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Interview w/ Carl Yates Perry - Part 1

Published 3/13/2020

Carl Yates Perry leads Square's developer business but made a few tough career decisions to get there. In today's part 1 of this 2-part conversation with Carl Yates Perry, we're digging into his career trajectory and how he knew when it was time to make the next career change.

Carl Yates Perry On The Web

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Transcript (Generated by OpenAI Whisper)
How do you know when it's the right time to leave your job? Even if you've been there for 10 years. This is one of the many things that I talk about with today's guest, Carl Yates Perry. Carl is a general manager at Square. We're going to talk about what that means and Carl's long and history career on today's episode. My name is Jonathan Cutrell. We're listening to Developer Tea. My goal on this show is to help driven developers like you find clarity, perspective, and purpose in their careers. One way that you can get a quick dose of all three of these things, clarity, perspective, and purpose, is to listen to the story of another developer or someone who has been working with teams of developers for a long time. And that is why we bring on guests like Carl to this show. This episode will be broken into two parts, so I encourage you, while you're listening to this episode at the moment that you think you have something of value, go ahead and subscribe in whatever podcasting app you're currently using so that you don't miss out on the second part and future episodes of this show that might provide you that same spark of value again. Now, let's jump straight into the interview with Carl Yates Perry. Carl, welcome to the show. Thanks for having me. I'm super excited to talk with you about your background, what you're doing at Square, but first, I want to rewind. You mentioned before we started recording that you have a little bit of an untraditional background coming into this. I'd love to hear a little bit more about where you came from and what brought you into the world of technology and building products. Yeah, happy to talk about it. Different than most people in technology, other than running to a number of people that have had, you know, as varied a background as me, but it's not the most common path. I think I always like to start off with the most important things I've been married for 22 years this year. Congratulations. Yeah, yeah, it's awesome. I have two kids, a son who is going to turn 12 this year and then a daughter who is going to be 15 this year. So the biggest projects in your life, right? Yeah, you know, it's funny because when I first became a father, basically, I told everybody that, and I've learned this over time, it's like the hardest, best job I've ever had in my life has been a father. It's taught me so many things and how to be a better individual for myself and for others. And as a manager and leader, you know, clearly understanding how to connect with people at different stages and different perspectives, being a parent definitely makes you think about problems at least for me in a different light and helps me try to connect more directly with people in their perspective instead of trying to bring them to mind. So, you know, it's been an incredible thing. It's been the hardest thing I've ever done in my life, but it's definitely a wonderful thing. Yeah, that's awesome. So yeah, so that's kind of my, the most important things about me, a little bit of background about me. I went to a small liberal arts university in Washington State, it's called Washington State University, ended up getting an English degree. I love reading, I love writing, I love thinking, I love talking about stuff and kind of end up falling into English. I went actually to go get a physics degree, but ended up falling out of leaving physics and moving into liberal arts in English. Oh, wow. Yeah, and my plan all along actually was to either largely to go into academia and become a professor and teach, you know, whatever I was going to do, whether it was physics at the time when I was in high school or later on as I moved into the English let to become a professor and teach English literature for the rest of my life at a university. And so, you know, I got to my senior year and, you know, luckily my advisor was the head of undergraduate studies in the program, his name is Jon Airstine and I told him I was interested in understanding what, you know, look like when I go get my master's, he's like, hey, take some courses. So I signed up for two courses and it was a huge turning point in my life actually. Probably kind of one of the three largest turning points in my life. I took the classes and I discovered I did not enjoy those classes. You know, there's a lot of really smart people in these programs obviously, but for the most part, at least as a young, you know, 22, 20-year-old person, the focus of it, what they talked about, how they were talking about just didn't resonate with me. And I realized I didn't want to go get my PhD or my masters and then PhD, at least in English literature, so I decided to leave and not pursue a master's program. That was a big decision for me. At the time I was dating my girlfriend who's now my wife as a set of 22 years and so we ended up making a decision, one, were we going to stay together and then two, if we stayed together, where