Soft Skills Engineering - Episode 116: Weekend Warrioring and Reaching the End of the Career Ladder

Episode Date: July 17, 2018

In this episode, Dave and Jamison answer these questions: I work at a growing start up, and while I was hired as a web dev, I have started working on unrelated but cutting-edge tech for the company during off hours. My boss has encouraged me to do this with monetary and office life bonuses, and he has reworked our business model to focus on it. The only problem is that our CEO overpromises and pushes me to my mental and physical limits for very short turnarounds. I still have to do my regular job. While I love the challenge, and love the company, I feel set up to fail. And the 40 hour coding sprints over the weekend are killing me. I feel like I’m setting a horrible precedent because somehow, defying all logic, I’ve met the deadline each time. How far is too far? Should I keep killing myself, or take the agony of defeat on a project. I’m currently working as a Senior Solutions Architect after a career progression that looks like this: Junior Developer, Intermediate Developer, Senior Developer, Junior Architect, Intermediate Architect, Senior Architect. In a recent one-on-one with my boss, we were discussing my future career options and concluded that the next step for me would be one of the following three positions: VP of Engineering, Chief Architect, or CTO. According to him, all three have similar levels of prestige, pay and influence, but vary in the nature of the job. Reflecting on this conversation, it dawned on me that I’m close to the final stage of my career. I’m currently 39 years old, so I’m now thinking to myself: Is that really it? One more promotion and I’ve successfully climbed the corporate ladder? End of the line. Time to retire. Nothing more to strive for (other than working on the most interesting projects). So, could you please talk about the software career progression, what to aspire to and how to measure one’s own progress once one has reached the top of the ladder?

It takes more than trying to remember the arguments to TAR to be a great software engineer. This is episode 116 of the Soft Skills Engineering podcast, and I'm your host, Jameson Dance. I'm your host, Dave Smith. Soft Skills Engineering is a weekly advice show where we answer all of your non-technical questions about technical fields like software development and also fail to remember the order of arguments to TAR, or even what they are. Actually, I heard a mnemonic. Have you heard of compressed Z-files?

Oh, that's a good one. And extract Z-files? That's a good one. I have not heard that. well now you have i can't i saw it on twitter i can't remember i'll try and look them up and give credit to them that's a good one but it it's not just that you have to know more stuff try now try and coming up with a mnemonic that lets you tar compress and then pipe to ssh and decompress and extract on the other side that's called google yeah that's the mnemonic all right

we have some patrons we want to oh yeah i was gonna i was gonna say we have some patrons to thank you should say that maybe we should simultaneously thank them but i need a creepy like cult voice yeah all right i'm just on patreon yeah i will say thank you thank you to all of our patrons this week we'd like to thank those that are donating at the illustrious level that gives them a call out each week nick cantar dimitro and neonilla david jackson ken howard sean clayton dustin coats thank you to each of you and if you'd like to join them you may go to patreon.com soft skills eng where you can contribute or hit up our website at soft skills.audio and click support us on patreon yeah we're pretty excited we've actually started working with a designer

and so pretty things should be happening soon so thank you for your support which makes that possible yes all right i will read our first question this is from an anonymous listener first love the show important preamble it's all questions i work at a growing startup and while i was hired as a web dev i have recently started working on unrelated but cutting edge tech for the company during off hours my boss has encouraged me to do this with monetary and office life bonuses and has reworked our business model to focus on it the only problem is that our ceo over promises and pushes me to my mental and physical limits for very short turnarounds i still have to do my regular job while i love the challenge and love the company i feel set up to

fail and the 40 hour coding sprints over the weekend are killing me i feel like i'm setting a horrible precedent because somehow defying all logic i've met the deadline each time how far is too far should i keep killing myself or take the agony of defeat on a project agony of defeat the agony of working 40 hours on the weekend sounds worse than the agony of defeat on a project which the company has pivoted to focus on but yet you are still somehow doing by yourself on the weekend yeah it makes perfect sense to me yeah that doesn't sound like your company has reworked the business model to focus on it it sounds like your ceo has figured out how to take advantage the whole company is now depending on your weekend time yeah sounds like a sustainable

