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

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

#33
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.

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

#34
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.

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

#36
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

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

#37
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.)

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

#38
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.

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

#39
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.

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