A considerable amount of the judging these days has been of people from past eras being assessed by the culture of today - for instance, the Boeing executive who resigned over an article he wrote 33 years ago.
Without focusing too much on that particular tree, and rather, looking at the forest - the question then becomes - how should people speak or behave, so that future generations won’t judge them negatively? This is extraordinarily difficult because it is almost impossible to predict how future generations will think. It would have been difficult for that Boeing executive, in the year 1987, to foresee that by the year 2020 the idea that women ought to serve in combat would be mainstream and that his views would be considered far out of line with orthodoxy.
One might respond, “The world is moving in a progressive direction, and the progressives are on the right side of history, so just say or do what’s progressive and you’ll be safe.” But even then, that is still very difficult. Who knows what “progressivism” will be thirty or fifty years from now? Sure, Trump will always be seen as bad, but plenty of issues aren’t that simple. There is considerable division within the political left itself; and who knows which faction will prevail. If the world has become vegan by 2060, will Barack Obama (and countless other people) be judged for having eaten hamburgers today? Will the trans movement still be going strong, or will it be perceived negatively by then? Will polygamy be as accepted as same-sex marriage, or will it be considered patriarchal? Etc. etc.
It essentially requires people to have excellent future-predicting skill, to the point where one can foresee how society will think and behave decades from now - and most people can’t pull that off.