Adam: You hear me through your headphones. I assume, so can you tell me who you are, uh, and what you do?
Jon: Yes. I’m John DeLamotte, and yeah, for the last about 10 years or so, I’ve been a software engineer. I’ve worked kind of all around and done a lot of platform-type work. So, stuff where I’m supporting other engineers at companies and working on the tools that they use.
Adam: And like, I usually like to tell people before we start what my thoughts are about the episode.
Jon: Uh huh.
Adam: But maybe you need to help me figure out what yours is.
Jon: I think it is kind of a story of like, putting my hope in something, and then realizing, like, it was very misplaced.
Intro
Adam: Hello, and welcome to CoRecursive. And welcome to 2025. I’m Adam Gordon Bell.
Today’s story is about career change in John’s life: trying to get a job at Stripe, working at Stripe, and eventually leaving.
It’s super fascinating. It’s a very candid look into identity and relationships, performance reviews, culture, and relationships. I don’t even know how to set it up. You won’t be able to predict where the story is going. I promise you that.
But yeah, it all starts with John trying to get a job.
Joining Stripe
Jon: I had a few friends who had worked with me at my previous company, and they worked at Stripe. They were like, “Hey, you should come get a job over here.” I thought Stripe was the coolest company. I was really actually particularly interested in it because they did sort of financial infrastructure. My dad was an entrepreneur, and he honestly, from the age of about, like maybe 12 or so, he kind of had groomed me to almost take over for him in his business, uh, in finance.
And so, until I was about maybe 25 or so, my life trajectory was, I’m going to go get a job in software engineering, and I’m going to work here for a while. Then I’m going to, like, take all this that I learned over here, and then I’m going to go work with my dad. So when Stripe came along, I was like, “Oh, this is perfect.” It’s a company I really respect; they have really high engineering standards. It’s got people I really like that are working there. And like, I could go like, actually see what it’s like to work in a real company that does, like, real financial money movement stuff. So it kind of ticked all the boxes for me.
Initial Interview
Jon: And I applied at Stripe. Yeah, I remember that was super nerve wracking. I was like way over prepared for the interview. I was like, I’d been writing TypeScript at the time for, I don’t know, maybe like six months or something, and so I had this impression of like, oh, Stripe, there’s such craftsmanship, such quality. I gotta make sure that I like, show up in the interview super well and present myself like I really care about craftsmanship.
So I had my IDE all set up. I was so focused on making sure that I had the testing and the types all right that I actually ended up sucking on the question. So that was tough. It was tough to swallow the failure there. I got turned down, and then I tried again six months later cause they were like, “Hey, you can re-interview in six months.” That time around, I made sure I did a bunch of practice interviewing beforehand. I was like, okay. I had talked to some other people who worked in big tech, and they’re like, “Yeah, it’s not really about demonstrating super high quality. It’s about solving the problem.”
So I allowed myself to lower my standards the next time to just be like, okay, I got to just solve the thing, and then I can iterate and make it better if I have time left in the interview. But really, I got to optimize for finishing the thing.
Decision to Join a new Team
Jon: Stripe is that they have several headquarters. They’ve got, they’re mainly in San Francisco and actually in Ireland. They got a big Seattle office and several others. But I joined in 2020; they had actually just established a Remote Hub. So they had made remote a part of their official policy. Kind of like you could be hired into the Remote Hub, and you could stay remote.
So I made it to Stripe, and I actually had a choice when I was joining. They were like, “Hey, we’re spinning up a brand new JS Infra team.” When a language gets a certain level of usage at the company, they typically form a team to support that language and kind of all the tooling and stuff around it. And they asked me, “Are you interested in being the first hire onto the team?” I was actually planning on joining the team that my friends at the company were on. They had an opening on their team.
And so I kind of had to make this decision: do I want to take the riskier, more difficult route of trying to help spin up a brand new team? Or do I want to go the safer route and just be on it? I took the riskier route because I was like, “What the heck? Why not? Let’s try it.”
And so, yeah, I joined the JS Infra team, and it was, the first year was pretty difficult, actually. I had a hard time with the team, getting our feet underneath us, and almost saying the words was difficult for me, but I’ll say it anyway: demonstrating business value.
Adam: The phrase was difficult because it was something that he was hit over the head with, again and again, by his manager.
Jon: They were like in, in all of my writing and my project proposals, in my planning stuff, in my like status updates for projects, there was always this push to be like, what’s the business value?
So it’s not an inherently bad thing; I’m just like, I have some baggage around it. It’s hard for me to say the words because I’m like, it had to be drilled into me so much, like what’s the business value?
What’s the business value?
Adam: The other thing John realized was that he had to work on his written communication.
Jon: Cause the company I was at before, like I had kind of, I’d been there so long, I didn’t really have to write much project stuff. I would kind of pitch it and talk to people, and then we would just kind of do it. And there was a lot of low process, but at Stripe it was really clear, like, Oh, it’s super important that we come up with real project proposals. We shop them around, we get feedback.
