CTO Wisdom with Charity Majors | Beyond the Program

Hey, listeners, Tim Winkler here, your host of The Pair Program. We've got exciting news introducing our latest partner series beyond the program. In these special episodes, we're passing the mic to some of our savvy former guests who are returning as guest hosts. Get ready for unfiltered conversations, exclusive insights, and unexpected twist as our alumni pair up with their chosen guest. Each guest host is a trailblazing expert in a unique technical field. Think data, product management, and engineering, all with a keen focus on startups and career growth. Look out for these bonus episodes dropping every other week, bridging the gaps between our traditional pair program episodes. So buckle up and get ready to venture beyond the program. Enjoy. Welcome to CTO Wisdom. My name is Eric Brooke. This series, we'll talk to leaders of technology at organizations. We'll understand their career, what was successful and what was not, and what they learned along the way. We'll also look at what the tech market is doing today. We'll understand where they gather their intelligence so they can grow and scale with their organizations. Hi, my name is Eric Brooke and welcome to CTO Wisdom. Today, with us, we have Charity, and Charity, give us your elevator pitch.

Hi, uh, my name is Charity, I'm the co founder and CTO of Honeycomb. io, which is, I would say we were the original observability company. Uh, we make observability for software engineers, um, and it's really about, you know, helping to accelerate those feedback loops that sit at the heart of every high performing engineering team.

Awesome. So how did you get started in technology? What was like, what was your journey to kind of like coding your first line of code or building something? What was the thing that really sparked for you?

Yeah, I grew up in the backwoods of Idaho. Very rural. I didn't have a computer until I went to college, um, and I went to college on a music scholarship. But when I got to school, I realized that all of the people who got their music degrees were still hanging around the music department and working very low wage jobs. And I was like, dude, I grew up poor. I do not want to be a poor adult. And that's when I found computers. Um, and I was really taken by the Unix command line. I've always liked words and the, the command line is just so expressive that I found it fascinating. So I'm sure that my first line of code was a bash script.

Oh, great. Um, okay. So when did you, um, tell us about your first kind of foray into kind of like being paid for kind of like the work that you were doing?

Yeah. In, in college. I mean, I'm old enough that back then they actually paid me to run the university systems. I was assistant men for the CS department, the best dad department, and then the university as a whole, they gave me root. I don't think they do that these days, but back then they gave me root. And I, and I parlayed that into a job at the local web development shop. And then by the time I was 18, 19, I got recruited to come down to San Francisco and I've been here ever since.

Awesome. Um, so tell us through your career, like kind of maybe highlight some moments before you got to management. And then obviously we want to dig in a little bit about your first foray into management.

Yeah, you know, I feel so lucky that I got into tech when I did when. You know, hiring standards were low, and if you were curious, interested, you know, they could find a job for you. You know, the world has changed a lot. Uh, I've been watching my little sister try to find engineering jobs, and I just feel so lucky that I got it when I did. Um, but I really, you know, as someone who, I did not, I'm a serial dropout, I've never graduated from anything. Uh, I, I really kind of made a career specialty of being sort of the first, Infrastructure engineer to join a group of software engineers, the startup, just when they're starting to get customers, things are starting to get real. And helping them sort of grow up and make reliable systems. And I, and I really, I love being an engineer. I really, I really enjoyed that.

So you, when you, you, you had a love for Unix, and then you obviously kind of went into infrastructure. What was it that was kind of like about infrastructure that really interested you?

Oh, the fires, the firefighting for sure. So I got my ADHD diagnosis in 2020 and so many things about my life make a lot more sense now. Like I tried being a straight up software engineer a couple of times and I always got so bored. You're sitting down. You're like, OK, I know what I'm building today. I know what I'm building tomorrow. And. Next week and next month and months after and it's just like my brain just like goes off. Uh, and for better or for worse, there are always fires to fight in ops in SRE, you know, things are, I have never been more calm than when everything is on fire. Everyone's freaking out. And I just like, I hit my groove that that is the best time to be alive in my mind, which is not an uncommon story. When you get to know folks in the SRE community, like There's a lot of us who are like, ah, I found a way to focus. Life hacks. Fires.

