Soft Skills Engineering - Episode 493: My boss one-ups my negativity and football engineering

Episode Date: December 29, 2025

In this episode, Dave and Jamison answer these questions: Hey Guys, long time listener, first time asker! At my BigCorp Co., whenever I talk to my skip level about my concerns, it seems we are playing the ‘Gloom Olympics’ every time we meet. I’ll mention I worked late, and he’ll counter with, ‘That’s nothing, I haven’t slept in three days!’ This repeated lack of empathy is demotivating and I don’t think I have had a fruitful discussion with him. How can I tackle this? How can I feel heard? I’ve decided to leave my current job as a software engineer at a large retail chain. This is my first out of university, and I’ve been here three years. I’m interviewing for two other jobs: one as an engineer at another large retail chain on a team, and another at a world renowned European football club. That job would be very different. I’d be the first internal dev hire ever, and I was told I should expect no other devs to get hired for 2+ years. I’d write my own tickets and review my own prs. The project would be to build a dashboard to manage the players - drug testing, injuries, rosters - internally. What should I do? Feedback & mentorship were central to my growth at my current job. I won’t have that at the sports club. My concern is I go to the football team, drink a lot of beer & have a great time, but after 3 years of being my own boss, I’ll think I’m the greatest dev ever but really not have kept up to date with modern trends, forgotten how to take feedback, and written a lot of 💩 code.

it takes more than using advent of code to finally learn haskell to be a great engineer this is soft skills engineering episode 493 i'm your host dave smith i'm your host jameson dain soft skills engineering is a weekly advice podcast for software developers who just don't want to be the ones who have heard of haskell but actually want to be the ones who have written it i think i've done this at one point and it's been long enough that i forgot all the haskell that i learned by doing advent of code i've also never completed an advent of code it's really three days of code for me okay yeah i mean the good news is that all you have to do in order to get all the value out of the haskell situation here with advent of code is learn enough to where yeah

maybe you forgot all the syntax you don't even know what a monad is but the feeling of superiority we'll never leave you yeah maybe i was born with it i was born to haskell i think they're all still available right can't you do all of the old ones i don't know from past years i feel like you can but i'm also not going to it's so it's such a cool project and i i love that people enjoy it and i wish that i also did it but not enough to actually do it okay you wish that you wanted to do it yes that is what i believe dave should i read our our patrons yes go for it thank you to ci issues sharpenty.io seth is begging for a review on his pr thank you for supporting us on patreon jameson you want to read our first question nice i am jameson this makes no sense

hey siri learn react testing at how to test front end.com balanced the parens but forgot the emoticons sad smiley face you can't fix stupid but you can put it in a container and hope for the best my actual name on linkedin is yami debugging the dark canny the mobile development ordinary first of his name quote or one equals one drop table meow mix j.cobb shandling hey dave and jamis on let's get our get our jams on record that soft that skill song soft skillet nation everybody sing along nice the missing semicolon christy the world's okay's programmer this is my list of reasons why messaging apps should insert a line break when you press enter instead of send message if the subs if the service org uses a subservice org and the controls at the subservice

org are necessary then quit your job nick molyneux if the service org uses a subservice org and the controls at the subservice org are necessary pretend it's not javier gonzalez chewy ted timbrel a single opening parenthesis dan from drone deploy never is not just a crater on mars flamingo emoji i like chicken i like liver yamix yamix please deliver swiss python okay i will measure the text bandwidth beautiful is better than ugly explicit is better than implicit simple is better kyle boss i can't see dodds pause for dramatic effect jenny kim the stochastic parrot ira chan jonathan king's nigh beautiful functional user documentation neil breen is the best movie director of all time will angel from drone deploy ho ho ho braden canes john grant britney ellick

and a closed parenthesis followed by a single closing parenthesis. Nice job. Thank you. Thank you so much. Every week, I'm a little surprised we haven't seen an obvious cross-site scripting attempt here. Maybe we need to reveal more about the tools we use to track all this information.

I assume Patreon is doing some kind of sanitization. If you want to test that, go to softskills.audio and click support us on Patreon and then do your best. And if it makes it into our spreadsheet and then into the other software we use and then you can have my cookies. I'll give them to you. Yeah.

