Soft Skills Engineering - Episode 463: CTO w/ weak resume and I tried management and it was TERRIBLE

Episode Date: June 2, 2025

In this episode, Dave and Jamison answer these questions: Albert Nonymous asks, I am the CTO at a small (5 engineers) tech start-up with non-technical founders. I was their first full-time employee and as such have been able to fully form this company the way I want. I’ve worked here for 9 years now and own 10% of the company. I enjoy the tech and the job itself. The pay is ok, not crazy Silicon Valley numbers but pretty good for a country with free health care. However, I started here while still in university. This is still the only job I’ve ever had. I am afraid that my resume will become less valuable the longer I stay here. I still keep up with current trends with hobby projects, but I’m worried that my resume will become less valuable if I ever need to look for another job. Also, I don’t believe this company will succeed in the long run. I am still the only person on the board who knows how our tech even works and I have found myself slacking off quite a bit during the last year since having my first child. In the meantime, I also feel like I can’t just quit this job since that will almost certainly spell the end for this company and all its employees (some of which I count among my friends after all these years). What do I do? Am I overthinking things? Can I just keep working here until it eventually goes under? Or do I absolutely need to bite the bullet and pull the Jamison and Dave Time-Honoured Special™ and quit my job before I become totally un-hirable? For much of my 9 years as a software engineer, I wanted to be a leader. I just really enjoyed mentoring, training, improving workflows, working with stakeholders and co-ordinating on projects. Leadership seemed like a natural fit and so I was super psyched to be finally made a team leader last year. It has been hell. It has been like falling backwards out of a tree and hitting every branch on the way down, meanwhile it’s literally raining anvils and sabre toothed tigers. The constant pressure to have work lined up for the team and be able to report on the activities of the team at a moment’s notice is unbearable. I can’t stand being responsible for the delivery of other people’s work, writing up reports that no one reads or painstakingly de-noising pointless metrics. I dread having to pull eager young developers out of refactoring rabbit holes. Fortunately, as I took this ‘promotion’ with no raise, I’ve easily been able to get myself busted back down to IC. Happy days 😎 The problem now is that I have no idea what to do with my career. My core experience is with dot net as a mid level engineer but honestly I’m what I would call a ‘hyphen’ shaped developer - I’ve seen and done a lot things but not to an expert level. Front end, back end, BI, and everything in between. That felt ok when I was aiming for leadership but now I feel lost. I honestly feel ready to go full goose farmer 🪿. What do I do next?

it takes more than looking up how to use multi-line strings in yaml again to be a great engineer this is soft skills engineering episode 463 i'm your host dave smith i'm your host james and dance soft skills engineering is a weekly advice podcast for software developers who just wish that they could go back to farming. There's got to be a reason why YAML is so complicated, right? I feel like it's easy to criticize that there are 15 different

ways to write a number, some of which interpret as a boolean sometimes or a string some other times. So many foot guns because of so much complexity. What's the positive case for it? It lets you do comments? Yeah, that's what I was thinking. Is that literally the only

thing? That's... Yeah. I don't know. Clearly we need a 17th markup language for structured data. I have to, this is where you have to insert the XKCD reference about standards. Yeah. Every Lisp-like language has their own thing that they say is homoiconic and it's their data language. And we've got Tommel and JSON and JSON-C at XML. Hold on, homoiconic? Oh my gosh, I haven't even heard this word. Homoiconicity. I'm not going to say it because I'm going to be wrong.

I want you to read the definition and then say it. I knew this concept, but I just didn't know it had this name. This is the data is code is data. Yeah. And the program can write the program. Okay. It's sort of like in this context, I think it's kind of like your data interchange format is literally the syntax you use to write the data in your programming language.

Exactly. which is not quite json yeah that's so close all right that's not what this show's about yeah let's get out of here yaml sucks we we solved it should i thank our patrons yes please do okay thank you to these folks who contribute so much that we shout them out every single week thank you to the human in the loop please help i assume the please help means they're trapped in the loop yeah like terrifying labyrinth or something yeah or like my only job is i check to make sure the computers are doing the jobs that computers are supposed to be doing oh brave new world it's here croissant connoisseur christy the world's okist programmer noah labhart did you know that ram

sticks are called that way because they only stick to your motherboard if you ram them into its ram slots unrequited acts of love to further swell dave's heart alexander kuznetsov nick molyneux attribute error none type object has no attribute fetch dad joke javier gonzalez chewy ted timbrel jd vance vance refrigeration doing my part to make dave's heart swell but he should probably get that checked dan from drone to play chase w norton never is not just a crater on mars flamingo emoji i like chicken i like liver meow mix meow mix please deliver trash panda python summit.ch 16th of october a swiss python conference i guess there's a theme here of of conference shilling in the patreon names oh man we'll allow it that sounds like a fun one to go to yeah