business model here's some free pizza there's a nice little perk for you buckle up the ceo's probably just probably he probably is going back with his ceo buddies and he's like look i have an experiment i'm gonna see how much free work i can get out of this engineer for nothing i can imagine the smoky back rooms cigars like there's some exclusive club that i've never even heard of and they're like guess what i made my employee do i told them that if they worked over the weekend the company would be totally successful i don't know this is weird i wonder how much pizza we're talking here because if it's like hundreds of boxes of pizza that could get interesting we converted your alley your hourly rate to these little seatsers five dollar pizzas

whatever that is i don't know 35 50 bucks an hour that's like a like 10 pizzas an hour yeah that's a new pizza that shows up every six minutes yeah like this is great for the first minute i wish i could get paid in pizza all the time so if you did that for 40 hours over one weekend how many pizzas would that be my gosh i'll tell you enough to retire on that's retirement pizza yeah just drop it off at your financial planner's office but seriously if you're doing this every weekend which i suspect you are not because doing this every weekend i think you would have already flamed out way before you could write this question but if you were doing 40 hours of extra work every weekend that's a full-time equivalent which means your boss is getting the

deal of a lifetime yeah i'm trying to hire somebody right now i would love to just pay them in pizza actually i wouldn't care because it's not like my money but i would be sad never mind it would be worse if you're starting up your own little startup and it was coming out of your life savings i think you'd be thrilled to pay with pizza i think i would if i were an evil human i feel like if i would instead feel bad that someone was working without getting paid this is really weird maybe that's why i won't ever be a ceo yeah this is why you don't even know about the club our ceo over promises and pushes me to my mental and physical limits for very short turnarounds so i could see that just being maybe maybe they're just really excited about new ideas and they just kind of get

ahead of themselves but then when they when they turn around and say by the way i promised this new thing in this field that you were not hired to work in that you don't know please get to work that that just seems dysfunctional if this was me in this situation on the receiving end i am such a people pleaser and i know you are too jameson this could be a case where the ceo is actually not telling you to do this but there is a little bit of room for miscommunication where you take his thoughts and his excitement about the idea well and the fact that he promised it to a customer to say why will i will i will not let this fail you know and it could be that the ceo is like well this is a long shot we'll see what happens and then you come back successful and the ceo is like

oh i guess it wasn't that bad you know and so that's what we call well if i were an economist that's what we would call an externality where the ceo is not aware of the pain he's inflicting just because he doesn't know that you look i mean you look for all from the outside you look like you're delivering successfully here but you know that it's actually super painful and exhausting and unsustainable but all the ceo knows maybe is every time i get excited and tell mr anonymous about a project, I get what I want. Yeah. Either way, I feel like the solution is the same. Either if they're doing it on purpose or if they're doing it out of ignorance, you have to say this isn't sustainable. If you want this to be my job, I would love to do this for my full-time job. I don't want

to do this and another full-time job. There are plenty of jobs out there. You can find a different job. Actually, this is a perfect time to take the eternal soft skills engineering advice. Quit your job and don't get a new one. You have two jobs right now. Quit one of them. Either quit being a web dev or quit being a cutting edge tech during off hours developer yeah yeah like if the company has truly reworked its business model to focus on it congratulations you have leverage yeah they sure do and you can say hey very truthfully it's not like you're holding them hostage it's i would be concerned about a business risk of if the company depends on this one person depends on just burning themselves out to complete projects that's not a long-term solution and it's not going

to work long term you're going to quit or you're going to fail because you're not in a situation where you can succeed so i think you have a pretty compelling case to say like hey this maybe started out as a skunkworks experiment thing it's time to grow up a little bit and treat it like a real thing yeah it's time to invest in it that's the term i think that you need to say is that we've been prototyping we've proven the concept we think there's business value now it's time to invest for real and what i mean by that is i need to be a not the only person working on this and b i need to be able to dedicate more high quality time to this instead of just my weekend and off hours which so far have been useful for cranking out a prototype but if we build a business on this it's going to

fail because you're going to get low quality you know cobbled together stuff that won't scale or won't sustain itself so yeah yeah i mean the the tight turnaround times and over promising that's bad that's normal bad yeah i mean there are lots of play that's that's the business model of agencies right like that's how they work but um the fact that you have to do this in addition to your other job is abnormal bad and ideally you would have neither of those but i feel like you could survive if that was your only job i um i think this developer this this listener is really afraid of failure and to the point actually that they're willing to work 40 hours in a single weekend to avoid failure and i gotta say i i look up to that your tenacity you know your let's just

use the word passion you're clearly a missionary not a mercenary right but i don't know pizza You're a pizza mercenary. But I wonder if it's the fear of failure that's motivating you so hard. Maybe it would be good for you to experience not meeting these crazy expectations. And, you know, what does it look like when you have an honest conversation with someone and say, I tried, I didn't meet the expectations, here's what I need to be successful. You know, that conversation is just totally lacking from this scenario. And I think it could really benefit everyone involved.

