Good thread, Matt. While I don't see a way out of the present dependence upon the division of labor (at least, none that wouldn't require generations to come about), I can see your point. There are times I would, personally, like to be able to at least make my income from all of the several talents I possess, thus becoming more self-actualizing, and perhaps providing a better lifestyle for myself. However, at the same time, I realize that I do some things better than others and so I might have to limit myself to just two things I do well: the one I'm employed at now (architectural drafting/CAD) and the one I aspire to (writing). I have other skills/talents, as well, but I don't believe I could generate much income from them.
I'm afraid that in our present society, most of us simply aren't equipped with the skills, knowledge and talents to build our own shelter (I could design my own, but I'm all thumbs with tools), make our own clothing, etc. The days of the self-reliant pioneer are long gone. Instead, today we are a society of wimps who, if the grocery stores ceased to exist, would starve to death.
Our dependence upon the division of labor is a lot like the dietary wrong turn mankind took 10,000 years ago, when we got off onto cultivating grains and domesticating livestock for dairy. In both instances, we've gone too far down the wrong road to turn back. In the case of diet, it's a sad fact that most of the world's population can't afford meat and, instead, subsists on a grain-based diet, replete with all the dietary illnesses that come with that, including rickets and scurvy. So, there is really not much hope for those in the Third World ever returning to a paleolithic diet. We in the affluent nations can afford it, so only a very small segment of the world's population will ever get back to eating the way our ancestors did. Same thing with the division of labor. We've gone too far away from the days when everyman fulfilled all the functions and executed all the tasks he needed to survive in the world. Today, most of the world are dependent upon others and those others are dependent upon us. But, consider that these two paths are what lead us to "civilization," in the first place. Without cultivation of crops and domestication of animals, we would have remained nomadic hunter-gatherers. It was this grounding in agriculture that allowed man to live in permanent settlements, which evolved into cities. It was the division of labor that allowed us to expand our civilization to unimaginable sophistication and complexity. The road back to where we were is harder one to follow than staying on the same path, at least as most people see it. As long as people are more concerned about where they left the remote and what game's on TV tonight than they are about learning the skills they'd need to survive in the wild, if they had to, we will probably continue as we have been, as sad as that is.