would we move? And so she's actually from the Bay Area where we are now and I was from the Seattle area, actually bread in Washington. And so we both had English degrees, you know, the cost of living between the Bay Area and Seattle at the time, especially was dramatically different. And so we were like, well, we just moved to Seattle. So we moved to Seattle and we started looking for jobs. And I ended up getting a temp job at Microsoft and my job was to log into an IVR or a phone system every day and transcribe the knowledge-based articles that people were calling in for and those are fixes that you needed for Windows or for any program you're using and I would package those up by hand and I would ship them to customers. And that was my job. Oh, interesting, wow. Yeah, it was a very manual job. And then I did a bunch of filing paperwork and stuff. But the thing that was really cool about this team was that somebody who had worked on the team previously had built a bunch of tools and they had moved on and were building actually tools for the broader organization now. And these tools that largely fallen into disrepair and stopped working because nobody was keeping them up to date and fixing them and addressing and adding new functionality. So I always love to learn. It's kind of the foundation of the way I think about my life and where I do. And so I was like, life is to get this out. So I started writing code. I'd done a little bit of coding in high school and then I'd done some web HTML, CSS, JavaScript stuff in college for some projects on the side. But you know, taught myself how to write code and VB, VB script, ASP and then ASP.net. So I actually improved and fixed all the tools and ended up like automating a bunch of their processes which had previously been manual now automated and the team was able to scale a lot more. And so I did that for a while. And then they started a new program called Technical Router Program and I ended up going there because it was in support in Microsoft as a full-time employee by this point in time. And it was more technical in nature. I was getting more kind of connected to customers. I'd be learning a lot so I went into that. And I ended up building internal tools for them and it eventually came a developer support engineer at Microsoft for kind of the web and for data access specifically. And that turned into being a beta lead for the early XML technologies, MSXML and other things that Microsoft was building. And so embedded with the product teams started working on the data access side as well with ADO and ADO.NET, LEDB, some old school terms for those people that had been around. And eventually moved over to the product team as a program manager on the data access team. Working on.NET mainly but did some native, you know, ADO work as well. And you know from there I was in the SQL Server team and just was able to like pick up a ton of knowledge and learning and started growing pretty quickly there. Became a lead program manager in data access and then became a group program manager running a couple of different technologies. And this was actually one of my first failings at my career actually as one of the best learning experiences I had. As a new manager that was growing kind of responsibilities and needing to hire more people, I kept getting pulled into the weeds by myself and wasn't kind of scaling and hiring people to come in and do that. And so as a result of my inability to scale, you know, my team and the organization, I ended up taking a step back. My manager was super helpful at the time and said, hey, we really need somebody that can go do this. We've been trying to get you to do it. I think it'd be great if you take a step back, go work with somebody else over here. Another one of my peers, but a good friend of mine, work for him and learn from him. And it was super interesting to go through that. It wasn't easy by any stretch of the imagination, but I learned an incredible amount of how to pay attention to what my job should be and what I should be doing versus what I am doing. Because I think it's an important thing to think about. And sometimes you get lost in the day to day and the hustle and bustle of your work and trying to resolve that specific issue your heads down on. And it's really important to take a step back and be intentional and identifying, am I doing the things I'm supposed to be doing? Or am I doing things that are taking you away from my core job? Especially as you scale and kind of take on more and more responsibility. I'll be it. Whether it's as a manager and having more and more people working and reporting to you and helping them or it's you just taking on more responsibility as a leader, it's critical to be explicit in those kind of analysis and decisions. So I did it Microsoft. I ended up moving back, you know, lead PM role and then a group program manager role. I'd done it Microsoft for 12 and a half years at that point. So I moved from somebody that was logging on to a phone and finally paperwork on a daily basis to a group program manager working on some really amazing stuff was specifically at the time working on the entity framework, which was a new object relational mapping technology Microsoft had been adding to the dotnet framework. And so we'd gone through a bunch of reorgs over the course of a couple of years and I'd never looked outside of Microsoft for really outside