Moral Math: A Conversation with Charlie Trotter

Hello. Thank you so much for tuning into Depricated Human. I'm Jess Lowry, your host. I wanted to thank you for listening. This is going to be our final episode of season one. I have recorded over 20 interviews with people impacted by mass layoffs, long-term unemployment, changes to the tech industry, changes to hiring processes. I want to thank you all so much for listening to this first season of Depricated Human. It's been an honor to have the opportunity to meet with so many people, many of them who are willing to come onto the podcast and record our conversation. There have been many that have not been recorded. And so even though some of you may not be named or have, you know, visibility and being a guest on an episode, I still want to say thank you for speaking with me over this past year when you're presented with what seems like an impossible situation. There are always going to be surprises to uncover and things to learn. And I love this episode with Charlie Trotter because in this episode, he actually calls out, through his storytelling of his experience, how kind of random it might feel as you navigate through the unknown. And we can't possibly predict the future and, unfortunately, in most cases, can't construct the future. But what we can do is stay true to our core selves of who we are, of what we value, of our purpose. And in that, we find direction. And in that direction, we find what the next thing is going to be. And so Charlie's story is not about a perfect next step. What he discovered is what was already there to begin with. Thank you so much for listening. I hope you enjoy this episode, and I look forward to you tuning in for season two in January 2027. Things are going to be a little bit different. We've spent a lot of time investigating what's happening, and now in season two, we're going to move into experimenting possibilities and creating new opportunities. Please reach out to me if you have any questions, comments, feedback, and enjoy this incredible story from Charlie Trotter. When people feel burnt out, they often assume they need an entirely new career. But sometimes the problem is not the work itself; it's the conditions surrounding it: the management, politics. Lack of control or responsibility without any authority. Charlie Trotter left a senior leadership role convinced he was finished with design consulting. What followed was not a carefully executed reinvention. It was a series of experiments, setbacks, and unexpected opportunities that eventually helped him enjoy the work again, but on different terms. This conversation is about separating what you know how to do from the system in which you were doing it, and recognizing that your next career may be a different configuration of the capabilities you already possess. Well, thank you everybody for tuning into Deprecated Human. I am very excited to have one of my favorite humans on the podcast today, Charlie Trotter. Charlie, could you please introduce yourself? Absolutely. Yeah, I'm Charlie Trotter. I've worked in consulting and software for about 24 years, design that long, and it's been an interesting journey. I'm not one of the people who planned their career arc, but I said yes to interesting turns along the way, and I'm generally happy with how that has turned out. So, how did you find design? Where did your career start? Well, the first design gig I got paid for was a logo design for my sister-in-law, who, she did lampwork glass beads. It was really beautiful stuff. So I designed a logo and a business card for her, and that was my first paid design gig. I'm an artist, and I grew up in a family of artists. I really wanted to pursue art, but part of my upbringing... And some hangups there made a proper art career not an option for a kid like me. And so I ended up just not going that path. And I was like, well, what can I do? And then there was an older guy that we knew who had his own freelance design business, a graphic designer, and he was like, Hey kid, you can retain all those artistic skills, and here's how you can apply it commercially. I was like, All right. But I hated computers at the beginning. I was like, I don't want to do it. I don't like computers. I can't imagine making art with a computer. It felt so limiting to me then. I just didn't understand because I hadn't been exposed. My mom loves to roast me about that, by the way, now that I've made the bulk of my career with computers. That's interesting. So you, when you hated those. But you, so you like almost did like an apprenticeship. Was it more like that, or— No, this was more a guy in our general sphere of my parents' friends, and it was, he's like, Hey, heads up, we went to his house one time and he showed me his setup, and he was also a fine artist. He was a painter and did a bunch of cool stuff. So I was like, All right, this guy's got credibility. Maybe it's something I'll consider. And so then I was like, Well, I guess when it comes time for college, maybe that's what I'll do. I didn't actually go a really strict design path. I didn't go to any of the design schools. I got a BA in advertising from University of South Florida. They were teaching us, I would say probably to be at like the director level less. There was like a copywriting course you could take and a design course you could take, but I didn't take the design course. So I was—I'm really self-taught. My next several jobs worked pretty key after college. I did have a really great designer bring me in. I was his only employee for a while, so I learned a heck of a lot during then. I had a good internship in college at an ad agency, and they were really great about making sure I was included and stuff. So yeah, which was a contrast because when I worked out of school, I worked the front desk at an ad agency and— I would ask people, Hey, will you teach me X, Y, Z, the designer, or like one of the old-timers, one of the owners, he used to do—he used to draw one of the comic strips, like a nationally syndicated newspaper comic strip for another—for an artist who was known for that strip, but he was a young guy who got brought in to draw it. That apparently happens often with newspaper comics people. I was like, Dude, teach me hand lettering, like the old-school style. And I brought in quill and ink wells. I was ready to go, and he just looked at me and said, No. And then he walked away. And I was like, No, I don't have time, just said no. And I was like, Dag. But then my next job, I had the opposite experience, which I think was the fork in the road that got me into software, because it was for a company that I didn't know at the time was a multi-level marketing company, but it paid better, and I got to be a designer. And I had one of the developers come to me my first week or so there, and he goes, Hey, if you ever wanted to learn HTML and CSS, I'm happy to teach you when we don't have other stuff to do. And I was like, What a difference, right? Like, in one arena, I was pursuing somebody, ready to go and asking for knowledge and guidance, and then the next one, it came and found me. And then I continued to find throughout software that same spirit in almost everybody I met. And I was like, Well, I think this is for me. This feels way better. Right. And that was even through some of my—the last agency I worked for as a full-time employee, like, was the most generous, I think, with its knowledge. That was whether it was a researcher or a PM or anybody, if I wanted to know more about it, it was like an email away, and we were meeting within the week, and people would just give