Building an empowered career w/ Jean Hsu & Cate Huston #261

Speaker A: Yeah, I think it's kind of darkly funny that ICs are like, I would be better as a manager and the managers are like, I would be better as an ic. And it's like part of that is just these walls are being completely squashed. You know, like a lot of the kind of AI based dev I do feels more than ever than being a manager. It's like, did you test that? How do you know it works? Why did this incident happen and how do we make it not happen again? Like, I used to ask these questions to developers on a much longer time frame and now I ask them to my terminal. But like, they're fundamentally the same and like one of the things that we are seeing with like, let's call it a productivity, individual gains do not translate to team gains and that is fundamentally a management problem. If you as a manager think that you're not responsible for that bit because you're not writing code and you're not doing your job. But then similarly, as an ic, if you think your job is to generate the code and you haven't figured out how to transform the output into impact, then you're also not doing a good job.

Speaker B: Hello and welcome to the Engineering Leadership Podcast brought to you by elc, the Engineering Leadership Community. I'm Jerry Lee, founder of eoc. And I'm Patrick Gallagher and we're your hosts. Our show shares the most critical perspectives, habits and examples of great software engineering leaders to help evolve leadership in the tech industry. One of the most powerful quotes that came from our conversation today is work life. Balance isn't about doing less work, it's about doing more life. In this episode, we're joined by Gene Hsu and Kate Huston to talk about how to build an empowered career. Gene and Kate are both engineering leaders who've transitioned into building a career portfolio of, ah, really interesting, interesting projects that to me represent the biggest opportunity and shift for engineering leaders right now. And so in our conversation we talk about this identity crisis intention that engineering leaders are facing with their careers right now and how to get clarity and build an empowered career. And so with us, they share the questions, the prompts and the experiences that have been instrumental to them as they've built out their own career portfolios. Let me introduce you to Jean and Kate. Kate is the author of the Engineering Leader, Fractional, CTO at TWIL and Engineering Leadership Coach. Formerly, Kate was an engineering leader at DuckDuckGo and automatic. Jean is a builder, writer, coach and fractional engineering leader at early stage startups. She was previously in leadership roles at Pulse, Medium and Range, and also built out a leadership development company focused on engineers amidst, um, their portfolio of different projects they're working on right now. They co founded DRI your career, a series of async courses to help you take control of your career with clarity and intention for listeners. They also offered a special discount code. So if you're Interested in exploring DRI your career, you can use the code ELCPodcast for 15% off any of their three courses. And we've got a link to DRI your career in the show notes as well. Enjoy our conversation with Gene Hsu and Kate Huston. Gene, Kate, I just want to say welcome. Thanks so much for joining us, uh, on the podcast. I wanted to kind of frame our conversation a little bit, uh, and why I've been really excited. So I have this hypothesis that AI is fundamentally shifting, like what a career looks like. And the way that you two are working right now, to me, represents a lot of what the future for engineering leaders may look like. My bet is that in, like, the next 12 to 18 months, there's going to be a lot more people that can explore more options like this, more, more creative career pathways in this kind of way, or maybe driven to because of some of the other more macro forces that are shifting things around in terms of what careers look like. And I mean, like, to summarize it, I also just think that the projects you both are working on are really co. Uh, and I think they also represent the future skills and capabilities that engineering leaders need to have. So there's sort of like these meta layers of, like, trends. And I think what you do, you two are doing also represent what it means to be an engineering leader now and into the future. What's your gut reaction to sort of

Speaker A: that synthesis, uh, Mao panic? Gene, I think he's saying we're trendy, we're trendsetters. Yeah, exactly.

Speaker C: Not face setters. Trendsetters.

Speaker A: Yeah. But I was telling Jean this yesterday that I think she makes a great fractional person because she's high confidence and low ego. And I do think that that makes many more options available to you when you're not trying to, like, hold onto something too tightly, especially when that thing is just going away.

Speaker C: Yeah. It's built into the engagement. Right. And like, I'm kind of like, you know, I'm working with the company two days a week. I think I'm doing a good job. Like, I think they do. They think I'm doing a good job, but, like, you know, If a month in, they're like, it's not a good fit. I'm like, when you get to a certain level in your career, it just feels like there are places that are a good fit. And then if it's not a good fit, it's like, cool. Wasn't a good fit. You know, like, there's still things to and learn. If it's not a good fit, then I don't take it that personally. Just how I've developed my career and what a company needs, I think maybe

Speaker B: to continue to frame maybe some things that people are experiencing. Uh, one thing, one idea that you and uh, we, us three were talking about was this sort of maybe identity crisis or this FOMO that people are having sort of across the engineering leadership and engineering function where there's this sentiment that if you're an IC that you probably feel like, oh, shoot, I wish I was an engineering manager because maybe that will give me more stability. Or if you're an engineering manager, you're like, shoot, I should have been an IC or I need to be an ic because that's going to give me more stability. And it's this weird sort of paradox where it's like everybody's sort of thinking like, oh, I should be doing this other thing because that's going to be, quote, unquote, more defensible or quote, unquote, more durable. Um, so I don't know what you both are seeing or how you might sort of name some of the experiences going on there. Like, what are your observations around that sort of sentiment?

Speaker C: Well, I think the upheaval is bringing up a lot of like, oh, did I set up my career well enough? Like, what if I had done this instead? So I think the overwhelming upheaval in the tech industry is bringing up these questions for a lot of people. And those questions have come up before, you know, regardless of AI. And yeah, but I think like, it's kind of this grass is greener of like, yeah, ICs are hoping they would be EMS. But I mean, the truth is I think anyone with engineering background is well equipped to navigate this shift. And this is one of, in one of our courses about navigating the AI shift. But like, engineers are trained to be adaptable, to learn new things, to learn new technologies. And I think it's easy to kind of forget, get that, especially when everyone's kind of forced to go through it at the same time, whether you're ready or not. So, yeah, those are just my, my thoughts on the, the shift.

