NOTE: I started writing this mid Marchish.
Here I am, 8 years later, standing on the edge of another precipice.
Moving to a new job. That smoke jump into the unknown.
You can read reviews, look up the executives, read their mission statements, parse through and try and evaluate the Glassdoor reviews. But in the end it's a gut feeling from the people you talk to. And now in the second year of the Covid-19 pandemic, it's not even 'meet people'. It's kind of sort of meet someone over zoom (with botchy mic output while both wearing what I assume are vietnam era chopper pilot headsets).
There is a groove to work. A familiarity with how things fit together, who gets back to you right away, who needs incessant prodding, what specific processes to ignore if you can at all help it, office politics (which I've so far avoided like the plague). So much of work is hundreds of individual other bits of works, the flotsam, the jetsam that becomes so much muscle memory that it almost doesn't exist. And you are left with the actual nitty gritty chewy bit that's the work that you are ostensibly paid to do, that hopefully you enjoy.
Moving to a new company is not only taking on and learning the core bit of work, but all that other sundry things.
Moving to a new company with no one to 'scout ahead' as it were, is, especially in the software world, a rather large scary jump. What does the 'unlimited time off' actually end up being? What are the horrid things they aren't telling you? Is this actually a 80hr/week sweat shop of doom with just excellent recruiters? You never know. The heterogeneity of software companies is so vast, I think that's the main thing that keeps tech folks where they are, if they are reasonably happy.
But it's time to move on, learn new tech stacks, work in a larger company, different industry. We'll see.