Ask HN: Did you regret staying at a job for too long?

I've also been at my current employer for a little more than a decade. I've been promoted to the 2nd highest level possible for an engineer without ever asking or doing specific actions to get those promotions. The last promotion would take actual direct effort, but I'm honestly not that interested. My salary is 2x-2.5x where it started as, and from a few brief stints interviewing at interesting places that reached out other people aren't willing to pay much more, and often less. We get a great work/life balance (wfh, 5 weeks vacation, 2 month paid sabbatical every 4 years).

I'm also very risk averse. I prefer being reasonably well known and trusted by the wider engineering staff here. I'm happy with where I am and have no intent of leaving. I mostly bring this up as a counterpoint to the people that say you can't have a good job by staying at the same place. Different places are different. Some of them are quite good. If you have a good thing, be willing to hold onto it.

With respect to not growing as an engineer, have you considered asking to switch teams or departments? I've shifted twice and each time led to a new set of challenges, but building upon my understanding of our systems.

I did the opposite - since college I've job hopped quite a bit between startups, SMBs, and the smaller end of public companies. Salary varied from ~100k to ~190k. Got laid off last year which I do attribute to being one of the newer employees.

I do feel like I would be in a better place if I had stuck around longer in some of these positions, but it's hard to tell at the time! Each change was to a better and higher paying job. I do feel like I got a good perspective on the industry but I hear about people who were my peers getting into management, getting into staff or distinguished engineer positions, assume they are having all their options vested, and they are probably ahead of me financially.

My understanding is that to make "real money" i.e. what a manager at a car dealership makes, or 300k+, the reliable paths are either getting hired at the google/netflix/openai/apple type companies, getting into management pretty much anywhere (check BLS.gov. Average salaries for managers even in older industries are above what a staff engineer at e.g. Pagerduty or Onesignal probably gets), or getting a good amount of stock options at a low cost basis and eventually getting to cash them out.

This does not answer your question exactly but to that point I would say hop on linkedin and talk to some recruiters, keeping your skeptical hat on for everything they say. A good manager of someone who's been productive for 8-10 years is not going to be surprised or annoyed that they try and see what the market is.

One last point, tech is especially sensitive to the fluctuations of interest rates. We are all subject to the whims of Jerome and depending on what he does in the coming months, the market for engineering talent may look much different next spring than it does now.

A few times. The one I regretted the most was the last year of my career in game development. We were asked to work the weekend once to get some features done. That turned into two weekends in a row turned into a full year of non-stop crunch. Programmers these days like to say how they're so "burned out" because they don't like the work. I was so burned out that I was mainlining energy drinks to stay awake. I developed adrenal fatigue. I still fell asleep in meetings. I have almost no memories from that year. I was a zombie.

The worst part is that it didn't matter. The game was so far off the rails that it never shipped. They closed down the studio soon after. They closed most of the company's offices with a year of the studio closing. 2-3 years after that, the company was completely defunct.

No employer has ever asked me to work that hard again. I would quit on the spot if they did. Life's too short.

Yes, stayed in the same place for 6 years, for no discernible reason other than I thought my opportunity was going to come, it never came, there were multiple changes in leadership and in the end the group i was in was dismantled and I could have been laid off (there were large layoffs just a couple weeks after I left).

So I'd definitely recommend staying sharp, looking at the market and moving when you think there isn't space for you to grow or change. Don't let your career stagnate with the business.

I'm a similar position as you in terms of job, salary and balance.

But this is my 5th job out of college and the longest I've been in a single job. When I hit my 4year mark, I started to think that the grass is greener on the other side and looked for opportunities here and there.

A few years in and I didn't find the right place that would make me jump ship. I have high standards and I can spot redflags based on past experiences in jobs in multiple countries.

I also found out that after I got older and accrue more responsibilities outside work, my job became a much smaller focal point of my life.

I'd rather be employed in an okay place, being paid a competitive enough salary (75% in the curve), and have opportunity to learn new things in the job and out, even if I don't love the field. As opposed to try a new job and risk being put in a toxic work environment and lose the balance I have now.