We do our due diligence before we actually start working on something. That was really clear; that was important. And that was something I was trying to get comfortable with. And I think my manager wasn’t wrong in the sense that, like, when you’re a smaller team in a bigger company, and people are looking at what you’re doing, they’re not really so much caring about the details. Like they kind of just want the TLDR, like what’s the value? The higher up they go, they’re going to look at a project proposal, maybe, and just kind of skim over it.
But the thing they really care about is like, what are you saying? How is this going to improve our business? You know, and say it to me as short and quickly as you can.
Bundler Project Success
Adam: About a year and then John starts to get the hang of things, and he lands on a project that is really impactful, where he could clearly demonstrate business value.
Jon:
And that was actually migrating our bundler that we used for our largest code base, which I think was something like five million lines of JavaScript. So it’s a big, big JavaScript code base.
And I was really hunting for that project to really sink my teeth into and show that I could really make a difference. And so I really poured my heart out into that project, and I worked a lot to get it done quickly. I remember in the first couple of weeks of doing it, I was really struggling because there was a lot of technical complexity around learning the new bundler and trying to see how I could actually replace it.
I had to figure out how to make locales work and how to write loaders for a bunch of different stuff because it was built for React Native. So there were a lot of confusing things where I was really trying to learn all this stuff. I had a hard time making tasks for other engineers. So I ended up doing a lot of heads-down work myself, and my manager was pretty clear that I didn’t do a good enough job bringing other people into the project.
I took somewhere on the order of 12 to 15 minutes to start up webpack in development mode, and that was super painful. Anytime you switched branches or did anything, you would have to go back through that 15 minutes, and it was rough. So I ended up migrating our bundler to a bundler called Metro, which is actually for React Native, but we were able to get it to work for the web as well. We got the time down to like, I think it was 30 seconds to start up.
It was a massive win, and so I shipped the project. It was a massive success. And then performance review time came around.
The Perf Review
Adam: John was in a strange spot now, where he was feeling anxious about this delivering of business value for so long. But now he had actually done it. He had landed a big impactful project, but it was pretty late in his first year. I knew there was a chance I would get, like, ‘less than meets expectations.’ But with the success of the project, I thought, well, surely, like, that will turn it around. Like, the impact was so high.
Jon: that will, uh, that will sort of cover over the mistakes that like I’d been trying to work on addressing, which was really around like project management.
Adam: But the meeting happened, and John didn’t meet expectations, and the reasons written all down in an official HR document were exactly what he expected.
Jon: When it first happened to me, I was in that kind of like that headspace of, like, Oh, what could I have done differently? What if I said this, you know, maybe if I try to do this thing, maybe it can kind of offset, you know, there’s almost this kind of frantic running around of like, how do I make this right? How do I make sure this doesn’t happen again? How do I? And at some point, I let that part of me slow down a little bit and just be like, man, this really fucking sucks. And I kind of let myself feel what it was that I was feeling.
I remember there was a moment where I, like, I have this little closet next to me, and there’s this little spot in it where there’s nothing. I remember I had such an emotionally difficult day at work after getting that review rating. I remember crawling into my closet and just like closing the door and just like letting myself cry. And it was like one of the few times I’d cried as an adult. And I was like, man, something else is going on here. Like, this is like, this is really difficult for me. Very difficult for me to have someone at work tell me like, you’re not quite good enough.
Adam: John’s own reaction. The strength of it. It was a big surprise to him.
Jon: Like, I should not be this impacted by, like, someone at work telling me, like, you’re not quite meeting expectations. Like,
it wasn’t like, you know, they’re going to fire me. It was just like, hey,You know, partially meets expectations was the designation I got
And that was a huge blow for me. I was actually quite shocked by how difficult it was for me. It was the first time in my career. And, you know, people might think this sounds melodramatic, but I’m like, it’s just how I felt when it happened.
Like I wasn’t choosing to be so deeply impacted by it, but it did impact me. It was really hard, like pouring my heart out into a project, like seeing success. And then like seeing that, like, it’s built, it’s getting our team a lot of attention and like, positive momentum And then getting like a bad performance rating
it was uh It was really difficult
Realization of Cracks
Adam: The work breakdown was a first for John, but really this was not the first time where he felt like things were suddenly crumbling. Something similar had happened a couple years earlier, but in his personal life. We were driving home one day and my wife was talking about some other family and something about parenting and how difficult it was.
And I remember this feeling rising up inside me where I had this insane urge to be like, “We’re not allowed to talk about other people’s parenting.”
