How do you know when it's the right time to leave your job? In today's part 1 of this 2-part interview, we're talking to Carl Yates Perry about his job transitions and how he made the decision to become the General Manager at Square.
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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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 kind of what that means and Carl's long and history career on today's episode. My name is Jonathan Cottrell. You're listening to Developer Tea. My goal on the 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. Thanks for having me. I'm excited to talk with you about your background, what you're doing at Square. But first, I want to kind of 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, I'm happy to talk about it. It's different than most people in technology, although I do run into a number of people. I've had 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, 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. Wow. The biggest projects in your life, right? Yeah. It's funny because when I first became, a father, basically I told everybody, 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, both for myself and for others. And as a manager and leader, 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. And I think that's something that I've learned a lot in my life. So it's been an incredible thing. It's been the hardest thing I've ever done in my life, but it's definitely been a wonderful thing. Yeah, that's awesome. So yeah, so that's kind of the most important things about me. A little bit of background about me. I actually 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 ended up falling into English. English. I went actually to go get a physics degree, but ended up falling out of leaving physics and moving into liberal arts and English. 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 English Lit 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's John Erstein. And I told him I was interested in understanding what, you know, it looked 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. It was 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, 22 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 master's and my 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 I said, 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 bred 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're like, well, we'll just move 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 aension platform and writeension platform and writeension platform and writeension platform and 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 had 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 what I do. And so I was like, well, I can figure this out. So I started writing code. I'd done a little bit of coding in high school. And then I'd done some HTML, CSS, JavaScript stuff in college for some projects on the side. But I taught myself how to write code in VB, VBScript, ASP, and then ASP.NET. And so I actually improved and fixed all the tools. And ended up 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. I was a full-time employee by this point in time. And it was more technical in nature. I was getting more connected to customers. I'd be learning a lot. So I went and did that. And I ended up building internal tools for them. And it eventually came a developer support engineer at Microsoft. For 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 and LADB. Some old school terms for those people that have been around. And eventually moved on to the product team as a program manager on the data access team. Working on .NET mainly. But did some native ADO work as well. And from there, I was in the SQL Server team. And just was able to 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 in my career, actually. It was one of the best learning experiences I had. As a new manager that was growing responsibilities and needing to hire more people. I kept... Getting pulled into the weeds by myself. And wasn't scaling and hiring people to come in and do that. And so as a result of my inability to scale 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. Worked for him and learned 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 head's 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 me away from my core job? Especially as you scale. And kind of take on more and more responsibility. Albeit whether it's as a manager. And having more and more people working and reporting to you. And you 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've been at Microsoft. I ended up moving back. Lead PM role. And then a group program manager role. I'd been at Microsoft for 12 and a half years at that point. So I'd moved from somebody that was. Logging onto a phone and filing 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 .NET framework. And so we'd gone through a bunch of reorgs. Over the course of a couple of years. And I had never looked outside of Microsoft. But really outside of the data access area. So I started looking more broadly. And wanted to see if there was a change. And something I could do a little differently. And one of my own managers. Who'd hired me into the program manager team. As a program manager from 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, you know, I told her I was looking. Was there anything around? And, you know, she said, Hey, talk to my head of product and program management. And see if there's anything there. And, you know, I went through the interview process. And. Then. I. 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. And this was back in 2008. Late 2008. And. Thought it would be an absolutely incredible opportunity. And so, you know, talk to my wife. And, you know, we had a great life. I had a really awesome job. But was looking for something a little different, more challenges. And so I jumped at the chance to do this. You know, to this day. I. I still have. Many of my friends. From. Who. Who at the time would joke with me about moving to work at Amazon. And that it was a bookstore. Right. And. Yeah. And that's kind of. You laugh. Actually. It is laughable. Because you think about AWS now. And S3 in particular. And it is a global scale. I mean. It's one of the largest. You know. S3 is. 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. Kind of moment in my life. Those. Three and a half years. I had never been. In a. Experience like that. In terms of the growth. And the challenges that were presented. And it was extremely hard. But. You know. Ultimately. Rewarding from a growth. And. Kind of learning opportunity. But. For me. At least. I became so wrapped into my job. That I just couldn't separate. Work from. Personal life. And was having a really hard time. Balancing. You know. My work life. And my personal life. And figuring out what the right integration strategy. For those two things was. And then. Kind of. You know. This. 