If you are not growing as an engineer, going to a new job might not help you and could be detrimental. It's much better to learn new things while you have the time to do so. Find an area you want to learn more, try new projects or courses, and have fun at your own pace.

I was in the exact same experience (and I'm also very risk averse), and I would say yes and no. Like most things it's complicated. But to keep it short I most certainly grew the most in my career – meaning in engineering, people, presenting, everything – by taking the plunge with a new role and the challenges it brings. You're forced to learn and adapt and taken out of your comfort zone.

I think even in a great company you are going to hit a ceiling that is hard to grow past even if the opportunity is there – there's politics, there's other priorities, there's always something that will get in the way. I found swapping job was the only way to "push reset" on that side of things enough to have that rapid burst of growth.

What I've very slowly learned is things tend to work out. If you've got some savings built up and not too much in the way of hard responsibility, I'd explore the option.

Both swe jobs I've had I stayed with for almost a decade each. I'm in a very similar position as you with similar stats. Though I am a bit older. I enjoy the predictability but both places had rounds of layoffs at various points in time and I have the concerns as you.

I wonder if staying for long stints looks bad to future employers and hiring managers. I do think the predictability hampers my drive to practice leetcode, build tech side projects, and practice interview questions.

On the positive side, I like being a subject matter expert and diving deep into a tech stack and code base and knowing it inside and out.

Do I regret it? I don't. The stability has given me time for non-tech hobbies and projects as well as the time needed to have a family.

It's a little tougher at my age and with a family to spend a lot of time on technical side projects but I make time for it. That would be my recommendation to you for concerns about personal growth.

Yes, I've stayed at the same company for over 12 years. My skills have atrophied and I make less than the median dev.

But if you have a good stable job, why would you leave? It sounds like you make good money and have good balance. What is the point of growing as an engineer if it's not applicable to your job or a future job you want?

Just enjoy your good job until it turns bad, or until the tech would get so outdated as to make finding another job harder.

Sounds like you’re in the perfect place, changing will almost certainly put you in a worse position. Don’t worry, enjoy life and try to grow as an engineer outside of your work if that is what you desire.

- left for a 2.5x salary bump after 1.5 years

- that place ran out of money after 1.5 years

- back at the original place, but got bored after 6 years

- let a recruiter talk me into a potentially more interesting place even if it paid less, left before hitting the 4-month mark for 2x more money

- left after 2+ years because the boss was a ginormous asshole and I was colleagues with Hamas (UN)

I regret step 3. As I was leaving there, a colleague asked me, bewildered: "why don't you just do side projects if everything's so easy and you're so bored?" And he was fucking right. I'd be done with work by noon Tuesday and then go tinker on some open source thing on Github or write on Medium or saw stuff at the country place. And so much more money would roll right in every year.

  > Did you regret staying at a job for too long?

Almost always

I was at the same company for seven years. It was my first job after college. Don't make the same mistake I made. I am now unemployed, and nobody wants to hire me because my skills are out of date. I have been without a job for so long that I have decided to take out student loans, and enroll in a boot camp. I've had to sell my car to afford this. My life is absolutely miserable right now. Remember, the people you work with are not your friends, they just want to exploit you to make money.

I actually came back to a place that I used to work at before taking a year long “break” to work on some freelance stuff (and moving to the city etc.), I regret it.

I got to work on some new things and met some new colleagues which was nice, but returning to a heavily abstracted monolith and a DB schema that doesn’t spark joy makes me want to do literally anything else. The people are nice and thankfully it isn’t a toxic work environment, but there are definitely disagreements and practices that I don’t agree with and that won’t change due to any changes just introducing more inconsistency into said platform.

Working on it tanks my velocity, which also tanks my morale, when trivial changes take hours and I’m never sure whether things will work the way I hope. I hate the type of project.

