there's a quote that I saw somewhere and I thought it was particularly powerful. I think Carter Cost was quoting somebody else and he said, becoming a manager is a transformation of identity. You go from getting satisfaction by doing things yourself to getting satisfaction by enabling others to do. And that is a dramatic and difficult change that the solo flyer fails to make. But because they feel like they're still delivering, they generally don't understand why then they're not progressing. So this is a skills gap. So the derailment archetypes fall into sort of three broad categories, which is personality and interpersonal things, which is Captain Fantastic. There is skills gaps and this one falls in there. This solo flyer doesn't have a rounded set of skills. And also there's wrong context where someone may be motivated by a particular structure and doesn't fit into the structure that they're in. When we go on to version 1.0, version 1.0 is that person who is highly skeptical of change. They came in and they were a superstar and they stayed exactly the way they were when they came in. Right. And as time and technology overtook them, they remained inflexible and therefore their skillset dated. They are comfortable in their routine. They don't like it when people come and change. I think every time I've joined a new company, I always encounter at least three or four of these people. Why are you parking there? People in your position never had to park there. Why are you doing this? People we've never had to do that. Why are you changing the font on this? We've never had to change the font, etc. I use small administrative examples, but this presents in small and very big ways. These people resist learning new skills that would help them adapt to a rapidly changing business environment. They resist new technologies that could help them perform their jobs better. When new management comes into the company and shakes things up, they often form part of a rear guard that resists that change. They like to call themselves traditionalists. They like to rely on the amount of time that they have been somewhere to really just avoid growing. There is a lack of curiosity in preferring the status quo and there is a need for curiosity in being a leader because you are meant to guide the organization towards progress and growth. Agility in your personal learning is the subtle skill of picking up on cues and changing one's behavior quickly. Version 1.0 does not have that. Version 1.0 might be motivated by fear, might be motivated by malice, might simply be contrarian. There are many reasons why a person could be like this, but they protect themselves by being rigid and aloof and acting with complete assurance. When they are challenged, they become quite combative and aggressive about their position and actually then behave like Captain Fantastic. This can really just happen because a person is afraid and I see it so often because by virtue of who I am and the things that I do, every time I've entered an organization, I have been a change agent or even a confirmation of change and it is almost normal, especially in the first year, to brush up hard against people who were in an organization before who are resisting a change that might make their lives better but that they are fearful of and it's a human thing and this is how it ends up in your blind spot because fear is a natural human feeling and you're trying to protect yourself. So that's version 1.0. Then there's the one-trick pony. The one-trick pony comes in and they are good at something, they are good, they are good at this thing and they become so good at this thing that it is all that they do. They become siloed, they become entirely focused on the idea that specialization is all there is to it. They get mired in details and start to lose sight of the bigger picture because all they want to do is this. They don't seek out broadening assignments because they have a specialty, this is what I do. Let's say I do law, I only do law, I only do compliance, I only do and now I'm using a personal example. In my area, there are lots of people who are only a company secretary, only do compliance, only do general counsel, general legal counsel, only do stakeholder management, right? These are all the things, only do BEE and this is the thing. When a person becomes that specialized, what happens when the world progresses and you encounter maybe someone like me and this could also happen to me too because the world continues to progress. You encounter someone like me who can do all of those things, right? What happens then when you only can do one of the five things? The result of being able to do only one thing is it's easy not to understand or to lose sight of the activities that create broader strategic value and I remember doing an assessment with my current employer early on and I've been working very hard on this in the background quietly but early on and one of the things that they said I needed to work on based on that assignment was the assessment was my ability to have a broad strategic view, to see the big picture, to stand away from the details and say, right, what are we trying to achieve? Leave the detail of this letter. The actual movement we're making drives us towards that goal, the one that we're trying to go to and my God, has it been game changing. A lot of what I've been able to do in this year in particular because when you're trying to grow in a particular skill, there's a period