most in my family have been able to

That's "old" money and "old economy" leftovers -- there are a lot of factors playing into the previous generations ability to retire that no longer apply to current and future generations.

For example:

• A lot of those in retirement now have things like pensions, which were guaranteed monthly income for life. Outside of government and union jobs, those are basically gone now. And will be even more rare in the future as those jobs are privatized to get out from under the pension burden or sent overseas for both cheap labor and no pension burden on the company.
• Many of current retirees have paid off their houses because the houses were pretty cheap and they tended to stay in them for life and not move around for jobs. Not so any more.
• In the past there were lots of blue collar manufacturing jobs that paid well, that pretty much anyone could get. Those are largely gone now. You could also make a living on a family farm in the past, that's pretty fucking hard to do now.
• Kids could be put through college for a few grand, not a few hundred thousand grand. Not so anymore.
• Houses in good school districts were pretty cheap. Most people lived in nice houses in good areas for modest mortgages. Now, people are spending half a million without blinking.
• Credit card debt is a massive problem.
• There was a lot less "stuff" to buy and they kept it longer, people paid $600 for a CAR and kept it for 10 years, now, we drop $600 on a new phone every year.
• There was the old idea that your kids, if they wanted something, went and got a job and paid for their own damn car at 16. Now, parents are supporting 40 year old kids out of their income/savings. Because they "want to give the kids everything."
• Etc.

In short -- the world has changed as has our attitude/lifestyle/goals, now, the numbers are terrible:

A third of people (36%) in the U.S. have nothing saved for retirement, a new survey shows. In fact, 14% of people ages 65 and older have no retirement savings; 26% of those 50 to 64; 33%, 30 to 49; and 69%,18 to 29, according to the survey of 1,003 adults, conducted for Bankrate.com, a personal finance website.