That said, it’s less about a particular workplace and more about greenfield vs brownfield projects, I bet some people thrive on maintenance projects, but I’d at least want to maintain a project started in the last 5 years or so, or at least something tastefully divided into multiple separate modules that don’t make my CPU hit 97C when compiling it and trying to run it locally. Oh and a DB that I can run locally in a container, ideally with data seeding from day one, being able to do that with projects that use PostgreSQL does spark joy and I can test possibly breaking migrations as much as I want.

I'm in almost precisely the same position as you.

Will be 9 years in December. I've been promoted three times and have the highest official position that an IC can have at this company.

LCOL area, $150-175k / year depending on bonus, fully remote, devil I know, good FTO policy and work/life balance, etc. Even some equity (that seems to have a lower-and-lower expected value as the years pass, but that's another story). Lousy health care insurance but apart from that they take pretty good care of us.

I don't have advice to offer, just echoing your concerns and adding a question: have you seen a drop off in recruiting emails / requests on linkedin that started around year 6-7 and got worse from there?

Around year 5 I was getting a dozen or more emails and linkedin messages a week. Now I get maybe one every two months, usually Contract or C2H offers at that.

Unclear if this is just the state of the market, my excessive time at a single company, the keywords / skills in my linkedin becoming stale - all of the above? I've tried to keep my resume / linkedin current with promotions, descriptions of what I'm working on etc. - nothing seems to help.

Would be curious to know what the experience of others are with >=6 years at the same place.

Well, the choice it completely up to you, if you are risk adverse because of family, debt, bills or whatever it's a point, otherwise you can't conciliate to be risk adverse and growing as an engineer at least during the first 7-10 years of work (unless your company investing you but doesn't seem do be your situation), you must take the risk and invest on yourself (trade money and safety for potential growing).

In the first case (you can't leave because of stability) i would consider to sneak into grey areas of your company where you can indroduce something new (new build system, refactoring and whatever), it will require more effort than usual and depending on the company is not 100% sure thy will reward you for this (consider the reward to be the task itself), this way can grow by applying those skills to real life problem, if you don't have obligations i may say, leave and find something else but keep in mind that in 99% of the companies you will find the same situation.

Anyway, side projects/blogging is what i would advice in every case, just a disciplined 30 mins a day makes the differece.

Yes, but because it was a toxic work environment.

If I was in your position I would not be concerned, I would be happy.

"Not growing" is subjective, the things I "grew into" 10 years ago are not relevant today.

Never, when it felt right. I'm in my mid fourties now, still doing web development and I stayed 13 years at a startup and am now celebrating 10 years at my current employer. In between I joined a somewhat well-known (prestigious) company which had a very toxic work culture, so it was a no-brainer to leave after just 1,5 years. Management was clueless, most people were awkward all the time, pay was very good, but I just couldn't stand going to work.

If the company values your work (not just by giving you an appropriate salary, but also acknowledging that you're a valuable asset and not just arbitrarily replaceable), gives you enough freedom and your colleagues are cooperative and nice to work with, why leave? You probably wouldn't leave your partner just because you've been together for a too long time, would you? ;-)

Yes. I had a very good job. If I became unemployed I would have no concerns about going back to that job if I had to. However, I should not have stayed there as long as I did. I kept looking at friends and family and seeing how their jobs were worse, so I felt like if I changed I would just be downgrading.

However, the company I was at for a very long time did not significantly reward me for my loyalty. Just small annual raises, that's it. Like any workplace, there were problems and annoyances that did not go away. No place is perfect, after all.

I have changed jobs twice since then, and it's been a big upgrade both times. I thought it couldn't be better, but it got a lot better somehow. I've been very fortunate, and I was able to negotiate very hard from a position of strength.

If I could go back I would have changed jobs a couple more times.

If you're just in a comfort zone in essentially the same role the whole time, it's not great. At early in a career, moving jobs every few years is a good way to get some diverse experiences and good raise.

However, if you have good domain knowledge and relationships, you might be in a good position to stay, and get into management, move around, etc. If you get laid off, you're get a pretty good severance (10 years * 1 month salary maybe).

