You have a classic case of the golden handcuffs. Been there couple of times. You have a couple options:

1. Ride it out and make it a better place. Be the person who improves Con #2. Usually, it takes a lot of time but it can be done by slowing making improvements toward a new stack. That will phase out Con #3. Help define Con #6 so you have some vision. Con #6 is caused by Con #1. Develop your resume with side projects OR using new stack at work (new stack in production code is worth much more in an interview)

2. Look at another job. You're right when you say other places are the same, but not all. If you find yourself preferring to be sick than to go to work, then it's hi time to change (been there) as you're not doing yourself or the employer any favors. You may need a change of scenery and the money is not worth it at that point. If necessary, take a money hit and move on.

A lot of it boils down to either money (which will come in time), or enjoying your job. If you're lucky, you can get both.

There are two important factors: 1.) is this dead end career or rather it will be possible for you to find another job later? A lot of money now in exchange of having trouble to find another job later on is a bad deal.

2.) How does the shittiness affect you personal life? If it makes you constantly angry and lashing out at girlfriend/boyfriend, you risk losing her or at least damaging the relationship. Factor that in. If it does not affect you all that much yet, then weight money against point 1

Edit: 3.) Is it fundamentally demotivating to you? Meaning are you loosing interest in learning more about stack you are using or learning new stack or doIng things well? If you risk to turn into complacent done in self defense, then run before it happens.

You neglect the scenario in which the overpaid employee could be married with dependents. When your kids depend on your paycheck, this is not such a simple matter, and making trades for "a lot of money now" doesn't seem like such a bad deal. When you're young and uncommitted, you can afford to make moves on airy idealism. You can't when you have something important riding on it. This is true even if you have a lot of savings or "runway".

I agree that he should find another job with reasonable pay before leaving this one, especially if he is in situation you described.

However, none of my three was result of idealism. I think that I am older then the average here and I have kids. As I got older, those three became more important not less. Including and maybe especially after children. Children benefit from father that interacts with them happily and normally, if the dad is frustrated and angry from work it is harder. If you damage relationship with spouse while you have children, consequences are more painful to fix then as if you was twenty and just figuring out whether she is long term material or not.

I have seen people who became demotivated and complacent drones - and it did became real problem and it caught them up. It is harder to get rid of bad habits at later age. Ageism is also very real, so the older you are the more careful you have to be at how you look to prospect employers.

If you have small children you have less time to learn out of work and less free time to just relax. That makes the choice of work more important not less. You can not just slack around dead end technology in work and then use evening to learn new things as much as before (lets be honest, that is what many people without responsibilities at home do).

Of course I agree that if someone can simply move to a better working situation, they should; that seems tautological. In practice, doing this takes preparation, and you can never really know what to expect until you've already made the jump. It's important to realize that going nomad any time work goes sideways will lead to a lot of instability over a period of years.

It seems a more tenable solution is to control the response to one's working environment and then seek to control/improve the working environment, leaving the mirage of greener pastures as a last resort.

"It seems a more tenable solution is to control the response to one's working environment and then seek to control/improve the working environment, leaving the mirage of greener pastures as a last resort."

That is when the work is somewhat acceptable, but not ideal. It is not when the work is "shitty" and its shitiness affects you. Most workplaces are not horribly shitty, really. Moreover, various people handle various kind of dysfunction differently. There are dysfunctions I handle well and can adjust to, but are also dysfunctions I handle badly.

Ultimately, if it is easy to control the response to one's working environment, then it is not really bad. And really bad workplaces exist and will affect not just you, but your family and future too. If you have been unhappy in school, afterschool clubs and all employers, then I agree it is you. If you have been happy up to now and it is hell suddenly, then it is the place.

If this is the latter, then it is good idea to seek new job immediately - that is not going nomad, that is looking at possibilities you have. Not doing so out of fear can be a mistake. You wont find good workplace if you are not looking for one. At minimum, once you take steps to find another job and know what is possible, you become objectively more in control of your life and will feel less trapped. Nothing bad can come out of that.

>There are dysfunctions I handle well and can adjust to, but are also dysfunctions I handle badly.

Point taken, but this is not an acceptable excuse. You have to keep it together for your spouse and children. Lashing out at them is not acceptable regardless of what's happening at work.

This attitude of "there are just some things I can't control" is pervasive and it's very dangerous. When we have people depending on us, we cannot allow ourselves to blame externalities for our behaviors.

>Ultimately, if it is easy to control the response to one's working environment, then it is not really bad. And really bad workplaces exist and will affect not just you, but your family and future too.

