What regrets/mistakes have you made earlier in your career?
Posted by BTTLC@reddit | ExperiencedDevs | View on Reddit | 99 comments
Posted by BTTLC@reddit | ExperiencedDevs | View on Reddit | 99 comments
bruno_pinto90@reddit
Relying on the company to grow/learn. Did it for 3 years and now have 1 year repeated 3 times. Just now i am dedicating time (at company time) to really learn.
f0reskinbandaid@reddit
Staying at my first job too long. It was 4 years of doing BAU support mostly for a legacy Oracle system. I would get to do some code changes every now and then which were just one liners in xquery. It was mostly lever pulling and SQL fixes. On paper now I have about 8 years of experience but really I have 4 and some change.
Educational-Heat-920@reddit
I've found that jobs will only give you small salary increases, whereas I've had 30k salary bumps from new roles. Switching after 1-2 years is the best way to get to comfortable money.
You also get exposed to new tech stacks and ways of working which helps you grow and makes your CV more appealing for the next role.
I've done e-commerce, agency work, sports, gaming and betting industry stuff. If I stayed in a single industry, I'd probably still be stuck there now
Floorman1@reddit
How far does this go though? Other than going to higher role titles (junior, senior, lead), can you realistically keep jumping for large bumps? I’m in a well paying senior role now around market rates, and other than going for lead roles, I don’t think there’s much to squeeze out of the market.
Educational-Heat-920@reddit
It goes as far as your willing to take it or as far as your ability takes you.
It's my advice for getting up the ladder out of entry level jobs. Do you want the responsibility of your lead? Once you earn a comfortable salary, work/life balance and job stability is more important than more money.
ReactionDry2943@reddit
I left my first job after two years. I learned a ton but I had no future there. I moved on to a company where I actually could advance, and I had a higher salary.
Shoeaddictx@reddit
I switched now after 2.5 years, more than doubled my old salary (I was underpaid).
Mr_Anderssen@reddit
I never used to take breaks and rarely took leave to just switch off. Burn out almost cost me my career.
Also I wish I knew a lot about Labour laws.
ceirbus@reddit
Just the usual Dunning Kruger - then I saw into the void and figured out how to sell solutions to top company stakeholders, c-suite, EVP, ect
The only mistakes I feel like I made were unavoidable just because you don’t know what you don’t know until you know, you know?
Kind-Armadillo-2340@reddit
My only actual mistake in this regard is not talking to more people sooner. There are plenty of people who will explain what you don’t know if you just tell them your idea. It’s a mistake I still make but I’m better at it now than I was early career.
ceirbus@reddit
I like to say “I’ll present the wrong solution to find the right one”
HatesBeingThatGuy@reddit
I'm a manager and my most powerful tool is: "My dumbass pointy head thinks this is the answer. Tell me I'm wrong."
ConcentrateSubject23@reddit
Not believing in myself and trusting the advice of others too much.
tan_phan_vt@reddit
This is me too...
I'm good and have affinity at certain domain and tasks, but what i'm good at doesn't resonate well with some seniors who got different expertise and background. They judged me and gave me advices and harsh criticism based on what they know and good at, its all about them not about me. I suffered for a while by listening to wrong advices that brought me nowhere, it was hard to get out after going the wrong path for so long.
Took me half a decade to pivot back to something that suit me.
tuna_safe_dolphin@reddit
I did this for way too long as well and sold my self short for well, more than a decade. But I did come around finally.
ConcentrateSubject23@reddit
What made you realize that you need to trust yourself more, what keeps you from doubting yourself too much now that you know you have this tendency, and how do you get over the regrets of being right for huge decisions yet not trusting yourself and losing out on large opportunities because of it?
SDplinker@reddit
Too long in toxic to meh jobs due to insecurity.
robhaswell@reddit
I spent too long working for "going nowhere" companies. Join somewhere that will help you grow.
AlmightyLiam@reddit
How do you vet this? I work at a big company, but I still feel like I’m not growing
ShroomSensei@reddit
First you need to know what "good engineering" looks like to you, then ask questions that can give you sneak peaks into it. I will say most companies fall into the middle, both literally and how you would interpret their answers. However there are some things that will SCREAM "holy shit don't join this team".