If you look around at senior management, you'll probably see a bunch of people who have been there 10, 15, 20 years and know everyone and everything... maybe try to be one of those. That's not something you can get with the job hopping strategy.

> Did you regret staying at a job for too long?

No, I stayed with one employer for almost a decade, until the product was "done."

I was able to get into more interesting technical challenges, and had a lot more satisfaction, as a result. There was no way I could get to the deeper (and more satisfying) points if I hopped out after 2-3 years.

THAT BEING SAID: No job is perfect, and I had quite a few frustrating moments. If I had changed jobs, would I have liked the new job more? There's no way to know! I can only state that I've taken two very horrible jobs, and left quickly. I wouldn't want to take the "this is awesome, but can I do better" risk when I already have a good thing going.

You are probably correct that you are stagnating. I've been there, and was happy with it for a while. But when it was time to leave, I had to work hard for about a year to skill up and prove that I could do modern tech stacks. It was a pain, but totally worth the effort.

At the same time, that salary is not bad for a lower cost of living area, so if it is stable and low-stress, that doesn't sound too bad.

I'd say that the question is whether or not growing as an engineer is a goal in your life, or if you are happy just working at your decent job, and then living your own life outside of work?

I regret not seeking internal transfer within my last employer. I "followed the flow" there for 8 years. Couple years ago I got less happy with project and passively talked with manager about "maybe switching projects in future" — yet stayed on out of laziness and liking the team. The point of no return was when manager/team started being unsatisfied with my performance too.

In retrospect, me unhappy + them unhappy = time to actively seek moving (which they'd still support back then); I stayed into a spiral of feedback => motivation => productivity => ... eventually I was laid off. I can't know how moving would have worked out but I regret not trying. [OT: and other passivity, not taking feedback seriously enough, sticking to WFH despite evidence it was challenging for me.]

It depends what stage in your career you are in, generally. Job hopping early on is a good way to raise your salary and get a wide range of experience. For more senior positions, where your projects are measured in months to years instead of sprints, staying longer is a good thing (imo). But either way, a decade is longer than I have stayed in any place - and had both regret for leaving a former employer _and_ regret for not having done so sooner. No silver bullet answer to that question :)

My advice: ride it out until something truly better/objectionable comes up. Growth is probably not best found at work, anyway.

I was in a similar position and left. I don't regret it, but I also didn't have a good balance. That place turned me entirely sour, I regret not leaving or addressing the building resentment earlier.

Now I don't have the social capital I had. I have to pass all these little interpersonal tests all over again, and I have no spoons.

I’ve stayed at all my jobs for too long (6+ years) and regretted it every time. I have been promoted but the pace is glacial. Upon reflection the right time to leave was always 2-3 years earlier, usually right after a promotion rather than stick around for the next. I will say that first ~4 years was always worth the investment, after that, especially when you hit your RSU cliff (if you have one), it’s time to go.

I've been working since my teens, sometimes many years at a job (~6 years at one, and would've stayed longer) or primary consulting engagement (10+ years). My only strong regrets about staying too long anywhere was a couple shorter situations, because they were in toxic organizations.

It sounds like you found a good situation, and hopefully you're also taking good care of your health, and pursuing a life partner and family if you think you might want that. For sustainability and/or personal development, can you find a way to grow as an engineer, and also (not the same thing) keep LinkedIn-marketable keyword skills, while remaining at your current place?

Or, by "grow as an engineer", do you mean you want to maximize your monetary wealth? If so, the most common way to do that has been to get a FAANG job. (Though that's being shaken up right now, with lots of layoffs. Also, the gatekeeping tends to be snooty and rooted in class, so being almost a decade at a much lower-paying job isn't going to help, unless it's in a niche they think is prestigious, like university research.)

I don't regret staying at my last role for 5 years but I do regret not spending more time looking and getting a better understanding of my value on the market while I was employed there. I wasn't underpaid but I certainly could've been positioned better to leave when I finally decided to. This is all recency bias of course but relearning how to interview was a difficult and humbling experience.

