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Federal taxes have been going down my whole life (born 1990 in the US). What era/region are you referring to where taxes go up?

Think state and local taxes. Depending on where you live and the type of business you run, they can add up quickly.

Also, the people I am speaking about were most definitely born before the 90's. More like 50's or 60's.

State and local taxes have been going up in many places. Often in response to decreased federal support.