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BOLDER & WISER with Peter Wang and Michelle Kraemer
The BOLDER & WISER podcast celebrates the messy growth journey and shares hard-earned wisdom from makers worldwide.
The B&W Podcast is based on the belief that
1) we are all work in progress, no matter where we are in life,
2) wisdom comes from honest reflections on our own journey, and
3) so much wisdom is buried in stories unshared.
Our first season highlights a wide range of unique operators that are leaders in their fields: from a Ukrainian jewelry entrepreneur, Head of audio at Adobe, to an Israeli founder of a billion-dollar company, design leader, leadership coach, personal finance leader, and more.
BOLDER & WISER with Peter Wang and Michelle Kraemer
John Costango: making changes at 50, realizing your true potential, developing your toolkit
In episode 2 of the Work-In-Progress Podcast, I sat down with my friend, John Costango, now an executive coach after 20 years as a successful Wall Street executive.
JOHN COSTANGO
https://www.aconnectedcoach.com/
John@AConnectedCoach.com
⌚️ TIMESTAMPS
00:40 Early life and education
08:59 Life goals
12:00 Teacher to Wall Street
17:21 Finding opportunities in difficult situations
24:46 Citigroup and the financial crisis
32:15 Importance of curiosity and seeing the Bigger Picture
37:53 Developing your toolkit
47:09 Making changes at 50
55:23 Flipping the script - designing career around life instead of life around career
Welcome to the Work in Progress podcast. I'm your host, Peter Wong. This show is created on the belief that we are all works in progress no matter where we are. In this episode, we dive into my friend John Costango's inspiring journey from a small town math teacher to a successful Wall Street executive, and now a leadership coach. John shares how to find opportunities in tough situations, how to move forward when life feels overwhelming, the benefit of being an outsider. How to embrace changes to reach your full potential and much more. Don't forget to like, subscribe, and share if you find our show helpful. I hope you enjoy this episode. John, welcome to the Work in Progress podcast.
John Castango:Thank you, Peter.
Peter Wang:It's so good to have you on. I feel that you have a unconventional path underneath a potentially conventional looking resume. And you've made some recent changes in life that I think a lot of our listeners would be very interested in the why and what you've learned so far. And one thing I like to do with all of our guests is ask them to introduce themselves first So John, how would you introduce yourself?
John Castango:Thanks, Peter. Yeah, so I'm John Costango. I'm an executive coach, a leadership coach, and I focus on helping leaders realize their true potential and also working with people who are thinking about making big changes in their career. Trying to understand what's next or figuring out how to take those steps. I've made a lot of changes in my career over time, as you've alluded, and done a lot of different things. And I really have become committed to this idea that everybody has so much potential in their lives and in their careers at every stage, if they are willing to look at it from the right perspective and take steps to propel themselves forward. And everyone can do that whether you're just graduating college or whether you've been retired for 15 years. And I love working with people on these challenges.
Peter Wang:Great. I think, we'll, I would love to dive into. The coaching aspect a bit later on. But I would love to zoom back a little bit, like in terms of your early careers and upbringing, how did you get, what was the career and life like before? The executive coach?
John Castango:Okay, you should know that. I'm 52 now, and my 50th birthday gift to myself was the gift of quitting and I quit a banking career that I had been working on Wall Street since the early two thousands in order to think about what was next. And I mentioned that because, you asked about life before coaching. It was a lot, right? there was 50 years worth of work. So let's see. I went to high school. Outside of Reading, Pennsylvania. Reading is a pretty small town in southeastern Pennsylvania. Most people know it because it's on the monopoly board, Reading Railroad. And that's, it's that seems to be where it peaked in terms of its fame. So a little town grew up in, went to high school there and went to college in central Pennsylvania at a liberal arts college called Dickinson College. And I chose Dickinson because it was a place that would let me do what I wanted to do in a sense. Because it was so focused on liberal arts there was a lot of freedom, academic freedom for the students to design their own paths. And I was really committed to this idea that I wanted to get a degree in math and a degree in English literature. Which is something that's a little unconventional. And a lot of places probably I would've had trouble kind of juggling both. And Dickinson embraced that concept pretty nicely.
Peter Wang:How did you pick those two specifically?
John Castango:As I'm looking back in life, I might be giving it more, more of a sense of story and agency than I felt at the time as a teenager. But what I remember is that I was really attached to this idea that I loved both of these subjects when I was in high school. I had inspiring teachers in both of those subjects when I was in high school. And part of me, I think just didn't wanna let that go. I enjoyed it. I was into it. The more sort of forward looking part of me realized that a degree in math and the experience that came from that, and the mental and cognitive development that came from that would be so a tool that I would be able to use whatever I chose to do in the future. And I was going to be a teacher. I knew I was gonna be a teacher and I wanted to be a math teacher. That appealed to me. And so that was, that part was easy. The literature part was more just that at the time was, that was my passion. I was really interested in it. It was a creative thing for me. In retrospect, what I realized is that introduced me to other cultures, other worlds, gave me a sense of, possibility and wonder and creativity and empathy which are skills that I've ended up using in the workplace a lot more than I ever would've anticipated at the time.
Peter Wang:That's interesting. Different people pick the majors depending on all kinds of reasons. Some of them, because they followed their parents' path; because their parents did the X, therefore they did y, the X may be slightly different variations of it. I picked computer science, electrical engineering, not because I knew that's what I wanted to do I wanted do design. I wanted to architecture design that space, but my mom did not want me to do that route. So she literally says, if you're not doing engineering, then you have to pay your own tuition. Oh. That was easy. Easy. Let me do, and my brother actually went. So we, I went to Carnegie Melon. My brother, who's one year 13 months older than me, he's basically this, literally, we were treated as if we're the same age. He went there for computer science, a minor in math, or maybe doubled in math. I said, I don't wanna do the same thing as he. I've been following him pretty much in my entire life. So instead I did something slightly different or electrical engineering, just so I can be different still qualify my mom's criteria. But then I found out, oh, silly of me, I should just do computer science as well because there's so much overlap. And then I, and then design, actually all the aspect of creative part came afterwards. Like a self exploratory why, just to have that urge to do so it's interesting, right? Different reasons.