I definitely overstayed my job as a system administrator. When I started, there was 40 hours of work per week, and I hung on too long, because it was something I was good at, the pay was outstanding, but it was unsustainable, as my workload gradually dropped to a few hours a week.

I should have either moved into other roles, or left the company somewhere around 5 years earlier, when I started feeling impending doom.

I would recommend updating your resume (or at least thinking about what you would put in it) and considering how attractive it is to other employers. The situation you want to avoid is being comfortable and respected in your current role for reasons that are not transferable (like knowing how to maintain some legacy stack), and then finding out you have poor options when your employer has layoffs.

Yes, promises of promotion that never happened despite taking on more and more responsibility and delivering. It was my first job out of school and in my naivety, I believed my results would speak for itself and office politics didn't matter. I probably stayed about 2 years too long until I finally started applying to other jobs out of frustration and got a substantial pay raise.

I spent 15 years with HP in their services division. I liked the work I was doing, even though I was slightly underpaid for it. I would have stayed there but they cut me loose back in 2014 with 50K other employees. They did give me a decent severance package (3 months pay with health insurance) but it was shocking how easily they just cut me loose after years of dedicated service. In the end they did me a favor; I've spent the subsequent 10 years doing interesting stuff for four different companies in that time. I'm in my mid 50s now and thinking about optimizing for a decent retirement sometime in the next 10 years. I don't know if I'll be forced to change jobs again or not.

Yes I regret being with HP for 15 years; I had a lot to learn to be marketable again after being there for that length of time. But since I'm working toward retirement now, I will probably try to stay as long as I can where I am.

Been 14 years at my ex employer. 9.5 employees, one chef and his chef in other company. Done shit and ripped my heart out for a penny of salary. Wasn't a problem until they employed a 52y old and she can't even do excel and shit so she started to do the boss and telling me and my colleague what we should do, without even understanding what we do.. after a while she got promoted. So we had 3 bosses. Then she started to bossing us two around and then they fired me because I spoke up and they needed to reduce to 9 employees. Me, who can do everything from a to z, knows all the problems and processes and who could do everything alone and actually have done that. The whole success of the company in the last 12 years was solely on my and my colleagues shoulders.

Leave early if possible. And just don't think they are your friends. They even didn't say thank you.

This regret goes both ways.

You might also regret leaving a great work life balance company and a boss who treats you well.

Slightly OT: don't underestimate the importance of having a good boss. 99% of the time, you either love or hate a company purely based on the individual person you directly work for.

Then you've won the lottery, for now. Congratulations!

It will be more difficult for you to find your next job because your position slowly morphs around you rather than what the industry is looking for. You should have a much higher emergency fund than normal for that case - you will have to retrain on your own dime when you decide to move on (or the company decides it's time for you to move on against your will, or the company changes to a culture you hate.)

You will likely need to take a step back in your career at that point, but you've already had the job for a decade and the difference between 8 and 16 years is the same at this point. That, and this is the worst tech job market since 2008, maybe 2001.

I also spent almost a decade at my first out-of-college corporate job. Had a great team, slowly shifted from company-specific ERP and niche client-server software to web development. It was very comfortable for a long time.

I left after internal changes started demoting my team to support and maintenance, HIPPO and all that. I don't regret staying there for how long I did: I gained a width of non-company-specific experience to find other positions. And turns out, I left at the right time, too: company was involved in a political scandal and my former coworkers are now officially "application configuration specialists" instead of "developers".

I find regret to be useless to me. It just keeps me up at night if I look back and ignore what’s with me in the moment. Learning from experiences is one thing, but feeling bad about choices I made in the past is useless because I cannot change the path I am on right at this moment. But I can step off it, or course correct.

If I find myself thinking “man I could have made a unicorn startup”, I pivot that internal monologue into “how might I start to build a unicorn startup”. In my opinion, the hard thing is listening to that internal monologue and really listening to what it is saying.