Along the same lines, it's not that it's easy to be reasonably pleasant in the midst of a stressful working engagement. But it is necessary.

I agree that there are some working conditions that are total non-starters, but it's unlikely that you'd find yourself stuck there; you'd walk out on day 1 or 2 and go find a real job.

Barring such conditions, I would argue that it is frequently more efficient to change the conditions at your current employer than to gain new employment. Remember we're talking in the context of an overpaid employee here, but developing the skills to do this instead of abandoning a company before your mobility is actually limited is a very smart thing.

> If you have been happy up to now and it is hell suddenly, then it is the place.

If the change is sudden, it'd be wise to inquire as to its nature and permanence before jumping ship. Sudden negative changes usually cause a mass exodus of skilled employees, so if you're already overpaid and the market is getting saturated with the resumes of your competitors, this is probably not a good time to jump ship.

>At minimum, once you take steps to find another job and know what is possible, you become objectively more in control of your life and will feel less trapped. Nothing bad can come out of that.

This thread is about overpaid people. Going out and looking is discouraging if you don't yet realize that you're overpaid and/or how difficult it would be to replace your current employer. You learn that your mobility is much lower than you thought it was, and this understandably creates a feel of being more, not less, trapped.

It is good to have an accurate concept of one's economic position, but you won't necessarily feel less trapped.

People are not gods and nobody is perfect. Your spouse, unless autistic, knows you are not ok even if you are not lashing out directly. If changing job is an option, there is nothing wron with doing it. More then excuses, (young) people I see insist on assuming they can handle everything and proceed ignoring reality.

Or to tell it honestly and directly, I prefer my husband to trust me and be happy at the job then seeing him unhappy every day and assuming I care more about salary then quality of time with me and children. I like to work too and I want to be useful to familly too.

What you advocate is effectively putting all your mental strength on employer.

These positions are not overpaid - the company pays that much because people don't want to stick around. Mostly because they are self aware and not stupid. If you are one of those who are unaffected, more power to you. However if you are, then you have to decide about prioritis - staying is about proving something to your self. It is not about family,so don't frame it as such. (It might still be ok if you realy really need to prove that thing - familly should be two way acceptance)

Also, badly managed companies don't value good workers. If you stick, they will not reward it. It is not that easy to change those companies. Again, it is ok to leave bad employer in exchange for less money. Unless you think your wife is some kid of gold digger uninterested in you.

If knowing accurate economic possibilities makes you unhappy, nothing will help you. Leaving is an option, really, and a bit less money in exchange of bit more good conditions are better for both you and other people around you.

I don't think it's simple. I know people that took as much as a year to find a job they liked while remaining employed at a poor workplace. However it is important, so even if it takes time and effort you should try to look for better work rather than accept the current situation.

> When your kids depend on your paycheck, this is not such a simple matter, and making trades for "a lot of money now" doesn't seem like such a bad deal.

Sure, until the gravy train ends, and it always does (layoffs, reorganizations, etc.), and you wind up looking for a new job with skills that are irrelevant or out-of-date. Unless you're within spitting distance of retirement, staying in a job that isn't growing you and preparing you for your next job (or, worse, might be burning you out) is a massive risk.

Yes, I agree that everyone should stay reasonably sharp. I don't think you necessarily need your day job to be on a "modern stack" to do this. Also, if you're overpaid for a software engineer, you may want to attempt to pivot to a managerial/leadership role where salary caps are higher. Staying at a "broken place" and making efforts to improve it is very valuable experience for that kind of career track.

The most important consideration is which point of your career you're in.

If you're early in your career, leave immeadiately. You are missing out on opportunity to learn from the best people and use that knowledge for decades to come. You will get severely damaged by the culture if you stay too long.

I'm in mid-career, and I work at exactly this type of company. I'm staying for a little while because I'm wise enough to avoid the nonsense and know when people are dead wrong and ignore their bad ideas. I'll bank some money and be in a good position to do a startup.

For someone late in their career who just wants to retire as soon as possible, it might be a good choice to stay.

Disclaimer: my view on having a 'job' is probably very different than normal. I don't buy into the your work is your life mentality that seems to be prevalent in the US. It may have something to do with the fact that I only recently (about 4 years ago) got my first corporate job, I had multiple companies before that.