Um, do you mind talking a little bit about how you think ADHD has helped you or hindered you in your career journey? Like, what are the things that you've learned from it?

Yeah, you know, I wish I had realized earlier that there was, I just thought it was really weird, you know, I was homeschooled my whole life. I didn't really experience traditional schooling. So I kind of just thought that I didn't develop the right habits or I always struggled with the sleep schedule. I always struggled with, you know, and, and so after starting Honeycomb in 2016, I, I, Accidentally had to become CEO for a while and my life stopped functioning like my everything just went to hell And in retrospect, I now understand that as an engineer One tool and I used the hell out of that tool. The tool is hyper focused, right? But I got interested in something I would never Dive into a hole and I would not emerge until I had figured it out, whether it was hours or days later, you know, and that tool got me a long way. And then when I became CEO, you don't get to use that tool, you know? And I, I'm not a structured person. I'm not a predictable person. I'm not a person and I'm not someone who can just like. muster through on willpower. You know, like my co founder, Christine, who structured people who can be like, at 10, 20 in the morning tomorrow, I will sit down at my desk and I will write an essay on X, Y, Z. And then I will be, I can't do that. I need fuel or I literally can't focus. Um, and so like a lot of my picking fights on the internet and the public acts of aggression over the years, I think just been. Attributable to trying to bomb my brain with adrenaline so that I could concentrate on something, but as CEO, I realized that if I had been awake for at least 30 hours or so, things kind of slow down and I could force myself to do boring things like expense reports. So I just basically for three or four years, I ran on no sleep, like sleeping every two or three days was the only way I could get myself to force myself to, which did not mean I was doing a good job on any of it, but I could sort of, you know, so like, it's, you know, I, I, I am very grateful for, um, the patience that the world has had with me and sort of figuring out my plumbing. And I hope that. I hope kids get to figure it out a lot sooner than I did, because tools, medication, God bless drugs, they are the best thing that ever happened to me. Even having a regular schedule, getting up every day, like delivering his promise, like, it's, it's night and day.

I really appreciate you sharing that, and I think also you've shown that even with that diagnosis, that you have been successful, and it shouldn't hinder or push people away. And having that diagnosis has really helped you.

Yeah, 100%. I mean, tech has long been a haven for neurodiverse folks. You know, there are a lot of ways in which it plays to our strengths. Just that sort of, you're a dog with a bone, you're curious, you're interested. If you can learn to like, align your curiosity and your interest with things that the world needs, it's a, it's a superpower.

Yeah, I concur. Um, so you've traveled a journey. Um, you've been like, so you did a kind of like an icy role and individual contributor role for a while when you first got to management. Like, what were the things that you had to learn?

Oh, no, I think I've learned so much more about being a manager since I stopped being an engineering manager. You know, like I think in the moment I was very reactive and very just sort of territorial and kind of, you know, I had just gone through this acquisition by Facebook and I wasn't very happy about it. I don't think I was, I wasn't really a team player in a lot of ways. And in retrospect, a lot of these things make a lot more sense to me. Um, but the things that I, you know, I mean, I think that the first thing that every new manager has to figure out is, is, is just like, You know, you became a senior engineer, presumably, and which means you learned to have, have, know how to trust your own judgment or know when to trust your own judgment and when not to, right? And when you become a manager, I mean, the first jarring fact is that you no longer know when to trust your judgment or not. You might be doing well, you might not be, you're probably going to feel like shit no matter what, right? You never get to go home at the end of the day, feeling like, yes, I did it, I built it, I figured it out, I fixed it. Achievement unlocked. You know, you don't get that feeling like, as a man. Over the years, you learn to look for those moments. They're, they're a bit more muted. They're, they're more unpredictable. They're more, it's more like someone will come to you and be like, Hey, that thing you did for me three years ago was great. And you're like, Oh, that does feel good. You know, but it's not like the dopamine hits that you get as an engineer where you're solving puzzles all day or you just leave work feeling just like high on life, right? It's not like that. So I feel like the first big adjustment of every new manager is just like, you're kind of like you're a beginner. You're a beginner again. You don't know when or where to trust your judgment and you don't know where to find your joy.