Speaker A: Yeah, I Think it's kind of darkly funny that ICs are like, I would be better as a manager. And the managers are like, I would be better as an ic. And it's like part of that is just these walls are being completely squashed. You know, Like, a lot of the kind of AI based dev I do feels more than ever than being a manager. It's like, did you test that? How do you know it works? Why did this incident happen and how do we make it not happen again? Like, I used to ask these questions on a much longer timeframe and now I ask them to my terminal. But like, they're fundamentally the same and like, this also comes to like, one of the things that we are seeing with like let's call it AI productivity is that individual gains do not translate to team gains. Right? And that is fundamentally a management problem. If you as a manager think that you are not responsible for that bit because you're not writing code, then M, you're not doing your job. Right. But then similarly, as an ic, if you think your job is to generate the code and you haven't figured out how to transform that output into impact, then you're also not doing a good job.

Speaker B: That sentiment that you're talking about of like individual productivity versus team productivity and like people, I guess, like misunderstanding their job, I think is so interesting because that almost seems like something that's been existing for a long time is that like people maybe don't necessarily know their job. I don't know. Like, what do you think about that?

Speaker A: Yeah, I mean, this is something that Jean and I talked about a lot in the em, um, course. Sorry, the engineering manager course. We put together and we really argued with each other in a productive, fun way until we got to this definition. Definition of NEM is the force multiplier of the team. And then this is what's interesting to us, like running the first cohort is the feedback on that is like, oh, wow, now I know what my job should be. Because nobody told them. They're like, your job is these eight people. Sure. And then what, you know, and so, uh, you. I think with all of it, we have to think about like, what does it turn into? Right? And the way that tech talks about things and like, in particular, the vanity metrics really take us away from understanding the actual impact. Right? So in the ZURP era, number of people was a vanity metric and it was a bad one. And now token spend is the vanity metric. It is also a bad one. You know, and what is interesting to me about both of these things is they're both input metrics. They have nothing to do with output.

Speaker C: Yeah. And I think it's a lot of um, how people think have thought about their own identity too. Like I was just telling Kate that I had, you know, tried to see if a friend of mine was interested in a role that I had come across and this friend was like, oh, I'm looking for engineering leadership roles of like 50pluspeople.org. This was a few years ago and I was like, oh, never mind, this is only a 20 person org, you know, and like that was the thing they were looking towards like the number of people in the org. And like, you know, going back to what Kate is saying, like I fundamentally don't care about that also because I don't have an impressive number. Because I don't have an impressive number. I like, you know, my own self defense part of myself is like, well that's not an important number. Let's just like do whatever makes sense for, you know, early stage startups. But yeah, I think it is fundamentally changing and having this like thing to focus on which is like ems being a force multiplier is like, that's going to be true regardless of what the tooling looks like, what your team size looks like. Right. I mean I think it's going to be challenging to be a force multiplier if you're managing 30 people. And that's kind of the model that some of these AI companies are proposing. But it is something that you can anchor to and like, okay, what do I need to do to be a force multiplier for the team?

Speaker A: Totally. I mean it wasn't just some of the thinking is so flawed. Right. Like the um, Jack Dorsey Sequoia VC post that was basically like middle managers are no longer needed pages of military metaphors. The middle m. The job of middle manager was routing information. And that is no longer relevant in the AI area. And I'm like, okay, sure. But like why is it AI that changed this and not when we like got the Internet and moved away from carrier pigeons? You know, like, it just doesn't make sense to me, you know, like, and so like there's just so much flawed reasoning that I'm like, okay, well I don't think this is true. And like it's very hard to find things that I think can be true unless you start coming back to the core principles which to Gene's point is like, as engineers we are trained to learn and adapt and we can learn and adapt again. And yes, it Kind of sucks when the learning adaption is forced upon you, but you can do it.

Speaker B: One of the main questions that I wanted to explore here because as you're talking about this, there's like getting back to the truth and like the core principles of what it means to be an engineering leader and also describing this sort of paralysis or confusion or these like shifting things that make it really hard for people to kind of reason, where do I go? What do I do next? Like, I don't have these like proxies of success that I used last time. Like, I can't look at like my org progression as the key indicator that I'm moving along in the ladder in this quote unquote right way. I'm using a lot of, you know, these kind of eye rolling metaphors for a reason. But, uh, I think this big question is like how to give people clarity and build an empowered career versus sort of sitting in this analysis paralysis. And a lot of people that in myself included or people really close to me, really get stuck in this like analysis paralysis of like, wow, things are moving so fast and things are going to be so different, but I don't know where to go or what to do. And like you just then sit and then things move around you and you don't know where to go. And so I wanted to kind of get a sense of like, you know, you both spend a ton of time thinking about what does it mean to have an empowered career, are spending a lot of time thinking about what does that mean right now especially. And so I wanted to get a sense of like, can you help sort of deconstruct what does an empowered career look like versus analysis paralysis? And like what people are experiencing right now. Like, can you speak to maybe that tension?

