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Anyway I haven't interviewed in a while!
I do feel like I would be in a better place if I had stuck around longer in some of these positions, but it's hard to tell at the time! Each change was to a better and higher paying job. I do feel like I got a good perspective on the industry but I hear about people who were my peers getting into management, getting into staff or distinguished engineer positions, assume they are having all their options vested, and they are probably ahead of me financially.
My understanding is that to make "real money" i.e. what a manager at a car dealership makes, or 300k+, the reliable paths are either getting hired at the google/netflix/openai/apple type companies, getting into management pretty much anywhere (check BLS.gov. Average salaries for managers even in older industries are above what a staff engineer at e.g. Pagerduty or Onesignal probably gets), or getting a good amount of stock options at a low cost basis and eventually getting to cash them out.
This does not answer your question exactly but to that point I would say hop on linkedin and talk to some recruiters, keeping your skeptical hat on for everything they say. A good manager of someone who's been productive for 8-10 years is not going to be surprised or annoyed that they try and see what the market is.
One last point, tech is especially sensitive to the fluctuations of interest rates. We are all subject to the whims of Jerome and depending on what he does in the coming months, the market for engineering talent may look much different next spring than it does now.
It will be more difficult for you to find your next job because your position slowly morphs around you rather than what the industry is looking for. You should have a much higher emergency fund than normal for that case - you will have to retrain on your own dime when you decide to move on (or the company decides it's time for you to move on against your will, or the company changes to a culture you hate.)
You will likely need to take a step back in your career at that point, but you've already had the job for a decade and the difference between 8 and 16 years is the same at this point. That, and this is the worst tech job market since 2008, maybe 2001.
And so if you have a solid job with people you enjoy working with, and management that doesn’t drive you insane, I’d be pretty hesitant to job hop unless you’re absolutely certain that the new firm will be better. There are many many ways to grow and educate yourself while still holding the same job - have you exhausted those yet?
Also, it's totally healthy to outgrow your employer and/or role. Nobody talks about this, but its true. (Why do you think the corporate ladder exists?)
Personally, I tend to have a shelf life of about 7 years at most companies. Which is a long time in this industry; they typically change a lot versus when I join. Usually I decide I want to work in a different domain after that time. The first 9 years out of school I was pure backend work, then I pivoted to compilers/low-level dev because I hated Rails so much, and now I'm eyeing full stack/indie dev.
Keep in mind it's a bad market for employees right now, so be patient in the search process. Good luck.
I'm also very risk averse. I prefer being reasonably well known and trusted by the wider engineering staff here. I'm happy with where I am and have no intent of leaving. I mostly bring this up as a counterpoint to the people that say you can't have a good job by staying at the same place. Different places are different. Some of them are quite good. If you have a good thing, be willing to hold onto it.
With respect to not growing as an engineer, have you considered asking to switch teams or departments? I've shifted twice and each time led to a new set of challenges, but building upon my understanding of our systems.
If I find myself thinking “man I could have made a unicorn startup”, I pivot that internal monologue into “how might I start to build a unicorn startup”. In my opinion, the hard thing is listening to that internal monologue and really listening to what it is saying.
(“deep thoughts, by Jack Handy”)