Jon: And I felt this like righteous indignation sort of rise up in me, and I was like, “Oh, we don’t talk about other people.” I remember feeling like it was so important that I hold my line. And so she was kind of shut down because she was just kind of trying to share about something that was difficult, some interaction she’d had with another family, and I remember us getting home, and like, I dug my heels in and I was like, I’m not kind of like back down on this. Like we can’t talk about other people. And I remember the fight lasted longer than normally our fights did; it was about two days long, which was super long for us; there was just that kind of tension between us.
Adam: John kept up his side of the fight. We don’t do this. We aren’t. These type of people.
Jon: I remember we were in our closet and she came to me and she was like, I can’t live with you like this. You’re just continuing to dig your heels in. You don’t want to talk about what’s actually going on. And I like can’t, I can’t live in a marriage like this. And she was like, I’m considering like taking the kids and going and staying with my folks for a while. It just really terrified me and I remember I just kind of fell to my knees and was just like, it was the first time I like let myself feel the reality of like, Maybe I’m not actually right in this scenario, and maybe there’s more going on than I realize, and like, maybe this could actually fall apart, which was a really kind of terrifying moment for me.
Adam: The next thing John thought about was his kids.
Jon: It’s it’s truly a terrifying feeling to be like, what would happen to my kids if something happened to us? And I just remember just the fear and the weight of that moment. And it kind of came at a time when like, I thought our life was really stable. I had sort of assumed, without thinking about it, that like I was safe and secure in my marriage and I, we had kids and so like it was sort of inconceivable to me that separation or divorce could ever be on the table.
I was kind of, I was about seven or eight years into my career, and I had a really good job. I had been there for about four years, I think, and I had accomplished a lot there. I was well respected, and I made pretty good money doing it, so we were very financially stable. I felt sort of like life was complete in some sense. And so to kind of be hit by that moment of realization that, oh no, this is, there’s actually kind of danger hidden where I’m not thinking it’s going to be, was really terrifying.
Adam: So again, John is in a closet feeling his life crumbling. Different because at this time, but yeah, he has to do something about it.
Jon: Well, I begged her to stay.
I think within a couple weeks, I realized, like, I have to do something. And she was like, I think you need to see a therapist, and that was very difficult for me to hear. I grew up in a very fundamentalist Christian home; there was always this message in our home that was like, God will fix it. And if you trust him enough, like, it’ll be fine. Like, he’ll always come through and always fix it. And so I sort of had this belief that I carried with me. Like, if you were to ask me, like, oh, that this person goes to therapy, I wouldn’t necessarily have said, oh, they’re weird or that’s bad or strange.
But when the moment came for me to go and do it myself, I was like, oh no, this makes me really uncomfortable, crap. But like, I’m sort of like I felt up against a wall in some sense because I was like, you know, I have to do something; things are starting to crack, and I think I need help.
And truthfully, though, like, it wasn’t an entirely altruistic motivation. Part of me was like, still believing, like, hey, my wife’s actually the problem.
And I’m going to go to therapy to placate something that’s not right with her because I thought I was, I thought I was solid. I thought I was super solid.
Therapy Experience
Adam: So next time John and his family were at church, he found that they had a list of recommended counselors, and he just started looking through.
Jon: And I literally just scrolled through the pictures of the people, and I was like, ‘Who’s the oldest person?’ That was my criteria for finding a therapist, and so I just found the oldest person on there and then, uh, ended up like reaching out to him. And, uh, so I ended up meeting with him in person, and it was probably about 10 or 15 minutes away from my house. And yeah, basically just, I would come in, we would have a 15-minute session.
We would start off, and he would ask me, like, ‘Hey, is there anything you want to dig into this week?’ Is there anything, like, really pressing? It was like, ‘Yeah, like, my marriage is starting to flounder.’ And I don’t know what to do about it.
He had some basically program that he would take me through, which is like, ‘Hey, we’re going to go through sort of learning about some fundamentals about kind of basic psychology and how the brain works.’ And then starting to like, talk about childhood development, and then sort of like actually doing exercises to be like, ‘How is it that I respond in certain situations?’ And starting to put language around what it is that I do when I’m in a situation that’s like difficult relationally.
Adam: John himself didn’t totally know what was going on. He was mainly in therapy to appease his wife. You know, he did have these internal triggers that cause these reactions, but he didn’t really have a ground-truth sense of whether they really were problematic.
Jon: And so he sort of introduced me to this concept, we are wounded in our earlier years, and that affects us more than we realize. And we sort of carry the resulting responses to those woundings into our present-day relationships.
And that, and he also started to talk me through like how it is that our brains actually work. The brain really is like an anticipation machine. So it basically takes all of your past experiences and filters them through what’s happened. And then it, it does some automatic decisioning before you even get the chance to start thinking about what it is that you want to do or behave in a particular situation.
So kind of starting to learn a little bit about what that was, was really wild to me, to even like consider the fact that some of my reactions, I don’t have control over in that rational part of my brain, where I typically do my spend my time thinking.