Speaker C: I'll uh, just start by saying empowered career sounds like such a huge thing. Like, oh, I gotta figure it all out, right? And I think one of the things that we do in our course DRI your career is to break it down. Like, okay, what are like just 10 things you want, right? What are like 10 things that you want? Could be work, could be outside of work. And just helping people become more and more attuned with what are the things that they intrinsically want? Because I think in the absence of that, it's just too easy to gravitate towards, okay, I'm going to move up the career ladder. I'm going to move, you know, into these bigger and bigger roles at larger companies. And the truth is that career ladder is getting, is like kind of getting Thrown out the window, right? Like, you would kind of float up it in like, 2018 to 2022. Right. Like, you kind of stick at a company, the company grows, the VC money is flowing. Like, you just kind of flow upstream and you get paid well, you get the amazing benefits. And now that's all getting thrown out the window. People are having to or they don't have to. But I, I think the path to an empowered career is to help people figure out what it is they want, figure out what they value. And so a lot of our work is like, helping, you know, doing values, discovery with people, um, helping them just figure out what it is that they care about. And then when they have those building blocks, then the next step feel a lot easier.

Speaker A: Part of that is when things are difficult, people start to look at what they can control. But, like, you could never really control capitalism. It's just when capitalism wanted you to believe it and when it benefited capitalism for you to believe in it, then there was this illusion of control, as you like, to Dean's point, floated up the career ladder. But now that stops happening and people like, how do I control it again? And, like, this is really our message. It's like you never, you didn't control it before, you don't control it now. If you want to feel empowered, you need to look at where you do have control and exert the energy you have in those spaces. Not in places where you have them.

Speaker C: Right. Not at work, where you're going through your fourth reorgan riff of the year. Right. Like, redirect that towards community projects or whatever it is that actually gives you energy back.

Speaker B: I'd love to get a couple stories from you both about what it looked like to get that clarity for your own career journey. I was wondering if you could maybe speak to some of that process of starting to get really attuned to what you want and then starting to orient around those things that you identified that you could control. Bring us in your journey. That's the, that's what we want to know.

Speaker C: Yeah, I think first of all, you need a little bit of space. It's hard to have space to explore and be experimental if you don't have any space. Right. So one of the things we talk about with our, uh, participants in our courses is like, how do you just, like, figure out your energy management so you can have a little bit left over for yourself? And so for me, that was leaving my last startup a year and a half ago and was like, okay, let me, let me take a few Months just figure out like kind of reset. After my youngest started preschool, I started to explore a little bit with tools, built like a few small apps, including like a community lending library and was just like very open minded with it of like, hey, let's try this thing out. And then sometimes afterwards I'd be like, oh, I didn't actually enjoy that as much as I thought or some things I would do, you know, spend a few hours doing something and then realize, oh, interesting, that was energizing. I want to do it more. And just being very like curious about it. Like at some point I was like, oh, I think I'm going to restart my coaching business and like build out, you know, get like maybe 10 clients. And even though I had that plan, I literally never told anyone I didn't post on LinkedIn. You know, I just didn't do the things that you would have to do to build out a coaching business. And I didn't beat myself up for it. I was just like, cool, guess I don't want to build out a coaching business. Like, where is my energy drawn? Because there are a lot of options. And so, um, fractional work was kind of similar where like, yeah, I took on a small engagement. I was like, I've got about eight hours a week. I mean the nice thing about fractional is like, no one actually knows what you're doing with the rest of your time and like a full time role where they can see your whole calendar. So I was like, hey, I've got eight to ten hours a week and tried it out, like enjoyed it and was like, okay, let me try on like a larger engagement. And it just is always kind of in flux. Like I don't really know what I'm going to be doing. Even now it feels like, okay, I have this empowered career. I still don't know what's going to happen in six months or a year. Right. Like, I think you have to be very comfortable with that ambiguity and trust that you'll figure it out.

Speaker A: Okay. Just to give you a totally different take on things, I guess that's perfect.

Speaker B: I feel like that's the best. The best way is to like to show how different.

Speaker A: I could tell you like a similar story, but I think, you know, a few years ago I was not really happy in my job. I didn't feel like I was learning. Yeah, I was just like, okay, like, what's going on? I tried interviewing elsewhere and then I realized it wasn't going to be better. And part of the reason why it wasn't Going to be better was because I have mainly worked in weird environments and my narrative about what I did, what it was that I was doing was not working. Right. Like, I had the other side of Gene's friends conversation where I talked to somebody and they're like, how can you be a director when you don't have at least a hundred people? And that company did a massive layoff. Dodged a bullet there. Um, and I decided that if I needed, if I wanted to, like, take control of my career, I needed to hold something back from my day job, which was really inclined to, like, suck everything out of me and do something where I could craft my own narrative, right? And this is really where I wrote my book. And in order to retain the space to write my book, I did not tell anybody at my job that I was writing a book until I had basically finished the book. Because as soon as people saw that I had capacity to write a book, it was like a, uh, lot more work landed on my desk. So I think doing it in secret was relate the strategy. But yeah, I, I thought about it. Like, I blocked off every Saturday to write my book, which meant. Because I couldn't just be like, oh, uh, whatever, I'll do the laundry on Saturday, whatever. It was like, no, on Saturday, I'm writing all day. And so if I need to run that errand, if I want to, like, have a social life, if I want to, I need to, like, draw some clearer boundaries and work, you know, not overwork, pleasing capitalism. I have to save something for myself.

Speaker C: Yeah, this reminds me of something you said earlier. Not earlier in this podcast, but earlier with me in general, which is like. Like, a lot of times people talk about, like, work life balance is just like, working less, but, like, figuring out what you want to do with the time outside of work. And then, right. Like, maybe it's like, oh, you have a really busy week. My natural tendency would be like, oh, let me not do any of the things for myself because it's such a busy week, right? But it's like, no, those are the weeks you need to schedule dinner with friends or, like, maybe a yoga class or something. So then you have something that you're looking forward to and, like, that also helps create that balance. But, yeah, creating that space to do the things you like and just constantly practicing that, like, okay, what is it that I'm drawn to? What gives me energy?