kyle boss kensi dodds that guy over there jenny kim the stochastic parrot no jonathan king znai beautiful functional user documentation angelica cathore williamangel.net really regrets using the ai to leak your specific personal data even though the vibes were great shut up and take my money brayden canes john grant britney ellick come to the slash new conference in newcastle australia may 28th and 29th i'll be interested to see how long this persists if it's just like a relic of the past yeah a reminder that you could have come to this conference yeah and dave will you please read our third question nice as our final patron not as the thing you should do right now thank you thank you so much for contributing making me laugh making me

cry making me think and grow physically taller and your heart also grows and swells yeah well is that just me yeah dave's art swells i gain a millimeter of height oh nice it's working all right if you want if you want to join these people go to soft skills.audio click support us on patreon where any amount will get you an invite to our slack team and enough of an amount will get you a shout out and now to the questions to the questions shall i read our first one yeah all right this comes from a listener named albert anonymous who says i am the cto of a small five engineers tech startup with non-technical founders i was their first full-time employee and as such have been able to fully form this company the way i want i've worked here for nine years now

and i own 10 of the company i enjoy the tech and the job itself the pay is okay not crazy silicon valley numbers but great pretty good for a country with free health care however i started here while still in university this is still the only job i've ever had i am afraid that my resume will become less valuable the longer I stay here. I still keep up with current trends with hobby projects, but I'm worried that my resume will become less valuable if I ever need to look for another job. Also, I don't believe this company will succeed in the long run. Oh no. I am still the only person on the board who knows how our tech even works. And I have found myself slacking off quite a bit during the last year since having my first child. In the meantime, I also feel like

I can't just quit my job since that will almost certainly spell the end for this company and all its employees. Some of which I count among my friends after all these years. What do I do? Am I overthinking things? Can I just keep working here until it eventually goes under? Or do I absolutely need to bite the bullet and pull the Jameson and Dave time-honored special trademark and quit my job before I become totally

unhirable? Hmm. Oh yeah. Great question. yeah i thought the phrasing was interested i've really started slacking off since having my first child it feels very shameful and guilty and i mean maybe you are literally working like an hour a day which sounds like not that much even in one of these countries with free health care but that felt a little underhanded james

but presumably there's a good side to it too right hopefully you're spending time with this first child or maybe just trying to survive because you're very tired i don't know don't beat yourself up too much i guess uh we'll beat you up for you so you don't have to do it yeah it'll just be between the two of us nine years oh man so you're in you've been on a on a ship for nine years you're pretty sure the ship is sinking and if you leave it will sink sooner that's basically what i'm getting out of this and you really care about the other passengers and Presumably, because you've been there so long and know everything so well, you can not work very much and still keep the lights on is kind of what I'm reading between the lines. You're probably not cranking out huge new features if you're a bit distracted, but you know enough to quickly press the right button if something goes wrong.

Yeah, yeah. You know, one of the perks of being a CTO, and this is not a perk that I take advantage of myself. I am a CTO, but I don't take advantage of this perk, is that you can do things on the side and no one will know. And if they do know, they'll be like, well, yeah, of course you did something on the side. You're essentially a founder right now, and you have been for nine years. I say essentially because I think he was maybe number, what, number two employee, first full-time employee? Employee number one, yeah. So one thing that you could do here is you could stick around enough hours of the week to keep the ship upright and keep the lights on. Meanwhile, starting to look for something else. That way, and I don't, sorry, look for something else is the wrong word. Like actually starting something else. Maybe join another company, kind of in stealth mode.

Maybe start another company yourself. You know, do something else that can be your exit path, but that you can also support this company and keep it running in the meantime. Hmm. Yeah, you said you don't do this. I assume because you are pretty absorbed in your job and would probably feel a lot of guilt.