Adam: So that was his personal life. He was in therapy. He was learning things about himself and his reactions. It felt like maybe he was getting better, that he could get through all this therapy stuff and be fixed.
But then, he had this poor review at Stripe, and the sort of breakdown that came with that seemed not ideal. And then it felt like the fact that his manager can’t be trusted, and there was this constant tension that caused.
Wife’s Health
Jon: There was some other stuff that started happening in my personal life too, which was my wife started to have health problems. She had an incident while she was driving, almost kind of like a panic attack, and that really started being difficult for her. She really started that year to struggle with anxiety for the first time in her adult life, and she couldn’t drive anymore.
And so I had just gotten my bad performance rating. She can’t drive anymore, and we have two kids. At the time, I think they were maybe three and four, or four and five, and they were going to two different schools that we had to drive them to.
I remember, like when my wife first started struggling with anxiety, it was another moment where I was like, Is this even real? Like, I remember her first really struggling with anxiety, and I was like, Aren’t we just making this stuff up? Like,
Adam: She appreciated this, I assume.
Jon: I did not vocalize that to her, but that’s what I was thinking in my head. You know? I started like, I started to really be like, am I gonna like, am I just gonna trust that like what my wife’s actually going through is actually legitimate? Am I like willing to start to take risks to validate what she’s going through and support her in that? And that was super difficult for me because I was still coming off that bad performance rating.
And I was like, well, crap, I’m going to have to like reduce my working hours a bit to be able to take the kids to school in the morning and pick them up in the afternoon.
And I’m like, I had started leading another big project, on the heels of that other one. And so it was this moment where I was like, am I willing to lose my job if things don’t go well in order to take care of my family well and to support my wife who is struggling? Like, am I going to take that seriously?
I did choose to start pulling back from work a bit. I reduced my hours a bit. I had to block out more periods of my calendar and just kind of, like, be more productive with the time that I had.
Adam: And then besides all this, right, John had really become paranoid about his boss. He was just afraid to interact with her, afraid to get more criticisms, afraid to see her name pop up in a Google doc that he was writing, you know, ready to give him some more criticisms.
The Balancing Act
Jon: Because there was this piece of me that was like, I was like, okay, clearly I’m not trusting my boss. Like I don’t trust that she has my best interest at hand, and that’s difficult for me now. And that’s the reality of it. But I was like, who do I trust?
Adam: Thankfully, there was someone on his team that he trusts that he had worked with in the past at a different company.
Jon: We knew each other. We knew each other’s families. And he had recently joined the team I was on. And I remember just like, kind of asking him like, “Can we sit down and just like work on this project proposal together?”
Adam: So they put together a proposal for the next big effort and that helped.
Jon: There was a piece of me that realized like, I really, like, performed super well and it didn’t work. So, like, what’s the point of trying so damn hard? and in combination with the trust that I kind of found in my friend, I think that sort of helped me, like, start to move forward, and be able to, like, let myself try again at work. in a way that was like not where I wasn’t quite pouring so much of my soul in, into it.
Adam: Not pouring everything he had into it was actually hard, though.
Jon: I think I realized that for me, work was really a core part of who I was. I remember like when I first became a software engineer, I love to tell people that I was a software engineer. I mean, this is like letting you, you all behind the curtain of what I feel when I would do things, but it was like be at a, a dinner event or something.
And it was like, in the back of my head, I’m like, I’m just kind of waiting for people to ask me what I do. Cause I’m like, you know, I’m a software engineer. It’s like, I thought that was so cool. And like, you should ask me about the projects I’ve done and the, you know, the millions of dollars or this or that.
I love the prestige that came with it in my mind.
And so that year was really difficult.
It was for the first time in my career, I had to make a decision like, am I willing to lose my job? I remember distinctly feeling that, like, am I willing to just, am I willing to fail?
Adam: And then John’s boss got promoted. He got a new manager that was a better fit, and also he just found some strength in just not caring.
Personal Growth
Jon: It ended up being the best year of my life. It was difficult; there was a lot of hard stuff, and I had to make hard decisions. But I found myself coming alive in ways that I did not realize were actually possible. I remember strange things happening that year. When I was a kid, I was always really bad at math. This was always a thing that was almost like this badge of shame I secretly carried around, which was that I did not know my times tables. I hated the fact that I was sucky at math. I had tried to relearn them as an adult, and I couldn’t get them to stick.
I found myself that year suddenly being able to do math in my head that I couldn’t before, and it felt easy. I remember I used to be really dependent on task lists. My wife was always like, “If I want him to do anything, it’s got to be on a list, or otherwise he’s going to forget about it.” Basically, our social calendar I let her manage entirely because I couldn’t handle a social calendar along with work stuff. That year, for the first time, I found myself waking up in the morning just sort of being aware of all the things that were going to be happening that day and being able to adjust and kind of plan accordingly. It was like I didn’t have to write everything down. It was almost like my brain was starting to do something different.