Speaker A: Totally. And, uh, like, you don't get work life balance by doing less work. You get it by doing more life. I know this because I worked In a wildly dysfunctional environment where the CEO is regularly the main character on the Internet. And there were people there who would just lose their minds. I was probably one of those people. And there were people who just managed to kind of maintain their equilibrium in the face of that. And, like, when I would talk to them, they'd be like, well, at the end of the day, I have my cats, I have my partner, I have my house, I have my cycling, I have my whatever. And I was like, oh, light bulbs went on.

Speaker C: For me, work is the way the work fits in. Their life is, like, much more boundaried and yeah, with different things.

Speaker A: Well, they have it. They have it in its place. They don't. I see their identity as their job. They see themselves as a person who happens to work at this place right now for like, more than a decade. Right, like, and yet they have not lost their minds because they have this broader identity outside of this environment.

Speaker B: Eric Rees, who wrote the Lean Startup, is coming out with a new book called Incorruptible. And it's like, how to build organizations or institutions that kind of are just like, not corruptible by outside forces, oftentimes, like the financial forces, sort of like these extractive forces like private equity that come in and disrupt your company and destroy the mission and, like, extract as much value as possible. One of the things that he was kind of talking about that I think really mentions, like, the power of space that you both are talking about. Well, I think the other side of it is like, you know, and talking about work life balance. Like, his argument is that, that we're not just in this era of shareholder primacy, where companies just exist to give returns to shareholders of the companies, but we are in extraction primacy, where these organizations get corrupted by these forces so that they just extract as much as possible from all of the different stakeholders. That's his argument. And he has a. His whole book kind of talks about them, like, what should you do about it? But, like, one of the small things that he had mentioned was like, you know, for you as an individual to create space, you have to think about, like, what is. He might have called it like his. Your ethical ceiling. Like, he was like, talking about assessing your salary and how much extra that you want to work, work. And he was like, you should think about, like, what is that actual ceiling that you need for, like, the life, the type of life that you want. And then don't do any more than that and give yourself that space so you can invest in your community, you can do these Other things that create more life. And so like, as you were talking, Kate, and you were sharing that quote, I was just like, so struck by like how you get work. Life balance isn't by doing less work, it's by doing more life. And I was just like, wow, like, like that is it. Um, so I know, I was just sharing that because, like, this is like this theme has come up to me twice this week of like, create space and do more life. So I don't know, I was just reacting to a few things that you both are sharing.

Speaker A: Are you gonna space and do my life then? Patrick?

Speaker B: I. I bought a surfboard. So, uh, there's, there's that. And yeah, I was just kind of writing down like, what are my rules? What's my manifesto in. In like a, uh, you know, a period of, of time off that I'll be taking. And it was like one was like, create over consume. And then I put like in parentheses. Like, no YouTube unless it's like in service of learning or the things that I want to create. Like, if I want to watch a YouTube video about how to collage my coffee bag art, like, I'm gonna do that because it's in service of creating. But then there's like some other stuff. But, um, I think that's something that's been really hard is because I have been working in a space where it's in service of a goal. But then oftentimes, uh, my trade off would be is I will spend all of my time on that and no time on cultivating life. And then all of a sudden you zoom out and you're seven years into it and you're like, you blink and you're like, I missed life. And so I just think what you both are sharing about how to help people identify what is it those things in life that they want to do to me really resonates. Obviously I did something cheesy. I wanted to share. I didn't know when to bring this up, so I'm going to bring it up. I did something cheesy. Um, so in service of DRI your career and building empower powered careers, I wore my favorite shirt that says, like, find your true north. Uh, and so, um, I was like that because that's it. Like, it's like, what are those things that like, you want to orient your life around and develop that, but it

Speaker C: could be really small. And I think it can sound daunting if you don't know what you want. I mean, I remember a time when I was just like, Overwhelmed with my three kids and just like, nothing sounded exciting. And like, it could just be little things like, oh, I'm looking forward to, like, making this meal, or like, I'm looking forward to having this conversation. Right. Could just start with really small steps or like, I want to create more space to go for hikes on the weekends. Right. Like, it can feel like, very daunting to be like, I'm going to have an empowered career. So just remember that you can start with really, really small steps. And then they do add up.

Speaker A: Yeah. I mean, the empowerment is also about what decisions are available to you. It's not really about whether or not you make them. And this was. Yeah, I mean, I think, like, Gene and I've talked a bit in DOI about, you know, my side of projects reached escape velocity. I, like, quit my job after our first cohort. But, like, everything I quit for had been going for like, at least a year before that. And that is how I created optionality to myself so that when the time was right for me, I was at choice.

Speaker B: Can we break that down a little bit more? Because I think that's a pattern that maybe on the outside, for somebody who's never started to cultivate those types of interests and experiments ahead of time, like, it may just seem so foreign. It's like, oh, how will I ever have capacity to even experiment in that type of way? Like, I'm thinking of, like, that barrier for people. Like, can you break down that cultivating that time to start to set the seeds for what the future projects that you're really excited about when they start to take cold.

Speaker A: So 2020, I took coactive coaching training. Um, because it finally went online, I didn't have to go to London to do it. Also, it was like, way cheaper. It was much more accessible. So I think I finished it in like 2021, maybe 2022. I started writing my book, which came out in 2024. I had, by that time, like, had my tiny coaching practice, which I called my profitable hobby on top of my work for like, multiple years. And then I had a book as well. Around the time my book came out, actually, I connected to Michelle, became an advisor there. Jean and I were talking about, I think the end of 2023, we started talking about, like, do we want to do something? And we were both kind of maxed out. But yeah, we just started having this weekly call where we're like, do we want to do this? Do we want to do that? And like, working through all these ideas. Right. And so then you Know, we shipped DRI in December, and then, you know, we put up a second course in March, and we are, uh, shipping our third course in May. And like, it seems like the momentum is like, really good. I mean, it is really good. I'm very excited about it because we have more time for it now. Right. But also it was like we spent a year, like, building all this force.

