The Technological Problems Of Retirement
But it's a definite problem either way: a pay-as-you go program like Social Security worked well enough back when we had a ratio of 16 workers to every retiree; now there's three workers for every retiree, and the ratio is predicted to drop to 2:1 in a couple of decades.
Much of the retirement-funding difficulty stems from a current technological glitch: "Caring for people too old and sick to care for themselves" is the only aspect of modern existence I can think of where machinery/technology/automation has ultimately brought us to a situation requiring more human labor than before, rather than less.
Consider the matter "People need clothing appropriate for the weather." Getting enough clothes for everyone -- even those too young, old or sick to work -- hasn't been a problem for decades, not when a modern machine can spit out more clothes in one hour than a human weaver and tailor working together can make in their entire lifetimes. "People need food" -- also not a problem for over a century; when famines hit today, it isn't because "there's simply not enough food to feed those people" but because "those people's evil government is keeping food away from them."
So for an elderly retiree (or any person of any age) today, if you ask the question "How much human labor and effort is needed to keep that person clothed and fed?" the answer is "very little, especially compared to the old days." (I've mentioned before how my current winter wardrobe, purchased in secondhand stores, cost me roughly one median day's wages in all, though in the medieval era a wardrobe that size would have been literally worth more than its weight in gold.) Feeding and clothing the elderly isn't the problem now; the problem is providing hands-on medical or everyday-living care they can no longer do for themselves.
And there, technology has (temporarily) made matters worse: we can keep people alive who would've died before, but now that they're still alive, we need to pay actual people to care for them, because our robot and mechanical technology isn't advanced enough to handle it. This wouldn't be a problem if we had Jetsons-level tech, where an ordinary middle-class family can easily afford a tireless robot maid that dedicates 24 hours a day to turning Grandma over so she doesn't get bedsores; changing Grandma's clothes, bedding and bedpans when necessary; helping Grandma if she falls down and can't get up ... but for right now, if Grandma needs someone to do all these things for her, it takes a lot of different people working together to achieve this.
A friend of mine pointed out that Japan has been developing robots for that exact reason -- their population demographic is aging even more rapidly than ours -- but so far, it's not going over very well. But Japanese robot technicians would do well to avoid uncanny valley situations by making "machines" rather than "robots." My dishwasher does not in any way look like a poorly paid immigrant servant scrubbing plates at the kitchen sink, and doesn't attempt to; it's a machine rather than a robot. And if I one day get so incapacitated that I can't even load the dishwasher myself, a machine that takes dirty dishes from the sink/my table and loads them into the dishwasher need not look anything like a person, either.
Indeed, in many ways robots would be preferable to actual human contact; if ever I get so dependent that I can't even wipe my own ass after visiting the bathroom, I'd much rather use a robotic asswipe machine* than need another person to do it. (*Though if it came to that, 'twould probably be easier to just install a bidet.)
Unfortunately, I have the gloomy suspicion it'll take us a couple of centuries before technology grants us affordable full-service robot servants, and that's not soon enough to give people today a good answer to the question "WTF can we do to pay for the whole Baby Boomer retirement thing?"