Compared to running your own business, having a corporate job is nothing. I can easily do the same work I used to do in a day and spread it out over a week. Make use of the fact that you can make lots of $$$ to save a lot and spend mental energy on side projects or hobbies. My side project for the last 2 years has been mostly raising kids but it may be an app or something else you work on the side. Instead of trying to 'climb up the corporate ladder' just try and leech as much money as possible while keeping your well being. Now that last part is important because if the job is stressful and you don't have the mental energy to do anything else than it's a no go.

But if it's chill, you get a long with your coworkers and the hours are normal and allow you for working on side projects, why not ride it out and maximize the $$$ return for that one day you decide to start a company/buy a house/start a family/whatever.

How dependent are you on the money you are making? Is that the main reason you would not consider switching jobs?

It might not be a popular statement, but money to a degree can buy happiness, comfort, and freedom. Unfortunately, it can be very addicting -- especially if you've adjusted your lifestyle to grow with an increasing income.

I did the whole golden-handcuffs thing for four years after I started disliking my job, but as soon as I "could" I quit to do my own thing. I gave up a very lucrative position, but my sanity and ability to work on interesting projects was worth far more to me. With my wife working we can cover expenses for us and our child without me needing to pull a lot out of savings each of month. It's been an adjustment spending less, more akin to a detox than anything, but we are both happier now that I moved on.

Went from imploded startup burnout to a job like you describe as a "secure way out". Went directly from burnout to bore-out, as I had to defend an architecture I never would have built like that but no means or resources to do it.

Still, 11 months of working there got me enough runway to fund founding my own thing together with a bunch of other people. 3 months later, shitty company went down the drain. 2,5 years later, we're market leader.

What you'll get there is smart money. If you leverage it properly, it might do you good. If you go there to stay longer, it will probably make you unhappy.

Your mileage may and will vary.

Good luck.

I'd wager monopolies and old tech correlate pretty well...

Consider industries that are growing for your next move: http://pages.stern.nyu.edu/~adamodar/New_Home_Page/datafile/...

Usually a lot more opportunities, a lot more shuffling around, and need good talent to continue growing.

Monopolies do not have a need to be innovative to stay competitive, so you'll be stuck with old technology for a while.

I was in a position i hated (dev lead with micro-manager), but i had extreme flexibility to take my time. took 2 years to find my next move, got a 12% bump in base, plus 5% more for annual bonus. I've loved it ever since, challenged every day, never looked back.

I am young, so while I have been in your situation I didn't have anyone to think about in terms of $$$. Your pros are good, but if you are feeling bad about cons 2, 3 and 6, I guarantee you it'll become worse as you start obsessing over it. I did not even have to worry about 4 and 5, and 1 was something I could live with because they were extremely nice people who were just trying to stick with (what I felt were) misguided values.

If you are not stressed, and have a lot of free time, it's a great time to learn something new.

So a few things. First, while it's not easy when you're highly paid, there usually are ways to get close to the same compensation somewhere else. You may have to be willing to come down, but you can usually find someone else to get you in the same ballpark. It just takes a lot of work (months). Building out a strong network is really important for this.

Second, politics is a constant any time you have more than 5-6 people involved. You must acclimate to this. It never goes away, and people are basically the same wherever they are. You can't escape this reality. Separating yourself from it just makes you an easier target (and having a high salary does that naturally anyway, so you don't need to get any bigger). Wherever you go, this will be the case.

When I was younger I used to hop around a lot; when the political situation would get hairy I would just nope out and move on to somewhere else instead of playing the game. Not only does that gets harder as you get more senior and enjoy more perks and comforts from your employer, but it makes for an unstable personal situation and most importantly, it doesn't really change anything. Your next employer will soon begin having all sorts of ugliness too, and you need to be able to navigate it.

You're probably going to be better off learning to play the political game and operate from the inside than to move somewhere else. It may take some hard work to counteract impressions made before your political awakening, but these skills are critical.

Take over. Don't let the inmates run the asylum anymore.

Sir, this is a thoughtful post, and thank you very much for sharing (my context mixed with your thoughts just fueled me the right way). Thank you, and keep posting!

Interestingly, I feel like this situation has some advantages over "non-shitty" work. The pros you mentioned are cool, it's nice to know tomorrow's meal is not at risk, and that's certainly not the kind of worry I want to have again.

But there's another hidden message in there. Monopolies with old tech, and no vision are industries potentially ripe for disruption. I bet if you look hard enough, you might find a need that translates into a start up.

Yep.

Pros 4.) Work like 32 hours a week and take as much vacation as possible and basically phone it in while they keep shoveling money your way.

You've got lots of time to look for a new gig at least.