John Castango:Yeah. And one thing we have in common is there was a little bit of financial control exerted in my childhood. My parents would use like threats about finances. Like your mom saying, you're gonna have to pay your own way to college if you, unless you do X, Y, Z. I had a little bit of that too. And one of my life goals early on, very early on was to get out from under that. And I mentioned I knew I was gonna be a high school teacher. I had a scholarship from the state of Pennsylvania that would help pay for my college. In exchange for a commitment to teach high school for a while. And that was a way of pursuing this very simple life goal that I had, which was get out from under any sort of like financial dependence on anyone else and be as financially independent as possible. And when I talked to young people today as they're thinking about their careers, I give people this advice, which is, don't obsess so much about what your career path is going to be or what your career goal needs to be, because frankly, there's a lot of unknowns there. Focus on three things. One is a life goal, like what do you want outta your life right now? Another is a toolkit that you can use to pr to move forward. And then the third is just your first step. Have the first step in mind. Be confident in the tools that you bring and know what your life goals are and make sure those three things align. And if you've got all of that, you're gonna move forward and then we'll worry about the next step after that first one is taken.
Peter Wang:That's fascinating. So Life Goal Toolkit and the first step, in some ways, the first step is somewhat dependent on the first, right? The fir
John Castango:Yeah, they're all inter they, they should all be interdependent and they should be aligned, right? Your toolkit, if your toolkit doesn't line up with your first step, like something's already off, that's not gonna help you. But my toolkit was a sense of confidence around being analytical and having gone through and gotten training in mathematics. So that was like core to my toolkit. Some of these other skills that came from the literature side ended up being important skills in the toolkit too. The first step was, I know I'm gonna teach. I knew that, so I didn't obsess about am I gonna teach for the rest of my life or not. I knew that was the first step focused on taking that first step, developing the tools, and making sure it aligned with my life goal. And it did, it gave me enough money to be independent.
Peter Wang:To be free. I know what's interesting in life goals, even though it's about life, it changes Stages of life,
John Castango:sure. Yeah. We're not
Peter Wang:thing for me.
John Castango:a single life goal forever. That's just our goal right now. And my goal right now is to have fun. My life goal right now is to have more fun now. It hasn't been that way for all 50 years. That's just where I am now. And I apply decisions that come to me through that lens of the life goal.
Peter Wang:Yeah. So you took a step of going to college with the goal of being more financially dependent from your parents, and then you became a teacher. How was that experience?
John Castango:Teaching was great. I was a math teacher. I taught in suburban Philadelphia on the, what's called the mainline, where there are a lot of, colleges and universities and wealthy, wealthy suburban Philadelphia folks living. So it was just, it was a really comfortable place to teach. We could really focus on what mattered, and there were very few of the distractions that a lot of public school teachers have to do, have to deal with. So I count myself very lucky there and formed some lasting friendships with colleagues and also with people who were my students at the time. And I've become friends with over the decades since
Peter Wang:And which grades were you teaching?
John Castango:taught ninth, 11th, and 12th grade math. So that was algebra that was trigonometry. Calculus, honors, calculus, those sorts of classes.
Peter Wang:Was the skill of teaching natural to you connecting with students
John Castango:No. That was not natural to me, actually. And of course I took education classes as in college in order to be certified as a teacher and all of that. The subject matter came very naturally to me, but the actual teaching, there was a lot of growth there. A lot of growth in that in terms of putting me into challenging situations and having to relate to students and meet them where they are and adapt to their learning style and adapt to what matters to them at any given moment while still propelling their curriculum forward. That took a lot of growth for me. In fact, I do recommend to people, if you're not sure what you want to do with your life, Do some of these programs where you teach for a couple of years just to get started because it's it can really give you a whole new perspective on who you are and how you need to develop.
Peter Wang:Oh, that's interesting. That's interesting advice. I haven't heard that one before. Yeah. Some people would say go into the service industry because by dealing with customers directly, whether it's sales, retail, or restaurants, you learn a lot about how to engage Maybe in this case it's like a variation of that, but Right, but differently
John Castango:yeah. It is
Peter Wang:that you value.
John Castango:of that. And and you can, on the benefit of it is you can also do a lot of good, right? Because a young, interested, excited teacher in a lot of these places can move the needle for real, for individual lives which is nice. When that
Peter Wang:Mm-hmm.
John Castango:I'm not sure you're gonna get that in a restaurant.
Peter Wang:Oh, that's true. Exactly. It's a different kind of level of impact. And so different role you play in the community as well, much longer term than the shorter term than you would. And so you were a teacher for how many, for a while?
John Castango:So I taught for five years.
Peter Wang:years. Mm-hmm.
John Castango:I had, when I first, the first year I taught, I became the advisor for the class of students who were ninth graders that year. So I followed that class as their advisor through their graduation. And and then they went to college. And then I went back to school. As I went back to teach the next year and I felt wait, all of these kids moved on and here I am and I'm still here. And it made me notice that, maybe this isn't me for the long term that it was enjoyable for a while. It was challenging but it wasn't going to be. The last step in my career. And so I started thinking about the next one.
Peter Wang:Oh, that's interesting. Where your students left and then you were, you felt like you were back again, that rotation. Oh, interesting. Okay. So then what happened? You were thinking about it.
John Castango:Yeah. So I was thinking about, what sort of changes would I wanna make? And the real deciding factor was I realized that I was bored
Peter Wang:Hmm.
John Castango:I had always made the commitment to myself that if I became bored with teaching, that I would find something else to do as if for no other reason, then it's just not right for the students. And I was probably accused of being a boring teacher at times. I think a boring teacher can still be effective, but a bored teacher can never be effective. Young people will see that boredom in your subject, in what you're doing in them. And that will keep the connection from forming that's necessary for real learning to occur. And so as soon as I realized I was bored with it I decided, time to leave and ended up getting a job at Arthur Anderson back when Arthur Anderson existed, doing actuarial consulting work, which basically you can do at the entry level if you have decent math skills that you can
Peter Wang:Mm-hmm.
John Castango:And first example of that toolkit sort of being applied in a very different format and moving me ahead.