So, yeah, I concur with all of that. It is, you go from competence to incompetence and it doesn't feel comfortable. Um, so what were the things that you would tell now a new manager? Here's the one thing you should focus on. I know it's very individual, it's context driven, but what are the things that you ask them, like a new manager, to focus on now?

Oh, well, that's a slip. You started off asking, what would you ask your, your past self, which is a very, I would tell my past self, if you don't feel like you could with your whole heart or most of your heart represent the company, you shouldn't be a manager. I never felt like I could represent Facebook as a manager. And so I was at odds with the system kind of fine for an IC in a lot of ways. It is not fine for a manager. If you can't do that. You should take yourself out of that role ethically, like practically, pragmatically, like the idea of managers as shit umbrellas, that is a flawed model. It is not good for you. It's not good for them. It's not good for the company. It's not good for anyone. If you're in a place where you feel like that's your only option, you should. Get the hell out of there, you know, at Facebook, I should have been an engineer. I should have rested, invested. I should have done my part. So I could have checked out at the end of the day, gone home, been with my sweetie, gone out with friends, you know, and as a manager, you can't do that. You know, you take a home with you. So much of it is emotional labor. You take a home with you. And which means that you have to, your job is to represent the company to your team. And if you don't think you can do that, you can't. Don't take the job. What I, what I tell new managers now, like who I think by and large at our company, I don't think have that sort of like tug of war of wills inside of them is much more just like, Oh God, I think some of the best advice I ever heard was from Simon Willison. He was like, you know, if you're, if you're a new manager or, or if you're not sure if you're a good manager or not, you know, you can be 90 percent of a good manager just by asking yourself, What would a good manager do? Just like, you know, whoever's in your mental model is a good man, just like, what would they do? And just do that thing. Because like, so much of it is just like being basic human being, following the rules, explaining things to people, you know, it's not like heroic sin glory and all that stuff that you can, you can get a long way by just like trying to be a basic, good human being and manager and investing in yourself, you know, not resting, you know, you're not an expert. Slip into beginner mind, ask questions, open up, be curious, be creative, you know, take advantage of the time for what it is. Like the final 10 percent of being an excellent manager is like a lifelong quest. So you're not going to get there overnight. You're not going to get there in the first few years, right? And so just like be fine with that.

Yeah, thank you. Um, so moving up the kind of the ladder or, um, is, um, like coming to a director where you're kind of managing other managers. Do you have any thoughts about that? Or did you learn anything in that part of your journey where you're managing managers but not managing ICs as much now?

You know, I think this is an under, under understood. Um, I think a lot of folks have this idea that being a director, director is like being a super manager or a super senior manager, but it's not, it's a whole different role. And the Delta between management and being a director is at least as big as the Delta between being an IC and being a manager. Now, this is not to say this is true everywhere because, uh, titles get very undisciplined, especially in startups and people are called directors and they do all kinds of things. But like my mental model of real directors is directors run the company. They're the ones that are responsible for taking the strategy, the decisions that are being made about resources by VPs and C levels, and making it actually work on the ground. So they're responsible for like the heartbeat of the company, right? Making sure that things are high functioning, that the wheels are turning, that people are performing up to spec, that bad performers are getting, holding managers accountable. Making sure that the communication patterns are scaling. Looking for, you know, it's a socio technical machine. That's never working perfectly. And, and it's, it's the job of directors to like, it's a lot of abstract thinking. It's a lot of relationship building. It's a lot of incremental, you know, work, but it's so important. And I feel like, you know, I'm actually like kind of, I may be writing a series on this and on our blog or something. Cause I feel like even lots of really great engineering managers don't actually really understand what it is that Upper levels are looking for in people that they want to promote to be a director, you know, and another aspect that I feel like a lot of folks don't really grapple with is that I feel like making career goals in tech is kind of like a fool's errand. I think that the best thing you can really do is like always be learning, be curious, be creative, be following, be aware of what you're enjoying and be open to opportunities because all of the interesting opportunities I've ever gotten that were changed my life. I was not expecting. I was, I was not gunning for them. But I was in a position where I was able to take advantage of them when they popped up. And I think that tech is so fast, you know, every step up the ladder that you go, there's at least an order of magnitude fewer openings. Which is the way it should be, right? So you can't always predict. You can try and put yourself in line to have a good shot at being tapped for a director, but you can't always predict where those opportunities are going to open up. Uh, so like, I think that like, you know, building a career where you're happy where you are, and you'll be happy if you don't move up to the next level is super important. Uh, and I think it is the people who are, who manage to find that joy, who tend to be tapped to do the next level of stuff.