- What does the team composition look like currently and for the future? Is it 15 oversea contractors and 2 senior engineers in house? Yeah fuck that.
- What's the tech stack for the project? Java 7 and Sybase? Yeah fuck that.
- What's the release process look like? On Saturday at 2 AM we manually log into the PROD server and FTP over the binaries to release it. Yeah fuck that.
\^ these are all real examples I have been told in interviews. Maybe not as explicitly as I am saying but you gotta read between the lines. My favorite questions are usually about team structure, tech stack, and the software development lifecycle. Those are all open ended enough that interviewers don't usually straight up lie to your face.
I cannot emphasize enough that you NEED to talk to the actual engineering team though. Not just the hiring managers, HR, and the random person who did your technical interview.
AlmightyLiam@reddit
Thank you for the detailed response, this is really helpful
gibdimkoofchji@reddit
You really can’t. You just have to go with your gut initially.
The big thing is if it’s not working for you, don’t be hesitant to look for other opportunities. It’s easy to stay in one place where you’re not getting what you want because of inertia.
robhaswell@reddit
I think if you know you know.
Wide-Pop6050@reddit
You don't learn as much if you're the smartest person in the room.
jl2352@reddit
Twice I stayed at companies long after I felt like leaving. At one I got a large payout, which was great. The other I ended up leaving feeling my time had been wasted.
If you feel like moving on, then move on.
MiserableIsopod142@reddit
i feel that so much. Im stuck with project where goals are not visible. It is frustrating and without growth. I once left a company because it felt exactly like this. Now in the new company it feels again like this.
proof_required@reddit
yeah I feel very similar. I only had one place where I got to work with a very smart engineer. Even though he was smart, he had no desire in any big tech stuff. But I feel like he was more of an exception. To find smarter people to work with, you need to generally go to bigger more sought after companies.
Cute_Activity7527@reddit
Big/small company has nothing to do with that. Great engineers work everywhere.
What you wanned to say is “work for winners”. Working for losers wont bring you any glory or wont make you proud.
ForeverPrior2279@reddit
Define great engineers? What's the point in time when you realise this?
robhaswell@reddit
Great engineers will share their knowledge willingly and effectively. It's best if there are enough people that if someone is full of shit then they won't get away with it. Really though, any knowledge sharing and discussion of ideas is a good thing. If you're left to your own devices you can bake in some funny ideas.
Factory__Lad@reddit
+1, but in many IT jobs, there is not really any pretence that they’re setting you up for success. You’re just framed as a shock absorber / auxiliary cost centre from the beginning.
Don’t be fooled by the brightly coloured beanbags :)
plastic_drops@reddit
You know the advice of you shouldn't take QA as your first job? You can use me as an example of what can happen if nothing works out. I've been stuck in QA for a long while (over a decade). I work as SDET but they just lump you with QA, so to everyone you're the same thing. I should've rejected the QA role a long while back and continued until I landed a SWE job.
eatacookie111@reddit
Not choosing this career until the age of 33
Owlofbohemia@reddit
May I ask specifically what is most regrettable about it? Apart from the lost time to hone the craft
eatacookie111@reddit
Money lol. But also I enjoy coding and I’ve never enjoyed my previous jobs.
speedisntfree@reddit
I really feel this. I wasted 10 years in aerospace engineering. The industry here in the UK is utterly miserable for pay, career opportunities and working conditions. If you are 60 years old and don't want to do any work it is probably a cushy job.
Scottz0rz@reddit
https://youtu.be/ULeDlxa3gyc
Leading_Yoghurt_5323@reddit
biggest shift is learning what to ignore… not everything needs to be fixed
chromalike_@reddit
Over indexing on stuff like design principles, tech debt, semantics of variables, classes, etc. This stuff is important but the best devs are doing this but not sweating about it so much. They are much more focused on driving the product initiatives and shipping stuff, testing the product, and learning about the product domain and doing competitive analysis.
Pineapple-dancer@reddit
My only regret is not getting in tech sooner. I genuinely love coding and building useful tools.
dryiceboy@reddit
Working too much and being on-call. It burnt me out. I don’t think it really helped my career move forward. On the other hand, things I did outside work have paid dividends e.g. learn non-tech skills, investing, and spending time with friends.