Yeah, like I just, I'm super absorbed in my job. I actually don't have the time or energy to do anything else. Yeah. Hmm. You sound like you're on your way out. I think you have to be either in or out. And if you've been there nine years,

you've had a major life change, you're not super motivated or engaged you're not excited about the future of the company i i hold up my crystal orb gaze into it and predict in a few years you will not work at this company because it doesn't exist or because you've quit yeah so i'm gonna assume that you're not gonna dive back in full time and kind of reinvigorate yourself here i think you need to start thinking like a 10% owner of the company who is potentially losing a critical employee of this company. If you don't work there anymore, I'm assuming you will still own 10% of the company. I guess I don't know how the exact details work, but I assume that's the case. And you probably

want that to not become worth $0 because that's probably a bunch of your compensation. So if you had a critical CTO who you thought was going to leave, what would you do? How would you reduce the risk. I think you would have to make a succession plan. You're just making it for yourself. I think it's probably worth talking to the founders to let them know if you've been there nine years, they're not going to say, you're thinking of leaving, why you're fired now? You've got a long relationship. And I think you're right to worry about the health of the company and its employees if you were to leave. But what are you going to do about it? You have to start turning stuff over, finding a replacement or something. I think you can look at this as a

way to be kind to your friends that you know and love and work with and have them have a smaller chance of all losing their jobs. And also cynically as a way to maximize the value of your 10% of the company. That's true. If you feel like it's not going to succeed and you're not going to go all in and say, well, and I will do what it takes to succeed. It seems like it would be worth more if you were to leave and someone else were to step in that had more engagement and was more motivated to make it all work yes and the you know i guess the question is why do you think this company is going to fail is it doomed to failure or with the right kind of people engaged at the right levels could it succeed and if that's the case yeah like why not bring someone

in to take over for you who you think could make it successful and then there's a chance that your 10 could be worth a lot while you also go find a satisfying and enjoyable job yeah and even if you You don't think it, even if you, yeah, I think there's the dual prongs of maximize the value of your 10% and minimize the risk to these people that you like. You don't want them to just all fall over. Now, one of the last questions that Albert Anonymous asked, if that really is your name, that'd be an awesome name if that was the case, is am I going to become unhirable? And I think the answer is pretty much probably, but not totally. So having only one job on your resume for nine years that you were the founder of definitely creates questions in the minds of hiring people who might want to hire you. It also creates an interesting skill set that might be minimally transferable to other companies.

And being kind of founder level for this long, it's kind of like, wait a minute, do you really want to go punch a clock for me and get a regular paycheck? Yeah, do you want to just like grab JIRA tickets after? yeah exactly it's kind of weird are you too used to getting your way and deciding how everything works and yeah like if someone came to work on my team as just a regular software engineer and all they had was nine years of essentially founder experience i'd be like i don't believe you i think you want to go found another company you're probably a bad employee like i don't mean as as in like a slacker or something but there's a certain amount of like i don't know rule following and you sort of work within the systems

and take orders well and that kind of stuff. And you might be too much of a rabble rouser. I say this as a dyed-in-the-wool rule follower myself. So that doesn't mean you get another job. I think you're saying it could mean you go start your other thing. Yeah, that's exactly right. I think, I don't know,

maybe that kind of ties into what I was saying earlier, which is maybe that is the right next step for you is actually start that thing. Now, I guess the question you got to ask yourself is, do I want to be a founder forever? or am I willing to go back into the regular workforce and try to find a company that will accept me through that transition yeah I think I agree with you that oh go ahead yeah and I think you probably could find a company that would do that but it's going to be a little bit of headwind

and it might not be you you might think well I'm clearly a staff distinguished principal whatever engineer because I I did it all here I built it all up from scratch and you might have to take kind of like a a level demotion below what you think you might be worth because i think people hiring will look at this and say this is kind of risky it's kind of weird and hiring is generally pretty risk averse can i keep working here until it goes under i mean sure you can also just do that yeah i think every year you continue to work here just amplifies the problem of transitioning into a quote regular job yeah the fact that you've worked here nine years means you already have approached things much differently than i did and i admire your ability to just stick with

it that long that's that's pretty awesome i think i would have a hard time staying if i felt like i wasn't going to be happy there if i wasn't going to get any happier there and i wasn't feeling happy about the work and it sounds like you're not yeah time to time to double down on those hobby projects see how many of them you can squint and say well this will enable ai agents this is a distributed database. Clearly it is for agents somehow. I think we've answered it. Have we answered the question? I think so. Interesting situation. Best of luck. Yeah. Tell us how it went. Shall I read our next question? Let's do it. Okay. This is from an anonymous listener who said, for much of my nine years as a software engineer, I wanted to be a leader. I just really

enjoyed mentoring, training, improving workflows, working with stakeholders, and coordinating on projects. Leadership seemed like a natural fit, and so I was super psyched to be finally made a team leader last year. It has been hell. It has been like falling backwards out of a tree and hitting every branch on the way down. Meanwhile, it's literally raining anvils and saber-toothed tigers. The constant pressure to have work lined up for the team and to be able to report on the activities of the team at a moment's notice is unbearable. I can't stand being responsible for the delivery of other people's work. Writing up reports that no one reads or painstakingly denoising pointless metrics. I dread having to pull eager young developers out of refactoring