Peter Wang:And that was the second step, if you will, or second chapter.
John Castango:That was the second step. And it's a whole big world out there, right? In the sense that, our clients, one of our clients was Enron back before Enron failed. And, you take this kid from Southeastern Pennsylvania who had been a teacher and not really seen a lot, knew nothing about business or finance or, energy trading or insurance companies or any of that. I didn't even know how to use Excel. Um, uh, I
Peter Wang:Oh, really?
John Castango:had never, yeah, we didn't, I never had to use Excel and it was a big wide world and some big changes. It was very exciting. Lived in, lived and worked in Philadelphia at that time. Got to travel meet other, comp, went to clients in Bermuda and, it just felt very
Peter Wang:Yeah. And that was a very almost formative years for you on the wall. You know, It's kind of entry to Wall Street. And so in some ways what's fascinating is it reminded me of myself when I, my first chapters, if you will, professional, was on in, was in New York, going to New York, and I did not know as much, I didn't know what the word is. Securities quite meant. There's technical securities and cinema safe and there's securities on Wall Street as an as. As a asset class. And what is securities? I still remember that thinking. Oh, how silly it would be years later how security. Oh, securitized. Oh, okay. And it was a whole different world. And so tell me a bit more about that. Cause I know you went through so much Enron, financial crisis. What was that journey like?
John Castango:So I, the first step was getting this job with Arthur Anderson. I was still in Philadelphia living there and working, but, starting to see the world through a very different lens and decided that the right next step for me was to move to New York. And that in a way became a bit of a life goal, was I was looking to be in a bigger city with a bigger social circle. And a bigger sense of sort of potential. And Philadelphia at the time, felt limiting in that regard. And so I thought, okay, I need to get to New York now. Now the thing is, how do I get to New York? And changing jobs was part of, finding someone who would, move me to New York and help me set up, my life there. And I had a couple of jobs in quick succession. In fact, the one that I went to New York to do ended up being a horrible misfire of a
Peter Wang:Mm-hmm.
John Castango:And the only good thing I can say about it is within six months I had a different one. So it accomplished its purpose but it didn't end up being the right fit for me at all. And so I moved to another one, and within a couple of years had several different jobs with different companies.
Peter Wang:Mm-hmm.
John Castango:The lesson that I started to learn at this point in my career though, that was. Really important to me later was that sometimes the best improvements in myself professionally came out of really bad situations. Screwups, right? One of those screwups was what happened at Enron. I was not at Enron at the time and was not on the Arthur Anderson audit team, which is where some of the real problems occurred. But I experienced the cult of Enron when I was there and remembered that sense later on in life about like, when things just don't feel right, like in your gut, what that feeling is and learned that acting on that feeling, listening to that feeling and acting on that feeling is really important. And as I was mucking about in New York one of the transactions I worked on in, at this insurance company, Ended up performing really poorly. And it performed poorly in part because it was exposed to credits like World com and Enron and others that, all went through a really difficult period at that time. And the deal needed to be restructured and we were all like trying to just figure this thing out. What is this thing? What do we do here? It's not in anyone's playbook. No one was expecting this. And out of that, there was a lot of creativity and a lot of thinking about the problem from different ways. Came some great opportunities for me, in part because people who were bankers on the other side of the transaction and the workout said to me after we were done, why don't you come work with us? Why don't you leave the buy side behind? Come over here to the sell side. We've got this business that's expanding really rapidly. And we could use people who like you, who come from different backgrounds and have different perspectives. And so I made that switch in the early two thousands and went to Wall Street and was there for almost 20 years, all coming out of like the screw up. And if that hadn't have gone poorly, I could have spent the rest of my career in insurance for all I know.
Peter Wang:Yeah, that's fascinating. So first, your life goal changed. To go to New York, you get there. It was not the dream job that you've always wanted, imagine to be, and you quickly make the switch, but also, you also made many other switches. When the door opened, when someone says, Hey, come to sell side or try this, was it hard for you? Did you have a feel like you had to leave something behind? What was it feeling like? Going from job to job? Role to
John Castango:hard. It was hard in the sense that I was taking jobs that I hadn't been trained to do explicitly, right? So I had a liberal arts education. I had tools in my toolkit, like I've said. But, I didn't go to school thinking I was gonna get a job in finance. I didn't know what finance was. I never took a finance, accounting or a business class in college. And so it was challenging in the sense that I just didn't have the same depth of background that other people at my level had. And, part of me was always like, afraid I'm gonna get, that's gonna become a problem someday. What? I don't know. I don't know. Is gonna be an issue. But it was a challenge in that sense. It, I've always been one to take professional risks. And I think part of what's made that possible is at some level I do have confidence that the tools in my toolkit are gonna be useful and that I've had some success, I've had success in the past, and I'll be able to figure it out. There is part of me that just is I'm gonna figure this out. But I wouldn't wanna say that it was without challenge or that, it wasn't scary at the time. It was. But I was always biased towards making a change rather than trying to clinging to the status quo and always go the other way.
Peter Wang:Yeah. That seems to be a theme bias for change, but also it feels like you have confidence. Your confidence is not about what this next step will become like certain level expectation, but it's more trust in yourself that you can figure it out, whatever this thing is.
John Castango:I think that's what we should all be striving for, right? Is less about. Saying, I can predict the future, which obviously none of us can, and increasingly challenged. But more about having confidence and conviction in our ability to deal with the sorts of things that are likely to come if we take certain steps, as well as a healthy skepticism of the value of not changing, right? So some people really clinging to this idea that I can not change, and the reality is the status quo is not an option. We always have to be changing. And so release that desire to keep things as they are, which is
Peter Wang:Mm-hmm.
John Castango:and say, all right, given things are going to change, how do I want them to change and how, like where do I want to go? And once you release that, that tendency to hold onto what you have, cuz it's not possible. It's a lot easier then to go in one direction or another. You have to go somewhere. So go.
Peter Wang:Yeah. There's two steps. Change is already here. Not changing is not an option. That's interesting. Yeah. So you also mentioned you didn't come from the finance background. I didn't either. I came from the tech background. Learning the space, right? How different lines of business, what do they mean, how do they operate? What does it mean to be a commercial bank versus right custodian and so on and so forth. How did become, and how did that different background actually help you to do your job better and stand Cuz Walls, oh no, it's very competitive space.
