I think progressives never thought about this because we banked on immigration and demographic change allowing us to win culturally and electorally but the issue is immigrants tend to be overwhelmingly male, that is how Trump won actually he won over a lot of Hispanic,Black,Asian and indigenous men who feel humiliated by a new culture, economy and world.
So what can we do rhetorically and policy wise to win more young men over ?
To your point, I think that there is a fundamental issue with how we talk about success and failure. We effectively target white straight cis men setting them up so that they can never really succeed. As the majority, at least in terms of social and political power, we recognize that they have significant privilege in our culture. We weaponize that privilege such that all successes are external (the system is pushing them up) and all failures are internal (must be something wrong with them if they can fail despite having all of those advantages). Everyone else, to varying degrees depending on how much social and political power we perceive them to have, has the opposite logic applied to them. We say that their success is personal and special because they do it in spite of the system working against them and we blame their failures on the system.
There is of course legitimacy to that reasoning. There are many roadblocks that, especially visible, minorities face that white straight cis men do not. That doesn’t make this mindset not problematic though. The biggest issue with it is that we apply the general to the individual. Does a rural white kid whose parents both work retail have more privilege than Jaden Smith just because of his skin color? That’s of course an extreme example but the point is that the totality of a person’s circumstances is more than just how their biology is perceived by the culture. Privilege does make success easier as compared to people in otherwise similar circumstances but it certainly doesn’t guarantee success or mean that successes don’t have to be worked for.