of the data access area. So I started looking more broadly and wanted to see if there was a change in something I could do a little differently. And one of my own managers who would hire me into the program manager team as a program manager for support, Alyssa Henry, was over at AWS. And so I reached out to her among a bunch of other people and she happened to be the general manager for S3 at the time. And so I told her I was looking, was there anything around? And she said, hey, talk to my head of product and program management and see if there's anything there. And I went through the interview process and they ended up offering me a job that to this day I still can't imagine why they offered it to me, which was I could be the technical program manager for S3. This was back in 2008, late 2008. And thought it would be an absolutely incredible opportunity. And so talk to my wife and we had a great life. I had a really awesome job, but was looking for something a little different and more challenges. And so I jumped at the chance to do this. To this day, I still have many of my friends who at the time would joke with me about moving to work at Amazon and that it was a bookstore. And that's kind of you laugh actually. It is laughable because you speak about AWS now in S3 in particular. And it is a global scale. I mean, it's one of the largest. S3 is one of the, if not the largest public cloud storage solution for objects. We were going through some incredible growth when I was there from late 2008 to early 2012. I was there for three and a half years. And over time I moved from the technical program manager role. I became the engineering manager for all of S3's public APIs. And really like we did a ton of amazing stuff there. It was a crucible moment in my life, those three and a half years. I had never been in an experience like that in terms of the growth and the challenges that were presented. And it was extremely hard. But ultimately rewarding from a growth and learning opportunity. But for me at least, I became so wrapped into my job that I just could separate work from personal life and was having a really hard time balancing my work life and my personal life. And I had a great, right integration strategy for those two things was. And then kind of, you know, I said there were three moments in my life that are kind of pivotal. There was a moment here. My daughter, one night woke up in the middle of the night and was having trouble breathing. And it was pretty bad. We called, you know, the doctors called the hospital. They didn't get back to us right away. To this day, I still don't know why I did this. I put her in the car and we drove to the hospital. It wasn't that far away, but it took 12 minutes to get there. Whereas if we just called 911 because it was fairly serious, it would have probably been faster. But I got there. And I remember it in this day. I'm in the car and I am pulling up to the emergency room and I park and my daughter says to me, daddy, I'm scared. And I said, sweetie, why are you scared? And I open the door and she says before I close the door, I'm worried I'm going to die. And so I opened the door. My driver, she wraps her arms around, wraps her legs around my kind of stomach, wraps her arms around my neck and is facing me. I'm holding her in front of me and I run in there and I said it's going to be fine. It's going to be fine. And it was fine. You know, to this day, we still don't actually know what the problem is. She goes around the NEPI pen. So it's a pretty, you know, we've gone and seen like five different specialists. We've gone to Stanford a bunch of times to see, you know, some of the world-class people there. And they just don't quite know what it is. But at that moment, I realized that, you know, I really need to prioritize time with my family at that point in time. And I wasn't able to do it when I was in Amazon. So I decided to leave. I had been looking and I ended up taking a role back at Microsoft. And I wanted to do something totally new because for, you know, 15 plus years or 10 plus years, I'd worked on developer-focused stuff. So I ended up working on the BI team and I was the group program manager for our group product manager at the time for Power BI. And we launched that. I worked there for two and a half years. We launched that in July. On July 24th, 2015, I still remember it to this day. It is one of the most successful BI services in the world, or at least, you know, where Microsoft sells. And it is a growing, fast growing service. And I learned a lot. It was a really great experience. I'd never worked at the top of the stack. So I did that. And then, you know, I wanted to go, I, after doing that for two and a half years, I wanted to go back and talk and work on developer-facing stuff. I really missed it. It's truly my passion, actually. And so I started looking around the Seattle area, actually outside of Microsoft, talking to people inside Microsoft, and a startup. Jon and Silicon Valley reached out to me and said, hey, we'd love for you to come and interview for our head of product position. And I was like, there's no way I'm moving down to San Francisco. That's crazy. We lived here for 15 plus years. We just moved to a new house. You know, but I thought it would be interesting to talk to them to see what it's like at a startup. They had, you know, six people at the company. So I flew down. And I