I've been giving them to the banners, but you can have them. Yeah. Dave, do you want to read our first question? Let's do it. This comes from an anonymous listener who says, Hey guys, long time listener, first time asker. At my big corp co,

whenever I talk to my skip level about my concerns, it seems we are playing the gloom Olympics every time we meet. I'll mention I worked late and he'll counter with, that's nothing. I haven't slept in three days. this repeated lack of empathy is demotivating and i don't think i have had a fruitful discussion with him how can i tackle this how can i feel heard have you had this experience where you

are trying to express a negative feeling to a superior at work in some way and get out negatived i can't say that i've had it with a manager but i've definitely had it with just regular people talking in normal social circles i think you could probably have this happen with a co-worker even if if you are lots of thoughts spinning off about this i wonder if i do this on accident by just being i'm on the offense what do you mean i just always tell you i haven't slept in three days and then you you assume i won't have empathy for you because i'm so tired or something like that i don't remember exactly what it was but i think i had this same type of experience when i worked at a big company where I was I was upset about something at work and the person I was complaining

to said that's nothing I have this thing that is even more upsetting to me yeah and it does suck if you want something to change if you're hoping especially if it's your skip level and you're hoping that your skip level says that shouldn't be and I will make changes to make it happen but instead I feel like it's a way of trying to shut down complaints yeah it could be and I wonder if there's a different way to express your complaint that isn't i worked really late and it made me sad like what what is underneath that do you have to work late all the time does that make you worried that the deadlines are unreasonable or like i guess that's the question like why are you saying this like why are you yeah i worked late like okay don't i don't know i mean i there

is ulterior motives right like sometimes you want your skip level to know that you've been putting in a lot of time i guess there's reasons for that yeah i i guess i'm assuming this is a complaint about a thing that they wish would change in some way, not a bid for recognition. But especially if it's a bid for recognition and it's coming across as a complaint, then it's really not working. Yeah, clearly.

Maybe it is. I mean, sometimes people just react that way, but they actually at least registered what you said, even though they also outdid you. Say, invite me next time. I would like to come to the work slumber party, please. I haven't slept in three days. The corporate provided cocaine

to keep you going all night or whatever. I don't even know how you can do that. Can I get access to that, please? Yeah. So you're saying I worked late and I wanted to work even later, but I just couldn't without some kind of stimulant. I didn't have enough business context to motivate me to stay up for three days. And I'm wondering if you could help provide me that. There is another solution here.

If you want to win the Gloom Olympics, you just need to make something really bad happen in your life. and bring like so bad that no one would ever dare to out gloom you and then bring that yeah that's nothing i hit the deploy button and i ended up in ukraine the wrong kind of deploy happened i got deployed yeah i don't know you could also just make up stories you know and then like every time you think you're about to get close to the end of your story then you just say and then and it just gets worse you tell a worse story you do about five of those and you just wear down your skip level manager so hard that they're just like i don't even want to compete with that i don't think i've ever talked openly with a person who has done

this but i have been around people who feel like they always have to one-up your suffering in some way and it makes me wonder i interpret that as shut up you wuss and suck it up look at look at how hard it could be yeah or everybody stop listening to them i should be the one you're listening to because i have the real suffering or something like that but i wonder what i don't know maybe that's not why they're doing it you probably can't ask your boss why your boss's boss why they're doing that yeah why do you always one-up me when i tell you all my terrible things that happen to me yeah it could also be you're dealing with a me monster do you know the me monster reference no this is a brian regan stand-up comedy bit where he talks about trying to tell some story

about something that happened to him and someone else just one-ups it. I think it ends with him saying, I really wish I was one of the astronauts that landed on the moon because no one could ever one-up me. Like, oh really? I landed on the moon.