me their time and help me understand what they did. I mean, there's the whole open source ethic in software. There's so much more that is about opening things up to people and sharing, and then having it be like the competition hits it from a different angle. Yeah, it's interesting because that's—I have a similar kind of story myself. I went to the University of Toronto, but I went as a mature student because I didn't go directly after high school. I worked for a year and a half and then decided maybe being a student wasn't so bad and I should do that. And I don't remember anything computer-related that, you know, it just—I wanted to make movies. Really? Yeah. Psychology, storytelling, you know, film studies at University of Toronto is not the hands-on film study. There's a different school downtown that actually teaches you how to work a camera. This was more of just having an opinion about movies. I had no idea what I actually wanted to do that would pay me money. And UX wasn't really a thing. I don't remember people talking about it until I was already doing it. Yeah. Yeah, we would have come up at a time that it got named along the way. Probably started out as something general like web design. Or do you remember the term new media? New media, that was hot, hot language when I was coming up in, yeah, my career. In general, your early twenties, or whenever you're going to college, the college years of the average person's life is such a weird time to ask them to make such a consequential decision because you just haven't been exposed so much yet. Yeah, but the other thing that's really interesting about it to me is right now, in this moment, a lot of people who are graduating from college are having a hard time getting hired. And what's different for me or interesting is that all the stuff that we were doing was all new stuff. But it was very inviting. It was very open source. It was very much like, hey, there's like a meetup group if you want to learn how to write JavaScript, go and hang out at this coffee shop at Wednesdays at eight o'clock, and people just teach each other. It was very accessible to get into the industry. But now it feels like you can't get an internship, you can't get a job. The openness of, let's bring people in and let's create jobs and let's create a profession, it's somehow protected or, I don't know, it's a weird moment that's so contrasting because it was all new when we were young too. These jobs didn't exist when we were in high school. Yeah, that's a shame about, like, internships being harder to get. I bring this up in almost every interview. For a long time, the hardest feature I ever worked on for an app was one that our very fresh intern helped me crack. Interesting. Because I was on my third sprint. It's one of those things where just when you think, oh, I got it. Yeah. You find the one thing that throws it all out of whack. And I was cycling on that, and she was fresh enough, and she was just like, what if we did this? And I was like, of course. And so everybody benefits from the interns, right? Like, what they lack in experience and general industry knowledge, they have in buckets in terms of fresh eyes that don't have the dogma and the, oh, you can't do that. That's why I'm not even going to think that thought or pursue it. So yeah, everybody loses if we take that out of the mix. Yeah, it's just getting exposure to real hands-on experience was a lot easier. I think that for me, one of the biggest differences, because none of these jobs even really had job titles, like webmaster. Like people had weird job titles. Webmaster, yes. They were, you know, very Dungeons & Dragons-esque. Yeah. Code words. They had some cachet to it. I find it weird that we're in this time now where people are having a hard time navigating entry into the job market. The other thing you said that I think was really interesting is what you learned from each job, and I'm interested to hear your experiences of how it changed over time, if you were to contrast that early beginning experience with more recently. Yeah. I mean, yeah, that early experience, even at that agency where I did have, you know, kind of a formatively bad experience with that, I also had some good ones where, like, they had regularly—we would probably call it something like a stand-up, but they called it like a traffic meeting. Okay. And it was just, we're looking at every—what's in midair right now, and getting exposure to just the machinery of—theirs was like a traditional Mad Men-style advertising agency. And so that was good. I kind of brought some of that with me. And each place, that software place was really good for me because I had to—the way that guy taught me HTML and CSS, he, when they got me set up with my computer, I think I was the only guy with a Mac, and they set me up with the full Adobe suite, so I had everything. And then he told me, I think in our first sit-down, he was like, Download this FTP client, I think it was Cyberduck, and download TextWrangler, a text editor. And this is all very different how this works now. But back then, those were the two things I needed, that and I needed a server to store stuff, which I think he, for years, he just gave me space on his personal server to just tinker. And it was through him that I published my first personal site. And he told me, though, in that first sit-down, he's like, Listen, if I ever even see Dreamweaver open on your desktop, I'm cutting it off. Like, we're not—I'm not going to show you how to do anything else, because I don't want you to use it. Because it, like, especially back then, any of the WYSIWYG stuff was—there was so much trash it put into the code that he was like, I want you to learn how to for real do it. I want you to understand the concept. So don't use a tool like that where it can allow you to do it. Without understanding it, which I thought was interesting. I didn't take that as a negative thing. That was, that felt like, it felt like somebody looking out for me. I feel like that's the thing people are being told right now about ChatGPT and AI. Don't, don't let it code for you, because you won't be able to understand it. Yeah. It's similar for a lot of things. I just started yesterday. I took my first piano lesson. Wow. I've been playing guitar since I was a teenager. I played professionally for a few years, had a running gig, and it was actually an organ player, incredible. He's an older fella. He's been playing since he was five, like, has forgotten more than I'll have time to catch up and learn. I got a little keyboard and decided I want to do it. Hadn't touched guitar in a year because I was burned out. Learned a lot about what, how to spot burnout over the last several years, because that's— so yeah, I hadn't played guitar for real in like a year. Wow. But I'm having to go back now and do stuff that, when you start out on guitar, it's easy to not do all the rigor, right? Right. I didn't sit— it was years before I sat down and, like, ran scales just so I knew them, so I knew where everything was. But now I'm doing that as I start this, and I'm like, this feels like, like I'm grown, right? Like actually, like running the major scale through all 12 keys is not the snooze fest it would have been to me as a kid. It's actually quite a meditative exercise, because you just lock in. I'm not expressing myself. I'm not doing anything. I'm just getting into the meat of my hands and my eyes, the knowledge of where those notes are and how the scales change shape as I'm playing. And so having that foundation of understanding why it's going to work later when in a lesson he's