Ask HN: Good salary but no career, what to do?

Hi HN. I'm in my early forties and I've been working for the last 20 years or so as a software developer.

For the past 11.5 years I've been working for the same company, first as a permanent employee working on premises, later remotely as a contractor and now through a 3rd company. The last 2 scenarios are only due to tax/legal reasons, for all intents and purposes it's as if I was still a permanent employee of that company. It's a non-tech company with a tech department of around 50 people, of which maybe half are devs.

I still have the same job title as when I first joined, senior software developer, and I haven't led any team or had anyone reporting to me. My salary is roughly 3.5x of my initial salary (despite having never asked for a raise), well above market here. Still, I'm treated like an errand boy.

I feel bad when I see everyone around making progress with their careers. Meanwhile my only promotion happened like 15 years ago, when I went from junior to senior dev. My salary is, I bet, better than most, but salaries are secret. I'm concerned about ageism and who will hire me when I'm 50 and haven't even led a small team.

I'm not sure how I can be so valued by the company in terms of money but not in any other aspect. I feel technically as competent as any other dev in the company (this is not a FAANG anyway), and I feel respected by my peers. I think I communicate well. I'm easy to work with, although getting grumpier by the day due to this situation (and age?). My bosses, including the current CTO, always say good things about me to the point of making me feel embarrassed when they do it in meetings with other people.

Some things that might play against me:

  - I'm a backend dev, and the main product is a web page. CTO has admitted that hurts with visibility.
  - I'm working remotely. The CTO of the company is very vocal against remote work.
  - I'm technically not an employee as of the last few years.

Other issues with this job:

  - The CTO says I report to him (unofficially, being an external worker) because I'm important, yet I spend months without speaking with him. I feel bossless. And I think there's little visibility of my work to work day.
  - Even though I have the opportunity to work on new semi-interesting projects here and there, I also have to maintain quite a bit of the old stuff that I inherited... I also have to do a shitload of reports (which I hate), as I'm the one with the better knowledge of the (decades old) DB.

Here in my country we have a saying, would you rather be the head of a mouse or the tail of a lion? Well I feel like the tail of a mouse here. Because I'd fully understand being the generic code monkey #478758 at a FAANG company where everyone's so good, but not at a small tech department after almost 12 years.

So I see two options:

  - take a huge gamble, and quit my job in the start or middle of a recession, and having just had a baby (I'd make sure to land one offer first of course). Lose two thirds of my income, or half if I'm lucky, which we can afford as the house is paid for, we have no debt. No guarantee that I can make progress or be happier elsewhere, especially starting from scratch.
  - keep my head low, swallow the little pride I have left, and keep raking in the money. Learn some more frontend stuff that at least will keep me more employable. In a few years buy a beach house, that would help with my feelings, hopefully. My girlfriend and mum think this is the best option, money is just too good.

I'm at a point of looking for professional help to convince me of point #2 as it's probably the saner choice. But I so fantasise with sending a resignation letter...