interviewed. While before I came down, I reached out to Alyssa Henry, who had been my manager at Microsoft and not my direct manager, but kind of my skip level manager at Amazon. And I said, hey, I'm coming down. Let's get together because we would do that every time I came down to the Bay Area. My wife's family lives here. And she's like, sure, yeah, let's do it. You know, why are you coming down? And I told her. And she's like, oh, you're interviewing. You should come interview at Square. And I said, well, I love Square, but, you know, I don't really want to work on that stuff. I want to work on developer technologies. And she said, well, actually, we're building a team to do that. And so, you know, fast forward, as it turns out, it's exactly the fast forward a couple of months. And I've been offered a job to be the general manager for Square's developer platform. When I joined, the team was five people, including myself. So it was a very small team. Yeah, wow. And it's been an absolutely incredible and wonderful and challenging ride over the last four plus years here at Square. Move my family down to the Bay Area. We actually live really close to my wife's family. So it's been great being able to spend time with our family. I love working at Square. I love the mission of the company. I love what we're trying to do with the developer platform and trying to help developers build solutions for sellers. Look, it really, really excited about that. And it's been absolutely wonderful. And I'd have to say at this point, it's hands down the number one best job I've had in my career. And so I've been incredibly lucky to get here. That's awesome. And that was a lot longer than I meant to. I apologize. Oh, no. It was so many things to unpack from your experiences over the years. And something that strikes me, there's a couple of things that strike me. Because I wrote down a question as you began talking about your career path. But then you went on to kind of answer this question as after I had written it down. And essentially, the question that I wrote down was, how do you know when and how to make these changes, these major career defining changes? And you mentioned multiple motivations for those changes. These totally change your life, like changing your job, changes your life, changes the way that your relationships play out. It changes perhaps where you live. Changes everything about, and it doesn't have to change everything about your life. But very often, just by nature of the amount, the sheer amount of time that we spend in our working hours, your job makes a massive difference on your life. And so it's interesting, there's multiple reasons that you made these decisions. And I guess maybe a follow up question that I have for you on that is, how do you know kind of what the threshold is? Or when did you, you know, because for example, the moving story about your daughter, incredible moment in your life, right? And it's this kind of pinpoint moment almost where it went from zero to a hundred, quite literally overnight for you. It seems, right? Yeah. But you know, in other ways, there's, you know, there's moments where you realize kind of over time that you want to do something different that you're interested in something different, perhaps at the end of a project, you're ready to transition. What is that kind of threshold for you? How do you make that call? Did you have a way of making those decisions? Yeah, I mean, I think it's tough. It's like the story with my daughter's super interesting in that, like I had been talking to people because I had, you know, I kept promising my wife, like, no, it's going to get better in three months and six months. And you know, it always got incrementally better, but I wasn't able to turn the quarter for myself. It wasn't an Amazon thing. It was a car all the AIDS parry thing. So, and at some point in time, I had to make a pretty, you know, significant choice in terms of how was I actually going to make it a priority in my life? That, that, that again was the ultimate choice. And it's interesting because like the day before this happened with my daughter, I had recommitted to staying in Amazon. I was like, okay, I can do it. Like, I can go do this. I will make it happen. Here's the specific things. And, you know, I, in my mind, I had kind of articulated the things I was going to do on a regular basis, and I was going to try to ask people to help me hold myself accountable. And, figure out ways, I need to hold myself accountable, but I, you know, I had done those things. And so, you know, there had been movement along kind of the timeline of me looking and, and identifying for me in the end, for the most part, except for that specific like this, this actually completely reoriented my view when that happened to my daughter. It's been about, you know, every, every so often. Maybe every year, maybe every year and a half, making an explicit kind of break from your day to day and looking at a couple of things. One of my mentors who works at Microsoft, he gave me some really great advice, which was, you need to make sure you're being explicit in your career choices. So, you know, everyone to two or three years, depending on what your arc of your career looks like to be clear, you need to do two simple things. So number one is, what are the things that you, you know, you want to be, you know, be saying you're successful at a year or two years