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. Was having trouble breathing. And. It was pretty bad. We called. You know. The doctors. Called the hospital. Um. 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. And it wasn't that far away. But it took. Twelve minutes to get there. Um. Whereas if we just called. Nine one one. Um. Because it was fairly serious. It would have probably been faster. Um. But I got there. And I remember. And to 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. Um. 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 open the door. I grab her. She wraps her arms around. Um. She wraps her legs around my. My kind of stomach. Wraps her arms around my. Um. 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. Um. She carries around an EpiPen. Um. 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. 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. Um. And. I ended up taking a role. Back at Microsoft. And I wanted to do something totally new. Because for you know. Fifteen plus years. Or ten 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. Or 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. Um. It is one of the most successful BI services. In the world. Or at least. You know. Um. Where Microsoft sells. Um. It is a growing. Fast growing. Um. 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. 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. It's truly my passion. Actually. And so. I started looking around. The Seattle area. Actually outside of Microsoft. Um. Talking to people inside Microsoft. And. A startup. Down in Silicon Valley. Reached out to me. 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. I thought it would be interesting to talk to them. To see what it's like. At a startup. They have. They had. You know. Six people. At the company. Wow. So I flew down. And. I interviewed. But 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. 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. I don't 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 a couple of months. As it turns out. Yeah. Exactly. So you 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. I moved 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. 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. Like. 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. No. This. So. It was. It was so. So many things to unpack. From your experiences. Over the years. And. Something that strikes me. There's. There's a couple of things that strike me. Because I wrote. Wrote down a question. As you began. Talking about your. Your. Your career path. But then you. 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. You know. How do you know. How do you know. When. And how. To make these. Changes. These major. Kind of career. Defining changes. Yeah. And. You know. You mentioned. Multiple. Kind of. Motivations for those changes. This is. You know. These. These. Totally change your life. Like. Changing your job. Changes your life. It changes. The way. That your relationships play out. It changes. Perhaps where you live. You know. Changes everything about. And it doesn't have to change. Everything. About your life. But. Very often. Just by nature. Of. You know. The amount. The sheer amount of time. That we spend. In our working. You know. Working hours. Your job. Makes a massive difference. On your life. And so. It's interesting. There's. There's multiple. You know. Reasons. That you made these decisions. And. I guess. Maybe a follow-up question. That I have for you on that is. You know. How do you know. Kind of. What the threshold is. Or when did you. You know. Where. Because. In. For example. The. 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. You're ready to. To transition. What is that. Kind of threshold. For you. And how. 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. The. Like. The story with my. My. My daughter. 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. In 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 Carl Yates Perry 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 in the end. Was the. The ultimate choice. And it's interesting. Because. Like. The day before. This happened with my daughter. I had. Recommitted to staying at 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 hadn't done those things. And. So. You know. There had been movement. Along. Kind of. The. The timeline of me. Looking. 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. Off. 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. Every one 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. 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. 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 T model. Which. From conversation with him. I'd love 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. In say. One dimension. But then they're not as strong. In many other dimensions. As you become more senior. This. 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. 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? Is like the first question I ask. Number two. Am I growing in my job? And am I being challenged. On a regular basis? And the number three is. What skills do I want to gain. Over the next one to two years. Such that I'm in a. 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. That 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 just 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 helped 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 I was 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 are. That have come up. And that I've been willing. To jump at them. And I'm willing. 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 winding rail. 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 a. Like a personal day off. That you can take. And go and spend. You know. Really kind of digging. 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. Is it actually. That you're learning. Or is it that you are. Experiencing new things. That you don't really want to. 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. It. In alignment with your goals. What you should be learning. And it really takes. Some reckoning. To. To kind of come to terms. With that. I mean. I think it's a really good point. That. Every role we have. Gives us the opportunity. To learn and grow. That. I think that's almost. At least in technology. I find that's. 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 established people. Is there. I think it's harder for. Younger. Or people. Or 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. I want to feel. I want to feel. Uncomfortable actually. I don't like feeling uncomfortable. 