Yeah, I concur. Um, so let's move up to exec level. Um, and so like either VP of it and kind of like engineering or CTO role, cause obviously it differs in many different places. What would you say is the. the magnitude or the changes that you really have to kind of like encompass at that point. I have

this thing that I keep chewing over lately, which is just like, out of all the C level roles in the world, CTO is the least formed. It's the, it's the only one that there isn't really a, a predictable pattern for. CTOs are all over the freaking map. Some of them are ICs, some of them are, Managers, some of them run orgs, some of them encompass product and design, some of them don't, some of them are, you know, some of them are like extrovert, they're all over the map. And when it comes to like VPs, I feel like engineering VPs have historically been sort of like the junior members at the table. Like they are not quite the top tier execs. Consistently, and I think that a lot of this is because The whole philosophy of having a high functioning exec team is that you co own and understand decisions that you make organizationally. So, like, the whole exec team needs to understand, okay, this is our marketing strategy for the year. Yes, we sign off on this. We own this together. You know, and I feel like people really struggle to do that with engineering. Some of this is the fault of Other execs who don't think that they need to learn as much about what makes good engineering orgs as they do about P& L statements. Some of this is historically the fact of engineering orgs who don't really try to convert their work into like the terms of the business, but there's been this big gap. And I do feel like the end of the zero interest rate era is forcing us to start to close that gap. And I think it's painful and awkward and uncomfortable for us. And I think it is so. healthy.

I wonder sometimes if we were to take like one area like delivery, who is responsible for delivery? Is it product engineering? Um, what are the factors that come into that? How predictable is software engineering in terms of like taking the SAS model as opposed to gen AI model for a second? Um, and that kind of like when you look at sales, they often have like a high level of predictability, not always because it's very much macro economic driven a large degree. What are your thoughts about like, how do we actually improve our performance in terms of delivery? Because that's usually what the exec care about from us. Like, are you and your team going to be able to do this on time? If time is a factor, time is

always a factor. Yeah. Yeah. You know, I feel like there are so many aspects. There is a higher level of unpredictability and engineering than in sales full stop. Um, but that doesn't mean that we can't. That we can't get much better at pointing at a place and saying, that's where we're going, getting updates along the way about how we're going at getting there, and trying to arrive there roughly on time, right? I think that like, anytime there's a big shakeup in your org, whether it's a hiring growth spurt, or a leadership change, or a re org or whatever, it takes time to like, you have to relearn all over again. Uh, but like, if we aren't focused on that consistently, we aren't going to, we aren't going to like, Level up. Um, I think I think there are a lot of really interesting that there are a lot of new startups out there that are kind of focused on giving. Engineering leaders visibility into their team without using that punitively and without using it necessarily. There's always a story behind it, right? Maybe this is what good tends to look like in terms of like number of PRs, etc. But like there's always going to be outliers. Some of them will be outliers because they are outlier individuals who Excessively helping the team, you know, move faster. Sometimes they're outlet, but it's always the starting point for a question, right? And I think that our fear of being tracked of having our, I mean, it's, I always forget the name of the law, but the law that once you're once you're tracking something, people will start to like adapt their behavior to deliver that metric instead of, you know, is a real thing. And so I think you really have to be careful with this data. You have to emphasize to people that yeah. You know, first, you're not looking at one metric. If you look at one metric or two or three, they're going to get game. But if you're looking at the broad Basket of behaviors, right? Things will start to, and if you're using them as the starting point of the conversation, I think they are, there's leading indicators and trailing indicators, right? And whether or not we hit our deliverables on time, it's always going to be a trail indicator. So a big part of the battle is looking for leading indicators that we can start to use to find these things before it's. Oh, shit. We said we were going to ship today and it's been, you know, a month, two months, three months, but nobody knows it. You know, that's what degrades trust, not missing by a week, not, you know, that sort of thing.