you talked about being a people pleaser earlier and it feels really good to say yes in the moment we've talked about this before and then the pain of having to deliver what you said yes to comes over time one thing that i've tried to move to as i as i try and improve from saying yes to too many things and not delivering is saying yes what will we give up to make this happen yeah like what's the trade-off and and if that that's a trade-off that you can decide or you can pass that up and say like, yeah, I can do that, but I can't do this and all the other stuff that I already said I was going to do. So tell me, help me, help me understand the priorities, which of these things is more important and which of these things are we going to drop to do this more

important thing? Yeah, I love that. That's such an important conversation to have, but it also takes a lot of groundwork or sorry, a lot of legwork to get, uh, to have that conversation in a way that your leadership can understand it and really make a good decision. I've often been surprised at the details that leadership is unaware of when it comes to ranking priorities against each other. You know, you really have to spell it out and get everything up on the, say, on the whiteboard at the same time so that they can actually make an informed decision about what's most important for the business. So you need to come prepared with a nice list of, you know, what's going on. And frankly, this is actually probably above your pay grade. I was

gonna say i would push back on that dave that's that's literally your your boss's job their job is to is to identify priorities so if if they can't do that then they're not doing their job it's probably i don't know it's not unheard of that they may not have done it that they may just be saying like all this stuff's important let's do it all but you should be able to say help me prioritize these things and if they can't do it they don't that's their legwork right like that's true as an individual contributor your job is to get stuff done and you can contribute and pass ideas up and and have a big impact but when it comes down to deciding like which of these important business goals is more important that's a ceo's job yep yep absolutely right and you should be

able to influence that it sounds like you're actually quite trusted yeah you know this person's coming to you the ceo's coming to you directly to get this skunk work stuff done and and so your opinion should have a lot of sway and don't discount yeah yeah for sure you can argue and you can persuade and present cases. But if the answer is they're all important, then the answer is none of them is more important than the other, which is not true. Yep. Well, has the question been answered? I think so. You're going to have to have a hard conversation. And I think you've probably gotten to the point where the pain of continuing is actually less or is actually greater than the pain of having that hard conversation. That's how I deal with my hard

conversations i just wait until it hurts more to not have it yep pushes me over the edge so that's where you are and good luck yeah it'll be better after no matter what oh yeah for sure for sure and this will be our next question yeah i was just gonna say this will be a valuable skill for you to develop and the next time you start sensing a situation like this you'll probably jump into this conversation a little bit earlier yeah all right do you want to read our next question yeah this one comes from a listener named julian who writes hi i love the show please keep up the great work. Thanks, Julian. I'm currently working as a senior solutions architect after a career progression that looks like this. Junior developer, intermediate developer, senior developer,

junior architect, intermediate architect, senior architect. In a recent one-on-one with my boss, we were discussing my future career options and concluded that the next step for me would be one of the following three positions. VP of engineering, chief architect, or CTO. According to him, all three have similar levels of prestige, pay, and influence, but they vary in the nature of the job. reflecting on the conversation it dawned on me that i'm close to the final stage of my career i'm currently 39 years old so i'm now thinking to myself is that really it one more promotion and i've successfully climbed the corporate ladder end of the line time to retire nothing more to strive for so could you please talk about the software career progression what to aspire to

and how to measure one's own progress once one has reached the top of the ladder i think we can talk about what to aspire to in a couple minutes right there's how deep could that topic creepy yeah not very deep i aspire to sleep well at night just chillax all day that is the good life i believe that was play-doh oh really okay yeah this is an interesting question on several levels one of the questions is about what is the software career ladder progression look like and then the other question is what does it mean when i have reached what i view as the top of the ladder what happens next yes i gotta tell you having stood on the top of an actual ladder it's not very fun super imbalanced all you can do is get down climbing the ladder is kind of exciting

i actually say that only half joking because you know i do not view my career progression as a ladder where i'm trying to reach the top um where i'm standing on the top of this thing and when i look at the the three things you've listed here vp of engineering chief architect and cto i actually see i see two parallel paths here vp of engineering and cto are effectively the same role in my mind um well actually i guess i take that back it really depends on the company but they're definitely on the same track yeah chief architect on the other hand is typically like a technical individual contributor role where you have a lot of technical influence but no reporting requirements by which i mean, no one reports to you, you don't have any management responsibilities, etc. Whereas on the