Speaker C: It's like a year coming.

Speaker A: Exactly, exactly. And now we, like, you know, because we have this framework and we have this way of working together and, um, we have this clear point of view and we know what we're doing. You know, it's like, like the last year was like an iceberg. Right. And now there's more above the surface. But, like, it was all being built

Speaker C: along and there was a lot of back and forth about like, I think we started off with like, Kate, because you had just, you had gone through. We had both gone through coactive training. And, you know, we had started with, oh, we'll have half day zoom workshops. And then we just made no. Similar to my co. My. My hypothetical, uh, coaching business. We just made like, zero progress on it. And then like a few months later we're like, yeah, I guess we don't. Neither of us wants to run half day zoom workshops, nor do engineers want to attend the half day zoom workshop.

Speaker A: Exactly, exactly. And so the format, the format was like a big unlock for us. And now we can just keep producing because we found the right format. We love it. And so we are now much more efficient in our, uh, discussing ARC for a few weeks, arguing about it, and then when we get to the arc, we ruthlessly execute.

Speaker C: Yeah, but I think it's hard for people who are used to being maximally productive and efficient to take that space to experiment without feeling like letting themselves not be super productive in that experimentation. So I had this framework, kind of different hierarchies of spaces where I realized that first I need to just not be exhausted. If you're exhausted, if you're like, okay, I've got an hour, like, I'm maxed out, but I've got this hour, or like, I have half a day off of work. And then people have like all these ambitious plans and you're like, literally just exhausted, right? You first, you need to have space to just be exhausted. Go take a nap, like, go lay on the floor, whatever. So, like, first for me is space to be exhausted. Once you're not exhausted, then you need space to do whatever. It's easy to be, to feel guilt around, like, Oh, I just binge watched the show on Netflix when I could have been been building my side business, right? Like, whatever. Just give yourself time to do whatever you want, whatever feels good, and then, like, space for joy. You know, the little projects that maybe you just want to do, you have no idea where they're going, or you want to, like, make something tasty for yourself, like, whatever, whatever brings you joy. And then I think once those have been somewhat satisfied, I find then I have space to be creative. So, like, if you have space, don't think, oh, I'm gonna just pop right into, like, being a creative person. Like, you kind of need some space, like, let all these other things out of your system first.

Speaker A: Capitalism is not very creative. You know, when I first liberated myself from my job, I was like, so excited, you know, I might have a new idea. It's like every few weeks. And now I've had at least three ideas in the last week. And like, it's like, oh, okay, like, this is when you can do something with your ideas, you end up having more of them, right? But when you can't do anything with your ideas, then you don't have that many. Right? And so this is the kind of momentum piece of what Jean's talking about is like, you know, when I, uh, left my job and I'm like, we're doing this. I'm like, okay, I think I have like three ideas and we'll just have to do them all, and then fingers crossed, something will arrive by the time we get through them. But, like, that's just such a limited way of looking at things, you know, like, now we have so many more ideas.

Speaker B: I find that when I'm in a space where I'm talking to people about ideas, though, it also then inspires or gives me permission to think more creatively. Is that like, that exchange, though, is also a gift? Because it's not just like, you know, that person is sharing your idea and they're looking for validation or creative partnership or whatever. But in a lot of ways, like, it's also inspiring you to go down that pathway for yourself too. And I think that's like the power of that conversation.

Speaker C: I do agree with what you're saying, Patrick, because I feel like a lot of times people go do their own solo thing, whether that's consulting or coaching, and it seems, you know, as you're coming out of full time corporate work, that seems like a dream, right? I think a lot of coaches do this where they're like, oh, if I could coach full time, that would be the dream. And then they get close to it and they're like, this is so isolating. I'm so drained. I can't just support people all the time. All of your work interactions are just supporting people. It's exhausting. And so I found that having a mix of my own projects that I can move forward or fractional work and then projects with one other person where we can collaborate. And Kate and I have been on our own AI ah, learning journeys. But having someone that you can kind of compare notes with or work in a GitHub repo with has been just fantastic. So I think for people who are thinking about going off on their own and like, finding even small projects that you can work on with others is key.

Speaker B: There's one particular topic that I wanted to surface which was this idea of like letting go of societal shoulds. Because I think as we're talking about this, like I find myself all this, all the time being like, oh, I need to do this thing for this reason, you know, like, I'm thinking of like the cliche narrative is like, okay, like I gotta have this job because this will help me then buy the house by this time, which will then help us raise a family by this time. Or like, you know, whatever version of it it is that for people, they feel like there's these like sort of self imposed, those pressures. So I think like, I don't know, could you kind of help share like in your mind like what is a societal should? And then how do you let go of societal shoulds in the context of like building an empowered career?

Speaker A: Interesting. I mean, I do think a big one is in tech, is you're supposed to live in one of like three places. I'm being generous because I want there to be one in Europe, but it's basically San Francisco, New York, if you're too cool to move to San Francisco. And then London. And I lived in London for a while. I'm banished from the US because you go to North Korea one time. And I don't want to live in any of those places really, you know, so I think this is a place where like, you know, if I was going to embrace the shirt, you know, I would have moved to the US before I went to North Korea. And I don't want to. I live in Ireland and I know that that constrains my options in some ways. And like there were times in my career with my partner, I'll be like, okay, like let's consider what we do want to put on the Table. But I always think about it, and I try first to think about it together with my partner as like, they should be in service of the life we want.

