Actually, this phenomenon occurs, due to the fact that TWO SEPARATE AND ONLY MARGINALLY RELATED THINGS ARE BEING CONFLATED.
The two SEPARATE THINGS, are
Actual oppression; and
The Politics of Oppression/anti-oppression.
The people who tell others that they ARE oppressed, even though they don't think they are, are usually fighting a larger battle, that is not directly relted to that individual; but their perception is that the only way to win that battle, is to insist that EVERYONE is oppressed.
And as some have noted above, it’s fairly common for people who are used to the “oppression” to fail to recognize it. Some actually take advantage of it, in fact.
But anyway, the reason for the impasse is that the argument is actually over different things, and the people arguing don’t realize that.
There’s an underlying, counter-Enlightenment, postmodernist assumption here, that truth is situated in the viewpoint, rather than being an objective phenomenon that can be debated using logic, reason, and facts.
Nobody “decides.” Truth is not an opinion, subject to change depending on your viewpoint. Given a specific definition of “oppressed,” either a person is or is not oppressed.
Certainly, their point of view is very valuable information, not to be lightly dismissed. But that doesn’t mean the conclusion they’ve drawn is accurate. A person who claims they are oppressed is, I’m sure you’ll agree, not automatically correct; a person who claims they are not is no more automatically correct.
I really wish this sloppy postmodernist approach to truth-finding would go away.
If 99% of blue people report that they have been oppressed, then it’s fair for a mauve person to say that blue people are oppressed, regardless that the 1% are saying otherwise.
Oppression is a subjective term. And identity is multi faceted. A minority or female person who is well off and educated, can absolutley feel and not be oppressed, because in everyday interaction it is the “wealthy, educated” parts of their identity which predominate.
A good example of this would be restrictive religious cultures. To greater or lesser extents many religious traditions place restrictions on followers (and sadly, women get the shitty end of the stick more often than not, homosexuals and other outgroups fair little better and sometimes worse)
By any objective analysis we’d label some of those behaviours and practices as a form of oppression.
Now a free choice by an adult to join such a religion or culture, with full knowledge of the consequences should be respected.
But it is quite possible that someone is so steeped in a culture or religion from a young age that they do not see the inequalities of opportunity or restriction. They may have accepted their lot and claim they are happy with it but if it is all they know can they be said to have made an informed choice? For such situations I think it is quite proper for those outside that situation to raise awareness that it doesn’t have to be that way.