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. And 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. A 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? You get access to 11 data centers worldwide. This includes their newest data center. In Sydney, Australia. You get access to enterprise grade hardware. S3 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 T. To get started today. That's linode.com. L-I-N-O-D-E.com. Slash. Developer T. All one word. And to get that $20 credit. Use the promo code. Developer T. 2020. At checkout. That's developer T. 2-0-2-0. Thanks again to Linode. For sponsoring today's episode. Of developer T. You know. It's interesting. You mentioned being uncomfortable. And I think that. There is the. There's. There's kind of two. Frames that people approach this from. Broadly speaking. I'm sure there's many more. But. Broadly speaking. There's. There's two frames. I think people. Naturally approach this from. One is. I think. Perhaps. Not. Not so healthy. So I'll just kind of show my cards. Right up front here. And the other one is. 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. Do. You know. Resound with. Maybe. Is against my values. It's uncomfortable. To me. Because. You know. In no uncertain terms. I feel like. I'm in the wrong place. Yeah. Right. Versus. Being uncomfortable. Because. You're. Having to admit. For example. That you don't know. On a regular basis. Yeah. Right. Those are two different types. Of uncomfortability. Yeah. I think people. There's. There's a little bit. Especially in the. In the United States. There's some. Some of the working culture. In the United States. Espouses that. The idea that. The first kind. Is the good kind. Right. Yeah. That somehow. Being. You know. Overworking. You're kind of. Earning your stripes. And. Even. You know. Accidentally. In cultures. Especially in startup cultures. There's. A. And I say accidentally. Because I don't think people. Are doing this maliciously. But. The. The accident is. Celebrating. The overworking. And. Or celebrating. The. That uncomfortability. When it's. Just not the right fit. For that person. Right. Yeah. To your point. You know. 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. Yeah. So I wonder. You know. How. Because. You might have. A mix of both of those things. In a role. And. You know. I think it's important. I wonder how you. Would think about filtering. Those. You know. The good. And. Uncomfortable. From the bad. Uncomfortable. Yeah. So. There's a. Like. There's all these Twitter. Threads. And wars. That are happening. Around the. Kind of. You know. Is overworking. The right thing. Or are you. You know. Are you doing it. For other people's benefit. Is it healthy for you. I think. I think the most interesting way. I think. Let me rephrase this. The way I think about it. Is 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. And he used the analogy. Of the. The muscle. And he said. When you stress a muscle. You can tear it. And you can. And. But you tear it. In more aggressive ways. Where it can actually. Cause damage. Whereas. When you stretch your muscle. Stretching actually. Causes micro tears. This is actually. How weight. Weight lifting works. Right. You. You stretch. And the stretching. Or the lifting of weights. Actually does. It ends up tearing parts. Of the muscles. And they repair themselves. And 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'm going to. I may choose at times. To. Place stress. In my life. When I'm performing. Those stretches. Or taking on those. Challenges that are stretched. Stretches for me. But I think again. It comes back to intentionality. A great example. You know. You've talked about startups. Like. You know. If you're going to sign up. For a startup. For the. For the most part. In Silicon Valley. In particular. There's definitely. Going to be an unwritten rule. Again. I've never actually worked. A startup. To be clear. I've worked at. Barely established companies. With Square being. The least established company. I've worked at. So. Yeah. So I've never put in the. Hundred hour. A week. Or 90 hour. A week. For. Months. At all. I've never done that. So I'm not. 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 an environment. Where it's required. And I think that there are. Aspects of unhealthiness there. If people knowingly. Choose it. And 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. And 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. You know. In some cases. Financially rewarded. In other cases. Growth rewarding. Career rewarding. So I think. You know. For different people. The. Love. Being in startups. Working that. 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. That I do. On a regular basis. And therefore. I have to. 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. Yeah. 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. 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. Is stretching me. Is the stress. That I choose. Yeah. To put myself under. Yeah. And in many ways. You know. Any job. That we are a part of. And for most people. This is true. You have a lot of. You know. Latitude. To move between jobs. If you're in tech. Most likely. Yeah. But any job. That I put myself. You know. I subject myself. To a particular job. In tech. It's likely. That. That. I have chosen that. But. Within that job. Kind of in a micro. Cosmic frame. The stress. That I am being subjected to. If I've chosen it. Then. That is. It's. Kind of the. The idea is. Free stress. Rather than. Stress free. Right. I don't want to be. I don't want to live my life. With. Without any kind of motivation. Right. That's. That seems. Boring. Quite. Quite frankly. Right. Yeah. 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. Or choosing. Of that stress. It's not even really about control. As much as it is. About electability. Yeah. I want to be able to elect. The stress. That I put myself through. Yeah. I think it's. Sometimes it's hard to know. What the stress is. You're going to go to. Go through. To be explicit. Like in a given scenario. I think what's most important. Is like. 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. 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. I think at least. Helps set you up. For a higher likelihood. Of. The stress. Not overwhelming you. And you being. Demanded. 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 kind of broken down. Which is. The outcome. Of. You know. Repeated stress. If not managed. Correctly. Man. There's so much good stuff. In here. I have. Kind of 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. You know. They knew all the right people. Everything just fell in line. For you. And. To your point. 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. So. I want you to take me back. To a moment. Where. You felt. Like. 