JM0ney@reddit
Actually believing that working extra hours would lead to promotions and raises. Believing that executives wouldn't try and screw me out of equity I had earned or taken in lieu of cash bonuses.
Healthy-Dress-7492@reddit
This is the most important lesson for random readers here to learn- the company is not your friend, they will duck you over in every way possible at every opportunity and literally not care. It’s about profit, you’re a tool, it’s transactional. There are unicorn companies out there where this isn’t the case but it’s best to assume it as a baseline.
LearningMyDream@reddit
Getting into this field with BCom degree , now going to reset my life again
chikamakaleyley@reddit
mistake:
thinking that i'd be a lifer at the first 'startup' i joined, 3 yr into my career
'startup' because, when i joined they were months away from a massive growth spurt. they were already successful
as a self-taught dev, and just kinda being 'comfortable' - it's a bad combo and I fell easy into cruise control, for 6 yrs, and then as a reorg I was let go and the result was I hadn't grown and I didn't know much about the technology that had advanced outside the office.
Yet, I don't regret this, because it had motivated me to be better late in my career, and so someone with 18 YOE - I'm not jaded, I have a lot of room to grow, and I'm still excited about tech.
JeanRalphioTheSecond@reddit
Basically I regret being afraid to look dumb, it slowed me down a lot at times. Asking tons of questions, working on stuff that’s over your head (with adequate support) are needed for growth
permatan_store@reddit
For me, it was honestly procrastination.
There were times I should’ve been working or improving, but I chose to relax, play around, and put things off. At the time it felt harmless, but looking back, it cost me progress I can’t get back.
That’s one regret that’s stuck with me till now.
Odd_Perspective3019@reddit
working under bad managers, you just lose out on growth and they change your way of working cause they cause so much self doubt in yourself
engineered_academic@reddit
OP next time you ask something like this add substance to your post with your own experience or its gonna get nuked. Leaving it up because there are some valuable pieces of info here.
Middle-Jury6078@reddit
OP code reviewed hard and almost got rerequested
BTTLC@reddit (OP)
Edited to add own experience
inqark@reddit
I suffered from “smartest in the room” syndrome. I had to learn everything myself with only online guides, articles, and videos as references for a lot of things. There was no one to really review my work that understood anything. I did my best but was slow. When I finally left I was lucky to join a larger company, surrounded by lots of great engineers and people that knew so much more than I did. I grew so much within just that first year that I started cringing at some of the decisions I made at my last company from just sheer inexperience. My regret was not having wanted more for myself.
BehindThePillow@reddit
I feel like I am where you were. After 1 year in my team I was somehow the one with the most experience. Now, 3 years in, I have never really had anyone scrutinise my work. PR’s are usually just approved outright, or approved after I explain my reasoning. No real feedback or tips. All I know, I’ve learned online as well, and there are no one in my current team that are willing or experienced enough to challenge my work or decisions. The positives are that I have become quite efficient at figuring out complex tasks myself, but as you say it’s still slow and I can’t really know if the stuff I come up with actually is a good way about it.
I’m changing to a different senior heavy team in a few months and I hope to get the same experience as you!
day_tripper@reddit
Never understood how to latch on to a superstar mentor to carry me up the ladder. Stagnated at senior dev for over a decade now.
Nobody wants to mentor an older person who finally understands tech skills are just not going to carry you and you absolutely must understand trade offs for tech decisions and how to “save” upper management by explaining those trade offs clearly and explicitly letting them know you are the font of knowledge rescuing them from screw ups.
tuna_safe_dolphin@reddit
Giving more than one iota of a fuck about any actual fucking company. The most important company back then, now and till I die is Me Inc.
laramiecorp@reddit
Sounds like an interesting company, where can I apply?
tuna_safe_dolphin@reddit
`cat your_resume.pdf > /dev/null`
beaker_dude@reddit
Chasing the next pay-jump. Choosing the job that payed the most VS what I would have enjoyed doing.
There were jobs that I turned down because the pay wasn’t good enough, but the work would likely have been enjoyable.