teaching me a song and he randomly starts calling out chord changes, and I just got to go. Which I'll be able to do thanks to that foundation, which I think is similar to what this guy was trying to lock in for me. Yeah. Yeah. One of the things that's been happening for me a lot lately is people wanting to show me the things that they're building with all these tools that we now have. And especially for the people who are not designers to be showing me their design work. And I think one of the main things I see is a lack of editing, where it's literally every single thought they ever had. How do I fit every single idea into this space? And not understanding the logic of progressive disclosure. You know, if you overwhelm people with too much information too soon, they can't orientate themselves to what are you asking them to do, or what's the point of this, and what are they supposed to understand? And it's an interesting moment when you hear so many people say, Well, anyone can be a designer, and it's like, yeah, anyone can be anything. It doesn't mean you're good at it. I think there's a difference between being able to do something and being proficient. And what I hear you saying is you're really kind of locking into that why we learn the way we do, why we skills over time the way we do, because the foundation is everything. Yeah. That and repetition. And we would talk a lot about that during the time where we worked together. That's when I first took on any kind of actual leadership role. I stepped into management. I was a creative director there. I got named two or three things before the end, but it was basically an experience director kind of a role. I never worked on a project with the people that I managed. I think maybe like one time did I ever do that. And so our one-on-ones was me trying to figure out, like, how do I get somebody from junior to senior level? Like, what's that path going to look like? I remember what happened to how I got there, but like... I did. I couldn't, like, write plot that on a map. It was just—and I think over time, what I finally started to realize was when you get to that level of expertise where you're a senior or principal, you have to—you internalize all these rules, especially in software, all the bits and bobs and when to invoke them and when not to. And you learn through research and through validation studies, and you internalize so much by repeating it. So all the rules get locked in, but the really interesting stuff happens when you're in a situation that is so complex and so difficult, and all the rules—it's like, where's your God now, right? Who's going to help you when everything, when all of your hammers break and you still have to solve it? Those are the moments. A few of those is what makes us into the senior players and the expertise. That's what builds your expertise, is when you think, I'm fresh out of ideas. I have no idea how I'm going to fix this. That you learn, like, you learn to calm down, like the most craven part of your brain that's trying to freak out that you're going to lose your job or be embarrassed or anything. And then you can kind of, when that quiets a little bit, and then you think, and it's usually something simple, right? Most of the time it's not like, Oh no, I figured it out. We actually have to split the atom, right? It's usually something simple that you're just too overwhelmed to see. So yeah, I think of that often on establishing expertise as I'm talking to even just my own kids, and they're—my older two have got jobs, and my oldest is in her second year of college and planning career, and has just now got like a shift lead position at the place she works. And so we have conversations about leadership and growth and management and all that. And it's just, yeah, it's really interesting to see. When those thresholds change. Yeah, absolutely. That makes me think of watching my kid learn how to play volleyball, because volleyball is very much a team sport. You could try, and there is a few kids on her team who try to just play by themselves. So they're, like, running out of their zones to just run in front of somebody and try to get the ball, and inevitably it never works out because you're basically removing somebody else's ability to be successful by trying to own all of it and do all of it yourself. And really, the successful teams in volleyball are the ones who set each other up for success. So you have to learn to work together in order to be really coordinated with that and do that well, and to be a good communicator and to not be led by ego. And it's so interesting to watch the kids learn the skills of volleyball, but then the real playing of it is all teamwork. Yeah, yeah. And that's one of the things right now that I feel a little sad about because we're losing a lot of teams on our, you know, different projects, or you're a designer of one, which was usually the case anyway, sadly. But you look at your career and see how things changed with the dynamics. How would you describe that over time? Yeah, you're right. I think it has. I mean, the—I don't want to put too much of it on the location, like in-office versus distributed, because there are ways to solve for that that can overcome it. But when I think about the times I really felt like I was on a truly diverse skill set team. Trying to solve a problem was, yeah, that was when I felt like we did work I was the proudest of. It was when I knew where the developers were, and I knew that the thing I was designing was not just like a—it wasn't the, you know, password recovery flow, right, like that you can do with your eyes closed. It was something more complex, and I needed to sit down with a developer and sanity check the whole thing. And so when I learned to submit myself to being really frustrated when a developer just rips it to shreds, and going, okay, that was actually a gift, right? I needed that information. That's going to make this design better. So, and the PM is also going to have a really good idea. And, right, to get over, like, the silly tribalism of your whatever your category is, having that collaborative space has been one of my favorite things, is when I look at a piece that's in my portfolio and I can't see the brushstrokes anymore, when I can't see, oh, that one was my idea, right? Because my ego just isn't wired to get anything from that. That's just how my mind works. I'm not keeping that score anyway, right? But when I truly have trouble remembering, that's when I know we really collaborated on this. Yeah. I find that really rewarding. I would say in terms of, like, how I'm working now, I do have a fairly collaborative process. There are meetings—I'm in regular meetings where I have a main stakeholder who has incredible depth of knowledge of their vertical, and then we've also got developers on the call that understand things we don't. And so I feel like I'm still working in that capacity now, even though I'm a freelancer and working through an agency, we're able to approach the best of that. But then there are other times I've got other clients that are like small, you know, mom-and-pop businesses that I do a Squarespace website for them, and it's just me. It's all up to me. But also, the level of complexity is really, it's nowhere near, right? I think you're also, at least in my experience, a very optimistic person. You can be cynical. There's definitely that side of you. You have a sarcastic kind of sense of humor at times, like the darkness is there, but always in service to the light. And, you know, working with someone, being able to work with someone who makes you laugh, and