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. Some moment. In your. In your life. Then. You can look back. And say. Man. That was. You know. Once I got out of that. That was a turning point. For me. Yeah. I. Um. The example. That I mentioned earlier. Kind of. One of the pivotal. Turning points. In my career. Was when. I actually failed. As a manager. The first time manager. Trying to scale. Organization. Um. You know. 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. That it was in. Which was. Inability. To deliver on. You know. The. PRDs. Or the specs. Or the. You know. The PR fact. Whatever format. You use. To define the product. Itself. I was like. Delving into details. Which was valuable. If I was. The frontline PM. That was responsible. For that area. And so. Um. It just felt like. I kept hitting my head. Against the wall. And repeatedly. Like. Not making it through the wall. And the problem. Was that. I wasn't. You know. 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. Also. I think. When you get. When you start struggling. And you start to. Well. At least this is what I find. For myself. When I start to get to. Spots where I. I'm either. Unhappy with what's happening. Or I'm disappointed in my effort. Or work. Or output. Or the result of something. That I had been working on. Um. 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. Um. I. I. I. Tend to. Better. Describe. And come up with solutions. For the problems I'm having. And. Through discussions. With multiple people. Um. I'm naturally. A person that likes to have. Kind of interactions with humans. And so. Those conversations are critical for me. And so. What you find though. Is when you get in these 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. And I think that's a huge mistake. I think it's a failure mode. That humans just naturally fall to. In many. In many regards. And I actually think. The opposite needs to happen. You need to find the support around you. People. You know. In my career. I've discovered. People are more than happy. To help out. In any. In many situations. And. Be a sounding board. Or give you ideas. Or even help you. With a specific problem. Right. And so. What I found. Um. When that happened was. You know. Luckily. My manager. And then. My co-worker. Who I ended up working for. And he became my manager. Um. Help. Kind of. Stop me. Like it required somebody to come in. Like look. You're 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. And 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 haven't. And so. I think that. Just. Just knowing. And hearing that. And being able to talk to them. And then other. 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. Um. That was the most useful thing for me. And I found it repeatedly. That when I start to. You know. Feel. Like I'm struggling. Or feel like I'm failing. Or feel like I have failed. And haven't met the goals. Um. I. 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. Ask for their perspective. Or if they. They weren't part of it. I start to describe the problem to them. Um. And 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 forwards. By speaking about the problems I'm encountering. Either. The. Specifics. Or the meta issues. And. Being able to. Kind of think through that. Um. I also do writing a little bit. Although not nearly as much. The spoken. Kind of conversation. Really helps me. Um. 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. That can be brought forward. When. You check your own. Perspective. Against someone else's. And. It takes a lot of work. Uh. I. In my opinion. It takes a lot of work. And you can tell me. From your experience. To develop relationships. Where people. Will. Uh. Will be honest with you. Especially in scenarios. Where that honesty. Is. Perhaps something that is. Uncomfortable to hear. Right. This is. You know. Of course. Um. Especially. You know. If for. For direct reports. It's difficult. To. To. 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. Right. Like. Yeah. That. That's hard to do. And so. You know. There's. There's mechanisms. For example. A mechanism. That I've tried to start using. Uh. In my. In my role. My current role. Is to ask. What am I wrong about? Not ask. You know. Give me some negative. You know. Give me your feedback. Right. But give me specifically. What I'm wrong about. Because. I can assume. That I'm not right about everything. Right. That's. That's a base level assumption. That I hope most people. Who are listening to this show. They can. They can agree with. Uh. You're not right about everything. Yeah. So I'd love to know. From your perspective. You know. What am I wrong about? So. Do you use. Some of these kinds of devices. Uh. Or. Or I guess. Um. Framing. In these conversations. To help you really dig out the truth. Yeah. I mean. I think. You're. You made a comment earlier. About finding the people. That you can trust. Um. 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 know. 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 parts. And so I think it's. That's the most important thing. Is to discover. Who those people are. Um. The other thing. You know. That I found. Uh. You know. Uh. Obviously. It was like. You know. Getting other. People are willing to share their perspective. On lots of different things. And. You know. They're not. People aren't going to go out of their way. To help. You know. In. In some cases. Right. But they're always willing to share their perspective. And their thoughts. And. And help you. You know. In some cases. Better inform your world view. And so I find. Um. People are always willing to share their perspectives. And. I think data is useful. And I think of people's perspectives. As data. And as you. 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 at her. I'm able to better. Articulate the world. I want to go to the future. The. The things I want to correct. And move towards. And establish a path forward. That I feel really confident in. Yeah. I really hate to say this. I've got to go to my son's. Uh. Parent teacher conference. Totally fine. I gotta 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. Totally fine. Let's. Let's put a pause on it now. Okay. I'm happy to do a part two. Like. 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 Carl. For joining me on this. And the next episode of. Developer T. Make sure you subscribe. In whatever podcasting 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 leno.com. Slash developer T. And using the code developer T 2020. It's developer T 2020. At checkout. Today's episode. And every other episode of developer T. Can be found at spec.fm. Today's episode was produced by Sarah Jackson. My name. Is Jonathan Cottrell. And until next time. Enjoy your tea.