(“deep thoughts, by Jack Handy”)

> I’m starting to be concerned that I’m not growing as an engineer

In general, to keep your mind healthy, it is recommended to continously challenge yourself and learn.

You could do this outside of work hours. Is that an option for you?

No, I regret leaving a high paying job at a large corporation while working remotely in a LCOL area to join a startup that failed dramatically. Now the market is difficult and the good jobs are hard to get. They say you'll only regret the risks you didn't take more than the ones you did, but that's certainly not true in my case because I would almost be financially independent now if I hadn't taken that risk.

Despite that, I'll probably do it again at some point because I don't learn lol

What about grow as an engineer with a hobby and you're golden?

At different times I've regretted staying too long and leaving too soon. It's a multi-dimensional problem and it's worth thinking through what you lose as well as what you gain.

It sounds like you have a pretty good situation apart from your goals to grow as an engineer. You might consider adding something, e.g. taking or teaching a course, joining or starting a group focused on learning, helping with an open-source project, volunteering to build a system for a local non-profit, etc.

  I’m wfh in a medium cost of living area. My salary is 140k and work life balance is great.

I'm not seeing much to regret there. Try 'looking for work' for a year or more, with no income and mounting debts, in comparison.

But be vigilant that the current job isn't a 'shrinking pond'. At least ensure you have 'up-to-date' skills. I would say 'in-demand' skills, but that seems like an oxymoron in today's market.

I don't think you have reason to be concerned. I concur with the comment about growing as an engineer as a hobby, but you're living the dream.

I stayed at a job too long but was in a different industry and making 59k in a high COL area and I was living in pest infested shithole. When I got laid off I pivoted to computer science. I don't regret staying because I am where I am now as a result - but I do regret not being able to leave on my own terms.

Absolutely. I wasted 6 years writing C++ and being miserable.

I can't imagine staying in a job for 10 years - the longest i've put up with one is 6, and i hated every minute. that was the first serious one i ever had though, and it did net me some qualifications which may have been worth having.

but if you like the job, you could stick with it, so long as you also learn new stuff you could a[[ly should the need come for change.

I thought I was making a good decision staying at a job I liked and not taking an offer for more money. I was laid off a year later.

I seem to only have long tenures (4 to 7 years, with 6 years average) and there hasn't been a single case when I left and wasn't having some remorse for staying too long and not leaving earlier. This includes my current position which I'm leaving after almost 7 years and wishing I would have left some two years ago.

I stayed for about a decade but moved out of engineering to PM and then to technical marketing, it was a mixed feeling. One one hand being for so long at the same company did not help me financially that much on the other hand changing jobs into totally new domains was not as difficult if I would have jumped companies.

in the exact same position. 10 years, currently 130k. Very good work life balance including being able to live wherever I want and having zero stress about work. At the very least I regret not continuing to learn the last 5 years. I probably won't give up this role as it's just too comfortable.

I regret leaving jobs too early.

There is experience to be gained from seeing a codebase and business evolve over time that can't be replicated by switching jobs.

Plus, you never know what a new job will be like. I ended up with a worse job 50% of the time I hopped.

I'd prioritize comfort and wlb more than anything else.

I've been "at the same job" for almost 15 years but the company been sold three times, fully bankrupt once, almost broke many times, grown to over 500 staff, layoffs to less than ten, IPO'd/re-privatized, etc

Anyway I haven't interviewed in a while!

Myself, yes I think the optimal number of years is 3. If your resume is filled with 1 and 2 year jobs, then you are no more value to the company than a contractor. But IMHO after 5 a company will think you have no options and runs cheap on you.

I was with an employer for 6 years, and I left because I felt like it was hindering my skill building and long term career development. In hind sight, that was the worst mistake I ever made.

If it ain't broke, don't fix it.

I haven’t had that experience because I have never been anywhere more than five years. It ends up being about 3 years on average because company gets acquired or does layoffs, or became toxic and I left.

This is why I left my last position. I'd been there for 7 years and realized that not only was I not growing or improving my skillset, it was actively deteriorating.