John Castango:It is. And I started to work my first job at Wall Street was at Citigroup in the early two thousands. And I had, I. I knew nothing about Citigroup, I didn't know about Sandy Weill. I didn't know about Jamie Diamond. I didn't know about Solomon Brothers and Liars Poker and all that stuff. I didn't know.
Peter Wang:Read all the books, the thing, the classic Wall Street books at the
John Castango:I just didn't and I went there and to answer your question directly, how did it help? I think it helped because I had a very open mindset about it all. I wasn't attached to this idea of Solomon Brothers and what it meant to be a trader at Solomon Brothers. And I didn't have a view that investment banking was somehow better than retail banking or that retail banking is where, the people who care about risk are and investment bankers or a bunch of sharks, like I just, none of that. None of that existed in my mind. And so I was able to just go with, go in the direction that things needed to go and learn enough about the organization so that we could put pieces together, connect the dots and so on. And part of my work at the time was assembling these fairly complex securities transactions that, really got into a lot of different parts of the financial markets, including mortgages commercial paper, and and bonds, obviously rating agencies and so on. And because it was all new and I didn't have preconceived notions, it was easy for me to look at things a little bit differently. That sounds nice, I assume. The reality is what I was working on were a b, s CDOs and the things that ultimately almost brought Citigroup. Down lost Citi Group, 50 billion and, caused, arguably caused, the credit crisis of 2008. And lots of humble lessons from that. I don't want to make it sound like, oh, I was doing this amazing stuff. It was hard work. It was interesting. I am proud of some of the experiences that I had, but it was definitely humbling to go through all of that and see it all blow up and be exposed for something very different than what we thought it was when we were working on it.
Peter Wang:Actually, this is interesting. We haven't talked about this before. So ironically I was also a Citi, but specifically in City Smith Barney On wealth management side. And that was actually the crown jewel in some ways within the city portfolio at the time. It's very stable. It wasn't connected to the other businesses that was at risk. When, I still remember the day when the city stock, when, I can't remember where it was, but when below a dollar, I was wearing a suit in this cubicle and it was, office was in incredibly quiet. The TV was on as usual, right. And we all see that we're all tracking our own stock when looking at it below a dollar. I looked around as if we all have this fear, but no one was talking about it openly with one another. And Lehman, I think I had already fallen. I can't remember the sequence of events at the time, was it? But it was a shock to me at the time. I did not know, wow, this is this bad. What is a shock to you?
John Castango:I would say that it was a shock. At that time when Citi's stock went, was at a dollar I had already moved to JP Morgan. To wind back a little bit, Around the end of 2006, I started to get that same feeling that I recognized from the time when I was at Enron
Peter Wang:Yeah,
John Castango:something wasn't right? Like that, that things had gotten wound up to a point where decisions were being made and things were being said that just didn't feel right. And I decided to that the market was going to probably get challenging. It was booming at the time, it was probably gonna get a bit more challenging and I'd rather be at an organization that had a more healthy respect for risk management is what I said at the time. And I thought that JP Morgan offered that. And I knew some folks who were there and were looking, had worked with before were looking to hire. So I made that shift. So I wasn't shocked that things turned. I had no idea they were that bad or that they were
Peter Wang:It's magnitude,
John Castango:I'd be a richer man today if I had been one of the people who knew that this was like going
Peter Wang:On the other side,
John Castango:So I had a
Peter Wang:did.
John Castango:but I didn't I had a sense, but I had no idea in a way.
Peter Wang:Yes. That was fascinating. Okay, so we were all both in the 08 crisis and actually because of 08 I had left financial services. I did my own pivot at the time, stepping out of it after the joint venture between Morgan Stanley and City Smith Barney creating Morgan Stanley. Smith Barney spent a year there in the jv. What was it like for you? What was your, some of the lessons?
John Castango:Yeah. So it was an incredible time. It was incredible for me because, like I said, I had moved over to another bank.
Peter Wang:Yep. Mm-hmm.
John Castango:bank had done its own share of these transactions. But I wasn't there when they, I didn't do them. And so I knew a lot about, I. All of this, but I hadn't done it there. And therefore, when things got bad and they let a lot of folks go, who had done those deals, they kept me around to help clean them up. What is this thing, people would add, what is this thing? How does it work? What can we do? Can we do this? Can we do that? And so I and a couple of other junior folks took on this role of cleaning this thing. And what happened very quickly as 2007 wore on and 2008 happened was the problems got bigger and bigger. Remember there was talk of contagion. First it was this little securities business and then it was all a fixed income and there was money markets. And next thing banks are failing and. The
Peter Wang:Yep.
John Castango:And so as the problems got bigger and bigger, they just kept asking me to get involved in bigger and bigger cleanup solutions. And so it was fantastic. It was just like one thing after another needed a lot of creative solutioning and hard work, and it was work no one else wanted to do. And I found it fascinating and fun for the most part and spent a few years doing that sort of work at the same time. Peter I had a real crisis, personal crisis around my role in all of that work, because I had been at Citigroup, I had been working on these transactions and if you saw the movie, the big Short. That was about that time and there were people who were portrayed in that movie who I know. And so I was faced with this sort of question. Do I say like, I was an idiot
Peter Wang:Hmm.
John Castango:I a fraud? It seemed like it was like I had to pick between one of those two things.
Peter Wang:That's interesting, but people saw you as a fixer in that, but you felt differently.
John Castango:Oh, sure. People saw me as a fixer in terms of my role
Peter Wang:Mm-hmm.