All jobs suck in their own special way. Improving your response to your environment (stoicism, seeing the humanity below the artificial surface of the company, seeking out the good people at your work place and working with them, etc.) is far more important for personal happiness than a specific job in the vast majority of cases.

Given the uncertainty we are facing in the world and economy, a high paying, secure job and a low burn rate seem like a very good situation.

save your money, invest it, get enough "FU" money, then keep investing until you have 10x your salary. And keep a positive attitude, try not to dwell on the negatives. You might find out it is like this everywhere you go. Its a matter of perspective. But the #1 goal is FU money, investment experience (whatever that may be), and a good work/life balance.

A good savings goal is 25x your YEARLY spending. Then you can invest to make about 7%/yr, spend about 4%/yr, and the extra 3%/yr should cover inflation. This should last 'forever' and you can work on whatever pleases you (or nothing).

http://www.mrmoneymustache.com/2012/01/13/the-shockingly-sim...

I am in the same situation. I took some good freelance job on the side and will probably:

-turn that freelance into regular job and quit the regular one

-try 2-3 good companies with remote options from my domain where I think I can be very good at and enjoy working. if I land into some of them, quit at least regular job and leave freelance as side income or quit that too initialy.

I find this question interesting because over the past year I've been reading everything I can find in the library about work, the history of work, pride of workmanship, craft, job satisfaction, motivation, and so on. There are two schools of thought (at least). On the one hand, some people strive to find a great job that's instrinsically stimulating and motivating. On the other hand, that can't be a universal human need: the world needs ditch diggers, too, right? So the other angle is that it's not what work you do, but why and how you're doing it that matters. Are you finding/creating challenges at work and growing in your skill? Are you using the excess money surplus for worthy causes, or are you squandering it on empty entertainment and vain pursuits?

I don't know which view is right, but the philosophy is fascinating.

You're not trapped by anything but the paycheck. You might ask yourself how much money it would be worth giving up to work in a better environment. Then see if you can find a job that pays at least that much, with an environment that is considerably better than where you are.

The problem is you never know if it is going to be better or worse. My experience is that it is mostly the same everywhere. What changes is the paycheck, company logo and the faces

The grass is always greener syndrome is very real. The reverse interview process is very hard to parse. It usually takes several months to know where you will be in the bell curve of work environment between "living hell" and "wow, I enjoy my work".

As opposed to staying where you are, where you do know it's going to be bad?

I may have gotten lucky at avoiding jobs that turn out to be stinkers. Hasn't happened to me in the last three job switches. (One turned into a stinker after I'd been there a few years, due to management changes. I left.) But I don't think that the odds are as bad as you seem to think they are.

But really, you have only three options. You can put up with it, you can fix it, or you can leave. You don't want to put up with it. You sound like you're asking for how to fix it, but I'm not sure that you realistically can. (Certainly I've never been able to.) That leaves only one option.

More seriously though, you should ask around people you know and trust about which workplaces they like. Not all workplaces are alike. Look at switching industries. Look at non-profits. Look at things you care about outside of tech, and go do tech in that industry.

Yup i have tried that but it backfired terribly as i have been moved later on to a different team and management structure.

Maybe the problem is with the constant between all these situations then...

Maybe or maybe not :)

That's my feeling as well. Sure you can move over to something else, but taking a pay cut is probably a mistake because the new place can be just as shitty (either right away or in the future), and now you're not even getting paid for it.

I don't really know what to do except save my money and move to the forest one day. Only half joking.

This is 100% the best way to keep your employees trapped. If you want to retain employees but your company sucks, paying them well above market will make it very difficult for most of them to go elsewhere. It's easy to say "Well, they can just save the extra money and get MORE freedom!" but that's very rarely how things actually turn out in practice.

It is important that potential employees realize this before accepting job offers with large salaries. That company is trying to trap you. You may choose to walk into that trap, but at least do so with your eyes open. The most despondent people I've met through the course of my career have told me that they're stuck at their company because no one else is willing to get near their salary.

Sounds like a bad case of lifestyle inflation.

Eh, sort of. How long are you supposed to only utilize half of your income, or half of your half? When is it no longer "lifestyle inflation" and instead "lifestyle baseline"? In theory, everyone would live at the average market salary (better yet, average individual income, on the bet that you'll always be of at least average commercial value) and save everything else to maximize their mobility, but almost no one actually does. The arbitrage between theory and practice is where most political tricks occur.