Adam: Somehow, this was related to the therapy to John taking his mental health, his wife’s mental health. Very seriously. To him recognizing that something in him was like a clenched fist, clenched with all this tension for so long that he had forgotten. And now he was starting to open up. Saturday to release that tension.
Jon: So, like, as an example, the math one is interesting. My, my mom was really good at math, and she prided herself on, being able to do math.
Math Lessons
Adam: She taught John math.
He was homeschooled, and she spent a lot of time talking about what seemed like very complicated subjects for an eight-year-old to understand. He couldn’t understand the mechanics of multiplication tables, but she was talking about irrational numbers and various things that he just didn’t get.
Jon: But I realized like that year in particular, I started to make the connection of like, Oh no. She didn’t care about me understanding math. She enjoyed appearing smart in math, and actually, she sort of lorded that over me. And so I felt immense shame as a kid around math. And I just kind of had to increasingly hide the fact that I didn’t, I couldn’t understand the fundamentals.
Adam: John hid that by cheating, secretly sneaking around the house to get the answer booklet and just copy down answers.
Jon: and it occurred, it started to occur to me that like, oh these things that I think I’m just bad at, I’m not actually like, bad at. There are reasons why. I feel so stuck when it comes to just doing math in my head, like there are very concrete reasons why that’s the case.
Healing
Adam: It’s a cool example because it’s like, yeah, sometimes you think that something is like part of your identity, but there’s actual tactical ways, like you just need to learn this thing. It’s not a disability, but just a skill to be learned, right?
Jon: Yeah, but really what I’m getting at is that the thing of like, there was something I tried to learn, but it was, I couldn’t get myself to learn it. So there was almost this block around the thing.
Adam: felt, it felt like a wall.
Jon: Because, like, I’d start to add numbers together and then they would just seem to fall out of my head. I couldn’t keep the context on them. It was like, it was more like that. It was like, oh, yeah, I could memorize my times tables. But something felt difficult around math for me in particular.
Adam: The concrete reasons were all the time that he spent just in fear and shame, trying to hide his lack of understanding of math fundamentals.
Jon: I didn’t have anyone to talk to about it. I couldn’t admit it to her because I knew it wouldn’t be taken seriously. And I didn’t have anywhere to go with it. I didn’t know what to do with that. And so I started to form another narrative around it, which was like, I’m bad at math. And I need to just, like, I need to, like, figure out a way to make sure that, like, nobody finds out that I’m bad at math.
Adam: Yeah, I mean, because if you think of your story, of trying to, well, of like having to find the answers and wanting to hide the fact that you didn’t know. Like, I assume there’s actually a lot of time if you add it up. Like, a lot of time that you spend worried that somebody’s going to find out.
Uh, like that’s what jumps to me is like that, that, that sounds very unpleasant, right? If I were to just spend a lot of time right now worried about somebody finding out about something, I mean, I would be a wreck, right? Like it’s not a pleasant thing.
Jon: Yeah, I think you’re right in that like, I had to spend a lot of energy to make sure that my mom didn’t know what was actually going on inside of me, which was that I was scared. I wasn’t going to meet the bar in school. When I actually started going to high school, I went from homeschooling into high school; I went to an actual high school.
I remember being terrified of going into a real school and being like, I’m gonna have to do math at this school. And like, they’re gonna figure out I’m a fraud but I couldn’t talk to anyone. I was terrified. And I had no one to talk to about that.
So it’s basically like, our brains are actually, they’re actually very dependent on each other. And as a kid, you’re very dependent on the emotions and the, they call it affect regulation. Which is basically like, your primary caregiver, one of the things that they do is help you to handle your big feelings.
Thanks, that’s what they should do. So whether you get really angry or really sad, like they’re meant to come alongside you and sort of be the stable brain that you don’t have yet as a kid, that you’re not able to actually do. And when that doesn’t happen, your brain actually doesn’t develop correctly.
Adam: So when John was able to see that as an adult, the wall was gone. It was like magic, and the numbers didn’t fall out of his head. And that just made him think more about his childhood and what other walls might be there.
Other Walls
Jon: You kind of know the feeling of it as a kid, but you can’t really put words to it.
My family was very, we had very strong opinions about, like, morals, and sort of what was right and what’s wrong, and what we do and don’t do.
Adam: And this was maybe at the root of that original fight with his wife about gossiping that ended in the closet.
Jon: We were told not to do certain things. We were told not to think certain ways. And so now I’m taking that same principle into that situation with my wife where I’m like, it was like, it’s my job to make sure that we are morally up to code. So it’s something that worked for me as a kid. Like I had to adhere to these moral codes, like I had to basically survive in a home where things were expected of me.
You’re like, I know if I go off track, like I’m going to be, I’m going to be shunned. And it actually did happen. Like one of my siblings was sort of like the black sheep of our family. They didn’t really fit the mold; they were sort of rebellious. And I remember them being ostracized from the family, and I remember thinking, like, man, if I ever did that, like I’d be screwed.