John Castango:JP Morgan. And, but I'm still focused on, what did what was my role in causing all of this thing, right? So here I am fixing partially I'm fixing a problem that I had a role in creating in a way, right? And so that was why my moral dilemma was, how do I see myself? Do I see myself as someone who was just. Stupid. Too stupid to know what was going on. Or was I a fraud? Meaning I knew what was going on and I was perpetuating this fraud on people and investors. So it took me a while to like work through that and come out of that as a whole person again. And the, what I realized was missing, I, I don't think I was stupid. I don't think, I know I wasn't a fraud, but what was missing was a sense of curiosity about the bigger picture. So I was just one of these people who was heads down, get your work done and make sure that your piece of the puzzle is right. But I wasn't curious enough, and I would argue that most of us were not curious enough to see the whole picture. Front to end. And in, in this particular type of transaction, it had to do with mortgage originations. And you know how people were able to get loans, maybe fraudulently, but those loans were gonna be securitized anyway, and the risk got passed along from one person to another. And I was sitting in the middle of all of that. And had I been more curious about how are these loans even getting to me? Why do they look the way they look? Are we sure that they're what they purport to be? Maybe I would've had a better sense earlier on that there were actually problems here. But that, that, that lesson around curiosity and seeing the bigger picture and making more connections was vital to me because then that really propelled the way I worked going forward. Regardless of what the work was, I was always asking those questions, i. What is it that I don't see here? What does a pitcher look like from another perspective? How might, what might we be missing? And those are those are great skills to bring to any problem.
Peter Wang:that's actually really, that's a really good point. I'm just getting a little reflection here too. It's a lot easier to not ask questions. I think most of us, even though we made sense, you said something before you said something was off. It takes effort to unpack it, to validate it right to to zoom out. And most of us is actually, and also we are not incentivized, I would say in our careers. We're not incentivized to ask the questions beyond this. We're very incentivized to go after the target that's being set for us. And that's actually maybe from executive point of view. And if we want, we're a founder or a company, we should be encouraging our people to ask more questions, show them the entire value chain from beginning to the end, right? That value chain once you unpack it, it's whoa. Red flag. what comes out of the end of it is not exactly what we want. Everyone was optimizing with fees they receive. By the way, I. You mentioned that movie, what's the movie you mentioned?
John Castango:big short,
Peter Wang:the big short, my two favorite movies is Margin Call
John Castango:the Lehman
Peter Wang:The Big Short.
John Castango:Yeah.
Peter Wang:I can watch those two. I think part because I was in that world without really understanding, like you, I didn't understand me, I was even further away. But two is, it is so real. No bank exists on its own, no bank or no, actually any fund. Beautiful, right? All of them exist in this, in a web, in a graph. So,
John Castango:It's fascinating and having been through it once, watching the events of the last, week or two have been really interesting and having been involved with the Fed and Treasury and in 2008 and looking at the moves that they took and when they were really decisive and maybe when they pulled their punches I've loved seeing kind of the government being able to react more quickly
Peter Wang:Yeah, then and last
John Castango:And I think that makes a huge difference. Hopefully
Peter Wang:hopefully. I know. Yes, hopefully the fear and the contain, the containment of it is effective. Okay, so we covered quite a bit already. We covered about your first two steps, if you will. And actually why I think we, we just covered now is this kind of realization of zooming out, be more curious. And I feel actually this sets a stage for the next stage of your life in a lot of ways.
John Castango:Yeah. That realization occurred, I don't know, call it 2009, 2010, somewhere in there. And the work that I started taking after that tended to be large scale cross firm programs or workout type situations where, things still needed to be fixed and cleaned up. So one of, one of the programs I worked on had to do with helping the bank deal with its mortgage backed securities litigation. So even though. Most people think 2008 was long behind them. Litigation moved slowly and the bank was dealing with a lot of plaintiff lawsuits claiming that the bank had sold them securities fraudulent fraudulently, different sort of legal arguments like that. And I was involved in setting up a team of business people, analysts, technology folks and other strategy types who we're gonna work very closely with the legal team in defending the bank against those against those lawsuits. Keeping in mind that the people on the people, the institutions on the other side were important and continued to be important clients of the bank. So it was a very like delicate process,
Peter Wang:It's a dance.
John Castango:defending the bank, also doing what's right by your client. And figuring out, is there a way to get through this where the client relationship is even stronger than before, as opposed to weakened by this by this litigious exercise that we're going through.
Peter Wang:Yep. And actually it also reminds me, it's a very complicated. Situation. It's not even a one-time event. It's actually over a period of time with the various parties interests, short-term needs, long-term relationships, right? Because we're all gonna coexist still. How did you navigate that? Did you have someone, some people to talk to? What was your, and solve this
John Castango:like JP Morgan, there's always people more important than you, right? No, there, there's always, you always have bosses and there's more senior people and stakeholders from different parts of the organization. There's a board, there's the C-suite, obviously all those folks. Yeah, is, was not a one person exercise at all. I had a boss who was fantastic and one of the best bosses I've ever had ended up being at various times the treasurer and the chief investment officer of the bank. An another person who I didn't report to directly then. As a woman who became the general counsel leader and was a boss in my final role at the bank. So there was tremendous amounts of support from senior people who had a depth of experience, depths of experiences that they could apply. And then there were teams of people working with me and working for me who did a lot of the heavy lifting and a lot of the thinking and the working. So it was a big it, it was a big effort for sure.
Peter Wang:Yeah, and I wanna talk about toolkit for a moment because I feel the toolkit you started with at the beginning and then through the next 20 years on Wall Street. How did that toolkit evolve?
John Castango:Yeah. So fundamentally it's the same, it's the same toolkit, right? It really is. I think the experience adds to that. And refines it. And over time you end up applying those tools in different ways. It's been a long time since I've, done any real statistics, for example. There are other people who do that now and do it better and all of that. But I still carry with me the ability to think numerically and statistically, to ask questions to, of data and about analytics and methodology and to understand more or less what's being presented to me, so that toolkit is still there. I'm just applying it in a different way. I think what's emerged that sort of new is what comes from the life experience that comes along with it, right? These realizations of what might really be important and how a change in perspective can make all the difference and where taking risk actually works to your advantage. And what happens when it doesn't. That only comes with time. It's hard to. It's hard to learn that in school. So the toolkit has evolved in that sense. I think as I, I started to take on more senior roles at the bank and more complex problems to work on organizational problems. I started to realize that tools that I needed to really develop more and that a lot of us need to develop more are those ones that if I went back in time, I would peg to the literature side of my training. The creativity, the empathy, the curiosity of the listening skills, the communicating skills that those were skills that were taking on a bigger and bigger importance in my toolkit for sure, in order to be impactful.