VP of engineering and CTO side, you're definitely on the management track where you have to deal with performance, hiring and firing, compensation, and a lot of other management things, which I've written down here, and I'll get to later. So I think the first thing you need to decide is which of those two tracks you want to pursue, whether you want to go into management, or continue on the chief architect track. And if you go to chief architect, you're you're basically doing more of what you've already done. But if you go to the other track, you have just stepped into a whole new universe that I promise you, you had no idea even existed. And you're only just beginning that career path. Having Jameson and I have both done management for a number of years,

and I'm sure that Jameson, you had the same experience I did when you started, which is that there is just so much stuff to be concerned about and work on on the management side that as an individual contributor, I basically had no idea it even existed. Yeah, yeah, that's very true. I would not want to be a CTO right now. I guess it depends on the size of the company. If it's like a five person startup, then you just kind of all look at each other and you squint your eyes and then the do-do-do-do, wah-wah-wah. And whoever loses the shootout is the CTO. Like CTO is just the title you give to the person you give all the work to that you don't want to do. But like an actual CTO at a medium or large size company would not be a job that I would be qualified for or

enjoy so depending on the size of the company i would question the jump from senior architect to cto because of all of the additional management responsibility that comes with that especially assuming senior architect doesn't involve a lot of management that's a safe assumption i think you jump there's definitely some benefit to having those deep technical skills but jumping from not managing to like chief technical manager person would be an enormous jump that you would be ill-prepared for in some organizations. Absolutely. And just to give you a sense for how ill-prepared you would be, I've just written down a little list here of the various things that CTOs need to be aware of and work with to do their job effectively. Do you mind if I just

rattle these off? Please. So finance, marketing, sales, accounting, operations, leading engineers, managing performance, compensation, hiring, firing, mentoring, scheduling, resource allocation, office space design team organization and the list goes on why would anyone want that job what a horrible job it's the top of the ladder jameson that's true view is so great from up there it usually comes with more money that's true i worked at a startup for my first job and my cto there there were like 10 people or something and we had a cto who's just like the most senior engineer person but he was very young and then we got a different ceo who is also very young. And it was basically like, that role was basically like senior engineer or architect. So

depending on the size of the company, maybe there's differences. Do you want to talk about this idea of career progression? I feel like implicit in this question is a linear up and to the right graph in terms of title and salary and influence and amount of stuff you get to do. And that's one model of career progression. You always pick the thing that is more responsibility, more prestige more money more more something yeah more more yeah but i think that's optimizing for more which might not necessarily be the thing that makes you happiest you can definitely pick a lot of there's a lot of different axes besides more words in your title or more impressive words in your title which usually come with more money you can you can pick a place to live you can pick

a team you want to work with you can pick a specific product you want to work on you can pick a specific technology you want to work in like there's just a lot besides how do i get to the next thing in in the ladder and i don't know does are you happier now dave am i have you how about this have you been happier more satisfied in your career when you feel like you've taken a step up the ladder no i don't know have you been less happy or like the same amount of happy or i don't know every time i've taken a step up the ladder so to speak it's been by accident i think I've just never really deliberately said i'm gonna go for that. I'm just not very ambitious in that way I've never really said i'm gonna take that step