also laugh through sometimes the absurdity or just the nonsense of certain kinds of workplaces and politics, that's why I remember you so fondly, because you don't get that all the time. Some people are very serious. Yes. Yeah, that's not my favorite. No. Serious. Not at all. Because I don't think it's, it's not as necessary as it sounds like it would be, right? It sounds like this noble path of being very serious and, you know, always in sort of mid furrow with our brows. Right, right, right. But why would you not want there to be some lightness about that? Even when it's serious work, right? Even when you're developing software where it's going to materially change somebody's workday or life, there's no, there's no reason to be bummed out. That's one of the things I think I've had to learn, and this is just human maturity, is realizing how can I not shut off the part of myself that gets mad at what I think is organizational injustice, things that just aren't fair to the people that have to do the work, how a project was sold, how the whole thing is managed, and then accept that that's the case. And that I'm not, at least at the moment, in a position to rage quit over it. Right. So how am I going to not bum out? How am I going to not bum you out? All those weird goose chases they sent us on. Sometimes I say, this isn't the Batman I wanted to be, but it's the Batman I ended up. Right. Like being good. Okay, yeah, if you needed me to drop into a situation with very little information and we had to do a deck and a sales pitch around it, yes, fine, I can help you. I can do that. Those are the weird gills I grew over being in a big consulting agency. I think about one of the design books I read early on. I think it was called Articulating Design Decisions. It was definitely one I wish I had read 10 years sooner. I think it's one of the O'Reilly books. I can't remember the guy's name, but I think he was local to DFW here because I met him at one of the local conferences. But there was a line in there. All of it was really great stuff about how to think about, you know, explaining your rationale, et cetera. But there was a section in there that really hit me where he suggested, take the user story format, the as a blank, I blank so I can blank. And he goes, fill that out for your teammates on whatever project you're working on. So the developer, the PM, the biz dev, everybody, the other designers. Because if you go home with a win and one of them doesn't, or if your win comes as a loss for them, like we're all trying to have our head hit the pillow at the end of the day and feel at least somewhat proud of what we did. Yeah. And if somebody else is really good at getting a win for themselves that is subtractive to the other people on the team, then everybody's having a bad day, or at least most of the team is and one person isn't. Right. That's what I use to check myself when I'm— Feeling the most frustrated with the machinery, the anger tastes good, goes down real smooth, but it starts to sour fast. And so you're just drinking poison. And so, yeah, I'm trying to keep sight of being a good teammate in all the ways that that, and every part of that meaning. The other thing I really appreciate about you is that you do have boundaries, because our time working together came to an end on your terms. You made that call, and I'm interested to hear you explain it, because obviously I know your story, but other people listening wouldn't. How did you transition from the bigger workplace that we were working at to where you are now? Yeah, good question. Man, that was such a weird journey. But honestly, all the milestones before it were just as unexpected and weird, so it actually fits in my whole overall thing. I stayed at that director level in the organization, had no interest. I saw what was waiting for me in the roles above and was like, Nope, you can keep all that. There's not an amount of money you can come up with that would make me want that. It was incredibly rewarding to have that team of direct reports, and there was this gravity to it where I was like, Okay, I have a responsibility to these people. And I saw it as, like, the order of operations of what I felt truly was my moral math of that whole thing was like, I have to work for them first and the company second. So I'm not going to sit here and go like, oh, I have to do this thing that's better for the company. And now I got to give them this bad news. I mean, there are times when I was like, yeah, this is actually bad news, and I'm powerless to stop it, but I tried. I yelled at some people above me on the ladder to try to see if we could stop it, and it didn't. And now this bummer is real. But one thing I learned, like, that was what ultimately what broke me was when I realized that these people I had come to care about so much, like, how do you not? Like, as a human being, you can't. If you're managing people and you truly have some responsibility over where you can help them grow as a person, as a craftsperson in your category, in their career, help them make more money, all of that, like, how do you not form an attachment? How do you not fall in love with those people? It'd be weird if you didn't, I think. And so that was what made it so painful in the end. So, like, my own, the futility that I got submitted to was different than when I had to, when I couldn't stop other people who I knew were in pain from being submitted to the same futility. It was different. I was like, I can, I'll eat shit a little bit, but I don't want to ask them to eat it. And so I just, I kept thinking I could do it for a little bit longer for them, for me, and I just couldn't. And so that was when I started looking. I think I started looking mid to late pandemic for another gig, and I had a spreadsheet. I think I probably still have it. I think it went up to like 54 different jobs I applied for. I was being really picky. I wanted remote work fully. I wanted to stay in the type of role I was in. And I just wanted out. I thought maybe if I work on the product side, I will not hate software. Because I got to a point where I was like, I don't want anything to do with any of this anymore. I don't want to design again. I don't want to be subject to other people's bad taste and then, right, like all of that stuff, I want out. It's too subjective and too painful. And so I started, when I finally got to a point at that, it was like application number 54, when it was not happening, that's when I was like, I need to—this is my message, right? This is the sign that I need to stop doing this, and maybe I need to start my own thing, whatever that is. And what was interesting during that time is how proof of, like, how—and I know it's, gosh, way worse now for people—but I would get, there was a few, it was like maybe five or so that I got down to, like, the last two people in consideration for a role. And it would always come down to something. A couple times it came down to how much experience I had with mobile. I was like, so I don't have a lot of vertical 16 by 9 screens in my portfolio, and you're worried that I will—that that's going to be the bridge too far? Like, that we will have all found the end of my abilities. Oh my gosh. And I was like, you guys understand, I was like, we—like, I come from, like, I'm a consultant. We do all of it. We do all of it. I've seen stuff that would make your hair fall out and been dropped into situations with no resources and horrible scope. And we had another two sticks to rub together, and we had to figure it out. And you think I'm going to get stuck on your mobile screens? And I