where you reach maturity in the skill set. Now that the skill set is reaching some level of percolation, I dare not say it's reaching maturity, I'm working on it still. Now that it's reaching some level of percolation where it actually has an impact, I realized that it's part of the reason why I was able to start the podcast. It's part of the reason why I'm able to say, for example, one of the things that delayed me was I was doing a special set of minutes and I was meant to deliver it two days ago. Old me would have delivered it anyway even if I wasn't 100% sure of the quality but I would not have been late. But current me understands the time that would cost the person I'm delivering it to, understands that his time is extremely valuable, understands that the two day delay is not catastrophic. In fact, it changes very little provided I do not interfere with his existing calendar. But taking that extra amount of time to make sure that the product I produce is quality is exactly what he actually wants and that has taken me a long time to understand. A one trick pony has a gap and it's written in quite a funny way in the book, it's mind the gap with a skill in brackets, so mind the skill gap. So this person is very good at doing what they're good at. They become so reliant on what they're good at, that signature skill, that over time unbeknownst to them, they become one dimensional and not promotable because you can only reach the top of your skill set and there's no way to go further from there. And you think, my God, but I'm so good at this, why is no one promoting me? So while version 1.0 resists change, one trick ponies don't realize they need to change, that they've over specialized, that they've become pigeonholed into doing one thing for their company. Their upward mobility stops because they've done the same thing over and over and over and haven't had a diverse set of work experiences that provides them with a broad strategic perspective. They don't understand how the departments function, other departments function. They don't grasp the activities that drive value. They think that their belief that we live in an age of specialization leads them to take the right approach 100% of the time, but they come to realize perhaps when it is too late, that that narrowness also narrows their option and severely narrows their promotability. So that's the one trick pony. And then last but not least, the whirling dervish. I see myself or I've seen myself in a lot of the archetypes to some degree, not 100%, but to some degree, but the whirling dervish, my God, this was a full frontal attack, a punch to the face. When I read this section, I very nearly cried, I'm going to be honest, because I saw myself. I had flashbacks of myself in past meetings, especially at the stage where I know that I derailed. I remember thinking, oh, my God, that was me. That is why I could not get my life together. That's why I did not get the directorship at the time. That's why. And what is the whirling dervish? Their tagline is, oh, my gosh, where did the time go? And it makes me laugh. A whirling dervish is actually a dancing man from Turkey, I think. Let me just make sure. But yeah, there are these guys who dance in white dress-like garments that have a red belt, and they sort of go round and round in circles, right? But when they're depicted in terms of the book, the whirling dervish kind of looks like a person wearing a very busy coat with things falling off of it as they walk, and their brain is like lots of little clouds of lots of little thoughts happening all at the same time. They're busy. They're busy. They're busy. They are busy. The whirling dervish, oh, my God, I hate doing this one, because it's like I'm attacking myself. These people are always out of time. They just don't seem to have enough time. They struggle with converting ideas into action. They lack good planning and organizational and task management skills. Therefore, they don't deliver on promises. It's very easy to say, I'll do this tomorrow, I'll do this tomorrow, and you don't deliver it, because they also have a problem saying no. A lot of people-pleasers fall into this category, oh, my God, this is so painful. The whirling dervish, right, needs to be in tune with the steps in the workflow process. They need to understand the proper sequence, how long does it take to complete a task, and who to include along the way. They need to be able to plan and prioritize tasks before a project can be started. They need to say no. They need to say no. They need to know when to do something and when to delegate to keep things moving. I was very bad at all of these things. I was very good at the technical knowledge. I was very good at understanding what needed to happen and how to reach the outcome. I was very good at producing unusual results, but, my God, was I whirling and whirling hard. I was whirling and whirling hard. If you think about it in the context of a meeting, usually a whirling dervish will come in at like one minute to the time in a flurry of, hi, hi, hi, how are you guys, oh, my gosh, there's so much going on, that sort of stuff. Usually things falling out. They don't have the notebook that they needed to have for that meeting. They wing a lot of things, et cetera. It's not a cute look. I didn't realize that I did those things until I read this section of the book. Then I called my best work friend from my previous job and I said, oh, my God, I read this book and I read