Yeah. Concur. Okay. So, um, when we look going forward, we talked a little bit about your career and that you moved through a honeycomb and you were the CEO for a while. Now that you're the CTO, um, I guess like when you think about it, what is success and how, what has helped you be Always

many people are different. And that's why I feel like It always starts with self awareness, uh, and just trying to be conscious of who you are, how, you know, your, your own, your own responses to things, uh, your impact on other people. Uh, I have not had an easy few years, and I feel like I've finally gotten to a good place, but like, I think a certain amount of, uh, stubbornness and tenacity is also necessary. Um, I, I feel like it's sort of the nature, blessing, the curse of leadership positions that everybody kind of thinks that they want to be one. You don't really know if you like it or not until you've done it. Um, and after this, oh my God, my dearest wish after this is to go be a staff engineer someplace. I just want to sit in the corner and write code and have it be someone else's problem for a while. But I feel very grateful for the time that I get to be in the seat and do this thing for as long as it lasts.

And so what were the things that help you in that, around you? Um, yeah.

Uh, journaling, um, writing, uh, I used to do Twitter a lot and it was really helpful for me in sort of working out external messaging as well as working out what I thought and felt about things. Um, I don't do it as much anymore. There's just too many places. There's like, what, Macedon, Blue Sky, and Twitter, and LinkedIn, and there's just too many, and I can't keep track. Um, but like, writing has helped me sort of externalize what's inside my head, and look at it from a new angle, and get feedback on it, and it's been invaluable to me. Um, I do not really, a lot of the standard advice like mentors and classes just really don't work for me. I have a lot of problems with authority, and anybody who I, this is not anyone else's problem, it's my problem, but anyone who I perceive as trying to set themselves above me, I automatically lash out at, which is not, not great. So, I consider everyone my peer, whether they're an intern, or a student. Or like fucking Elon Musk or everyone's my peer, right? That's just how I make my way through the world. And realizing that about myself was a very healthy thing. I don't mind if other people think of me as a mentor. That doesn't bother me at all. They're still my peer to me, right? So like I said, I think a lot of it is just about understanding your internal. Because when you're in IC, you have, you have much more of the luxury of not having to be on all the time. It's okay. Your mistake, the higher up you go, the more Your internal struggles become, it's so easy for them to be externalized and become other people's problems. And if there's one thing that I really can't abide, it's people in positions of leadership who make their problems everyone else's problems. It's so irresponsible. It's not okay. People do it all over the place and it's hard not to. So I feel like, you know, the thing about you need to apply your own oxygen mask before you can use it on others is so real.

I really love that analogy. That's a really good one. Um, is there a problem that you're looking into and trying to figure out at this time?