Peter Wang:Yeah. Yeah, that's fascinating. I can tell you relate to that the problem space evolves, actually changes from technical problems, let's say ahead of you, that you can solve on your own to people problems. For the majority, after certain level, it's all about communicating, listening, coming together, being trusted, trusting, but also know the hedge and so on. So that's fascinating that, and that's very hard to learn at school, but it's true. The better writers, though, I do find the more articulated, the critical thinkers that can also communicate becomes a very important skill.
John Castango:And I think you know, a person who is by nature willing to exercise curiosity, just something as simple as curiosity. When you like, pull that apart, there's a lot there. If you are curious, you do not think you know everything. You
Peter Wang:Right.
John Castango:do not think that you have the right answer. There, there might, you might not even have this view that there is a right answer, right? But, so just being curious allows you to be open to all sorts of possibilities that if you're, if you are attached to your preconceived notion of what the right answer is, then you're not gonna be curious. And so why bother if you're curious? People respond with curiosity as well. And so if you're having a conversation with someone and you appear curious and you just wanna understand them and know more about what's going on and hear their perspective, they will tend to be more curious about you and what you think and what your perspective is. And then you have a much richer dialogue and a much greater potential to actually come up with something. A solution or an idea or a way forward that any one individual who isn't curious, might never have gotten to.
Peter Wang:That's such an important point. Yes. Staying curious. Actually, this is probably, I was thinking back to you being a unquote outsider, not coming from the background, but staying curious allows you or allow you to be trusted. Cuz trust is a big thing right? To say, Hey John, can you come and help us with this? That is placing a lot of trust on you.
John Castango:It's also a great position to have if you're thinking about your own career and risks that you might be willing to take. So I got accustomed very early on to not knowing as much as most of the other people in the room about any given topic. And sometimes those people worked for me and sometimes they were my peers or whatever. It didn't matter. I got accustomed to just not being the one who knows the most. And I had to learn that when I was a teacher, which is a little ironic because
Peter Wang:Oh
John Castango:well then you do know, you're the teaching the subject, you're supposed to know more than them about the subject, which I probably did, but I certainly wasn't the smartest person in the room. And I had, and I got comfortable with that. Like I used to say, I love teaching people who are smarter than me. They're like doing my job for me. And there was this willingness from an early on to be like in this position of not knowing and in this position of wondering and being curious about what could happen. And with that mindset, I was much more willing to take jobs. Where someone who was really attached to knowing all the answers or feeling like they were the master of the subject would never have taken. So I took jobs that didn't exist before, so there was no playbook as to how to do them. I liked to take jobs where I was challenged to learn something new and to take jobs where it wasn't really clear what a good outcome would be or what the next step would be after that. But having conviction that we'll be able to find a good outcome and then there will be something else to do is a lot easier to have if you're naturally like curious and don't think that you know everything or that you even want to try to know everything.
Peter Wang:reminds me, what are the barriers to being curious? Why is that hard? It seems so easy for children. For example, I have three kids and they're curious, ask questions. They, and they actually make me more curious because the way they ask questions or I didn't know that was a question, but they presented as a question, make me realize actually this is a question in the statement. What do we lose that? And one of my own hypothesis is, I don't wanna say education, but I think from engineering point of view, as example as engineer, we're trained to come up with bulletproof answers. Solutions. So you lay out all the possibilities from Edge case, from case zero to the Edge case, and that's how we train and grade it on and so on and so forth. And I realize that along the way it's working, was working against me because I have a tendency to solve the problem first, figure it out, sharing it, then have a discussion versus figuring, having the discussion first, then collectively solving the problem. So I can see that's one, at least from my own world, my background, I know it's working against me from a curiosity point of view. I wonder if there's anything else
John Castango:I think that comes, I think education unfortunately can do a lot to squelch curiosity, right? Because people are rewarded for having the right answer more than they're rewarded for having a lot of questions. That's just
Peter Wang:The right question. Yeah.
John Castango:Early on, you get a lot of that. I'm generalizing, obviously this isn't true everywhere, but I think it can happen pretty early on. And then there are certain professions that develop standards that are maybe good for what they are, but don't lead to people developing their curiosity and being willing to show their curious nature. Curiousness is then seen as not knowing and not knowing is seen as a weakness,
Peter Wang:Mm-hmm. Yep.
John Castango:in, in law, for example, in litigation, which I've learned a lot about, the litigators will say, never ask a question you don't already know the answer to. And I'm sure that serves you well if you're taking a deposition or you're in a courtroom. But that doesn't serve you well in the rest of your life because a lot of the questions aren't answerable or no one will ever know the answer to every question. And if you try, then you're not gonna go anywhere or you're gonna refrain from asking questions that, that really would've benefited everyone to be asked. And so sometimes professions build up these standards that squelch curiosity to.
Peter Wang:that's right. That's fascinating. Yeah. Don't ever ask questioning. Wow. That just if you have that filter, how many questions can you ask in life? Interest. Okay, let's skip forward real quick. Actually, that's full circle really, cuz at the beginning we talked about this 50th birthday, The importance of it than that year. Let's talk about that.
John Castango:Yeah. Yeah. My 50th birthday would've been in Oct was in October, 2020.
Peter Wang:Mm-hmm.