realized, like, it was not that they couldn't— Do the rational math of understanding that's not a real problem. It was that they were stuck in, This is a box I have to check because mobile's really important here, and I'm nervous because I have to justify this decision. And if something ever goes wrong, there'll be a record of all the people who had that box checked and you didn't, right? So it's now this weird, I don't know, narcissism of small differences kind of a thing where I'm like, Do you understand? I say this all the time of our folks that we knew in that place, and really anybody who spends enough time in consulting to get good enough at it. But if you give me a researcher, a developer, and a good PM, we could regrow hair with enough time. Like, we will figure it out. Like, it doesn't matter whether it's software or not, the deliverable, like, because there's something about that mix. I'm like, okay, I've seen that repeated enough times. I'm not going to sweat whatever the situation is. But I just couldn't get through. So I was like, well, what's something where some of these skills would translate? And so then I ended up getting into apparel decoration, is like the official term for it. So I like embroidery and screen printing. And I spent some time researching the viability of that. I built this little building I'm sitting in now. It's a 12 by 16 shop in my backyard on what had to be a house-grade foundation. Interesting. It's bomb-proof. There's a piece of equipment that's going to come in here that weighs as much as a car. Interesting. So we built it. I ordered this machine from Japan. It was beautiful, a six-head embroidery machine. And so that was my plan, is to stay employed, slowly grow this embroidery business. I didn't want to start with screen printing because the gear to do that was, A, it was way cheaper, so it would have been easier, but it was a massive, it was like an order of magnitude different footprint physically. Okay. And I'm like, my wife still wants to park in the garage. Right. So, and it would cost a ton to, like, get air conditioning in the garage, or I'd just die here in Texas without it. Right, right. That's where we started, and I found a local partner who gave me a wholesale rate on screen printing. So then I started doing that for—I did that for, I think, about two years while I still worked at that agency. There was a while that I would work eight hours at this desk where I'm still at now, and then I would get up and I'd go inside and have dinner and then come back out, and I would do a run of, you know, 100, 200 shirts or hats or whatever. Yeah. And it did a really great thing for my brain because nobody was debating me about whether slide five really got to the ROI, you know what I mean? It was none of that nonsense. It wasn't a feather in anybody's cap. It was, Is the logo on the garment? Yes. Good. Done. Yeah, yeah. And the repetitiveness of it was healing me. And so I just finally got to a place where there was one day I came inside after a particularly—it was like a last straw moment with a person at the company that I regularly dealt with, and my wife and I, I wasn't just going to do it. Like, we need to agree on this. I'm not the only one who lives here. This is going to affect all of us, for good or ill, and we've got four kids. And so we were just like, We'll play it by ear. We'll negotiate, and when we're both sure, that's when you'll jump. And I came in one day and I was, like, so outside of my body upset about this interaction, and it was one in a string, and I could see my wife seeing me. And then when I got done telling it, she just, like, grabbed me and she was like, You got to quit now. This can't keep happening. So yeah, then I put in my notice, and I bounced, and we got a killer tax return that year because we had bought a $55,000 piece of machinery, financed it, and somehow the way the taxes worked out, we got a big return that was going to float us when my, you know, pass for the next first couple months while I really dug in and tried to sell a lot of jobs. And then I didn't sell a lot of jobs. So yeah, it was tough because marketing is really difficult, and it's a very different discipline. While I can create all the deliverables for marketing, like actually doing that effectively is a totally different muscle, and I have not worked on that one. And I don't regret—eventually we sold the business because it was not buying groceries happily. We had, you know, family that was able to help us when it was lean, when we needed it. But that first year out was our leanest year yet. There were some financial vehicles we pulled the last bits out of and did everything we could, and finally got to the point, okay, this isn't working. I'm going to have to start doing freelance work again. Yeah. And it was just little stuff here and there. I audited one one day just so he could see if I knew what I was doing, and it was like my body knew that I was in a situation that I knew exactly what to do in. And the client was there, and I, again, I was not on the clock. I was just there to observe, but somebody turned around and asked me a question, and it's like a switch flipped, and I went into consultant mode. And then I did work with him for close to a year, and that helped me get back on my feet. And through that process, I was like, wait a minute, I remember hating this. Right. Why doesn't this feel the same? I'm actually enjoying that I'm good at this, and I'm enjoying doing design work again. I didn't think I was going to enjoy that again once I went into management. And I did. And then I found there was an agency here in town that I had actually applied for, and the day they were going to send me an offer, due to some economic circumstances out of their hands, it actually made sense, like real sense, for them to not actually offer me the job. But it was at a point where I was in probably some of the most pain. Yeah. Where I wanted to get out of where I was, so I was gutted. My two best friends came from out of town and surprised me and just stayed the weekend with me. But it was that agency that reached out to me once I started freelancing again. I was like, hey, we've got this part-time opportunity with one of our clients. And then a few months in, they were like, they want to bring you on full-time, and this is going great. And I was like, I can't believe I'm just, like, literally designing data-dense enterprise software screens and actually loving it, and it's quiet in here, and I have a low amount of meetings every day, and the agency's paying my hourly rate, and they're marking it up, and everybody's getting it. Everybody's happy in the equation. And I was like, wait, the client gets what they want, they're happy. Like, we get along great. We're doing good work. The agency's happy. I'm like, what an arrangement. I never would have thought to start doing this. Yeah. I was literally just in a survival mode going like, where can I get the next little bundle of bread money? Yeah. And so then it just kind of came together. And then once it went to full-time hours... Then I'm like, oh wow, that's 40 hours a week at my hourly rate. We're like, that's what the project actually needs. That was the agreement, and that's what I need to bill. And there's enough work for it. And I'm going, this was it. I think I needed to not be in management anymore. I needed to return to design, and there was a way to enjoy the work, even though I still see all the stuff that I saw organizationally at the other places that were frustrating and insufferable and all that. Like, all of that's going to be true forever in every