Yeah, what if you just said that in response to your skip level? I haven't slept in three days and you say, well... I landed on the moon. I landed on the moon. I was part of... I was on the set crew

that faked the moon landing. just kidding i wonder what percentage of the population believe that i believe very wholeheartedly it happened and was real but it's not zero it's yeah i've known some people that believe it's fake well anyway we'll get to the bottom of it right now maybe we'll take a few minutes i do think that you know every once in a while when someone asks us a question rather than answering the question directly i think we like to address a premise that was baked into the question. And here, one of the premises is that you should be sharing these kinds of concerns with your manager in such a way that they feel like it's appropriate to respond by just

one-upping the concerns. And I think it's possible that instead of just complaining about something, and I don't want to completely trash the listener here, that's not my intention, but someone could characterize what you did as just complaining. Instead of doing that, you could actually be asking for a change. You know, like let's reverse engineer or work back from how you ended up working late and then talk about ways that we could prevent that and then share those ideas with your skip level manager. Yeah. You know, maybe that's a more productive thing. At the very least, they have to respond to your request instead of responding to your complaint with a bigger complaint. Yeah. I agree that there's something beneath I worked late

that you could express more explicitly, and hopefully that would elicit better feedback. If you believe that you should never work late at your job, this could be your boss's boss's way of saying, no, no, sometimes you work late. But you could also find that out if you say, hey, I worked late and I didn't expect to. Help me understand the expectation for when you really grind through and work late and how often that should happen in a year. Is it a rare thing? is it every sprint deadline we just do whatever it takes to meet it yeah exactly help me think about how do you see it i guess as as you go up in big corps especially you you will probably tend to encounter more people who work as a bigger and bigger proportion of their lives though so

you'll probably get about this specific question you'll probably get it'll just get worse and worse but yeah yeah no the the the farther up in the tree you are towards the the roots the more of your life is offloaded to other people that you can pay with the money that the company pays you in order to spend more time working yep exactly have we answered this question i think so my advice in a nutshell is figure out what you're trying to achieve in these skip level one-on-ones and find direct ways to achieve them they're probably limited in time probably limited in frequency so it's even more important that with your skip level you go right for the right to the heart of the issue rather than beating around the bush yeah and if it is just recognition you want

you can say that you know yeah you might feel weird saying it and that might be a signal that maybe you shouldn't be asking for it in this way but let that awkwardness be a guide yeah that's my advice great we've done it dave should i read our next question i was hoping you would this is from an anonymous listener who says i've decided to leave my current job as a software engineer at a large retail chain this is my first job out of university and i've been here for three years i'm interviewing for two other jobs one as an engineer at another large retail chain on a team of engineers and another at a world-renowned european football club that job would be very different i'd be the first internal dev hire ever and i was told i should expect no

other devs to get hired for two plus years wow i'd write my own tickets and review my own prs the project would be to build a dashboard to manage the players drug testing injuries rosters etc internally what should i do feedback and mentorship were central to my growth at my current job i won't have that at the sports team my concern is i go to the football team drink a lot of beer and have a great time but after three years of being my own boss i'll think i'm the greatest dev ever but really not have kept up to date with modern trends forgotten how to take feedback and written a lot of crap code nice use of the poo emoji by the way yeah on the last word there oh duh tough decision i don't think it is oh i think this is so obvious you just go no way

no way do you do not go to the sports team so do you have any clues about whether this person is a diehard football fan it i don't know it seems i'm assuming so but like why else would they consider it yeah because people who work in sports who aren't professional athletes generally have worse jobs and lower pay ah yes because there's a population of enthusiasts so the supply and demand is a little bit different it's the same reason why a lot of video game jobs are kind of crappy because there's an army of people who want to make video games there's an army of people who would love to work at this famous european football club yeah yeah i would not do this in a million years it would might be a cool experience to tell people that i worked at this

club and i bet it's not gonna go great and i'm frankly astonished that they would hire a full-time internal software engineer to build this thing for them instead of yeah use a different thing i might even ask them in the interview process hey why are you not just using a contract agency to do this and if they go yeah oh good idea you got your answer yeah on the other hand it would be really cool to do greenfield where it's just you i mean i don't think it would be great for your career but it would be really fun i'm not even thinking about that part i think it's it's 100 about the go work in this there's probably a word for this type of industry an industry that people want to work in because it yeah it's fun a fun industry i'll use that word yeah there's an there's an

intangible in your paycheck that doesn't show up in money yeah it's like non-profits often have some amount of dysfunction and lower pay and different resource constraints partially because a lot of people want to do this meaningful non-profit work and then yeah yeah i'm not even thinking about the i think there are ways you could get feedback and and anchor yourself a little bit so that you are hopefully staying up to date but i personally i'm trying to think of what would say this person's a diehard football fan or soccer fan as the inventors of the sport like to call it. Is that true? Would I do that equivalent thing? I don't think so. I also don't know what it would be, but I don't think I would go work as a fan of the thing the company does