Adam: And, but like, why does that matter just because it did to your, your family or
Jon: It matters because there was this, I had a belief as a kid that I didn’t realize that I believed, which was basically like if I didn’t adhere to a certain set of beliefs about the world, morals, I would essentially be cast off.
Like I would be ostracized. Even though they would say things like, “Hey, we love you, no matter what, we love you unconditionally.” But I knew somewhere inside of me that actually wasn’t true. There were things I could do to cause me to be separated emotionally or physically from my parents.
I had to make sure that I behaved in a particular way in order to keep their approval, in order to keep my, basically to survive.
Adam: Unpacking and rehashing all this childhood stuff sounds traumatic. Like I have no experience with therapy myself, but my initial reaction is, like doing all this, would just make things worse. You’re just rehashing things. You’re re-scarring yourself. But actually, for John, it had the opposite effect.
Work and Personal Integration
Jon: That year, I actually ended up having a super successful project, and come the next performance review, I got an exceeds expectations, and I got like a huge bonus and extra equity. You know, my boss sent me the sort of PDF thing before our one-on-one, and I remember looking at it, and I was like, I got like… seeds? What? I was like, it was just one of those moments where I was like, what’s happening here? This is so wacky to me. Like, I’ve started working less. I’ve started not giving a shit as much. And suddenly, like, I’m doing better, and the project is going really well.
I found myself too, just even being able to, when I ran into roadblocks in the project, I let myself be really honest about the things I was hitting that were not going well. I was like, oh crap, this is, I made a bad decision about this piece of tech that I used. My normal inclination would be like, okay, I need to fix it, and make sure to figure it out really fast. But I was like, hold on, I can take a step back and write a document and just say, Hey, things are a little off the rails here. Here are all the options I’m aware of. These are the different paths we could take. These are the trade-offs I’m aware of.
And like, just share it with my team way earlier than I did before. So I could tell there was this, not as much fear in me about being like, I can expose what I think are failures to my team, and it ended up making the project go way more smoothly because I was able to talk about what was going wrong and really solicit kind of the collective knowledge of the team and figure out how to move forward on something.
Adam: But I feel like, did you ever have any fears? I feel like that panic-motivated work is one of my superpowers. Like, okay, I don’t know about X now, but in a panic, I’ll quickly learn it.
Jon: But like, actually, like, probably the whole rest of your team are feeling the same thing. They’re also probably worried about like, Oh, somebody realizes that I don’t know this thing about this thing.
Cause like tech is insanely complicated. There’s so much stuff. You can’t know it all. when someone starts to step forward and be like, Hey, I actually don’t super know, but here’s what I do know. And can we all like kind of work together to, can I get some help? I mean, it’s basically saying like, Hey, I need some help. And here’s what here I’m going to lay out everything I know. But I’m going to like, I’m going to take a risk and say, like, I need some help. and what I found is that like, that actually builds a connection in the team that otherwise wouldn’t be there because otherwise everybody’s kind of going around silently thinking, Oh shit, I got to like know my stuff or peer competent. And we actually end up just sort of almost not, we’re not really trying to one up each other, but we’re just sort of trying to avoid the fear. Whereas if we just allow ourselves to be more open about what it is that we don’t know, it can actually build stronger connections that have a, that make a project actually and a team be more, together
and like do better work.
Things Change Again
Adam: So everything is great. Now, John and his team have bonded and found ways to grow together when they don’t know something. It’s a huge change from that first year when he did everything himself in a panic, trying to find business value. And also he and his wife are closer than they’ve ever been. So it’s like, everything is solved.
Jon: I was like, man, this is awesome. Like. Such a good year, you know, I’m able to do math in my head, and truthfully, like, it was even to the point where I was like, things started smelling better to me. This is weird, but I’m like, and even colors, I was like, noticing more colors. I was like, this is so cool, I was so excited at the end of that year.
And then all of a sudden, I remember waking up and feeling like I had lost something. It was very strange because I had all this forward momentum and I felt like I got that review and then I felt like I hit a wall. And, I kind of started to be like, really, unmotivated. in work, in life.
I remember, yeah, just laying in bed and being like, I don’t want to get out. Some days when it was really bad, it’s like I would sit at my computer and I would like, try to do a very simple task. And it was like, I couldn’t muster the energy. And I think, you know, I’ve heard people describe that as like burnout, basically.
Adam: This depression was actually kind of aggravating.
Jon: Like if I put in all this work in therapy and like I’ve done all this stuff with my wife and we’ve been through like rough times and we’re like still together and, like, growing closer. Like, what’s the point if, like, I just am gonna get randomly slapped with depression? Like, I think that was very un, uh, demotivating and difficult.