from now? And then also, what are the types of roles that you want to go and have and fill or take on that help you both be able to successfully say those things, but also leverage some of the strengths that you have? He talked a lot about something called the inverted team model, which from conversation with him, I'm glad to understand, it's something McKinsey like brought about early, like in the 50s or 60s, where, you know, there are lots of people that have, really amazing strengths and say one dimension, but then there are not as strong in many other dimension. As you become more senior, this can actually help you accelerate very quickly early on in your career, because you're so massively amazing at this one or two things that the weaknesses that are kind of across the broader set of skills that you have aren't as prevalent and they're not as big of a blocker. But as you become more senior, take on bigger and bigger responsibilities, like the missing skills that you have there are actually massive and very problematic, and so you should be explicit. So, you know, every one to two years, I look and say a couple things. One, am I enjoying my job? It was like the first question I asked. Number two, am I growing in my job and am I being challenged on a regular basis? Number three is, what skills do I want to gain over the next one to two years? It's such that I'm in a spot where I feel more confident that I've grown as an individual, that I'm becoming better in the areas I want to become better in, and if there's specific skills that I'm struggling with and I'm not as good, am I trying to improve on those? Or am I okay with keeping them that way? Those are the three things that I, you know, I started doing later in my career, you know, about 10 years ago, based on feedback from a couple of different people. And I think the core for my decision making, you know, is as I identify like, I'm not really happy. I don't think there's the opportunities in my current role that help me fulfill kind of the growth areas and trajectories I want to have, I then start to look more broadly about what challenges are out there. And you know, there's a, there's a gentleman I worked with, Microsoft, his name's Amir Nets, he's a very senior individual at Microsoft. And when I told, you know, everybody's leaving, he's like, you know, congratulations, Carl, this is great. He said, you know, it's great to see you grabbing at the opportunities that are presented to you. And in my career, I have been incredibly lucky. I really think that luck has played a big part in my career. I think sponsorship, I think hard work, I think a lot of other things as well, but luck, the luck that there are these opportunities that have come up and that I've been willing to jump at them. And I'm only going to jump at them because I want to keep growing and learning and being challenged. And I think that's, I know that's like a long, windy rail, but trail, but I think that's how I think about evaluating whether this is the right job for me now. Am I growing? Are, am I being challenged? And am I going to be in the spot I want to be in a couple years from now? Yeah, that's such a good framework. And I'm imagining that this is almost like a personal day off that you can take and go and spend, you know, really kind of digging into those questions and getting to the truth. Because I think for a lot of people, the superficial answer that you might have kind of a gut response to, may not be enough to answer those questions, right? It's like, well, of course, I'm learning. But is it actually that you're learning or is it that you are experiencing new things that you don't really want to carry forward, for example, right? You might be learning something, but it may not be functionally what you should be learning or, I guess, an alignment with your goals, what you should be learning. And it really takes some reckoning to kind of come to terms with that. I mean, I think it's a really good point that every role we have, give us the opportunity to learn and grow. I think that's almost at least in technology I find that's the case. Absolutely. And there's so many opportunities in technology. Like, you know, I think about engineers or product people in particular, but lots of others. Like, you have, especially in the Bay Area, you can go anywhere you want to. You can go do lots of different things. So there's that opportunity for at least to style as people is there. I think it's harder for younger or people are people trying to break into the space. And so making sure you understand what's critical for you, you know, we only have this level of kind of cognition and ability to engage, you know, as long as we're alive on this earth. And so the question is, what are you going to do with that time here? And when I think about my career explicitly, I want to be stretched. I want to feel uncomfortable, actually. I don't like feeling comfortable, but I want to feel uncomfortable. Because when I feel uncomfortable, I know that I can't just keep doing the same thing over and over again. I've got to think about the problem in a different light. I need to approach the problem from a different angle. I need to grow new skills to be successful here. And I think as I do that, or anybody does that, actually, it helps them in their current job, right? Or that future job they want to go after. And so, as I said, I think a lot of