place. And I still spot that stuff, but it doesn't get to me. Like, I don't know, I don't think there's armor or anything, but like it doesn't—those little darts don't make it as far in anymore. Yeah, I feel a lot freer with it. I also found a marketing agency approached me through a friend, and so I'm doing some stuff for them, and that's fun because it's like more traditional graphic design. Like I'm back to some of the original stuff I wanted to do, like logo design and stuff like that. So I'm going, wow, who would have thought that just being a freelance designer was going to be the thing that was going to make this a viable option for me again. Yeah, I think it's interesting. It's a great story because a lot of people, I think, can relate to it from who I've spoken to and just the things that I've observed and the time that I've been doing this podcast, where a lot of people ended up in what they call fractional work, you know, whether you call it freelance or fractional. Some people talk about it in terms of like a portfolio career where there's a bunch of things that you do for income. Sometimes they're related, sometimes they're not. And for some people I've spoken to, it's unthinkable to not be a salaried employee. It's just absolutely not. They cannot compute it. But when you are able to figure out a way to make it work for you, you can end up making more money, and you can end up doing more work that you like. Yeah. In fact, so I was that guy at one point. Real easy to be that person when you've got kids and responsibility and a mortgage and all of that. Like, I never even, like, upgraded our house. We're still in the first one we bought. I want to be buried in the backyard, and I want to discharge admission and give tours. But, like, I hate moving so much. I wouldn't move into a palace if I had to actually pack a box. And so, like that. But yeah, it's easy, right? Because that's very compelling, because that gets into this security. Like, it's easy to imagine an interruption to your bread and your shelter. But the problem is, especially now, like, I think I would say to that other version of me, like, look around. Is it so stable after all? Right. Where are you now? Exactly. Yeah. And the whole, even coming on, even recording this podcast, and I thought, oh, I've got some things that would be officially a bad business attitude for me to have, right, if I talk about them. And is that going to be a problem, right? Am I going to regret doing that? Will opportunity be withheld from me in the marketplace? Right. Because that's always the hovering threat. That's why you're a good soldier in the organization. That's why you don't, you know, complain as much as there's cause to. And you want them to give you more opportunity and more money, right? And you don't want them to withhold it from you. I was, toward the last few years, I was aware that I was in a position where there was a really good reason I was not even getting asked to consider a promotion, and I actually preferred it that way. I was like, jokes on them, right? Because I don't want it, and I get to speak a little freer. But when you, yeah, when you realize that that's not as stable as you thought it was, then what's left is when you're, like, you're regulating all your behavior. And you're managing yourself, and you're this version of yourself that is a person that makes them want to give you opportunity because you don't want it withheld, and you don't want to speak up too much because you don't want a future employer to withhold the opportunity. The problem is, you were a good employee, and you were part of a layoff, thanks to a variety of factors, and they're still withholding the opportunity anyway. Right. So they're going to withhold the opportunity at some point for reasons that, you know, protect their investments. So the only delta there is your dignity of speaking up and calling bullshit bullshit, and not eating it, right? So something changed for me when I realized I can be a part of this machine that even, let's say I even fundamentally have a problem with the way this whole capitalist machine works, right? There's plenty of drawbacks to it, but it remains the only workable option for me, as I said to you before, until people start hiring decorative hermits to live on their land and be eccentric, my perfect job doesn't exist. And so I have to be participant in this machinery. And I think that the way to do it is keeping your dignity helps to manage your blood pressure, for one, because you realize, like, I don't have to get this worked up about this, right? Unless somebody's being, like, actively harmed, right? Like, that, of course, is different. But, like, just the run-of-the-mill of all of it is not buying into the language. Don't buy into it. It gets real culty really fast. Oh, we do this here. We try extra hard here. We value excellence here, right? All of that stuff, where you hear somebody speak and you're like, I don't talk like that. I don't want to talk like that, but I'm going to because that is part of this whole thing. You don't have to do that. You can still be A good teammate. If you're a decent human being and you want to not bum out your partner that you got staffed on some ridiculous jobs with, right, you have to regulate yourself. That's what is going to make you deliver good work, not the weird culty idea of excellence or any of that other nonsense. Like, that's not what's going to make you do good work. That's what's going to make you be afraid to lose a job. And now fear is animating you, not a concern for the people around you and a basic desire to go like, I would love it if I felt good about the thing I made, which means I got to try. I got to block off my focus. I got to do it right. I got to do all the things you got to do. And so when you, you can exist in that space that might even be contrary to some of your deeper beliefs with your dignity still intact if you just go like, I don't have to be, I don't have to consent to being a part of this cult. I don't have to receive this motivational speech and pretend like it meant something to me. I'm just going to keep showing up and doing my work and being a good teammate. And I bet for the most part, nobody will notice a difference but you. Yeah, and I think that's such an interesting perspective in this moment for so many people because there's this need for belonging and this need to be part of the group and part of the tribe and to speak the language and to emulate one another. But what I always liked about consulting, one of my favorite things about it was that I got to leave a client that I didn't want to—like, the project would end and we would party. There was some client projects that it was such a celebration that it was over, and you got to share in that, you know, shared experience with the people you worked on that project with. And typically we all kind of—it wasn't like a secret society or something like that, but it was sort of like you went through war together and you kind of went through a battle together. And I like that part of consulting because You are always presented with different things, and I think that mix of projects and clients, it keeps everything fresh, and it also keeps things from being stagnant or stale. But especially with these corporate environments, you don't have to live there. You just, you're just like a, you know, a vacationer. Yeah. And that's what, you know, fractional work or freelance work is, really. It's just like, hey, I'm here as long as it's mutually beneficial. But if at any point it's not, I can and will find something else. So they have