I had to leave in order to protect my career.

Every next company hires you for your particular expertise that you are able to apply from day one. None of them are interested to invest in your growth. You do it on your personal time.

I've actually had the opposite experience.

I left a great job where I was well liked for a small raise. The new job sucked and everything went downhill.

Unless it's a giant leap in pay, stay where your at

I regret that I was born before jobs (the "work or starve" kind we have now) are made obsolete, so in that way I regret keeping every job for any length of time.

If you're asking this type of question, you should be looking around. Everyone needs some amount of comfort, but stagnation/continued disengagement with the work indicates that you might not mesh well with what the org is now (vs when you were hired), who you've become, or that you are [no longer?] a great fit for the role.

Also, it's totally healthy to outgrow your employer and/or role. Nobody talks about this, but its true. (Why do you think the corporate ladder exists?)

Personally, I tend to have a shelf life of about 7 years at most companies. Which is a long time in this industry; they typically change a lot versus when I join. Usually I decide I want to work in a different domain after that time. The first 9 years out of school I was pure backend work, then I pivoted to compilers/low-level dev because I hated Rails so much, and now I'm eyeing full stack/indie dev.

Keep in mind it's a bad market for employees right now, so be patient in the search process. Good luck.

“… but I’m starting to be concerned that I’m not growing as an engineer.“

What are you looking to grow into? What is growth to you?

What’s your general outlook around what you hope to get out of this?

I stayed at one company for 11 years, also my first job. Worst choice ever. The company was bad, I was not growing, it was detrimental to both my and my employer.

General comments:

I have stayed too long when things were crummy. They didn't start crummy; they became crummy as things changed. (Companies are only good to work for until they're not. Just about nowhere is good forever.) You can tell when things have become crummy, but you can remember that it used to be good, and so you're tempted to ride it out. Do that, but only for a few months. After, say, 3 to 6 months of no improvement, it's time to have your resume hit the street.

On the other hand, if you have good pay, good people, and good working conditions, think hard before you leave that. It's not easy to find a place that will be an improvement. My advice would be to ride that out as long as it keeps being good (but see previous paragraph).

Specific advice:

Are you concerned that you're not growing, or do you feel that you're not growing? That is, is this a head issue, or a heart and gut issue?

If you feel that you're not growing, if you feel that you need to be doing more for your own sense of satisfaction on the job, then go to your boss, and tell him/her/other that you feel that you need more responsibility.

On the other hand, if it's not bothering you at a gut level, if it's more a "should" or expectation that you think other people have for you, then maybe take a look at what you can actually do now. Are you really not better than you were a decade ago? Five years ago? Do you still write the same bugs you did then? Do you still get stumped by the same questions you did then? Can you handle bigger designs than you did then? Are you really not growing, or are you just not seeing that you've grown?

It's really easy (especially on HN!) to see "yeah, I started Facebook at 19" or whatever, and feel that at 30, I should be able to do more than I can. But that's not a realistic standard of comparison, and not a realistic expectation to put on yourself.

Absofreakinglutely. I mean, my experience isn’t rosy like yours, since you ask: my regret is threefold.

First, I regret being naive. I grew up with the idealistic notion that if you are loyal to a business, they will be loyal to you. Reality: businesses actually ran like this are nearly extinct. Either way, when it comes to money, you can’t really trust people in a business arrangement to look out for you. Also, as I am now over-the-hill, I’m finding that someone with a long tenure and experience at one place is a liability. Bean counters want to replace you with someone cheaper and more expendable. Younger employees think you should retire and get out of their way (buddy, god willing I still have several decades to go and I’m not even sure I will be able to retire). Prospective hires think you have years of baggage and bad habits (which is likely true).

Second, I regret sacrificing the prime of my health and time eating shit at places I didn’t like for extravagant promises of equity. Equity is good and worth working for, but only if it’s worth the price you must pay today. Others may disagree, but I have found it’s not worth living in hell for the next 3-10 years even if that could potentially net me millions. And of course, there are no guarantees. The world could end, I could die any moment, or the company could go tits-up. My first startup experience netted me only $2000 for 12 years and a lifetime of regret… particularly over preferring to keep working rather than spending time with my father who later died.

