When you are working for a good company that values you, and embedded in a good team that also values you, there is a bonding that occurs that goes deeper than your average commercial exchange. If you have never been in this position, you may not understand the emotional difficulties involved in watching such a place slowly burn to the ground. Old timers usually still feel loyalty to those of their coworkers who are still sticking around; if the poster's boss is a good leader and strong advocate for them, which it sounds like they are, this can be even harder. People build a lot of loyalty towards good leaders.

Sure, it's emotional stuff, and the purely rational actor would dip without question. But having emotions is healthy and normal, even if it means they sometimes lead you to somewhat suboptimal situations. Of course, it can reach a point where people get locked in out of fear of the unknown, just like bad relationships. But it's rarely as easy as just saying "Okay, time to leave."

I can't find a single thing to disagree on in your excellent comment but there's one more nuance:

"When is the time to let go?"

This goes for all areas of life: intimate relationships / marriages, employment, being part of a hobby club that's not the same anymore, local community help (donations, voluntary labor etc.).

We the people are extremely bad judges of when is the right time to leave -- and 99% of the time we leave way too late. Usually after getting some deep emotional scars as a bonus.

In hindsight (which as they say is 20/20) every time in my life after I left any kind of interaction between me and other people / companies, it was well after I should have. But only in retrospect.

I gradually learned to recognize the signs and started to escalate problems early. And if they aren't addressed, leave early.

Life is too short to keep a death grip on things that are poisoning you. It seems every one of us learns this lesson very late in life.

This is all a story. How do you know when you should and should not leave? Everything happens on time. You always leave at the perfect time. You can create a false narrative in your mind and say “I should’ve left two weeks or two years ago;” Or, you can be thankful for the way things are and have the attitude that everything always happens the way it is supposed to.

At least in the context of my life experience I will disagree somewhat. I have this way of intuiting when I have made the most out of a situation or an interaction (especially when it comes to paid work) and time and again, without fail, I have noticed that due to emotional immaturity I have stayed well after the point at which I stopped learning and thriving and started getting poisoned by various bad (new) conditions.

But don't get me wrong: I am doing my very best not to live with regret and make myself better utilizing those past lessons -- as you said. But analyzing it back in time, I know that I actually had the right mindset but was too weak to utilize it.

Sure, but just because you went through periods of getting “poisoned“, why does that mean you stayed too long? Everyone goes through trials and tribulations. You’re making an error by assuming that leaving before the poisoning means you left on time. You always leave on time. The poisoning is part of the bigger plan of life. There’s never a need for regret, for everything happens exactly the way it’s supposed to.

If only somebody would have told him that leaving once you learnt everything you could is a nice idea. But we don't seem to get such lessons, but rather have to learn them ourselves, right?

I wish I could believe that but still... in retrospect, it seems you are correct.

I don’t claim to have all the right answers, but I am a psychologist, and I have spent many years learning how to not think. All of the errors, mistakes, and failures in my life can be viewed as lessons I was always supposed to go through. A perfectly positive attitude charms our brains into properly regulating our internal physiology. Anxiety and the other negative internal states (mania, depression) typically can be cured by changing our internal dialogue and our perspective. One thing is for certain: you and I didn’t make this world. We didn’t invent people, trees, viruses, or love. We are part of a bigger picture. I compare it to being an actor in a movie. Why critique the scene? Why look back at previous scenes and wish they were different? Why hope for better scenes in the future? The script is perfectly written. Just read your lines. Play your part right now in the current scene with all of its ups and downs.

Prioritize your health. Go your pace and accept the consequences. Always feel satisfied with your choice.

I suppose my biggest issue is actually accepting that reality might not be as malleable as I thought. It's an extremely hard thing to accept even to this day (and I am hitting 41 y/o very soon).

Prioritizing your health is an absolutely sound advice every time. I started doing that and even if the improvements are small and hard to feel just yet, it still feels great to feel better than two weeks ago.

If poster's boss is advocating for them (or reporting that they are) without any effect, it's a fairly hollow gesture.

If you respect me as an engineer, you do what needs to be done to address my genuine and valid concerns. If you can't, I can still like you as person, but you've ceased to be an effective leader. (I hold myself to that same standard with the teams I lead as well. I'm only as good as 9 parts what I deliver and 1 part what I wish I could deliver.)

I've also seen the opposite. People leaving way too early. Younger people usually who were jumping ship way too fast. Then they were miserable at their new job and jumped ship again. Not good on their resume at all.

I think they didn't realize that they had actually found a truly awesome company by chance and were witnessing its conversion to 'normal company'. Nothing more, nothing less. But if you ask me it was still totally bearable. The devil you know type of situation and hey, I'll let them pay me f they keep wanting to. I can still jump ship if they turn from normal company to actual evil (like introducing the kinds of perks that try and bait you into working 80 hour weeks and thinking it's fun and worth it and normal) company. I can still jump ship then.

> If you have never been in this position, you may not understand the emotional difficulties involved in watching such a place slowly burn to the ground.

I have been in that position before - that’s why I’m asking

I stayed 11 years at my previous job because it was fun and we were shielded us from a lot BS.

Honestly, I was lucky enough to negotiate my total compensation around 3 years ago before the acquisition using an offer I had.

So while I'll never see another raise again, I have very decent overall total compensation, especially for the cost of living where I'm at.

The other side of it, is that I have about 3 months of vacation built up. The TLDR on that though is they tried to take it from me about a month ago (carry over policy that I was told I would be exempt from). I told them straight up I would leave that day, so they reneged in the end. But I have no clue how they wouldn't assume I'm going to just take it this year and look for another job.

So my play now is to enjoy the compensation while looking for another job.

I'm also pulling back heavily in my support to the organization, which is tough because I'm not used to putting in less than 110%.

I'm trying to look on the bright side though. I think this experience may have cured me of my tendency to be a workaholic.

I obviously don't know what company you are at or what 110% means in that context. However unless you're Ar a FAANG type company I would venture that 110% is waaaay more than your regular coworkers put in. Probably at 50% levels if you are lucky. Personally I am lucky to work with lots of bright people that put in their 100%. But even there we have 50%ers.

So my advice: put in your 110% for 90% of the time (or something like that :)) I do this periodically. When required I'm there 110%. Done with something at 2pm Friday? Yeah well today I'll just call it a day instead of fixing yet another bug from the backlog that wasn't even in the sprint.