John Castango:probably a year and a half before, little two years before my husband said to me one day, you're miserable. making me miserable and you need to fix this, and you don't know him. And so you don't know how shocking this sort of a statement is coming from him. But it's shocking cuz he's not, he's a very non-confrontational purpose person. And I don't think he's ever read me the riot act before. And so I really took notice of that. Wow what am I not. Seeing here. And yeah, I knew that, work was hard and I felt like I was a little bit in a little bit of a treadmill and all of that. But he really encouraged me to say are you enjoying life? Is this fun for you because you're not acting like it? And and to say you need to do something about it, which was a good call to action for me. And what I decided was, you know what, there's more that I can do. I have a good career here at the bank. There's gonna be no shortage of problems. If I wanna be the person who gets sent in to solve problems, I can do that until I retire. But what else might there be? And so I set on this path to figure out, what else might there be? What else? Might I want to do. And tried to separate, fantasy from reality in that as well. And so it was a several year process, Peter, of detaching from what I was doing and attaching to something new. It
Peter Wang:And. That took a year and a half, a year
John Castango:a couple years. Yeah, it took a couple years. I gave my my boss a good amount of notice. She does not like surprises, so I didn't surprise her. And planned to leave in early 2020 and because of the pandemic and other things, it's, we pushed that out by a few months. But I left the bank in September of 2020, so just shy of the birthday mark. So I gave myself that gift right on time and then took a year. To figure out what I wanted to do next. And I was very deliberate in that. I knew myself well enough to know that if I didn't give it some time and distance, that I would probably just say yes to another job in banking. And if I was gonna have another job in banking, I wanted to be sure that I was, I had looked at all sorts of options and I was choosing that deliberately, not just being pulled back, by this sort of gravitational field. And so getting far enough distance so that I could see the landscape well, as well as resist this sort of natural pull back into the thing that I had been doing was important to me. And I gave myself a year for that.
Peter Wang:Yeah. I actually, I love that analogy of the gravity because I think all of us are being impacted by different gravity forces, but we're not as aware of them. Career is definitely is one. There's a sense of inertia, the sense of gravity and getting far away from it takes time, takes effort, mind, space, actually. Not beyond my aspect time. Even people you talk to, cuz we tend to talk to the same people, then you're still the same circle. It's still in that world to get away from it. That's all. Some people are literally traveling, right? They say this is six months sabbatical and so on. To get, then come back and say, okay, what's my new perspective after being away? Um, I think a lot of people can relate to that. So now for you, when did coaching emerge to be an option for you?
John Castango:Yeah. So during that first year away, I had told people. Don't even call me with job opportunities. I'm gonna say no to everything. I don't care what it is. So that I could get that space, the pandemic was right in, in full tilt at that time. So we didn't do a lot of the traveling that we wanted, but I did have a lot of time to spend at home and read and explore sort of areas of my life and being that I hadn't touched in a long time and I went down a few dead ends around what I wanted to do next. Cuz everything seemed like a possibility. And since I wasn't talking to people about specifics, it just was too general. I took a different approach one day about, I don't know, maybe about July or August of that first year being away. So towards the end and I thought, look at all of my career to date. All the different jobs, which we've talked about a bunch of them. Some are very different. Being a high school teacher, being an actua consultant, working on Wall Street, being a banking executive, being involved in litigation. All these things were very different. But is there something about each one that I liked? Cause I liked every job or I liked every career role. What did I like? And is there a common thread? Because if there's a common thread here that should, that's good data, that should tell me something about who I am and what I might wanna do next. And I'm so glad I took that approach because what immediately popped out was I loved the opportunity to work with people who were at some sort of developmental cusp in their life or in their career. And to help people through that to guide people through that. And the mode took. On different forms. Sometimes I was a teacher, so it's obvious. Other times I was a manager and I happened to be a manager who took a lot of interest in people's careers and tried to help develop people on my team. Other times it was, a more senior person, a manager of managers or someone who was involved in mentor programs or what have you. But that was the part of the work that always really got me excited. And when I look back on that, I'm like, wow, that was fun. I love that part. But other than the, education classes I took, in ancient history, I hadn't really ever been taught how to do this stuff. I just did it. And it was never like my full job. It was just part of what I took on as part of my job, right? And so I thought, okay, here's my idea for my second year away, go to school to learn more about this, whatever this is, and investigate whether it's something you would want your job to be a hundred percent. And that led me to coaching very quickly because, this is what coaches do. It's a different mode of delivery than giving advice or consulting or managing or what have you. But it's the same sort of thing, helping people who are at developmental cusp in their life or career, make that step. So I went to school at the Hudson Institute for Coaching in Santa Barbara at a program. It was about a year long part-time program where I learned a lot about, adult learning and development and psychology and stages of life and all these things. And also got a sense of what it would be like to be a coach for a business.
Peter Wang:mm.
John Castango:really just got attached to that work. I love it. It's fun. I enjoy working with people. We get to do remote sessions. I meet people in person and it's just been giving me a lot of excitement. It's also allowing me to work on my life goal, right? My current life goal is to have more fun, right? I am tasking myself with developing this business and this new career, but doing such in a way that it supports my life and my life goal. For the last 30 years, I've designed my life to support my career goals in a way, right? I lived my life based on what my job required of me. And I'm flipping the script a little bit at this point. And that's my own challenge cuz it's easy for me to think, I'm gonna dive into this and beat the crap out of this and put my life to the side. But I'm not doing that this time.
Peter Wang:My mind went back to that gravitational analogy where your life was orbiting around career versus. Life is now in the center,
John Castango:Yeah. Yeah. It's a Copernican revolution,
Peter Wang:Yes,
John Castango:We're now revolving around the sun, which is the life and the career is gonna support that. And, I do want to say I have a lot of gratitude and humility about this, and the path that I've taken. It is easy to look back on it and say, oh yeah, this makes a lot of sense. And boy, it was all, such brilliant thinking and strategy and so on. Reality is there are a lot of steps that you don't know how it's gonna go. And it may or not have been so brilliant, but, it's gotten me in places that I like. The gratitude comes from having the opportunity, the safety net. The economic flexibility to take some of these stages, take some of these risks that I've taken and I recognize not everyone has that. And so in coaching it's about trying to find what people's goals are, understand what holds them back and what might be in the way. And helping them release as much as bad as possible at the same time as drawing on the innate resources that they have, but recognizing everybody's situation is different. And while they can't necessarily take the exact same path as someone else there is a path to take and there are ways to advance through that. And a coach's job is to help discover that.