Speaker C: For me, going back to what we talked about earlier with the kind of default, you know, floating up the career ladder, like, the societal shoulds come from a place that serve the system. If everyone thinks, oh, we should progress on this career ladder, we should make, you know, we should found startups like feed the VC ecosystem. Like, that actually doesn't benefit the individual. Like, no one came up with the, uh, engineering career ladder out of like, hey, what would make an individual feel, you know, maximally, um, happy in their career? Right? That is, that is absolutely not how the career ladder came to be. It's just like, how do we have this pipeline of people that will fuel these growing companies and, and like, growing profits for stakeholders and investors? I think one metaphor I keep coming back to is, uh, I read this book, how to Do Nothing, which is fantastic. And one of the early, uh, stories she talks about is this tree in Oakland, which I have yet to go visit, but I want to go, like, make a journey to it. And it's this, like, super gnarled oak tree, like, not straight at all. It's apparently growing on, like, the side of a hill. And, um, she talks about how all the pine trees that grow straight up are perfect for being mined for lumber. And so, you know, they seem like they're doing really well and then they get chopped down and it's these like, really gnarled trees that are unuseful to anyone else but are actually thriving in their own lives. And so I think about that a lot of, like, how can I thrive but not, like, just feed the system? But what. What shoulds are things that I actually want and what are the things that are actually the system is telling you to do it because it benefits someone else. So really just, yeah, being a little bit more discerning of the shoulds rather than just letting them be that, like, critical voice.

Speaker B: Were there some shoulds that were, like, really clear to you that was like, oh, this is like, when you kind of were going through this exercise, like, were there a few that, like, surfaced where I was like, oh, this is a should that I need to let go of? And actually, here's what's really important to me.

Speaker A: I mean, there are shoulds that people will tell you, like, especially if you're a woman or a person of color in this industry, they will tell you you should be grateful, you should work harder, you should be patient. To get to the next level. Like, they're not even shoulds that are internalized. They're shoulds that are, like, pretty implicitly told to people. And then if you go and look at the data, we have massive gaps in terms of equitable pay. It's like, well, really, who is benefiting from these shoulds? Because they are straight up exploitation.

Speaker C: Yeah, I mean, a should I really let go of, but, like, I feel like a lot of people feel is like, oh, I should go work at an AI startup and work like 6 days in office in SF because the jobs are going to be gone and in like five to 10 years. So now's the time to like, hoard your wealth. Right. Like a one that I feel like the bear. You feel that too?

Speaker B: That's so weird. Oh, my gosh.

Speaker C: Yeah. And I'm like, come on, I'm trying to lead a leisurely life. This shit is not helping me.

Speaker B: No, I totally. I totally relate to that. So I want to switch up a little bit to kind of the frameworks or in how you both approached building out your career portfolios so you've been able to sort of share some of the different projects and the ways that you both collaborate together. What I kind of want to get into is like, some of the mental models that have helped guide you as, like, you've been building. And both of you are probably approach it very differently. So, like, I know, you know, Kate, I'm kind of teasing up, like, you know, how you approach building bets and how that sort of array, like how you organize things around that. And then Gene, like, for you, like, sort of the experimentation and just like the exploration, the curiosity, I kind of wanted to, like, tease out those sort of mental models and how those have led you down different pathways.

Speaker C: Something I learned about myself is like, if I don't want to do something, I just won't do it. And so, like, really the most important thing for me is to figure out what are the things that I actually want to do and then figure out if I can make money doing them. And so I think a lot of my energy has just been going towards that. Rather than like, oh, this is a thing, let me now set up a system to run it. Because if I don't want to do it, I can set up the system and I just won't. I just won't do it.

Speaker B: Well, that makes sense. Don't set up the system unless you're willing to do it. I get that.

Speaker A: Is this why you don't use all the systems? I Make for you.

Speaker C: Meanwhile, Kate, Kate keeps gifting me GitHub, uh, repos for like, chief of staff so that I can post more, which, which has helped. I feel like if the systems help you do it, like, there's kind of a middle ground where if the systems make the things you don't really want to do more tolerable so that you do want to do them, like, you know, it can work.

Speaker B: Well, I think, you know, maybe we'll deviate and then Kate will get into the bets. But like, you both applied this in a really interesting way with dri, your career. And I think one of the things that you've talked about is it has made the things that you probably never would have done happen in a lot of different ways. And like, it sounds like social media is kind of one of those examples. So I don't know if you can kind of talk about maybe some of the ways that like, these tools or like these systems that you've kind of built for yourself have just made like, work that you never would have even touched or, like, maybe not considered doing, but, like, you just never would have had time for interest for, like, it just like, lasts on, on your list. Like, how are you applying in a way that's like, allowing you to do the type of work that you never would have done before?

Speaker C: I mean, number one is like, building the platform, right? Like, I had experimented with like, the community lending libraries that had like, auth and email notifications. So then by the time we were working on this course and I think I literally had it to do to look into, like, teachable, you know, all the major, like, course platforms. And I was supposed to go through, look at the prices, look at the features, and then suggest one. And then around that time, I had started putting, I started moving off of chatgpt and into Claude code of like, okay, let's put all of our content in, you know, local repos that we can share, and then that way we can run Claude code. It has all the context to like, update our content. Once it was like, literally once it was local in my, like, in my directory, I was like, like, wait, it's already here. It's in a GitHub, huh repo. I can just have quad code, the platform that we can then, you know, have exactly what we need. And we don't have to pay the 150 bucks a month. We can just have it be exactly what we want for our course experience. And that's something I never would have attempted to take on. Kate. I mean, Kate's now probably contributed more to the platform than I have. But, like, I don't think either of us would have at all considered running a, uh, course. Platform. Platform.