Those resources have an expected value and a present value. At some point it is reasonable to decide to open it up a little bit more. Most people aren't going to max out their income overnight, but give them a couple years and they'll have moved to a nicer neighborhood, etc. Why? Because they could, and once you've filled some basic savings obligations, it can definitely be worth more to live somewhere better than to watch as a number you never intend to touch increments.

That said, sure, most people lack the discipline to live at a market salary instead of the salary they get paid. That's why this is a great way to trap employees. You keep clean hands and all the blame can be shifted to the employee, even though it's understood that it's very unlikely that the employee will actually account for the fact that any other position will entail a 40% pay cut.

Consider the possibility that other companies may, contrary to expectations, be willing to pay equally well. I'm not claiming this is absolutely the case, because I don't know your definition of "pays well," but at least it seems possible.

Here's how i'd access the situation,

- less money, no learning: leave immediately, you will feel much better.

- good money, limited learning: most of the jobs fall under this category for experienced people, use your spare time to learn new things. look out for new opportunities don't rush.

- good money, lots of learning: you must be starting out. for people with years of experience this will be momentary, enjoy while you can. look out for the next gig.

Most important thing here is never stop learning and continue to do what you enjoy most.

All the other things around: shitty management, inexperienced teams (jerks), politics, etc don't waste your energy and time unless if you have a "good" manager to work with.

If you're in your 20s, leave, for anything else really.

If you're in your 30s and have family/big bills and/or a side project/venture, stay put, try to not be bothered so much and bank money. If not, leave and do something better with your time.

If you're in your 40s, find something better (that gives you future leverage) that can pay you equal. At 40+, high pay is not a leverage for future employment (it's a liability IMHO).

If you're in your 50s, ride it out as long as possible and save as much as possible.

If you're in your 60s, why are you still enduring this?

Save up some money, get an offer at another company that you think will enjoy (even if for less money), and bounce. Life is too short to work somewhere you hate.

I'm in the same situation and decided yesterday that it is time to take the risk and do what will make me happy: go back to school. I managed to save quite a bit in my 3.5 years working at my current job so I'll be fine with the reduced income that we'll have moving back to a smaller city. After you've saved enough (which is hard to determine), pull the chord. You'll feel much better.

You have to decide which is more important FOR YOU. If you choose money, you can do things with it in other areas your life which makes you happy/satisfies you. If you choose a job with better management, technology, etc, you will be happy in your job.

I choose the better job (better people), because that's what I spend most of my day and everyday frustration doesn't worth it FOR ME.

I think only you can make this decision. If the cons don't effect your personal happiness or mental health, than I see no reason not to stay. If the job stresses you out and you feel your skills will get stagnant, I would recommend quitting. You can always use this job as a stepping stone to a better job.

This is a "feel good" answer that is statistically very unlikely to work out.

I'm not the guy you replied to but I agree with him. It's not really unlikely to work out if you approach the problem deftly, he just states the plan in simplistic terms.

Also, if you hop around a lot, you'll realize that these problems are not constrained to one bad company. You'll run across it basically everywhere if you wait long enough. You might have a boss who protects a "good culture", but when he's gone (voluntarily or not), it's gone.

For career stability, you have to learn to play this game and operate within its constraints, or you'll spend your whole career on the proverbial run.

The problem is that software people think empirically, as their job requires them to do so. Most other people do not do this, and in fact, most others would be disadvantaged if they did do so, so they have exactly the opposite incentives dictating their thought processes/structures.

STEM-types like us assume that "convince people" means show them the evidence, make our most stringent and convincing arguments, and demonstrate the clear superiority of the approach we've advocated.

Unfortunately, very few people are equipped to process such arguments from an objective or fair perspective. Advocacy for your theory's superiority is heard as "admit MY superiority". The theory and the personality proposing it are naturally and automatically conflated. Quite reasonably, colleagues are opposed to such admissions when that's the message they're hearing.

Not only are there the standard tendencies to interpret such behaviors in this manner, but there is the additional factor that all of your peers/colleagues are also performing image calculations in the context of their own careers. Even if they know that your intentions are pure and that your arguments are solid, they still have to protect against the opponent who would walk in to the bosses and say "borplk embarrassed that guy really bad the other day", failing to observe and/or communicate the egalitarian/cooperative context.

This is the part where people normally say "Well I would never work somewhere like that!" Yes you would. You do. It's unavoidable. You can't overcome human psychology (which is just a thin veneer on human biology). You must learn to cooperate with it.