rabbit holes. Fortunately, as I took this promotion with no raise, I've easily been able to get myself busted back down to IC. Happy days. The problem is that I have no idea what to do with my career. My core experience is with .NET as a mid-level engineer, but honestly, I'm what I would call a hyphen-shaped developer. I've seen and done a lot of things, but not to an expert level front end back end bi and everything in between that felt okay when i was aiming for leadership but now i feel a little lost i honestly feel ready to go full goose farmer with a goose emoji nice what do i do next have you ever heard of a goose farmer no is that are the geese the crops or are they assistants in the farming or are you turning into a goose there's so many

farming while a goose that's gonna go goose farmer what could it mean yeah if someone said a cow farmer i would assume they meant like a cattle rancher i mean i would assume they were turning into a cow and becoming a farmer yeah you know whatever you can interpret that that's the ambiguity in in the language that's why you need to express this as code so it's unambiguous it clear oh huh it's a vivid metaphor falling out of a tree while deadly things are raining down on you yes raining anvils well the thing about falling and heavy things raining is they don't hit you that hard when you're both falling that's true that's a fair point it's not maybe he was trying to soften the pain of management yeah maybe the branches are there to break your fall

yeah imagine how much it would hurt if you fell without hitting any branches yeah and then you hit the ground and then all the anvils fall on you yeah some of these sound like things that suck about this job not necessarily about management and some of it sound like things you maybe don't like and could get better at or could just decide you just don't want to get better at the thing you don't like. Yeah. I mean, a lot of these things are just kind of baked into the job of management, you know, like being responsible for the delivery of other people's work. Yep. That's management. Yeah. That's, that's the job. Writing up reports that no one reads. That's just every job. Really? No, but I, I definitely have had a job where that was the

case. It was a government contracting job and I had to write these weekly reports and I actually started hiding little, um, invitations in the reports. I'd be like, Hey, if you read this sentence come to dave's office to get a prize and one person did a program manager came and got the prize oh i was like wow awesome yeah i don't think i write up reports that no one reads maybe those are like pr comments or something but there's not a lot of hierarchy so maybe that's it maybe i don't have a fleet of bosses above me that i report to that demand a bunch of stuff that doesn't matter or painlessly denoising pointless metrics yeah that kind of sucks it sounds like a big company yeah maybe that's what i'm getting from this oh man the the one

sentence that just really resonated with me was i dread having to pull eager young developers out of refactoring rabbit holes oh one of the things that i really have disliked about management is right in this this wheelhouse which is i hate telling people not to do something that they really want to do yeah it's this tension between business needs and engineering wants slash needs yeah that that is where i feel a lot of tension too where if i were an engineer i would i'd probably say the same things about how i want to do this and how we need to do it and also boy do we not want to pay you money to do that right now it sounds like hmm no idea what to do with my career You could just try again later. Say, well, I'm an IC for now. Hyphen shape, no idea where to go.

I love the hyphen shape developer. That's so funny. This is a reference to the T-shaped developer. Yeah, where you're broad and you go deep in one area. Yeah. What if I'm just broad? I'm just hyphen. I'm just the top part of the T. Yeah, that's so good. So yeah, I mean, I think this was stated pretty explicitly, but I want to make sure it was clear. This person went into management, hated every bit of it, and then got themselves demoted back down to individual contributor, and now just kind of feels aimless and lost.

Like, I thought I had my goals and desires all lined up, and then when I actually got what I wanted, I absolutely hated it. So now I'm back at square one. What do I do? Honestly, this sounds like a positive outcome. The no raise thing is paying off now because it was easy to bounce back. Yeah. uh nine years did they say how long oh i imagine it wasn't a super long time if they were able to bounce back also and they learned a bunch of stuff about themselves yeah so that doesn't sound too

bad yeah i mean it kind of the cliche thing to say would be to quote thomas edison who said like no i didn't fail a thousand times i just learned a thousand ways that didn't work or something for the light bulb i don't remember the exact quote but you know now you can add to your list one more door you definitely don't want to walk through so it's like good progress and isn't life really just a sequence of walking into the wrong doors and then trying desperately to get out yeah or convince yourself no actually this was the right door yeah exactly there's two ways to be happy yeah you can either walk out of the door and find the right door or just convince yourself that this door is great i've fallen in love with this door after reflection