my stuff has to do with luck and timing. But I do think the constant focus on growth and challenges and taking on new opportunities when they present themselves has definitely been rewarding for me and has turned out quite well in my career. Today's episode is sponsored by Linode. You can get started on Linode today with a $20 credit. If you are a new user to Linode, and if you're not a new user to Linode, then you already know how valuable this credit can be. Because the plans on Linode start as low as $5 a month. What do you get for $5 a month? The access to 11 data centers worldwide. This includes their newest data center in Sydney, Australia. You get access to enterprise grade hardware. This three compatible storage option and the new Next Generation Network. Linode delivers the performance you expect at a price that you don't. On top of that, you also get root access to your server. You get an API that allows you to orchestrate that server, as well as a Python CLI. Beyond that, you can even get dedicated CPU plans or GPU plans. Go and check it out. Head over to Linode.com slash Developer Teato get started today. It's linode.com, l-i-n-o-d-e.com slash Developer Teaall-more word. To get that $20 credit, use the promo code Developer Tea 2020 at checkout. It's Developer Tea 2020. Thanks again to Linode for sponsoring today's episode of Developer Tea. It's interesting. You mentioned being uncomfortable. I think that there's two frames that people have purchased from broadly speaking. I'm sure there's many more. Broadly speaking, there's two frames that I think people naturally purchase from. One is, I think, perhaps not so healthy. So, I'll just show my cards right up front here. The other one is certainly much more healthy. The one frame is, I'm uncomfortable because I'm stressed or because I am doing something that I don't resound with. Maybe it's against my values. It's uncomfortable to me because in no uncertain terms, I feel like I'm in the wrong place. Versus being uncomfortable because you're having to admit, for example, that you don't know on a regular basis. Those are two different types of uncomfortability. I think people, there's a little bit especially in the United States. There's some of the working culture in the United States. It's the idea that the first kind is the good kind. That somehow being overworking, you're earning your stripes. Even accidentally in cultures, especially in startup cultures, I say accidentally because I don't think people are doing this maliciously. The accident is celebrating the overworking or celebrating that uncomfortability when it's just not the right fit for that person. To your point, you were probably also quite uncomfortable when you were having to stretch and make compromises on the time that you were spending with your family. I wonder, because you might have a mix of both of those things in a role. I think it's important. I wonder how you would think about filtering the good uncomfortable from the bad uncomfortable. There's all these Twitter threads and wars that are happening around the kind of is overworking the right thing or are you doing it for other people's benefit? Is it healthy for you? I think the most interesting way I think, the way I think about it is it's actually a friend of mine that I worked with in the SQL Server team told me one day he said there's a difference between being stretched and being stressed. He used the analogy of the muscle and he said when you stress a muscle, you can tear it. But you tear it in more aggressive ways where it can actually cause damage. Whereas when you stretch your muscle, stretching actually causes micro-terrorism. This is actually how weight lifting works. You stretch and the stretching or the lifting of weights actually does, it even sets tearing parts of the muscles and they repair themselves. I think that you have to be conscious of how much stressing you're doing and how much stretching you're doing. Stress is not the most healthy thing. It can be beneficial in certain instances to be clear. But oftentimes the way I think people need to look at the problem is how I'm going to stretch myself and I may choose at times to place stress in my life when I'm performing those stretches or taking on those challenges that are stretches for me. But I think again it comes back to intentionality. A great example, you've talked about startups. If you're going to sign up for a startup for the most part in Silicon Valley in particular, there's definitely going to be an under it in rule. Again, I've never actually worked to startup to be clear. I've worked at barely established companies with square being the least established company I've worked at. So I've never put in the 100-hour a week or 90-hour a week for months at all. I've never done that. I'm not speaking from a point of view of experience here. But I do think that you can choose to take on time-bound situations where you work that. But I don't know that I would enjoy working in environment where it's required. And I think that there are aspects of unhealthiness there. If people knowingly choose it, I think that's the key for people is knowingly choosing that. And knowing how long they're willing to put up with that, I think that there is totally within their ability to make those decisions. I just not sure that people know the trade-offs to be frank. So I think it's tough. There's lots of people I've worked