It's tiring how much the media and casual discourse treats "millennials" as one gigantic person, but then again generational cohorts are a planning tool because large numbers of them engage in similar activities around the same time. This greatly impacts markets, culture, and circles back around to influence lots of other aspects of life. It also leads to more pressure and (generally) fewer opportunities on those who have fallen behind.
As much as we deride or wish to discourage people from comparing themselves to others, falling behind (in terms of timing or attainment) compared to the median member of a cohort confers a disadvantage towards further progress that would follow the same formula. This is particularly and literally applicable to millennials: after all, the entire generation was told to follow a formula, where getting to college was the first step, and any further clarification of one's ambitions would be expected to materialize once that baseline was cleared.
Now that they're all firmly of working age, it's clear that following that formula blindly -- as if it were just one of those "this is how the world works" societal norms that everyone does, like brushing teeth or obeying stoplights -- was a mistake. But the message was fed by their elders, the same people who are now helping them out if they're able.
And if one had poor parents or hardly a shot at getting to college, what were they supposed to do? They came of age at a time when blue-collar work was precipitously falling, all the well-paying high-demand careers demanded years of education, and years of coddling and lack of substantive discourse about the middle class's economic realities have resulted in a generic, aspirational message like "follow your dreams". Higher education was positioned by public policy and combined wisdom as a tool of opportunity, how was one to know that predatory-sounding trade schools may have been a better bet? And if public policy drove young people towards those schools instead, would we now have tens of thousands of HVAC technicians and automotive mechanics and cybersecurity professionals working in food and retail?