this about this whirling dervish and I think that's me. I thought she was going to say, no, it's not. She was just like, oh, I cried a little. I was shattered, but then after that, and that's about three years ago, after that, I decided how can I make this better? Over the last three years, I have been deliberate about thinking before I say yes, about being mindful not to throw out a, oh, I'll do it just now, or I'll do it tomorrow, or I'll do it because I do it very easily. I've been mindful to say, okay, this takes this long and I'll get back to you within this amount of time. As difficult as that has been for me, what that then does for the people who are dealing with me is it makes me more reliable for them. It makes me more dependable. They understand what I'm doing. I'm not whirling and causing confusion. I'm becoming a steady force and that is what people need when they're working with you. That is what people need when you're in charge of them. I'm still working on these skills, but now I know what I'm bad at and because I know it, I have been to a course about managing my time. I've been to a course that teaches me how to manage my outlook and I'm not talking about reading emails. I'm talking about how you can truly weaponize outlook as a tool of efficiency. I've been able to now do this podcast. I've been able to now write the newsletter. I've been able to spend quality time with my kids. I've been able to do better at work actually because all of a sudden, I don't feel like I don't have time 100% of the time anymore. Also, the other thing that would present as an effect of being a whirling dervish was that I would work extremely hard just to the tip of burning out and then I would crash and I would need some recovery time and then I would do it again and then I would get really sick and then I'd be like off for two weeks because I'm trying to get or I'll still come into work because I never took the time off because I didn't have time. I would have pneumonia. I would have this. I was forever ill because I was running my body into the ground, over committing left, right and center. When I stopped that and I learned to become comfortable with a productive no, I found myself producing more which is an absolutely mind-blowing thing. Instead of running around like my hair is on fire and I remember this, I'll tell you the story in closing. I remember in my early days, I would run into the office every day. I don't even know why I was running. I just never had time. I would park my car, come out, grab my bag and I would run through the security checkpoint because we have security checkpoints. One day, one of the guards, she's a woman and she says to me, you know ma'am, this thing you do of running around, it's not a good look. She said it in vernacular. It's not a good look. It makes you look like you're one of the juniors. You need to walk, walk. I remember the next day I came in and I walked to my desk, such a small thing but it made a dramatic difference. I remember turning around and saying to her, do you see me walking? She did a little clap. It has stayed with me. Ever since then, I deliberately walk into a room. I do not run in in a flurry. And today, I was coming from the bathroom and I was walking and I heard some of the cleaners speaking to me behind me and one of them said to the other in vernacular again, I really like this woman. She has gravitas and I thought I have arrived. But the point of this is this, once you understand what's in your blind spot, you can do something about it. That is the true strength of facing the discomfort of understanding what your derailer is. Understanding what your derailer is, is not about attacking you or making you uncomfortable. Understanding your derailer is about understanding what you need to do better, how you can do it better and preserving that potential and living up to that potential in the best way possible. It really is about empowering yourself. I don't even have time to tell you about Carter Cost's actual derailment, etc. Maybe we'll circle back in a few months and talk about that aspect of it. But for now, I hope that you will take some time to figure out what could possibly derail you because if you don't know the answer to that question, you might be surprised that a derailment will cut you off at the knees and will cut your career off at the knees and you never saw it coming. Thank you so much for listening. If no weapon formed against me was an episode, it would be this one because my God, I think I've attempted to record this 10 times. It's been everything from jet lag to failing to say coherent sentences because I hadn't slept for three days. Then I finally managed to sleep, but then it's Nate's school calling, it's the kids waking up earlier than usual, it's this, it's that, it's this, it's that. I've had to delete it multiple times, but I was going to record it no matter what and here we are and I hope it has been useful to you. Have a wonderful week. Make something beautiful. If you like podcast, as always, I am receiving more and more feedback from people. Oh my God, thank you so much. Makes my day. Sometimes it makes me cry because I'm just talking to a computer and knowing that this makes a difference somewhere to someone, changes the meaning of this thing for me because that is why I do it. Thank you so, so much. Please keep talking to me, like, share, subscribe, tell a friend about it if you really like it. I really appreciate each and every one of you.