with that have worked at startups. And I've really enjoyed it. And it has been, in some cases, financially rewarded in other cases, growth for a warning, career rewarding. So I think for different people, the love being in startups, working that level of pace is super engaging and exciting for them. I've never had the opportunity to do that myself. One day, maybe I will. But for me, it's more about stretching myself. And that's where the level of uncomfortable comes from. Because I'm in situations that I've not necessarily done or know how to do on a regular basis. And therefore, I have to look at the problem differently. I have to come up with different solutions or I have to approach the problem and leverage the people around me to be successful. So I definitely think that's more the vein that I've experienced it in than the stressing side. It's happened, but it's been intentional most of the time. Yeah, I think you're hitting on the most important thing there. Right at the end, at least in my experience and in my career so far, is that the stress that I feel is stretching me is the stress that I choose to put myself under. And in many ways, any job that we are a part of, and for most people, this is true, you have a lot of latitude to move between jobs if you're in tech most likely. But any job that I put myself, I subject myself to a particular job in tech. It's likely that I have chosen that. But within that job, kind of in a microcosmic frame, the stress that I am being subjected to if I've chosen that, then that is kind of the idea is free stress rather than stress free. I don't want to live my life without any kind of motivation. That seems boring, quite frank, right? But I do want to live my life in such a way that stress is not coming at me from all angles without my control or choosing of that stress. It's not even really about control as much as it is, about electability. It went to be able to elect the stress that I put myself through. I think it's sometimes hard to know what the stress is you're going to go through to be explicit in a given scenario. I think what's most important is I'm willing and know that I'm going to be stressed. I don't know what the stresses are going to be and I don't know what the forces are. They're going to come at me to cause that stress. But making the decision ahead of time that you're going into that particular situation in your career or that role, knowing that that is going to be there, I think it at least helps set you up for a higher likelihood of the stress not overwhelming you. You being able to manage through it and figure out how to be successful and grow through it as opposed to honestly end up being fatigued and broken down, which is the outcome of repeated stress if not managed correctly. Man, there's so much good stuff in here. I have a slightly different question to ask you. People who are listening to this, they might hear someone that they think kind of rolled the dice perfect every time. They got all the right opportunities. They knew all the right people. Everything just fell in line for you. To your point, certainly there's a lot of luck involved for a career like yours. But I'm almost certain that that perception of everything just falling in line is not true. I want you to take me back to a moment where you felt something kind of like a dark place, a moment that you didn't know what to do, perhaps you didn't know what the way forward was. Some moment in your life, then you can look back and say, man, once that got out of that, that was a turning point for me. The example that I mentioned earlier, one of the pivotal turning points of my career was when I actually failed as a manager, the first time manager trying to scale organization. It felt like I was trying to do all these things when in reality, I wasn't doing the most important things to get the team out of the spot that it was in, which was inability to deliver on the PRDs or the specs or the PRFAC, whatever format you used to define the product itself. Instead was delving into details, which was valuable if I was the front line PM that was responsible for that area. It just felt like I kept hitting my head against the wall and repeatedly not making it through the wall. The problem was that I didn't know where the doorway was. I was hitting the wall. I wasn't going to the doorway that was there. I wasn't leveraging the people around me. I also think when you start struggling and you start to, at least this is what I find for myself. When I start to get to spots where I'm either unhappy with what's happening or I'm disappointed in my effort or work or output or the results of something that I had been working on, for me, the way I manage through that, that's most effective is talking to people and engaging them and getting their perspectives and hearing their thoughts. That helps me better inform my perspective, my thinking. I tend to better describe and come up with solutions for the problems I'm having through discussions with multiple people. I'm naturally a person that likes to have interactions with humans. Those conversations are critical for me. What you find though is when you get in situations where you start to beat yourself down or you start to feel like you're not succeeding and that you're failing is you actually tend to close down. That's a huge mistake. I think it's a failure mode that humans just naturally fall to in many