The Team
Adam: Now John and his team were in this great place where they shared their difficulties, and they tackled them together. And although this wasn’t a technical difficulty, it had nothing to do with JS infrastructure, but it was affecting the team because he wasn’t getting much done, so he had to call a meeting.
Jon: And yeah, I remember going into that meeting just feeling sick to my stomach, like queasy, like, Like, I can’t believe I’m going to go say this to the, to my coworkers. It was so nerve wracking to me,
like, to actually admit to them, like, hey, I’m struggling. and I’m like, I’m, I have help. I was,I was still, seeing a therapist at the time and trying to work through that. But it was kind of just admitting that I didn’t know exactly what to do or what was going on. so I remember going into that meeting and just sharing it with them. And they were all like extremely supportive. I was like, honestly shocked by the level of support that people had for me. Like people talking to me afterward, like setting up meetings and talking and just, it was like really encouraging to get that level of support. And that,That, even in and of itself, like, helped for a while.
And then another few months went by and I wasn’t doing well again. I was like, shoot, I’m struggling again. And I remember talking to my wife about it. And by this time, like she and I, like we’d, we’d stayed together. we’d gritted our teeth and like started to work through some of our stuff.
And like, honestly, our marriage was better than it had ever been
at that point. it’s one of those things where you’re like, you go through some deep shit and you come out the other side and you’re like, I didn’t really know this woman as well as I thought I did.
And she’s actually really amazing.
Adam: That’s awesome.
Jon: And like it, I need, like, we’ve needed to go through the hard things in order to like, start to peel back the layers where we can actually start to see each other. Well, so it was at that time I started feeling like really supported by her. And I remember talking to her about struggling at work again.
And she, I remember sitting with her and she was like, I think you should ask for some time off. Just like, take a couple of weeks just like let yourself rest. That was another really scary thing for me to ask. And of course, like my, they were very supportive. I was able to take a couple weeks off.
Father
Jon: And it was at that time that … Oh, do I want to share this? Um, yeah, you know, I do. I do want to share this.
Toward the end of my, toward the end of my time off from work, I kind of made this connection that like part of the reason why I was so attracted to Stripe in the first place had to do with my dad. And kind of like what I had been groomed for.
Adam: John cared so much about Stripe.
He reacted so strongly to things that this company, because of his dad, because some part of him. The part of him that idolized Patrick Collison really wanted to impress. His dad.
Jon: And, I had started to be really honest with my parents about some of the ways that things were hard for me as a kid. And that was a difficult process.
And toward the end of my time off, I remember at that point in my, in my journey, I had started realizing like there was, there’s very much in my family, but kind of a stronghold around work. My dad was absolutely a workaholic, and it cost our family dearly. And I think, like, sort of, a lot of this story is me replaying the same thing that he was doing, even though I had sort of vowed not to ever do that.
Adam: So John decided he needed to talk to his dad about his work and his lack of presence in John’s life, especially in his childhood. Because like, if that was the root issue behind these work struggles, why not tackle it head on.
Jon: It’s just happened over the phone. When I called him, he was actually on a business trip. We had a time schedule to talk. I called him at the time. He picked up the phone, and I could hear someone in the background, and he was like, “Oh, hang on. I’ll end this meeting in a minute.” I was like, “Dad, this is really important. Like, we need to talk.” And so he’s like, “Oh, it’s okay. I’ll call you back in 15 minutes.” Twenty minutes goes by. I have to call him again. He’s still in the meeting, but he’s like, “Oh no, the meeting’s over.” I’m like, “I can still hear the guy in the background. You don’t understand. This is like our relationship is on the line here. I need to talk to you. You gotta stop your meeting.”
And it almost was this moment of like, that was my entire childhood summed up in a moment where it was like work was everything. And he could not pry himself away, even for a discussion with his son. That was extremely difficult for me, but also very important for me to realize that was what I had felt as a kid. I was straight with him. I was like, “This is what’s going to happen for us to reconcile.” And as soon as I touched the work thread, it was like, within minutes, he had gone to, like, “We’re done. We’re absolutely done.” Almost like, “You’re not my son.”
He actually ended up disowning me. And that, I remember that it felt very, it was such a final moment for me. It was sort of this moment of realizing that all the things we talked about earlier in this conversation, where I knew this, I had this sense that if I stepped on some toes, I would be cut off. I knew that if I addressed the work situation directly, it would mean that I was cut off. And that would be it. And it turned out to be true.
Grieving
Adam: John was cast out. He had questioned his dad about work. And that was just unacceptable.
Jon: And that was, that brought a lot of grief for me, and a lot of anger that I like had never really allowed myself to feel. But it’s just like, it’s almost a sense of, like, as a kid, you know, something’s wrong, but you don’t know how to put words to it. And then you kind of like eventually come to this point where you’re like, “Oh, no, there actually was something wrong there.”
And then there’s the grief that comes with that when you realize the truth. The truth of what our relationship was.