Yeah, um, I have just, uh, taken over responsibility for our AI strategy. This is probably the most boring and predictable answer in the world, but, um, I am excited about it because, you know, I, I, I'm excited because I think part of what brings companies to Honeycomb as customers is our reputation for engineering excellence. You know, I think we've, we've really tried hard throughout our entire history to share what we've learned about what makes for high performing teams, what makes for predictable, consistent software delivery, what makes for happy team. Um, it's what's made it easy for us to recruit, even when, you know, in the days when everyone's, you know, fighting for engineers, and it's, and it's brought a lot of customers to us because they trust what we say about the future. And up until now we really haven't said much about AI and I think that's starting, starting, it's about to start to hurt us. And it's time for us to start talking about where we think the future of AI fits into the world and how people should be preparing for it, how they should be hiring for it, how they should be building. So over the next few months. Um, we are not only starting to build some things internally that use AI that I'm really excited about that I can't really talk about, but also we're planning to put out a drumbeat of material. It's just engineers talking to engineers about how to apply. Good software engineering principles to non deterministic systems, which is something that nobody's really figured out. You know, there's all of this hot air and thought. I hate that term thought leadership. It gives me hives, but all these people just like thinking out loud all over the place about how great or how bad everything's going to be. And I'm so irritated with that. I just want to hear engineers talking day in the life of the engineer. How, how am I using this for good? How's it screwing with me? How can we make some progress here? Uh, and my hope is that we can earn some credibility with folks who are using LLMs and building models in the way that we already have people who are just built writing code.

Yeah, it's a fascinating space. It feels like an industrial revolution and like, realistically, every CTO is going to have AI as part of their journey going forward. It's some

combination of industrial revolution and giant fucking bubble and nobody really knows what the percentage is yet in some sense It's very clearly like a trillion dollar solution looking for a trillion dollar problem, which we haven't found yet We found a lot and that my friend can't quirk who works at honeycomb it I should attribute that but I would say that it Stuck with you like that's so true. Lots of little like ten million dollar problem Maybe a million dollar problems, you know Well, you know, I probably, no, not so much. So how much of it, how much of each is it going to be like TBD?

Yeah. Yeah. Concur. Um, I also want to point out that I found, um, I'm going to be careful of the word because I don't want to give you hives, but like some of your articles and blog posts are excellently written and have definitely helped me think farther and wider. So I definitely recommend our viewers check out your blog because it's very good. Okay, moving on. Um, what's it like? You talked a little bit earlier about working in the exec and it's a lot about, you know, as a business, we're like the one team and our job is to kind of align on that. What are the things in hindsight you would say that could prepare someone for their first exec role?

Oh, that's a really good point. I think that for engineers in particular, you need to understand how this works. You need to be curious about the business. You need to, you know, I think we get so deep into tech for the sake of tech and even tech, tech's affecting the business, but just like, like when I started Honeycomb, I did not know the difference between sales and marketing, much less demand gen versus product marketing. You know, I didn't, I had never heard the term product market fit. I didn't know that categories existed, you know, and I was phenomenally ill prepared and it was very hard to recover from. And I think that You know, if, if you want to lead engineering or you really need to learn about how, um, and most engineers don't, uh, and, and there's a, there's this kind of ingrained snobbery that a lot of us have, you know, Silicon Valley is infamous for thinking that engineers can do everyone else's job. You know, and while I would, I would still hold, I think an engineering background prepares you for that. Incredibly well for a range of careers, only a few of which involve writing code all day. It teaches you how to think and debug and it gives you this really, you know, and having a technical orientation where you can trust your own judgment to some extent. It's just like it's currency in this world. Uh, but you have to care as much about the business as you do about technology in order to be pretty exact. Another thing I would say is that, you know, a thing that I think that In order to co own, you know, each other's decisions, I, there was a, there was a moment when Honeycomb, I think, kind of crested a thing that we had been, where we had been messing up for a long time without realizing, where we were just like nodding, going, yeah, that sounds reasonable, and moving on. And when we started going, no way. What exactly do you mean by that? Wait, are we using the word enterprise to mean the same thing? You know, just like digging in to make sure that what's in our head? Because otherwise you're going to be surprised, right? And, and being able to like early detect those areas of misalignment. My friend, Emily Nakashima, who's our VP of engineering, wrote two of the best blog posts I've ever read on becoming a VP of engineering. And she talked about how creating alignment It's a buzzy, buzzwordy sounding thing, but it's like so much of what the job is. Just making sure what is in people's heads is not just the same words, but the same concepts, the same ideas, the same priorities, the same, you know, learning to get you that spidey sense when something is not on the same page, you know, and how to resolve it is so critical.