regards and I actually think that in the office it needs to happen. You need to find the support around you. People in my crew, I've discovered people are more than happy to help out in many situations and be a sounding board or give you ideas or even help you with a specific problem. What I found when that happened was luckily my manager and then my coworker who I ended up working for and he became my manager helped stop me. It required somebody to look at your failing. We've given you feedback. You're not doing the right thing. You continue to focus on these details. You're not solving these problems. Here's where the team's blocked. They're going to be worse off in three months or six months if you don't go solve these problems and we've asked you to and you have it. I think that just knowing and hearing that and being able to talk to them and then other peers or friends of mine to get outside perspective and data and viewpoints so that then I can start to synthesize and articulate what my perspective is and feel confident that I can establish a path forward. That was the most useful thing for me and I found it repeatedly that when I start to feel like I'm struggling or feel like I'm failing or feeling like I have failed and haven't met the goals, I kind of take a step back pause and like look at the problem and then I go to the people I trust and I start to ask questions for their perspective or if they weren't part of it I start to describe the problems to them. That's always been a great tool for me and it is the most powerful tool for me is more clearly being able to articulate and form solutions to the problems and path forward by speaking about the problems I'm encountering either the specifics or the meta issues and being able to kind of think through that. I also do writing a little bit although not nearly as much as the spoken conversation really helps me kind of dig through that and understand what the right path forward would be. That's excellent advice. I think there is so much that can be brought forward when you check your own perspective against someone else's and it takes a lot of work in my opinion, it takes a lot of work and you can tell me from your experience to develop relationships where people will be honest with you especially in scenarios where that honesty is perhaps something that is uncomfortable to hear. This is of course especially for direct reports it's difficult to pull out feedback from a direct report that hey you know what you did this thing and it just really wasn't great for me. That's hard to do and so there's mechanisms for example a mechanism that I've tried to start using in my current role is to ask what am I wrong about? Not ask, give me your feedback but give me specifically what I'm wrong about because I can assume that I'm not right about everything. That's a base level assumption that I hope most people who are listening to this show they can agree with. Not right about everything. So I'd love to know from your perspective what am I wrong about? So do you use some of these kinds of devices or I guess framing in these conversations to help you really dig out the truth? Yeah I mean I think you made a comment really about finding the people that you can trust to kind of explore these things I think that's critical to having candid, open and honest conversations because some of the conversations especially when you're struggling are hard and you need to have kind of honest voices and mirrors that can show you parts of the reality. It's not the full reality but the parts. And so I think that's the most important thing is to discover who those people are. The other thing that I found obviously is like getting other people are willing to share their perspective on lots of different things and people aren't going to go out of the way to help in some cases, right? But they're always willing to share their perspective and their thoughts and help you in some cases better inform your worldview. And so I find people always willing to share their perspectives and I think data is useful and I think of people's perspectives as data and as I at least kind of take my view and then I get the other data which is other people's viewpoints and then I kind of work closely with my trusted network. I'm able to better articulate the world I want to go to the future, the things I want to correct and move towards and establish a path forward that I feel really confident in. I really hate to say this. I've got to go to my son's parents to come right back. I've got to be there in 10 minutes. But I love this conversation so if you want to continue it I'm happy to do it. I just can't right now. Oh no totally totally fine. Let's put a pause on it now. Okay, I'm happy to do a part two. I defer to you to what you think is best. Sure. Thank you so much for listening to today's episode. Thank you again to Karl for joining me on this and the next episode of Developer Tea. Make sure you subscribe and whatever pie-casting app you're currently listening with so you don't miss out on that episode. Don't forget to get your $20 worth of credit by heading over to linno.com slash Developer Tea and using the code Developer Tea 2020. Just develop a T2020 and check out. Today's episode and every other episode of Developer Teacan be found at spec.fm. Today's episode was produced by Sarah Jackson. My name is Jonathan Cutrell and until next time enjoy your tea.