PopeyesPoppa@reddit
Idealizing compensation over everything and not accounting for trade offs. I discovered I’d much rather have less compensation to be in a role that has interesting work with great people.
Far_Mathematici@reddit
Not grinding to FAANG or adjacent during the glorious pre 2023
solidiquis1@reddit
I became a director of engineering at an org with 20 engineers with 3.5 years of experience as a self-taught dev. I don’t necessarily regret it, but I learned real quick that I wasn’t wise enough yet to lead. I then became IC again after a year at a new startup and 2 years later am now a tech-lead. Little bit of a course correction.
Outside-Storage-1523@reddit
Not pivoting to system programming as soon as possible, and delayed the majority of my learning after my son was born.
IsleOfOne@reddit
I'm all too familiar with this. I think it's quite common. Now that you've already blown it at your current company, use it as a training ground, then move elsewhere and make a concerted effort to do better.
My experience is proof that over time, you can learn to identify what leads you to self-sabotage in this way, and nip it in the bud. Better yet, you can learn to do the opposite :)
BTTLC@reddit (OP)
Ha, yup. I recently started a new role at a different company, and right now just sitting back and learning how why things are the way they are here. But going forward here, will definitely be a bit more selective on rhe hills I’ll die on :)
throwaway_0x90@reddit
The biggest mistake I made was staying too long in my first job, long enough for it to start making me bitter and angry and nearly tanked my career.
But also I learned a lot from that job and that experience became my litmus paper test for all other jobs. Once that feeling of frustration returns, I always knew it was time to quit and never think about sticking around hoping it'll get better.
jtonl@reddit
I didn't finish my high school in order to get a degree. Sad to say I can't work for regulated industries such as finance or work abroad due to the paper requirement. Though 15 years later. I'm in a stable job with good work life balance.
Nezrann@reddit
Wait like you have a degree, or you never finished high school so you can't/couldn't get one?
I assume the latter because ftqI dropped out in 11th grade, went to college, graduated, and had no problems getting into medtech.
Even-Jellyfish-9417@reddit
Taking >1 year contracts instead of holding out for full time roles. The experience section on my resume is too long. Nobody reads it all, I'm sure. I look like a flake.
Free-Huckleberry-965@reddit
I left a stable, but boring, company for the big raise and startup experience. Four jobs later and I've been laid off twice, burnt out, and my resume is ruined. I could have had a decade of slow, predictable work at normal wages with the boring company but gambled on getting the big TC.
greensodacan@reddit
How is your resume trashed? TBH when someone stays at the same company for more than five years, I start worrying about title inflation and lack of breadth. Not necessarily a red flag, but not a green one either.
Free-Huckleberry-965@reddit
2016-2018 Company 1
2018-2021 Boring Company
2021 (9 months) Company 3 (laid off)
(6 month gap)
2022 (3 months) Company 4 (burnt out)
(8 month gap)
2023-2024 Company 5 (contract ended after 12 months)
(10 month gap)
2025-2026 Company 6 (laid off)
greensodacan@reddit
Eh, everyone's having issues getting callbacks though. I mean yeah, it sounds like the startup world wasn't great, but you've got 2 years, 3 years, some rocky contracts, another year, long gap, another year and a half....
The average probationary period is six months, which you're passing, and everyone knows layoffs are completely out of your control. I wouldn't consider your resume trashed, but maybe find another way to frame that last ten month gap. Say you were working with smaller clients or something.
The market's been rough, and smart companies don't hire contractors for long periods. It looks like that's just the space you've been occupying for a bit.
FlailingDuck@reddit
Never believe pushing for better is a mistake. Striving for better can very well be better than settling. I'm sure your resume can be made a lot more spectacular than a job history of 1 company.
Free-Huckleberry-965@reddit
I have three 6-month+ gaps on my resume since covid, and I'm currently unemployed again. I appreciate the sentiment, but I'd rather have a job or recruiters returning my calls.
FlailingDuck@reddit
I understand my friend. I just put years on my resume, not months. I also have 6+ months gaps, but job history of 2023-2024 then 2025-2026 is enough. I am fortunate enough to be in work atm. All the best.
diablo1128@reddit
Staying at my first job for too long.