Third and finally, I regret surrendering to my poor self esteem. I’m a college drop out, a nobody from a nobody town, working at small to mid sized businesses, and I think I’m merely ok at what I do. No one in their right mind could or should hire me. The job I recently left paid a very good salary, full remote, I had 10 years of seniority, I had lots of respect and could throw my weight around, all I had to put up with was incompetence and nightmarish stress. Since I have no self esteem, I felt I deserved that trade. It’s been eight months since I left, and I’m struggling to rebuild my confidence and control my anxiety.

I have mostly had the opposite experience (quit jobs too early) because at the time I didn’t understand how many firms are mismanaged, disorganized, or just plain hostile to common sense.

And so if you have a solid job with people you enjoy working with, and management that doesn’t drive you insane, I’d be pretty hesitant to job hop unless you’re absolutely certain that the new firm will be better. There are many many ways to grow and educate yourself while still holding the same job - have you exhausted those yet?

Decade? I regret staying in my first job for two years instead of one.

Sounds like you need a side project where you can explore new skills.

Unless you’re very lucky - typically it is not a smart choice to stay longer than 2-4 years at 1 tech company. In current situation.

People who stay longer only encourage employers to keep old salaries as is while buying new workforce for the market price.

sounds like you made what most ppl seek and probably grown enough as an engineer as to invest more in yourself. like pickup new 'hobbies' or meet interesting ppl

it's only bad if you don't like it

I only saw people regretting staying for too long when they whined about the job for years before actually leaving

I'm rn =P

Yes, but the situation was much different than the one you have found yourself in.

As an "intern" I found myself at a very small company - literally just my boss, his son, and me. I was the only programmer. I loved the autonomy that came with being the only one who knew how to write code, and they were in desperate need of it. There was a lot to do, and they had a dream I believed in. I worked there - sometimes I even slept there I worked so late - for five years. They ended up giving me a salary of 48k per year (in 2006) and no healthcare or benefits. I worked every weekday and most weekends, lost contact with friends and family, and ate terribly because I wouldn't even take time to try and make healthy food. Spent those five years cramming shitty fast food down my throat every day.

There are several warning signs that are hopefully plain as day to people reading that.

1) an "internship" should be tightly directed learning under a mentor. If you are the only software engineer at your "internship" what they are really looking for is free labor.

2) No software engineering job should pay 48k in America.

3) No full time job should go without health insurance.

4) Under no circumstances should a person work 60-80 hour weeks, but particularly under that horrible pay and no benefits.

I stayed because I felt a misguided sense of loyalty to them, and because their desperation to make their small business work meant that I got a huge and diverse array of systems that I got to build, and I got full autonomy to build them. There was something deeply addicting about that: addicting enough that I didn't even think about how my finances were crumbling and I hadn't seen a doctor in half a decade.

I finally woke up from my addiction when I started encountering health problems and couldn't see a doctor.

After a lot of soul searching, I left - and instantly upon finding a new job realized just how badly they had abused my naivete and sense of loyalty. I make many multiples of that income now, but I will never regain the lost health, lost friendships, and years of earning potential.

My advice to people is that, no matter how fun the work involved in the job ITSELF is, you need to still take an honest assessment on a regular basis about whether it is worth it. Even a very fun and fulfilling job can be killing you, or underpaying you, or distancing you from your family and from other opportunities.

In your situation, you are earning a reasonable wage and it sounds like you are not being stretched thin by it. Feel free to look around, but I don't see your situation as dire or necessarily in need of change.

I don't think people can realize how bad the "inglorious" side of software engineering can be. That isn't to say don't look and see if you can find better, but recognize that you are already in a great situation. And also one where you can either comfortably look for a new job or do your own side projects to learn and grow in ways your job might not be providing.

Nope. I follow a very simple rule: you should be earning, learning, or leaving.