Ask HN: What was your biggest business mistake?

Trying to "pay my dues" as expected and/or manipulated by an older generation particularly of middle-management. That may have been the way things worked for them, but more and more of the U.S. employment space doesn't work that way anymore and hasn't for well over a decade.

Employment in the U.S. is becoming de facto class based, and if you permit yourself a) to become over "classified", and b) to let such a role mis-direct your energy in inefficient directions, you can seriously screw yourself.

Neither am I a fan of the know nothing hotshots that e.g. were being parachuted in as excessively paid management consultants. But that resentment doesn't negate the above fact.

Look for the exceptional person who really is competent, and cooperative, and build your relationships that way rather than through whatever formal hierarchy. And keep yourself prepared to jump ship; don't paint yourself into a corner, especially financially.