The point wasn't the same as that of St. Francis of Assissi, who saw poverty as being intriniscally groovy and something you "offer up" to God. Instead, it was simply an attempt to cut out all the stuff that makes life annoying in order to hold onto the stuff that makes life worth living. So a Daoist wouldn't take any pleasure in being cold, dirty or hungry---like some Christian saints. But he would be happy to wear straw shoes he wove himself because the hassle involved in doing what you have to do in order to afford expensive leather boots wasn't worth the effort.
And it is a bit of a misnomer to talk about Daoist "poverty" anyway. Real poverty in ancient China involved starving to death or being pushed around by bullies---none of the Daoists in the stories were into that. Instead, it was more about choosing to create your own definition of what is "acceptible" and living by that code instead of having to accept those imposed upon you by others.
But if someone chooses to do this, it can cause a lot of social problems. People invest a great deal of their self-definition and sense of self-worth in the things they own. Think about the pride people put into their cars, houses, clothes, etc. If you honestly don't care too much about this stuff, these other folks can sometimes be really offended because they see your way of life as statement about the shallowness of theirs.
Even if people say that they aren't too concerned about the things they own, I find that more often than not they are consumers of experiences. That means that if they don't go on about their house or car, they end up bragging about the trips they've been on. Sometimes this can involve just going to lay on a beach in the sun at a Club Med resort. But more often it's the people who do adventurous things like backpack across India or do wilderness canoe trips that talk like this. But no matter how much they protest about the intrinsic value of travel, it always strikes me that the real value for them seemed not much different from the sort of guy who brags about how groovy his sports car. The "story" about travel is usually the most valued part of the experience, and ultimately going on trips is about buying a story to wow your friends.
If you question the ultimate value of this sort of travel "one-up-manship", I find that people often retaliate with the line that "if you haven't travelled, you can't possibly know what you're missing". As a matter of fact, I have travelled a bit, even if not very much. I just never really found anything all that groovy about it. Buying a ticket to China and touring Daoist Temples, for example, is no substitute for spending years practicing taijiquan, meditating and wrestling with ancient texts. Even someone who travels "like a native" or works in foreign aid projects can easily come away from the experience, IMHO, with only a very limited ability to understand where they've been. After all, many colonial "old hands" were convinced that they totally "understood" places like India and Vietnam---even though the history of the 20th century proved them completely wrong. And these folks didn't just go on a two-week excursion---they sometimes spent most of their lives surrounded by these other societies. This fact comes about for the simple reason that wisdom doesn't simply come from experience, it comes even more from the process of self-examination.
For me, when I listen to the tales of travel overseas I constantly find myself thinking about the oceans of jet fuel that get burned so tourists can brag at parties. I don't see this as being any intrinsically better than the elephants and people who used to suffer horribly so people could own ivory gee-gaws from the Congo . People who strive to become one with the Dao almost inevitably become aware of the interconnections between the way they live their lives, and how it affects other people around the world. Above my kitchen table I have a translated poem that I pulled from a Daoist teaching text: Journey to the West, it refers to exactly this sort of connection.
Hoeing millet in the noonday sun,
Sweat drops on the ground beneathe the millet.
Who understands that of the food that's in the bowl,
Every single grain was won through bitter toil?
In ancient China the wealth of the elite scholarly class was all based on taxes raised by poor peasants. So even the most modest silk robe and the smallest sinecure of so many bushels of rice per year ultimately came from the sweat of someone toiling away in the hot sun. Deciding to chuck away one's honours in order to live a life of simplicity could be seen as an act of signficant moral courage.
Like most things, however, there are complexities.
The Confucian worldview believes that one's primary responsibility is to your family. And how this was expected to work out was through bonds of obligation that place a person as a link in a chain that connects to both parents and children. The greatest sin that a man could commit would be to not provide male children to continue the family name. Only slightly below that would be casting away all connections with your parents. And only slightly below that would be not marrying. And eventually, only slightly below that would be to not move heaven-and-earth to provide financial security for all of these people.
Similarly, I think that a lot of people don't understand how much social pressure is exerted today upon people to ensure that they stay on the treadmill. Parents are often experts at laying guilt on their children to live up to their expectations. Moreover, deciding to "opt out" of the rat race means that you end up with a lot less resources to do things like jump in a jet airplane in order to fly across country for a family reunion. And doing without a car can mean that a person can't visit mom for Christmas dinner because she lives in a place that is inaccessible by public transit. This can result in a lot of stress, as for many modern people---just like ancient Confucians---"family is everything".