at like a, I don't know, the company that makes my favorite video game or favorite bouncy ball or something. I'm going to write software for the bouncy ball factory that I love. Okay. I have a motorcycle and I really like it and it would be kind of cool to work for that company okay maybe i would do it i don't know you found your place that's a much bigger company though and they have a way they they certainly have a lot of software people that already work there yeah so i think it's that the inherent incentives around working at one of these industries combined with the fact that you'd be the only dev makes me say heck no so in other words if it was just if it was a cool industry that you love or a cool company that you love

and there were lots of other developers you'd be more inclined to go yeah join our team of software engineers that maintain this really cool product. And you kind of just deal with the fact that maybe you'll make less money, but you get to do some cool work, but you're going to deal with a lot of things for the first time. Yeah. I don't know. What do you think though? Yeah, no, I'm totally agree with you. For me, the only factor here is that you'll be working alone. I think you're going to burn out. I don't think I've ever worked completely alone at a company ever. and just the prospect of showing up doing my work nobody understands you you're definitely going to be the outsider you'll constantly be having to explain yourself to a company that

to a group of people that just don't really get why you're there especially if you're tracking things that the players then learn are harmful to them and their careers you know now it's like going to be really awkward yeah i assume this is for some kind of like their development teams or I don't know how it works. And I assume you're not tracking like someone I've heard of's drug testing result. It's like the amateur teams or the youth teams that are affiliated somehow.

I don't know. I don't think it'd be fun at all. Yeah. In fact, I recommend people, generally speaking, when you're looking for a software job, the best jobs are those where the software you write is why the company exists

and it's why they make money. If the software you write is just some ancillary thing, like a quote, necessary evil in the eyes of management, it's just never going to be a great place to work that's a great point and that's the case here right the product is the players and the ticket sales it's not you yeah and then that that just that's not a complete deal breaker for me though but that combined with working alone as a deal breaker in fact working alone itself might be big enough to me for to be a deal breaker especially if i'm kind of early in my career yeah wow this might be the fastest we've just agreed very

clearly on one side of the question just like that it's interesting we have slightly different reasons but yeah we're both pretty firm don't do it but also i don't like soccer that much so who could say i know i don't know if i let you know this jameson but i for the podcast i uh recently put out an offer to hire our only software developer to manage our drug testing database for your drug tests ah okay it will come up positive for l-carinitine whatever is on this energy drink can that i've never like i couldn't tell you what it actually is okay good to know boy does it make me feel briefly good and then bad later i guess so it really does fit the profile yeah i guess it does yeah

my dad is late 60s grew up on a farm in idaho and one of the things i admire the most about him is that he continues to learn and develop new things and one thing he did a couple years ago was decide out of nowhere to become a really big soccer fan okay so he just picked a team and decided to start watching soccer and got really into it and followed the team and i think the team he picked one stuff that year so he was really pumped about it so this question made me think about him maybe he would go work for this team yeah i think it's so cool that yeah golf is the only sport that has had a place in his heart for his whole life never really liked sports that much at all besides golf and then all of a sudden he's just i'm into soccer let that answer the question for you all right

have we have we answered this question i feel like we have is there more detail to discuss here i don't know i mean the other job frankly doesn't sound that awesome i cut out some details it's a different tech stack but same business vibe but maybe that's enough to help you learn and grow i think you'll just by default learn and grow by moving to a different job yeah that will happen you find what is institutional knowledge that you developed and what is skill that is transferable which is a good thing a good meta skill to learn you also learn which processes and principles and things that you think are inherent to all software development are actually just a one team thing yeah that's a great thing to learn is is there's no one way to do it yeah you can do it wrong in

many different ways right and right in many different ways there are many wrong ways to do software development there are no right ways to do it but there are many many equally enjoyable wrong ways yeah what can people do if they want their own questions answered dave i think they can go over to soft skills audio and click the ask a question button where you can fill out our form and see if it is cross-site scripting resistant it's really close to the place where you put your patreon name actually it's not even not even the same company but in any case it's a good test of our security systems which aren't ours at all but we love it and we thank you so much everyone who does this the question flow is strong vibrant and absolutely beautiful so

thank you for keeping those coming yep thank you thank you we will catch you next week