to treat you better too. They want to keep you because it's easier for you to leave. And your hourly rate, whatever it is, is a great shield to nonsense because you don't have to—there's no, my favorite thing about freelance work, and this is what spoiled me to ever go back, is nobody—there's no internal initiatives. There's no Q3 goals for things, and I got to make a deck that doesn't mean anything to anybody except it's a feather in somebody's—right? Like all those wild goose chases that weren't actually meaningful, I don't have to be bothered with any of that. If they're going to pay me to do it, I might consider it, but they don't want to because they know, oh, we're not going to ask him to do that. Not because I can't, but because they don't want—yeah, it's too expensive. And then they get religion pretty fast about what's worth asking me about. I feel like that really clarifies the whole relationship of going like, look how happy you are, and look how happy I am, and we don't—I don't have to be a part of this. There was a time I remember, man, I'll never forget this. I was on a project, and it was when I realized, like— Okay, as much as I want to get out of this, I think I have to be in the consulting side. I think I'm a consultant for life and not a product side person, because we were on site with a client and there was some request, I don't even remember the details, but something was like, we need this thing turned quickly and it's going to be a lot of work for one, maybe two people to do. And the director on the client side turned to us and asked us about it, and I think I was the lead on the project. And so me and the PM spoke about it. We looked at each other and I was like, well, everybody on staff that would help you with that, we'd be past our hours for the week. And at least at the agency I was at then, I know this isn't the case everywhere, but like we had to get approval to do overtime. Right. And for the, at least for me, I was never pressured to work it and not bill it. They were like, no bill the time, and if we can sell more, we'll sell them overtime or rescope. So that was our plan. And so I told her, I was like, well, we could see if we can get approval for overtime if that would help. And then she goes, no, that's okay. And then she turns to her own employee. They were traveling to a place where they were having an internal conference somewhere, and she turned to him and goes, you can do it in the, you should have time in the hotel tomorrow night. You can knock that out. And I was like, oh my God. He and I could both do that work just the same as each other, but one of us she knew she couldn't ask and one she knew she could. Right, right. It's leverage, right? You actually have leverage. And that's the thing that most employees lack, especially at this moment where you feel like you can't say no to anything and they know that. So then they ask you of things that are... Not really reasonable. I mean, when you and I were working together, I was working at like three in the morning on certain engagements with clients that were on the other side of the world. And I'm a parent. Yeah, I'm a parent, so I'd be up at three in the morning running a workshop and then go to sleep for a couple hours and then wake up to make breakfast and lunch for my kid, take her to school, sleep for a couple hours, and then get back at it. I remember one of my engagements where I worked with people that were from, I think, McKenzie, and we were having a late dinner, as you do, because there's no end point. You work as much as you physically can. And they turned to each other as we're working and eating dinner that they were so relieved to not be at home because when they're working on a project from home, they have to explain to their partners why they're not available for dinner, and it's like a whole thing. And it's so much easier when you're traveling for work because you don't have to explain your time to anyone and you can just work without worry. This is the mentality. And I think when you are able to find your leverage again, you also can find your sanity. And then it sounds like you also then can find your way back into the work on your terms, which made you like it again. I'm aware of what I was able to say no to, but I also know there were some of our peers that were not. And so that ability was not evenly distributed for, like, all of the above reasons, right? So yeah, that's—I don't understand. I don't know how somebody could get that that doesn't have it, because I don't fully understand why those experiences were different for any of us. So yeah. I think of this all the time that, like, I don't—I think we spoke about it earlier—that, like, I don't, I'm, the situation I'm in now that I'm enjoying is not because I'm smart and I laid out a great plan and I executed a great plan, or because I have some acumen that somebody else could benefit from. It's, it just happened to work out like this. And so I've got to want to be careful to say when I have had things that I thought went well or didn't go well, that it was not—that I'm not saying, hey, do this like I did it and you'll be fine, because I couldn't tell you how I did it. It just, this is the way it happened. And I've got really good friends that it didn't happen that way for. People who are by a factor or two better at this than I am, who remain either unemployed or really struggling with the situation. And I'm like, well, this is not—this is just, this is just blindfolded darts. I don't know how any of this is working out, but at least for me to have the understanding of this is how—this is a way this could get configured, that I'm not miserable and the people around me aren't miserable, and I can feed myself and my family, and it's working for now, and I'll figure it out when it doesn't. I'll say that the good thing that I feel like those of us who've had the—who have known the happiness of working in consulting for a sufficient amount of time, that crucible does equip you to improvise. And even when I don't—even if it dries up, like, I just know I'll figure it out because I've figured out other more complicated things that didn't seem like they were solvable at the time. And okay, it'll be a, you know, might be a bummer, might be tough, might be lean again. But I'll figure something out. But especially, like, whether it's, like, the inability to get hired somewhere because of what's going on in the industry or what, like, the—like, what are you going to—there might not even be a role for us for how long, right? Because of AI. So if you don't want to do what some of our friends are doing, where they're like, Oh, I'm going to take advantage of this technology to make my own products and sell those in the marketplace and do all that. Really great. There's some smart people with great tastes and good instincts that are doing that. But what if that's not—what if you don't want to run a company? Right. I don't want to run a company. I just want to be a designer. And so what's on the table for us? Which is why, like, I've talked to a friend of mine, another alum from our old employer, who is actually looking to exit the industry because of AI, seeing the writing on the wall. But she was talking about, like, content creation, which I've always gone like, I enjoy being on social media. I'm a ham, so I like performing. I like doing little funny bits or music or what have you. But it's never really gone anywhere. It's just fun for me. And so she was starting to look into it and go like, actually, it's like there's a difference between wanting to be the tip top of all of that and then