Yes, I was getting promoted, have my name as an inventor on granted patents, and all that good stuff, but it was a private non-tech company in non-tech city. I wasn't learning for the best SWEs in the industry, I was learning in a top down management style company that was stuck in the 90's.
The company created safety critical medical devices using c and c with class style c++. Python was also used for testing. I 100% learned a lot at this company, but it only took me so far. I feel if I jumped 4 years in to an actual tech company I would have learned a whole lot more than staying for 15 years.
razzmatazz_123@reddit
safety critical medical devices seems like a great niche though. Couldn't you jump to another medical device company? or even to other domains that needed embedded systems devs?
diablo1128@reddit
Personally I don't want to jump to another medical device company. I would like to work on something different that needs my skill set.
I've tried doing this. I've applied to companies working on smart devices, wearables, fitness trackers, autonomous vehicles, etc.... I rarely hear from these companies and when I do I always seem to get to final interviews and then a no offer.
I feel like the problem is I don't have the domain experience, for example, a role at an autonomous vehicle company could be on the path planning team. Well I don't know path planning and would have to learn on the job. Chances are there is somebody that already has real world experience with that and has the same coding skills as myself. I'm not going to wow you in an interview with my coding skills. I feel like I'm average at best for the industry, not tech companies.
The closest I've been to an offer was 2 times over the last 4 years at Apple. I interviewed for the health team and for the "final interviews" after the virtual onsite. I didn't get an offer and the recruiter said I did great and it was just bad timing. I take that to mean I was literally send best and a back up option if other candidates passed on an offer.
VizualAbstract4@reddit
Probably the same mistake I'm making now: not really connecting with the development community at large.
I rarely, if at all, discuss code outside of my 9-5. I'm either writing it or reading it.
That said, I like to think I'm doing something right: if this is the 2nd startup I help found and it's also turning out to be successful.
The employees we hire onboard fast and thrive quickly.
But overall, this is my 6th job as an engineer and I've been writing "code" since I was 14, paid for it since I was 21, and I'm now 42.
But yeah, I see my peers go to conferences and attend talks and discussions and I sometimes start to feel a bit regretful that I don't participate.
But I guess from my experience, whatever they learn becomes outdated in a few months time anyway.
droi86@reddit
Left a nice stable job in the great resignation period, I got a 40k increase and then got laid off 8 months later when they ran out of free money, since then I've been in crappy contracts and I'm training my replacement right now, I'm pretty sure I'm being laid off in a few months once the training is complete
FlailingDuck@reddit
Not realising earlier some people do not have your best interests at heart and actively allocate time to ruining your chances to succeed.
LyfsDiary@reddit
I worked for 3 years in my first company despite the fact that it was dead in the waters with 0 income. Even when I got a different job, I decided against switching because the CEO pleaded me to stay and convinced me that he had grand plans.
After that, I switched to another startup and then another startup. All of them underfunded. I should've taken a career break, upskilled and applied for better companies instead of these lowest hanging fruits.
I could've earnt a lot better but more importantly I spent my youth solving nothing-burger problems, which I could've better utilised by building things that were actually useful for people.
Early_Rooster7579@reddit
Worked in FAANG for too long early on. A brief few year stint in startups made me a far better engineer and programmer.
Being able to just do things and figure it out rather than follow some dictated perfected process helped a lot
gibdimkoofchji@reddit
I moved from startups to faang and the difference is so ridiculous.
Start ups teach you to do so much more. No one is coming to figure out v what the hell is going on in production. You have to do it. No one is coming to figure out some weird ass bug in some weird ass library for you. If you want something built, you have to build it
FAANG is kind of the opposite.
Early_Rooster7579@reddit
Yeah, you can become super silo’d in FAANG and end up struggling to work outside the ecosystem thats been created for you
Bricktop72@reddit
Believing good work would get me promoted.
GoFastAndBreakStuff@reddit
Shunning opportunities that involved meeting up with people, customers, partners - building a network. Don’t bury yourself behind the screen. Get out there. Get good at it.
Asya1@reddit
Staying too long at garbage company
Agitated_Marzipan371@reddit
Not addressing mental health issues
dotnetdemonsc@reddit
My biggest mistake was believing in the saying “Become irreplaceable.”