Peter Wang:Yes. And as you were going through how you help people, it reminded me of that framework at the very beginning. You said three things life goal, toolkit and the first step. Does it feel like you're actually applying that framework when talking with people? Like what is your life goal right now? What's your toolkit? What can you draw from? What you need to add, and instead of first step to that goal. It's very, it's interesting. It's almost like a full circle,
John Castango:Yeah, it's exactly that. And people have such a rich toolkit as adults, especially, people I work with are successful adults. They've had good careers, they've raised families. People are resourceful and they have a lot in their toolkit. They don't always see it. And people can be sometimes a little disassociated from a life goal. So asking people what their life goal is. Sometimes that's the coaching work is to even figure out what your life goal might be right now. And in terms of the step, folks sometimes get over overly concerned about what all the steps need to be, as if there's some way of mapping out every future step. And so yeah, we work on what would one step be that you could take now, right? Let's not be overwhelmed by the questions of every step, but what are some steps? What's the first thing you can do? What small step can you take? And just those simple approaches can help people see the path more clearly.
Peter Wang:Yeah. My father-in-law, like to say one foot in front of the other, like that feeling, it's actually hard. I personally have struggled with that too because I tend to like to see, predict map out scenarios and when it's life, it's really hard to map out scenarios, especially as you get older actually, because a number of paths and the
John Castango:There's so many. What's interesting is there are so many possible paths, right? And there always were, it's just as we get older, they, it seems more complex and we see more burden down with, a lot of things. And shedding some of that weight and being a little having more conviction about the ability to find your way as you move forward is sometimes all it takes to really get people to propel through a feeling of being stuck.
Peter Wang:Yeah, culture a lot of times make you doubt yourself. If you look at self-help books or magazines, right? It's all about how they have achieved their world. so much better way. Therefore, here's a gap and you need to do all these things to get there. So meaning you never apply enough. Versus is the opposite of, okay, I do have skills, I do have resources, I, I can, and I have and take stock of that. It's actually easier for kids to write down those things than for adults, ironically. You talk about your husband giving you that kind of jolt that you needed. How has coaching helped that relationship in your own personal?
John Castango:Okay, your question presupposes something.
Peter Wang:Yeah. Oh, you're right. I should stay curious. I should reframe it.
John Castango:so how has that helped? We have to ask him maybe. I think that without question coaching has made me much more self-aware and so much more attuned to what's going on internally. What's going on internally might be impacting what I'm saying or doing, or act how I'm acting. And that self-awareness is of great value in any relationship, right? Especially one as fraught as like with your spouse. So I think in that sense coaching has been helpful. I do have to try not to coach him. It's easy to fall into this realm of oh here you need a coach, and how about I coach you right now? And, and remembering that's not always helpful or what's needed. And I assume any sort of helping profession has this, has this sort of tension in it. So that's been new for us to work through. But the self-awareness on my part I like to think can only help in any relationship.
Peter Wang:Can In all of us. A hundred percent sir. And I'll go back to the question. Cuz I was thinking about the three things, right? The life goal, the toolkit and first step, when people have a hard time coming up with their own life goal, what do you say to them? How do you help people? It can be so overwhelming. What is my life goal?
John Castango:Yeah, this can be a lot of work. For some people it can be a lot of work. So it's hard to, it's hard to boil it down. But one useful distinction for a lot of people, especially in the sorts of professions that you and I have come out of, is to distinguish between achievements and aspirations. So achievements are time bound things that we can get that others will see, a promotion a certain title, a certain amount of money in the bank, a type of car, whatever, right? These are sort of achievements. Nothing wrong with achievements and achievements can be motivating. And they should be, but an achievement is not a life goal. So a life goal is more of an aspiration. It's a way you want to be. And it's different. It's not something you're just going to get to at some point and make a mark. It's a way that you aspire to be, which is a continual, like a continuous thing. I want to be financially independent that's, yeah, sure. You can feel like you've gotten there, but there's a lot to that. I want to be a great parent. And good son, those are life goals. It's not like you get that mark and then you're done. It lasts. And for a lot of people, they have trouble answering the aspiration question without just giving achievements.
Peter Wang:Because we're so used to.
John Castango:We're so used to being conditioned. I'm trying to get this thing and the lie is, once I get that thing, I'll be happy. Or once I get that thing I'll be satisfied. But achievement always needs more. Cuz once you, every time you get a raise, how long before you think you deserve another raise? Right?
Peter Wang:Yeah. For Gen Z. I'm kidding. No, this is difficult.
John Castango:And part of the work is to help people understand what do I, who do I want to be? What do I, what am I aspiring to be? And independent of what I should be as someone tells me I should be, or what someone needs me to be or what I want to achieve? And developing a sense of that can be an important first step in
Peter Wang:Yeah,
John Castango:lot of this work.
Peter Wang:and that goes back to your point about being curious because we're so used to people telling us, and a lot of times our actions and our decisions are subliminally affected by people's expectations of us, and therefore that's why we do it. So let's bring this to a close. Thank you so much for sharing your story and a lot of learnings. If people want to contact you, John, what's the best way for them to reach out to you?
John Castango:Yeah. So the easiest thing to do if you want to reach out to me is either to email me, I'm at john a connected coach.com, or even better go to the website, a connected coach.com, and my contact information is there and there are ways to get in touch with me. And I welcome that. I'm also on LinkedIn. I'm the only stango on LinkedIn, so I'm very easy to find and I monitor that. And that's a good way to communicate as well.
Peter Wang:And we'll, I'll include that in the show notes as well. Any last words of wisdom? For the listeners out there.
John Castango:Yeah, I think what I would love people to know and by this I mean it's a general statement. It's not only true for executives or people who have at the end of their career, this is true for everybody, is that, you have more agency and freedom and potential in your future than you might think. And you've got the resources internal and external that you can draw on. And the irony is, the more successful people are, oftentimes the more complicated and harder it is for them to see all of this potential because they define themselves more and more narrowly over time and get boxed in by their expectations. But there's just tremendous potential in all of us, and you can see that by looking at things from different perspectives and by taking steps, like start taking some steps and see where they go.
Peter Wang:That's a very powerful, and that goes back to achievement versus aspiration too. Cause we get boxed in by achievements and we can't see what our aspiration is, which is actually what should be the gravitation force that drives, that poses forward. John, thank you so much for your time today and um,
John Castango:This has been great. I love talking about these subjects and happy to anytime.
Peter Wang:great. Take care and hopefully this will be a great episode for our listeners to
John Castango:I look forward to it.
Peter Wang:Take
John Castango:All right. Thanks Peter. Bye.