I remember when traveling my first journey with domain driven design, and one of the things it talks about is ubiquitous language. I'm using the same words across the organization. And I remember asking each of the exec at that time, what is revenue to you? And every answer was different. And that really highlighted to me like, Oh, how much conflict and extra things do we create because we're using words?

Yes.

Yes. Okay, cool. What does an interaction with a board look like from your perspective? Like, what, could you demystify that a little bit for people that don't

know? This is something that is near and dear to my heart, and it's something that I think that a lot of mythologizing goes on around. So Honeycomb, we've actually done something, I think we're the first company in America to do this. We have an employee, a voting employee board member on our board of directors. We've had this in place for three years, and part of their role is to attend all the board meetings, even the closed sessions, and then they present the board deck that we present to the board back to the company in the next, all hands, and they talk about what they saw, what they heard, and I think a lot of people expected this, this position to be one of like employee advocacy, or, or that there would be like a Opportunities for the employee board member to speak or something. People don't realize that that's not what boards talk about or care about. Um, they talk about numbers, sales numbers, sales efficiency, you know, how much, what's your zero cash date, marketing numbers. You know, they do a certain amount of debugging, like slightly closer, but like it's all, I don't even talk in board members, in board meetings, hardly ever, right? It's really head of sales, the head of marketing, COO, CEO. And they're talking, they're talking about things that are not what employees care about for the most part. You know, things like, you know, how's my rap? I mean, I'm overstating a tiny bit, but like the kinds of things that like, I think employees think boards will talk about. So, honestly, like, I've been doing a little bit of a tour to be like, what has been the impact of this experiment and everyone, a lot of folks have said, you know, what I think I've learned from this is that I don't care about this information. It's not, I would be okay if this experiment went away because I found out that it's really boring and I don't want to think about all this stuff, but I tune out during the updates and I'm like, okay. Thank you for your honesty. I do think that like there's a, there's a subset of folks, primarily people who are aspiring to upper management for whom it is really interesting. There's a lot of details that are honestly pretty dull if you, if you aren't like thinking about that or caring about all the time and it can be very anxiety producing too. So it's, it's, I used to operate from the principle that, you know, full transparency on everything. That's what builds trust. And. In theory, I still agree, but I also have come to respect that it's so easy to just drown people in details that it makes it hard for the things that really matter to just stand out and land as hard as they need to with them. So I'm still kind of trying to figure out how to thread that, you know, to give people enough information that like, I fully 100 percent believes that like, if you're an employee, you have a right to understand how the company is doing. When are we going to run out of money? What's our strategy? How are we, you know, but I also. I've come to respect that not everyone wants to know all that stuff. And so, yeah, I don't know. It's an interesting, it's interesting. It's an interesting sort of like needle to thread.

Yeah. Thank you for sharing that. Um, in

I mean, obviously everybody is like AI, AI, AI, and I'm already getting so cynical about it because it's like just because you put AI that doesn't make it better. Honestly, I think I can say with some confidence, if you can compute the answer, you should compute the answer. Because if you can computer it, it's going to be a better, faster, cheaper, and more reliable answer than anything. An AI answer is a guess. You know, and guesses aren't better. There are some problems for which this is like the only answer or an easier or faster answer, but like for, you know, it's so frustrating to me right now. Cause I'm looking at the observability industry and people are just like, dashboards with AI. And it's like, yeah, but that's because you didn't collect the context. You can't calculate the answer. So you're guessing the answer. That's not. A plus, that's not a good thing, you know, and I think that, you know, so much money is chasing all of the AI promises right now that it's inevitable, but I think there's already a well earned, well, a sink of cynicism that's sinking in across the industry and I am pretty irritated with it. Is there