Spoiler: you may not be replaceable, but you sure as hell can be done without.
iamalnewkirk@reddit
After 30 years in tech, I've made many mistakes.
As a software engineer, I fell into the trap of becoming zealous and dogmatic about the tech stack du jour when I entered the industry. This caused me to inadvertently become narrow-minded.
Given where we are today with AI agents capable of producing quality software across various languages, more people will naturally become polyglot developers. However, it took me an inordinate amount of time to get there. This loyalty to my first programming language also caused me to not shift when the industry shifted to new technologies, which cost me opportunities.
As a people leader, one of my biggest mistakes was taking opportunities for title and financial gain rather than being intentional about domain and career trajectory.
A clear example of this: once upon a time during a final interview, the co-owners explicitly told me that they maintained an intentionally flat hierarchy and culture. They were hiring me as Director of Engineering, but made clear I did not have the authority to unilaterally reward or discipline my reports. I recognized this as a case of responsibility without authority, yet I ignored that red flag for title and money; and yes it did come back to bite me in the ass.
ValueBlitz@reddit
No need to be loyal to a company.
They will not hesitate to cut 10% of the workforce before an investor conference just to show they're cutting costs, so why should you work weekends for no extra pay?
Gamazarr@reddit
Playing the “corporate” game. I always felt like people who acted this way were so cringe (still are). I was just so bitter, but changing my mindset to just faking it, I’ve seen more raises/bonuses and favoritism.
Factory__Lad@reddit
I left a really interesting project to join a dot com that didn’t really have much of a business plan, just because it seemed too much of an adventure to resist.
18 months later all was dust
We did have some adventures though, and the original company got into trouble for unrelated reasons, so the regret minimisation framework remains intact.
callimonk@reddit
Believed in myself a bit better. I didn't get help for my mental illness and stayed in some pretty toxic relationships. Yes, I know, you're asking career-wise - both of these things resulted from a lack of self-confidence, and that impacted my career early on.
It took me too long to get my shit together. I was tired all the time, and that level of exhaustion and illness affects the ability to learn as well as the ability to get shit done. I still deal with ME/CFS, but there's a difference between having it treated and not.
A lot of people see the Dunning-Kruger side of people being overconfident.. I think under-confidence isn't a great thing, either. But, I'd come out of a ton of trauma, didn't really have much of a childhood, and had a lot of bricks stacked against me. So, I came out all right. I'm better now, and investing myself in confidence-building hobbies has greatly helped.
Oh, and I wouldn't change how many video games I played. Well, maybe a little bit. But online gaming helped me network with some great people who have truly been the wind beneath my wings in this career.
raulmonteblanco@reddit
This is minor, but at one point my manager asked me how I would feel about a title change. The title would have been accurate for what I do but also sounds less cool. I realize now that that title probably paid more though.
Dreadmaker@reddit
Early on, being too precious/defensive with my ideas. Definitely a large part of that as a junior dev at the time was that when it came to implementing something, I was good enough to figure out a way to do it, but not necessarily the best way - and when a senior dev would say ‘why don’t you handle it this way’, I would often default to making up some kind of bullshit rather than saying the real reason: ‘I don’t actually understand what you’re proposing because I’ve never seen it before, and I don’t know how to do it that way. If my name is on the thing, I have to understand how it works, so I’m doing it my way instead’.
I would have probably grown faster and learned more if I had been more humble in those cases and just literally said that - ‘I’ve never seen this before and I’m uncomfortable with it as a result - knowing that would you still recommend I do it that way and can you help me to implement it if so?’ As an experienced dev at this point, I know that whenever I’m making a suggestion to a junior like this, there’s good odds that I’ll need to help them with it and teach them - which I’m actively signing up for in making the suggestion. And that’s fine! That’s how everyone learns.
To all of the folks out there who fight about implementation from a place of fear/not wanting to admit that you don’t know about what the other party is proposing - suck it up and take the opportunity to learn. You’re going to be a much better engineer for it at the end of the day.
Lazy-Cloud9330@reddit
What's to regret? Mistakes are how you learn.
Tired__Dev@reddit
Mostly self taught, so all of them.