I'm gonna go for it and the times when I have okay I said never but there have been a few times where I have thought about that and worked on it and you know what the process of Taking that step and trying to move up in that position. It just hasn't been all that satisfying to me Yeah, I don't know. What about you? I think there have been times where i've deliberately said like I want this kind of job. Well, that's different from move up on the so-called ladder yeah i don't know i feel like i'm trying to say something without saying it trying to to hint at it without saying it so i'll just say it instead i i guess

why do you want to do these things i i don't see i mean it's a limited amount of information in a question so you can't put your personal philosophy and hopes and dreams and stuff but i i would question the value of moving up so to speak for its own sake like what what do you want to do that that would enable and that might also clarify which if you do want to move up which are those roles you want to take if you want a larger technical influence or if you want if you really want to influence like the culture of an organization and its mission or i mean there's there's things that come with these roles and are those things that you want or do you just want the roles for their own sake or do you want more money or i don't know i feel like identifying what you

on out of it would would help clarify what direction to go and it also might be none of those directions right maybe you want to spend more time on your hobbies or with your family or away from work and then like turns out after you've been a senior architect maybe it's pretty easy to go back down to just be like an individual individual contributor you can just chillax and do good work and then go home yeah or or maybe maybe you have very specialized experience that lets you go like found a startup in a field that you have deep technical expertise in and that's none of those things, right? That's like founder that becomes something else, depending on how that founding goes. Yeah. And that, that I think is where the possibilities really expand. You know,

I mean, just, just because you had the title CTO doesn't, or VP of engineering or chief architect, that doesn't mean that you've arrived and that you've checked that box off on your ladder of progression. You know, there's so many things you can do within that area to, to satisfy whatever it is you're looking for. You know, like for me, for example, I would really like for my next role to be something like on the on that spectrum, something in like the VP of engineering or CTO role, because what I found is that I really have enjoyed growing teams. And I really would like to do that from scratch, where I take, you know, nothing, a start of an idea, maybe a business partner and grow a team to fulfill some need, and be part of that growth from the very beginning.

So that's what I want to do. You know, so there's so many options there. Yeah, you know, just because you have that title doesn't mean you've really arrived. There's so many different directions you can go from that point. And I think you could spend your whole life learning how to be a good CTO or VP of engineering and still maybe never actually tick that box fully. I like what you said there because it focuses on skills, not necessarily external representation of those skills. I care a lot about getting better. I do care what my day-to-day is like. So I care about my role in that it affects my day-to-day but I feel like once I'm in a role I focus a lot on what can I do to go from being really sucky at it to less sucky so that's and that's enormously

fulfilling to me and how do you measure your progress along the sucky to less sucky spectrum every day I think boy I just suck at this and then at the end of the year I'm like you know I suck a little less even though every day I felt like I suck I'll write a book about it that's my scientific progress evaluation philosophy yeah i don't have i don't have a good system for measuring it besides what i feel like maybe that's one of the things i need to improve that uh i still feel like we haven't really addressed this like what to aspire to and how to measure one's own progress that's part of the question i think that at this point in your career well okay let me just say this i don't think people generally get a lot of satisfaction out of aspiring to the next title

or the next rung on the career progression chart at your company. I don't think that gives deep abiding satisfaction. What I think does give satisfaction is experiences you want to have and challenges you want to overcome. And so I think if you could identify those kinds of things,

challenges you want to tackle, like starting a company or like growing a team or like successfully mentoring someone to do something they want to do that's challenging, stuff like that, I think you can derive great satisfaction from. And that's the kind of thing you can put a goal on, I think, and say, I'm going to do this.

But it's not necessarily going to be achieved with a checkbox on a career progression ladder that you would read in like a corporate policy. Yeah, we've talked about the hedonic treadmill on this show before, I think, right? Oh, yeah. Yeah, it's been a while. That's true. It's the idea that you quickly adapt to your improved circumstances. So it'll probably make you happy for a little bit when you if you get a promotion and get a pay bump. and and then you'll just kind of go back to the same baseline level of happiness you're at before it uh yep yeah we adapt really well to good things it turns out and then just the baseline of our expectations is now raised to wherever we are so i agree with you dave i think it is unlikely that

you would feel an enduring sense of accomplishment for having achieved one of these titles that will be enough to satisfy you if you're pursuing something and you're just going to look around and be like what's the next thing and it kind of sounds like that's what you're thinking ahead of like once i have this what's the next thing and maybe that's when you turn inward a little bit yeah maybe and it gets more challenging right because there's not this clear path you know you have to do a lot of growing up i think yeah where you really have to say what's important to me because you know to this point you've been able to follow a pathway that was specified by others and they've said this is what we value and now you have to say what do i value and that's a much