Speaker A: No, totally. I mean, it was kind of amazing to me because I woke up one morning and you were like, so I built this thing and I was like,

Speaker C: I was in Mexico City for like a wedding. It's amazing what you can do when you don't have kids with you for a weekend.

Speaker A: Yeah, I was like, I was focused on some content stuff and then Gene was just like, intern Claude and I, and then they just kept producing all this stuff. I'm like, wow, this is amazing. Yeah. So now we both work on it, which was, um, we had to adjust some things to be able to both work on it. We moved our entire development flow into GitHub. And then I, I realized, you know, when you have a product, you have to engage in self promotion. Have you heard about this? It's outrageous. It's not a strength for either of us. So I, um, was like, okay, how do I make Claude our, uh, social media manager? And so I wrote this tool that brings in all your social media, it structures it so you can dump it in Claude in a prompt and it can just coach you and be like, this is what's working, this is not what's not working. From there you can figure out what your content guidelines are, what your content structure should be. And so this is my latest rejected present for Jean, which is, I sent her a content strategist and also an engagement manager. So it helps us just basically do social media more efficiently, but also to do it in the way that we want to do it. Right. So it's not going to be like, gee, you must write about this thing that you don't care about. It's like, based on the things that you do write about, like what's working and what's not. And here's like a, ah, Wildcat is very grounded in what you're doing, which is being good for me at least, because I don't want to do many things that give me the ick and

Speaker C: engineers do not want to be marketed to like that. So absolutely, it's not effective anyways.

Speaker B: And as you're describing this, like, this is the opportunity that I think for engineering leaders and anybody who has a significant technical background right now is that there's this like, unique positioning where if you get really clear on, you know, what you value and the things that you want to do and the types of experiments in the areas that you're curious with, like, you actually have, like, a much more empowered ability to make those a reality. Like, as you're talking about it, like, you know, what I infer is, like, why you're building DRI your career is because you deeply value helping people connect to, like, what model motivates them or just, like, what do they deeply value? And to, like, orient and align their life around that, including, like, your job, which helps, like, you know, power that. And it's like, this is an expression of, like, a deep thing that you both really care about, but then you have, like, the tools to do it in a way that you. That, like, in a way that you. You want it to be, versus having to kind of default to other people's tools and platforms. And I think, like, to me, that's like the special part, like, the most unique part about being an engineering leader right now is, like, if you get really clear about what you want, you can focus on those things because you've got all of the tools and things that you need to do that now. Um, and so for me, I'm like, that's like. That's like, opportunity of, like, what does a future career look like? It's like the just, like, the ability to, like, really directly align your actions in spaces and missions and projects that you care about. Like, it just seems like you can do that more now.

Speaker C: Yeah, I mean, you can ladder up to it, right? Like, I think for me, one of the. You're asking about mental models or frameworks. For me, I was kind of, like, coming out of, you know, postpartum year with my youngest, and I knew that I wanted to get up to speed with what was, you know, the newest in AI tooling. But I know that wouldn't motivate me to be like, oh, let me go get up to speed on AI tooling. And so I just found some, like, random project that I wanted to build and did it in, like, a day. And I think if the framework, the mental model I had was like, I'm not going to come up with the idea and then go build it. Right? Like, I need to build. I need to get in the practice of building so that, like, by the time I have an idea that I really do want to build and maybe is, like, income generating, my confidence in building will be at the same level. And so, like, I created, like, a Trader Joe's snack box builder, and then I created this, like, community lending library. None of this, these were, like, businesses, but I was just like, hey, let me learn how to Build my confidence that Claude can do things like auth email notifications, right? Like all these kind of things that are just beyond a static site. And then by the time, uh, the course platform came around, like my, my mental model or my hypothesis kind of proved itself, which was like, oh yeah. I was like, this is, this is something I can build. Like, I know how to do this.

Speaker A: Yeah. I mean, the other thing that we have done with this, which is incredibly engineering, is that we have essentially scaled one on one coaching, right? And we have not done it by like TR an AI model to coach people, right? We've used AI to build a platform. We've used it to make it faster for us to kind of make our ideas high quality and shippable. You know, it is incredibly useful in audio editing. And then the actual coaching aspect remains very human. We read everything, people submit ourselves, we comment back ourselves. I find it really disappointing in this era that the things that are being most talked about being done with AI are, uh, like building things to build faster with AI and just like AI ing it, you know, like you have a problem, you stick it in some AI and like, whatever. And actually what I find much more interesting is to come at it from a human leverage perspective and say, how do we use AI to do something that is still meaningful, where the human part is still human and where the bit that doesn't really matter, like the quality of our JavaScript code up to a point is just, you know, done for us in a very short amount of time.

Speaker B: And I think that's what I'm after is how can these. Like, I think this is like the ultimate question that I've been sort of like wading through the forest of narrative and everything going on to be like, how do we align these things? And the concept that's come up this week is like, for human flourishing. Like, like, how are we aligning our engagement with these tools and like allowing ourselves to do these types of projects in a way where it's making us more connected, it's making us healthier, it's building better relationships. Like, it's allowing us to be more better humans. And I'm like, that's like, that's the goals. Like, how do we, how do we create alignment there?

Speaker A: Yeah, I totally agree with you, but it's also choices about how you use it, right? Like when I wrote my engagement manager skill to kind of help me engage more on social media, I'm just building managers for myself now. Like, so, like, one of the things that I pointed out was like, pull out people's wins so that I can congratulate them. And not just because then I say congratulations to the algorithm, but because I genuinely want to know them and say congratulations. And like, that piece is human. Like, it doesn't it matter if, you know, a tool surfaces versus me reading my entire feed and catching it? Like, I don't actually think so.