In effect, when the old-time Daoist chucked away his career to live a life of frugality in the countryside he was jumping off the treadmill and leaving his family to fend for themselves. I don't think people who read books about these characters often understand how crazy and wild this life choice really was.
In a related vein, if someone walked away from the Confucian "rat race" they were also turning their back on the Confucian "safety net" too. If you bailed out of your responsibilities to your family to live as a hermit in the countryside, they also turned their backs on their responsibility to help you when you got old and sick. The idealized vision that we have of the wise hermit never shows him sick and starving. In "Star Wars" style Taoism, Yoda never gets sick and starves to death in his lonely hermitage. But this had to have happened all the time in ancient China. (Ordinary people starved to death all the time, after all.) Other things happened too. In Bill Porter's book on modern Chinese hermits, Road to Heaven, I recall him writing about a young woman who helps out an older Daoist in a hermitage. One day she went out to fetch water and was attacked by a leopard----luckily she was carrying a glaive for self-defense and killed the beast. Life before the welfare state was plenty darn scarey in and of itself, anyone who decided to turn their back on society altogether was going into a much scarier place.
So why do people turn their back on the rat race?
I suppose the obvious reason is because it is a "rat race". We only have so many years to live our lives, so why not enjoy at least some of it? And, as I have pointed out above, if we participate in a "system of exploitation" aren't we ethically bound to try and extricate ourselves from it?
If we start thinking about our obligations to others and the insecurity that comes from the frugal life, then the issues become a little more thorny.
The more I think about it, however, the more I come to the conclusion that "security" of any sort is more of a mental construct than an actual, real thing. In our modern economy a steady job is increasingly beyond the reach of most people. We all know that the physical health of either ourself or those we hold near and dear is also something that simply shouldn't be taken for granted. Even closer to the vein, we should also remember that our mental health is also something that can evaporate without warning.
In effect, all we really have to rely upon is the specific, particular moment of "now" that each of us currently inhabit. As we progressively move away from it in time we have less and less cause to assume any sort of stability or continuity. I suspect that the ancient Daoists understood this fact and had developed their own sort of personal accomodation to it. Perhaps the best known statement to this effect that modern Westerners know of comes from the New Testament:
That's why I tell you: Don't fret about your life---what your going to eat and drink---or about your body---what you're going to wear. There is more to living than food and clothing, isn't there? Take a look at the birds of the sky: they don't plant or harvest, or gather into barns. Yet your heavenly Father feeds them. You're worth more than they , aren't you? Can any of you add one hour to life by fretting about it? Why worry about clothes? Notice how the wild lilies grow: they don't slave and they never spin. Yet let me tell you, even Solomon at the height of his glory was never decked out like one of them. If God dresses up the grass in the field, which is here today and tomorrow is thown into an oven, won't (God care for) you even more, you who don't take anything for granted? (Matthew 6: 25-30)The Jesus of the Gospels seems to have believed in a literal Father God in the sky who would make everything right after we die. Like most modern people, I simply cannot believe in such a thing---it just seems too out-of-step with everything else we know about the universe.
But Daoists were different. Many of them did not believe in any sort of conscious existence after death. And those that did seem to have believed that this was reserved for a very lucky few instead of the many.
It seems to me, therefore, that most of these frugal-living recluses probably didn't believe that there was some sort of "cosmic insurance" policy in their hip pocket that would make the consequences of their life choices disappear at the moment of death. Instead, what I think they did was gain the ability to see beyond the comforting illusions that sustain almost everyone else (e.g. that bad things will always happen to the "other guy".) Once you do that, I suspect (for I'm not there yet, although, I think I get glimpses once in a while) that you realize that everything we do ultimately involves walking a high-wire over a bottomless void.
Once someone realizes that his life is not much more than a short existence on a high-wire anyway, he also realizes that doing without now in order to be better off sometime in the future is not much more than a case of gambling a sure thing for what might turn out to be not much more than moonshine. Wisdom comes from learning this fact in your bones. Serenity comes from becoming happy with it.
Personally, I think that I'm well into the "wisdom bit" but seem to have a significant bit more to go before I end up in the "serenity" part.