anything outside of AI that you're seeing at the moment? I mean, yeah. I

mean, I think it's a really interesting time. You know, there were a few years there where, you know, there was such hot competition for talent. It turns out everyone was overhiring. You know, and, and now I think that I think that I think the move towards efficiency is a good thing for like it's a little bit pain growth is fun, right? It's fun. It's hot, you know, but like, it's not always healthy and growth for the sake of growth is not a good thing. And I think that all it's learning to talk about are. Our work and the language of the business and actually justify it in terms of real needs that we're really solving in a competitive way is really, really good thing for all of us. I feel like, you know, engineers are the engine of modern businesses, the innovation engine. You know, we push, we push markets forward, we push technology forward, we push, we push companies forward. And. We're too expensive to be, to just be put in the corner or in a closet and given tasks, given tickets, right? Smart companies are inviting and encouraging you to come above the value line so that our creativity and our problem solving is being used to address, you know, at the very, at the very top level, what are we building? Why are we building it? Who are we building it for? Um, and so. You know, I feel like engineers who feel like they're being taken for granted and treated like, you know, little monkeys, take a ticket, find, find new jobs. They exist.

Thanks, Charity. Um, in terms of like your entire career, we talked a little bit about what's helped you grow and what's helped you scale. And you've talked about the writing and how important it is. Um, it's, and I definitely appreciate, as I mentioned, your blogs. Um, it's kind of like having an RFC out in the wild and it's like, oh, wow, look at this thinking. It's kind of interesting. Are there other things that you? like have helped you along the journey. Um, and I know we've kind of like covered some of them, but I just want to give you a bit of space in terms of What's helped you scale?

Therapy.

Very good answer.

I think therapy is, if you are in charge of other people, I think therapy is an investment in yourself that everyone, everyone should do, you know. I've tried a lot of things. I've tried, you know, having coaches. I've tried, I read a lot, some might say compulsively. I, I think I find a lot of value in reading about things that are not about technology, like books about ethics and religion and just sort of like practices. I think there's a lot of wisdom there that is not just of the moment, life hacks, you know, but is a little bit deeper. And I think that as some of us, you know, I really love what Will Larson says about how we have, each of us has a 40 year career. I think it really changes how, we can be so like, like little mice, you know, just darting from moment to moment, year to year. But like you have a 40 year career. How do you think about the arc of that time? And whereas the first 10 years, I think for everyone is. learning and soaking up and just like upskilling like crazy. Like after that, I think that once you get some power, what are you going to do with it? You know, what is the legacy that you want to leave? Like you want to have an impact on the people. I was just talking to this guy, I won't name him, but like he's an exec and he was talking about the place that he works and how he got kind of disillusioned with some other They're living up to their own values, but instead of just quitting, he was like, well, I'm already kind of mentally out the door. Why don't I see what happens if I stick around for a few months and just try to hold people accountable on the board, my peers, you know, the rest, the rest of the execs, the other folks, just what happens if I try to hold up a mirror and go, is this how you, and I was just, I got chills. I was like, what is the point of power? If you just perpetuate. whatever got you here, right? Can't we do better for each other? And I think zooming out and looking at the arc of history and looking at, you know, people who have been thinking about ethics and morality and the good life, you know, for longer than technology has been around can be really grounding. for sharing

that. Last question. What do you do for fun, Charity?

You know, during the pandemic, uh, actually just a year, year and a half ago, I got cats and This is so cliche. I grew up on a farm where we had lots of animals, but we ended up eating most of them eventually, so we never really like bonded with them. Uh, but having cats that like to snuggle with me, I've always struggled with sleep schedules and like a regular, you know, and it has been, it has been wonderful. I look forward every evening to laying down with those cats. fuzzy little fuckers and just like petting them and falling asleep and it's in this charity.

It's been awesome having you and describing your journey and some of the wisdom that you've learned from it and your openness about your experiences. I really appreciate it. Thank you. Thanks

for having me. It's been a great, great fun for me to

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