actually making a living. There are options for doing it that you can do on your own terms. And I was like, Huh, how about that? I'm thinking, what if the—because I had a real dark night of the soul thing over the summer for a couple of months where I just felt this hovering dread of going like, my gig's good now, but— There are also people for some of the teams in this client that I work with who send me, like, AI mockups, like that, or I drag an index file into Chrome, you know, into the browser. It's a working, you know, quote-unquote working piece of software. And I'm like, they just prompted this. I'm going, okay, this actually makes your request a lot clearer to me than if you had just sent me a few bullets in an email. So, but I'm also looking at that and going, it can't be much longer. And so what will I do? And what if at the end, like the stuff that I, like, the stuff that's on the table that is not as easy for AI to do is the stuff that I wanted to do from the beginning, but was told was not a responsible path for somebody who might want a family, a musician, or whether I pursue comedy or whatever I want. And I'm like, wait a minute, that's what all this content creation stuff is, is performing. And who better than people who have been in software consulting to absolutely find a way to kill it in that space? Like, we can create all kinds of high-quality assets on a nothing, right? Like with—and we know how to present, we know how to talk, we know how to be funny and interesting and charming because we had to win clients over, all of that stuff. Why wouldn't we consider that? Except that the reason is because you're like, well, that's—I don't want to be influencers or cringey. That's—you'll see people talking about getting over cringe all the time, and I'm like, that sounds also weirdly culty to me. People will make fun of you for this. You got to get over that and do it anyway. And I'm like, I've been in that club before in a couple of other arenas in my life, and I don't want to do that again. But at the same time, what hit me was, haven't I already done things that are more cringe than this? Because you know what I've done? I've written annual goals using the SMART method. Okay, yeah. It's cringey to me. It is, yeah. I'm a grown person. If I want to do something, I just do it, right? I wanted to learn piano, so I bought a piano. I know how to learn, right? I know how to, especially from this industry, I know how to quickly acquire working expertise of information and get in. It's like, I don't need goals. I just need it to not be stupid, and then I'm going to go do it. I'm going like, we've all done really cringey stuff, but we've done it under an umbrella of a stable, respectable job versus doing something we find cringey or not cringey when we're trying to make our own path. I've done more embarrassing things than this in pursuit of the nobility of a steady check. All bets are off now. Forget it. I'm not going to let anybody—I'm not going to wonder if some old coworker is going to go, Look at him. Look at this. Look at this guy. Look what's happened to him. I agree. It's kind of having to get over the definition of success. I think a lot of people have kind of created a definition based off of how things were when they started their career or when things were at their best, and they kind of had an aspirational goal, whether they articulated it or were fully conscious of it, maybe not, but you kind of had this idea of what success looked like and what your life was supposed to be at a certain age, at a certain season. And the idea, like, you know, even for me, I started in UX primarily in SEO, so I optimized websites back in the day. Yeah. Yeah. And so my dad has a hotel, and he was like, Do you want to rebuild my website? And I was absolutely thrilled to because, like, you know, my dad's been helping me a lot, and it felt good to be able to do something for him. But it also was like this very full circle moment of like, I'm designing a WordPress site. So I built it, and it was like, wow, this is very humbling to come back to where I started. But it's also incredible that those skills didn't go anywhere. They're all still in me, right? And, yeah, it's not something maybe I put on my LinkedIn, but there's just so much more in all of us than whatever our job title was. Yeah. So why not just explore it all? I love this conversation. Yeah, likewise. Yeah, I loved that you came on. Thank you so much for your time. Absolutely. Carly's story does not offer a formula. He had support, relationships, and fortunate timing that many job seekers don't have. But it does reveal possibilities beyond the traditional choices between finding another full-time job or starting a company. A contract or fractional role with a small client or maybe a return to an earlier skill can create income while showing you what still fits. It does not have to become your permanent identity. It can simply be the next workable step. A job title may disappear, but a profession may change, and the capabilities developed across a career will remain. The question is not, who will hire me? It's also, where else could what I know be useful, and under what conditions could I enjoy using it again? Thank you for listening to the first season of Deprecated Human. Over the course of 20 interviews—actually, there's been more than just those that I've recorded—but we together have heard from people navigating layoffs, long-term unemployment, changing professions, independent work, and the loss of identities built around jobs that no longer offer the security they once promised. These conversations confirmed that people are not struggling because they stopped being capable or valuable. They are trying to move forward through a hiring system that often cannot recognize transferable experience, while work itself is being reorganized around automation, contracting, and new sources of income. I am deeply grateful to every guest who trusted me with their story, and to everyone who listened, shared an episode, or heard part of their own experience reflected in these conversations. Deprecated Human will return for a season two in January 2027. This first season was really about listening closely enough to understand what people are experiencing. The next season will focus on applying what we learned. We will explore how to move through uncertainty, identify the capabilities that remain valuable, test possible directions, and create a working life that is not dependent on one title, one employer, or one predetermined path. These practical guided resources will be available exclusively to subscribers. Until then, remember that not knowing what comes next does not mean you have nothing to move towards. It may simply mean the next version of your working life has not been designed yet. Thank you for spending this season with me, and I hope you tune in in January. Until then, I wish you all the best through the holiday season, because I know that can be hard for so many people that are unemployed and struggling right now. I know that we don't talk excessively about politics in this podcast, but obviously the system that orchestrates these outcomes is something that makes our lives better or worse. And for those of you who feel a little bit more hopeful because of what we saw in the midterms, I hope you can hold on to that through the next couple months. And in January, things will shift. There is so much to look forward to. And so many people who love you and support you and want you to succeed. So take care. Make sure that you reach out to people and let them know how they can help you.