Speaker B: I wanted to close the loop. One, one thing. So, Kate, bring us into how you apply bets. Like, I'm trying to understand, like, how you choose bets, size and scope and things like that.

Speaker A: Yeah. So it's like risk profile. Right. So when I left my job, I figured out what my, like, absolute minimum bar was. And so I want to meet that each month. But then ideally I would like to make more money than that. But, like, if I hit that minimum, then I'm winning. I'm not dipping into my savings account and as long happy, like, you know, I can do that. Right. So then I want a relatively solid bet that kind of covers the minimum. And then I won probably my fractional work. Um, and then I have this kind of medium bet which, like, could go really well or could go really poorly, which is doi. And then I have space for like this third bet, which is I try to optimize much more for learning. And, like, really, it probably won't pay off, but, you know, for dead, it would just be for me. So right now I'm taking this MBA essentials course and then that's where I'll put my, like, more unhinged raccoon themed most projects that go in that bucket. Right. And so then I end up trying to apportion my time, like, across these three things and one of them has a pretty set, like, do this work, make this money, and then do I like, ah, we are always just trying to, like, do the right thing for the people who would benefit from it. And, you know, then fingers crossed, it works. But you can't know. You have to build it and hope for the best. Right. And then my own mad stuff is just for my own creativity and learning.

Speaker B: I just really appreciate the intentionality of the model there in terms of like, you know, ultimately, it's like we want people to walk away with a little bit of a idea of the pathway to build an empowered career. So final thoughts on how somebody can apply all of the lessons that we've talked about today to help them build an empowered career.

Speaker A: Just core, like, what choices do you have and what choices do you want to be available to you? And how can you be honest about those choices. Right? And part of that honesty also comes back to money. Because if you are always telling yourself that nothing is ever enough, you are constraining your choice set. If you can kind of really understand what is enough for you, then your choice set will be more real.

Speaker C: Mine's similar, I think, like, as engineers, we're really trained to think about scalability. Like, how would this work at scale? And the truth is, for your career, it doesn't have to work at scale. It just needs to work for your individual career. You don't have to have 10,000 people having the same exact career. And so there's probably some version that is off the beaten track, not just climbing the career ladder. Uh, that will give you enough money, will energize you in the ways that you want to be energized, right? Like, it doesn't have to look like what other people are doing.

Speaker B: We have a couple rapid fire questions to dive in with both of you. I got a preview into some of your answers, and I'm really excited about it. So the first rapid fire question, what are you reading or listening to right now?

Speaker C: Okay. I just read this book that apparently falls under the genre of cozy sci fi, which I was like, yes, I need some cozy. I need some cozy vibes right now. It's called Psalm for the Wild Built, and it's very good. It's like, explores the kind of interactions between machines and humans in a very. Just a very heartwarming way, which I'm

Speaker B: going to add that. Feel like I already did add it to, like, my library. Um, it also sounds like a folk album too, so I was like, that's great.

Speaker C: It's also very short, which is nice.

Speaker B: I love it. What about you, Kate?

Speaker A: I just finished powerfully likable by Dr. Kate Mason.

Speaker B: Next question. What is a tool or methodology that's had a big impact on you?

Speaker A: Systems designed as a discipline? I feel like I annoy Dean so much. I'm just gonna have to go and, like, find a therapist after this.

Speaker C: Mine is just, like, returning to first principles. I feel like there's so much uncertainty in every. Everything's kind of. There's so much upheaval that, like, just going back to, like, okay, what makes sense? What are we trying to solve? How will this solve the problem?

Speaker B: Next one. What is a trend that you're seeing or following that's interesting or hasn't hit the mainstream yet?

Speaker C: I mentioned this earlier, but, like, how can we use AI to figure out how to work less? How can we work less? And be do more. Human flourishing, I think is the phrase you use, Patrick.

Speaker A: Mine is AI Cost management. Like lower cost local models. I feel like that's going to become increasingly necessary. And I am curious, curious about last question.

Speaker B: Is there a quote or a mantra you live by or a quote that's been resonating with you right now?

Speaker A: Mary Oliver, what are you going to do with your one wild and precious life?

Speaker C: I've been playing this game with my kids, uh, called fortunately, Unfortunately. I think it came from that Chinese story of like the, the guy who's like horse gets her and then his son doesn't go to. It was like, oh, fortunately, this, unfortunately this. We've been doing this with the kids where one person says, fortunately, oh, fortunately we have no school today. And the other person says, well, unfortunately, like it's raining outside. And then it just. Yeah, it's just a hilarious game to play with anyone really. You don't have to have kids to play.

Speaker B: It's a fun, creative.

Speaker C: Although with kids it really goes towards a very poop centric story.

Speaker B: Always, all the time.

Speaker A: I love it.

Speaker B: Um, Kate, Jean, I just wanted to say thank you both for just being able to spend the time. Well, I think one for your work to help people live a more empowered life. But I think too to be able to spend time together and to share what you've learned and how you're building and the choices that you've made, it really means a lot. And I hope that people listening, uh, are able to make different choices and I think more deeply, like going back to some things we talked about, like deeply reflect about what they want, be honest with that and make time for more life. I think if that, if there's anything that somebody does make time for more life. So thank you both.

Speaker A: Thank you, thank you.

Speaker C: Thanks for having us.

Speaker B: If you're listening to this and you're wondering how can I connect with other engineering leaders in my city? Pull up your phone, write now and go to ELC Dot Community. Click our chapters page. You can see that on the menu on the left. Find your local chapter and click Join. We're hosting virtual and in person events all the time and this is the best way to help you get involved, expand your network in your city and support your leadership and career growth. So pull up your phone, head to ELC.community join your local chapter and get involved.