i i think a thing we have said a lot in this podcast is that you learn a lot more about what it means to be a great individual contributor if you are in management ever because you learn what you hope everyone that reports to you would do to make your life better totally you also mentioned how much you enjoy a lot of these leadership things so i think one way to look at this is say you know i might be a hyphen shape developer in terms of technical areas of expertise but maybe maybe my t what's the name of the i don't know uh is that the stem the root the trunk stem yeah maybe maybe my maybe the trunk yeah i like trunk because a tree has a trunk and tree starts with t and yeah it's okay all right my t trunk is uh kind

of like getting stuff done ability not not necessarily the raw technical problem solving but the the leadership skills to accomplish a technical task with a group of technical people without having to be their manager but still i know who to talk to about the thing and how to push on something to make it go faster i'm not i'm making all these specifics up but you can you can maybe double down on that area if that's the parts that you liked and you don't like all the parts you described good news now you don't have to do any of those parts yeah you can just do the stuff you liked awesome but it feels like the tone in this question is kind of existential Like, oh, my gosh, I don't know what to do.

I'm going to give this up. Yeah, sort of like, well, what do I reach for now that I don't have this goal of, well, I want to be in management? Yeah. It's time to achieve some kind of Zen enlightenment where you realize there is no management. I don't know. Yeah. That happiness was not in achieving the goal, but in the journey. Oh.

The journey of finding your way back to the same place you started. But yeah, I guess you have no journey now, though. No idea what to do with my career. Maybe the problem is you haven't gone deep in any area. Maybe the hyphen is the problem. Yeah, I was kind of thinking that. Maybe you just get to pick and say, well, I haven't tried this yet. I haven't tried going really deep into something.

And that might be a cool way to grow. Maybe go read a book about something really deep. I don't know. Yeah. I don't know how you learn stuff. Read a book, maybe. it felt okay when i was aiming for leadership just reading the question back i do think there are trade-offs and it can be useful to go super deep it's it's nice to have a broad overview

to be in engineering leadership but also i think there are engineering leaders that have gone like super deep into spinning hard drive device controllers somehow and like i think there's broader things you pull out of that super deep knowledge too hmm i have no more words i feel like my advice on this is pretty generic like yeah it's just like no it's fine just get back to work and do your tickets it's fine yeah get back to work and do your tickets but do them better now because you're a manager because you've been a man and find find something to get excited about in tech look here's what you can get excited about every day you wake up you go to work you join your stand-up meeting and you look at the poor sucker managing your team

and you just say, ah, that's not me. All right, no blockers. And thank goodness I'm not running this meeting. No blockers. Exactly. Yeah. What I accomplished yesterday, didn't have to manage this team. Today, my plan is continue not managing this team.

Yeah. This is bad timing to say quit your job, but I have found a source of renewed passion in a product i'm excited about or a team i'm really excited about or something so maybe you can find that if you're at a big company some way to shake it up a little bit could be useful or barring that a bigger shake up although that comes with all these caveats right now when it's a little bit tough out there yeah maybe that is what needs to happen here it's less than a goose farming i mean you did bring that up that is always an option take your your tech earnings and

buy some property that's ripe for goose farming and become the world's best provider of down yeah or the best goose that farms other unrelated crops it's like organic right there's something about the crop that is about how it's produced not just how much it costs your brand is goose made yes a goose picked these beans and a goose literally picked these beans it will taste better because of that oh have we answered the question yes and we supported local geese yep as we always do a core value of ours actually i grew up in minnesota and i hated those things there were canadian geese everywhere and we would chase after them and chuck rocks at them and they would get back at us by pooping on literally

every square inch of grass in the whole state oh man they are the weed of the fowl family yep well that means we've surely we've answered it now that we've yeah i think so i've revealed my ancestral hatred of geese another hot take by jameson yep you're gonna get a lot of hate mail this week like like you did a few weeks ago geese can't type i'm safe what about what about their allies yeah i i hope they have none i'll find out you're gonna wake up and find your lawn covered in goose poop we did aerate our lawn and it gives me flashbacks it looks like yep okay what can people do if they want their own questions answered go over to softskills.audio and whether you're a goose or a human fill out the form available from the button that says ask a question

we must thank you so much to everyone even if you're a goose for submitting those questions because, boy, they're just wonderful. I read these questions and I just think, I'm so glad I'm not some of you. Just kidding. Just kidding. A lot of you are in really challenging situations and we just want to honor you

for the suffering and struggle and say thank you. Please keep the questions coming. We appreciate it. And if you are a goose, tell us how you defeated our advanced goose captcha that is meant to prevent you from submitting questions. We will tweak it.

All right, thank you for listening. We will catch you next week. I'll see you soon.