> If you get rejected somewhere and then accepted somewhere slightly lesser, you know you pushed yourself as high as you could go.
No, you still don't know even that. For every person reading this comment, there exists at least one job "lesser" than their current one where, if they were to apply to today, they would get rejected (and not just on the basis that they're overqualified).
Your statement imputes way too much rationality and efficiency into society—a sort of just-world hypothesis applied to the narrow domain of the job market and those who hold the keys into any given organization. Organizations are made of people, and people can be dumb and irrational. The kinds of people who have the final say on whether to reject or hire aren't exempt from this. The decision to reject can be as uninformed and arbitrary as it is logically sound.
The same principle applies to successful hires, too. In fact, that's the reason why it's possible to get rejected even for jobs where the application process should result in a hire. Companies hire people, find them to be worse than expected, but keep them around anyway because, while the powers that be definitely wouldn't go back in time if the opportunity to do so were available and hire that person all over again just the same, it's still too much work (or it's perceived to be too much work—again, people do not make optimal decisions) to get rid of them. Good candidates who get rejected are a casualty of organizations hedging their bets to try to prevent this from happening too much to them.
Or you had some "in" at your current job that you may not have somewhere else.
I've done fine at my last two long-term jobs but I also very much got them because I knew very higher ups who answered an email right away.
It actually encourages me that a lot about the hiring system is pretty random. Otherwise the big tech employers would just skim the cream except for people who really don't want to work for those employers. As it is, there's enough randomness that lots of good people end up at other companies.
I think it's a pretty reasonable assumption, even if the ordering is strictly personal (some people would take a job with better work-life balance instead of the better paying one, some would make a different choice, same thing with technology stacks etc.).
The second premise also seems to be true, though I would phrase it in a descriptive rather than prescriptive manners - the choices you make regarding job offers reveal your preferences ("the ordering of jobs").
Having no "job ordering" would result in people taking jobs based on a coin flip, wouldn't it?
This isn't true at all in my opinion. Hiring criteria are so vague, subjective, and interpersonal fit is also very subjective, that failure isn't a direct indication of one's ceiling.
If you get rejected somewhere and then accepted somewhere slightly lesser, you know you pushed yourself as high as you could go.
If you apply and get accepted and just take that job... then who knows how much higher you could have aimed.