Adam: What, what are you grieving?
Jon: I’m grieving the fact that I never really had a dad. And that I needed one really bad. And that I came up with a lot of strategies to keep myself functioning in light of that. And that basically, like, most of my life I’ve lived out of those strategies. And it hasn’t worked very well for me in the long run. It’s wild, it’s, um, it can kind of just come on at times. Just the sense of, like, deep sadness. And that’s sad. It’s sad to come to your life, like, I’m 36. It’s sad to get to that point in your life and realize you had it all wrong. Like your sort of whole perception of things was just, was just off. It’s very sad.
Adam: But like also you are, I don’t know, like I, I, I feel, I feel the need to, to, to argue against you and be like, but no, you’re, you, you know, you have your life and it’s worked and here you are.
Uh.
Jon: I mean, it’s… it really is, Adam. It’s the thing of like, it’s hard to put words to. And in fact, this was a big barrier for me to allowing myself to feeling, to start feeling things again, which was like, that perception of success is almost a barrier. It is like there’s this piece of my mind that’s like, oh, I don’t deserve to feel that way because I have a good life. I have all the things, like I’ve paid well, I’m this and that. I don’t deserve to feel sad. And there is almost this sense of, like, this barrier that happens. I’m like, oh, other people have it way worse. I shouldn’t feel sad about this.
But the truth is, like, when I really, like, let myself feel it, I’m like, nah, deep down I am actually really sad. I may appear very successful, but I’m still very scared. I’m still very sad. I’m still… I’m still, like, I’m, in many ways, a boy like struggling to figure out what it is that I’m doing.
Exploring New Opportunities
Adam: So now John’s time off has gone from restorative to, yeah, I don’t know what, like a bereavement process. And then he’s got to get back to work.
Jon: I thought sort of I had, I was like, okay, I’ve like, in my mind, I was like, I beat the final boss. I said the thing I’ve been afraid of saying to my dad forever. Like it’s, it’s, I’ve achieved it, so I should be pretty good. I did well again at work for a while, and then eventually things started to kind of unravel for me again. It’s like my mind wouldn’t even run. And then kind of the inability to focus again came back, and I was kind of like, well, crap, I’ve already like taken some time off for this. I’ve already done all the things I think I could do for this.
I remember like again, sitting down with my wife and having a conversation. I remember we were sitting on our back patio and we were just kind of sitting and like contemplating this decision. Like, what do we do? And I looked at her and she was like, I think you need to quit. And, you know, it was funny because at that exact moment, there were some people walking by a path next to our house and we overheard the conversation. This lady, she’s like, Oh man, I have this friend. She loves her career. She’s really good at it, but she just had to quit. That was when I decided to leave Stripe and not really knowing what I was going to do next.
Psychedelics
Adam: It’s what makes me think of this thing with the VCs who were upset on Twitter. There were startup founders who were taking psychedelics, like ayahuasca or whatever. Then just deciding to leave the company, and the VCs were like, “Ah, we need to stop this.” This is not a good thing, right? And probably, I mean, maybe it’s not like traveling to Chile and taking ayahuasca in the jungle. But like, probably those people were broken in a way that made them very successful.
Jon: Hmm.
Adam: Something happened to them and they realized that wasn’t good. And the VCs are like, “Oh my God,” he doesn’t want to burn the midnight oil. But yeah, maybe, maybe the realizations are valid. Which, is to say, like, yes, you, you’ve left Stripe, but maybe that’s not the important thing.
Right.
Jon: Yes. I think so. I think so.
I wish I had like a great, um, wrap up to this whole thing where I’m like, and I hit the top of the mountain and there I was and I achieved enlightenment, you know, or this or that, but I’m like, it’s more complicated than that.
I hope that, you know, people listening to this, if they take anything away, it’s just like I, I believe still that, that, that we do matter as, as people, as individuals and, and we are each as individuals worth time and effort to explore and understand and really come alive.
Because I think, like, when we do come alive, and it’s, it’s something that motivates me. And it may end up being a fool’s errand. But, I guess I’ll die trying.
Outro
Adam: So that was the show. Yeah, John left Stripe and he found something else. And yeah, he’s sad about his childhood and about his father. He’s profoundly sad. But he’s also happy to have removed these layers of tension from his life, you know, that he didn’t even see before. So thank you, John, for sharing your story.
If something that John shared resonated with you, maybe follow in his footsteps, become curious about your own feelings and reaction to things. Learn more about yourself. What could be more important than that?
You can learn more about John on his website. I’ll put a link on the webpage for this episode. And thanks to supporters who keep me at it. I hope you liked this rather emotional deep dive.
If you want to join the supporters and show your appreciation for the show, go to corecursive.com/supporters. We also have a pretty awesome Slack channel that you can find on the website. A great place to hang out. Until next time, thank you so much for listening.
Sticher
Overcast
Jan 02, 2025
51
min