Once you internalize this perspective, you are a) finally operating on the same level as many of your peers (especially non-STEM peers), and their decisions make a lot more sense; and b) room to effect change becomes visible much more readily. The opening of the playing field is especially potent in software-heavy companies, because, as discussed above, most software devs are very naive when it comes to office politics. If you're willing to practice it, you can frequently crush with minimal serious opposition.

I appreciate the explanation and I get it. My point still remains that from a practical standpoint you are statistically unlikely to be able to cause significant change as a low-level employee no matter how you go about it.

A lot of these companies are intentionally and systematically dysfunctional. You can have all the charisma in the world, they are not interested in changing.

And when your official role and purpose is not to shake things up, you wont be allowed to shake things up.

Again, notice I said statistically, not absolutely.

That's the defeatist perspective people are arguing against. It's like saying "there is a bug in this compiler; you won't be able to compile that." True, you won't be able to pursue exactly the same route, but you don't just accept that there's a bug. You find a workaround and get the result you need.

People can and should do the same thing in the office. The entire point of politics is to navigate the hierarchies that impede access to what you want.

Thank you for taking the time to explain what I meant in my overly terse terse post.

Sometimes you can change it, other times you can not. You are not the only person trying to influence culture and oftentimes the culture became that way because someone is actively trying to keep it so. In that case, you start from disadvantage and not everyone is equipped to do so - it takes great social skills.

You also become threat to established people as you are trying to change the culture. You need to be ready for ugly politics and bacstabbing tactic when it happens. Really bad cultures are result of upper management values and incentives they put in place. If upper management rewards (whether on purpose or as side result of other goal) the behavior you consider bad, then your attempts to make situation better man end up punished.

"Be the change you want to see." doesn't really refer to creating external change in others. More generally it means you exact change in the areas you have autonomy in, improving whatever your measure of quality is. Ideally it'll become contagious, but if not, hopefully it has improved your life in some way and you can feel good about your proactiveness.

Ive made this exact thing happen. It helped artificially that I could make changes without anyone else's buyin for a time, but over time and with persistence I was able to make sweeping changes with no authority whatsoever. Its hard, its grueling, but its not impossible.

My rules of thumb:

- When young, it's ok to take bigger chances. It's more interesting that way.

- Try not to quit a job unless you have something else to keep you busy (and pay your rent).

- When you have a significant other, kids, and ailing parents, these jobs are great. You will know when the time comes.

- Politics are in every job.

- Above all, learn patience!

I picked money when i accepted this job ( worked for a startup that i liked a lot ) in order to support my family. And while they are not depenndent on it that extra money is making everyone feel more secure.

Honest question: How much $$$? Are you sure you're paid more there than elsewhere? The market is still very hot for senior developers, and most of the top companies I know of are willing to match current stock with theirs, even in the low millions (over 4 years).

I would take the opportunity to work on some open source projects or throwaway learning projects in this time.

This is a perfect opportunity. Get your work done but invest your energy in something else so you don't get "bored-out".

Try having all of the above and getting crap pay! Unless the job is actually causing you mental anguish I recommend you stay and find your hapiness elsewhere or until you find a better equal paying job.

well if you don't need to be present all of the time and the employer doesn't have crazy IP over your work, and if you're somewhat entrepreneurial, fly low, work fewer hours and try starting your own business!

flying low is SUPER important. you will need every ounce of your mental capacity to pull this off.

spend an hour or two in the mornings on sales/networking/outreach. "work." spend your evenings building your product.

Yeah. Not exactly the same situation, not a monopoly. But yeah, it's well paid and it sucks ass in a lot of the same ways.

Care to level-set on the tech stack? How "old" is the old tech stack?

Is it "old" like Rails 4? J2EE? COBOL? Mainframes?

Not that "old" but shitty. Lots of spaghetti connections to a different systems. No documentation and none seems to know how it should really work.

Sadly, that is not out of ordinary. Learning how to achieve in such environment would be useful to you.

I think you've described just about every organization > 5 people.

Just curious, how would one fix #2 without some amount of #3? 4,5,6 would bother me most...

Best advice I have is to work on stuff outside of work using a more current tech stack so when OP does jump ship they will be able to transition smoothly and not end up in the same situation.

Yeah but you do not learn it by migrating the inherited legacy app you do not fully understand to a stack you also do not understand that well.

You can't see how much money you're losing by staying in a job you hate.

I actually accepted this offer because of the money offered. I worked for a startup before which i liked a lot but they paid below market avg ( while being extremely profitable)

Do as much as you can to improve the place then move on.

you should probably put a throwaway contact email on your profile - you might get some interesting inbound that is well paid but not so shitty ;)