harder question to answer i think yeah and i don't think that's a thing that only happens once you become cto or vp of engineering or chief architect i feel like i feel like i don't i could not see myself doing my boss's job i do not think i have the skills or personality or ability to perform at the level that my boss performs at so effectively i feel like i've in some ways reached the top of the ladder here so what i'm doing is growing myself not saying like how do i get to that next rung because it feels kind of like not a thing huh interesting i don't know maybe that's just fear or something. But my point is that this can happen at any point in the rung, not necessarily just at the top. Yeah, I think I think you're right. I think at the top, there's a forcing

function because there are no more rungs, right? Yeah, yeah. Especially I mean, people that get there are usually very high achieving, very motivated, very used to exceeding expectations and like exceeding targets and yeah, accomplishing tasks. And then what's the next target? Yeah, good point. Let's do it for pizza on the weekend. Yeah, go get a job. Think of all the pizza. Be two CTOs at once. Weekend CTO, daytime CTO. Yeah, that's the next challenge. See if you can do it and only work for pizza as a CTO. Try to find a company that's actually willing to do that. You can check that off your list. I've done a really good job at it. Now I'll see if I can do a really bad job yeah this is a deep subject that it is there's there's plenty left to explore oh for

sure for sure and i mean julian says he's 39 years old and i'm gonna assume julian started his career in his young 20s so you know 17 18 years of experience at this point um you know most people work until their 60s so you know you're looking at 17 or 18 years into a 40 plus year career yeah so this is a very important question to answer and i think for some people the answer might be a whole new career you know like i've gotten everything i want to get out of software engineering i'm going to go try something else yeah and that's becoming more and more common i think not i don't see a lot of people leaving software engineering but i do see what the trend that i do see which is common is that people will change careers completely you know multiple times

in their life yeah yeah i have a i have an acquaintance who changed from medical imaging to the oil industry like just completely pivoted and it's very satisfied really yeah interesting i don't think i could ever be good at anything else i feel that way too when the zombie apocalypse comes dave i'm gonna be like do you need any like requirements analyzed and maybe i could write some tests for them and they'll be like brains and then i'll go run to my neighbor's house yeah find all of my neighbors who have real skills and mooch off of them i'll build you like an app to manage your shotgun shells your inventory my family the internet doesn't work so it's really good that it's a progressive

web app it works offline except without the internet or stack overflow i couldn't program anything anyway so crud we're screwed better start backing that up yeah everyone some people you know the prepper movement where they store food and supplies yeah we have to be internet preppers for when the internet's gone i'm gonna archive wikipedia archive stack overflow we'll be great i've got my mission well have we answered this question i don't think we have but i think we've given you the best we can which is search your soul young julian you'll do great thank you for asking this question this is a really deep one that has caused me to reflect on my own life and career so yeah i appreciate it even if we didn't help you i helped myself so at the end of

the day isn't that why we do this show i don't know if you're joking or not but it is like you can listen if you want i just want to talk to dave all right what can people do if they want to listen to me talk to you some more about their crest about their problems just do whatever you did to get here in the first place if you want your own questions answered you can go to softskills.audio and click ask a question it'll end up in a google form that we take a look at every week to draw questions from thank you so much

to those who have submitted you you are the lifeblood of the show you keep the show going so please keep those questions coming we're working through them we've actually answered more questions now than we have in our backlog so yeah you do the math on that one yeah the proportion of questions to questions answered is changing that's right it's dipped over one wait it dipped upward what's that uh i don't know up into the right newfangled dance move kids are doing that i don't know so on that note i i would like to say this question is the kind of question that i think would be best answered by a lot of different perspectives and voices rather than just ours and you can add your own answer on our website if you go to softskills.audio

and then scroll down to the episode uh what is this number whatever this episode number is 116 uh and you can comment right there people do read those and sometimes some nice comment threads get started we would love to hear your thoughts on that and share that with others Because I think this is the kind of question that really benefits from a diverse set of perspectives Unlike most questions, which are fully answered by just I I agree with you. I'm I mean, I don't know I'm relatively early in my career still in the scheme of things like julian has more experience than me So i'm just i'm just rambling. It'd be great to hear somebody who maybe maybe someone's done this, right?

They went up to cto and then dip back down. We're like, here's what I learned when I did that It'd be cool. All right. All right. We'll catch you next week Thank you.