I think one the challenges with being happy at a job is that every job where you are happy is a single change away from being a job where you not happy. Your manager could leave. Budgets or Prioritizes could change. Your org structure or upper management could change. Your team and org could be great, but suddenly your competitor changes strategies and you have to pivot to face that. Even an unexpected change in your personal life could change what you need your job to be.
And change in inevitable. At every job I've been in, it takes me 6 months - 1 year to really settle into it. And by that point, there's always been at least 1 major change that had some impact on my job.
If change is inevitable, what does it mean to find a job that makes you happy anyway?
>What are the concessions you made?
I've given up finding a job that makes me happy. But I do now strive for a job where I'm not miserable. One realization I had about myself is that I need to be in a stable environment with a stable schedule. Constant fires are hazardous to my mental health. I now work as an ant in a big company. I feel like my work is useful to the other people in the company who consume it, and when I stand up from my work computer at the end of the day I can disengage my mind and focus on personal stuff (family, hobbies, etc).
The compromise for me was that I never saw myself as a big company person. I worked for a decade in fast paced consulting roles that were exciting. And I burned out badly, both from overwork and repeated violations of my ethics. There are days when I really can't believe that I'm willingly working in a big company and I'm dealing with some byzantine process that has taken 6 months to fix a small thing. But then I hear from a friend who works for a startup and he tells me about the CEO texting him on Saturday morning. Honestly, the byzantine process is less stressful.
I'm not trying to say you need to work in a boring big company job. What I'm trying to do is give an example of how something you fear (for me, working at a huge company), might be the thing that you need right now. Don't dismiss things just because you feel like "That's not me."
>What are the red flags (or the right signs) to tell you a job is the right one?
To me there are two big things.
1) Your need to agree (for the most part) and get along with the people you work with and your manager. I think this is extra important when you are a manager. This is important because you want your values and ethics to be aligned with the place you work. You need to ask a ton of direct questions in the interview. I think the right people will understand why you are asking and respect you for it. The people who you don't want to work for will see it as a red flag and you won't get the job.
Of course, this doesn't always work either. At my current job the hiring manager quit and left between the day I signed the offer and my start date. Thankfully the team got a new manager who is great.
2) The pace you need to work has to match the pace of work at the company. Fast, slow, whatever - make sure they match.
>Did you manage to reform a shitty job in something at least tenable?
No, never. At multiple jobs I stayed longer than I should have trying to make things better. What I should have done is stopped caring, worked a pace that allowed my mental health to stabilize, and moved on.
>I can't get out of bed, am tired all the time. Sometimes on the brink of tears. I'm at a spot where it's very obvious to me that I'm depressed, it's impacting my family life.
I've been there. Personally, I think the jobs that cause the most damage are the ones where you find yourself constantly feeling like the decisions being made make no sense. Or worse, are unethical. I once worked for an EVP who constantly pushed for us to spin stuff and put stuff in slides that my team (I was the manager) thought was BS or lies. I used wake up and feel nauseous with the thought that things would be shown to the president of the company saying it came out of my group. Leaving was the only solution.
>Despite spending more and more time carefully picking a job, it always feels like I'm either deceived, or missed some stuff I should have caught earlier.
It's stupidly hard to find a job with a working environment that suits you. Nobody is allowed to just be honest about what's good and bad about their job. The bad is always re-framed into something that doesn't seem that bad. And sometimes the things that you hate are things that other people love, so they can say "X is good" when actually X would be terrible for you. Lots of people are expert bullshiters when it comes to getting a candidate to take the offer. The reality is that the job interview process is just the trailer for the movie. And there are a lot of terrible movies with great trailers. Don't beat yourself up about it.