Democratic Socialism can work and has for many years in Europe, Australia and New Zealand. While I totally disagree with the basis for socialism and the thought of collectivism in general, I would much rather have a society where I have way more personal freedom and more socialized government (healthcare, retirement, higher minimum wage etc) than have a total free market system with no personal liberty which is where the US is moving. Ireland, New Zealand, Hong Kong (if considered a free country), and Australia are considered more "free" countries. In some indexes the US is down as low as the 40s in freedom from the government! It is quite an eye opener when some countries that you travel to seem more "free."
Socialism is not compatible with personal freedom because it imposes economic rights or a right to goods. Under any kind of socalism, freedoms must be taken from some and given to others.
Take socialized healthcare for instance:
"An alleged “right” to health care, like all other economic rights, imposes positive obligations on the parts of others to fulfill that right, and thereby necessitates the violation of other rights like the right to property. A “right” that is in conflict with other rights represents a contradiction that is resolved not by some crude moral balancing act, but by recognizing that economic rights themselves do not exist."
http://www.objectivistcenter.org/cth--1297-Right_To_Health_Care.aspx
"Let's begin by defining our terms. A right is a principle that specifies something which an individual should be free to have or do. A right is an entitlement, something you possess free and clear, something you can exercise without asking anyone else's permission. Because it is an entitlement, not a privilege or favor, we do not owe anyone else any gratitude for their recognition of our rights.
When we speak of rights, we invoke a concept that is fundamental to our political system. Our country was founded on the principle that individuals possess the "inalienable rights to life, liberty, and the pursuit of happiness." Along with the right to property, which the Founding Fathers also regarded as fundamental, these rights are known as liberty rights, because they protect the right to act freely. The wording of the Declaration of Independence is quite precise in this regard. It attributes to us the right to the pursuit of happiness, not to happiness per se. Society can't guarantee us happiness; that's our own responsibility. All it can guarantee is the freedom to pursue it. In the same way, the right to life is the right to act freely for one's self-preservation. It is not a right to be immune from death by natural causes, even an untimely death. And the right to property is the right to act freely in the effort to acquire wealth, the right to buy and sell and keep the fruits of one's labor. It is not a right to expect to be given wealth.
The purpose of liberty rights is to protect individual autonomy. They leave individuals responsible for their own lives, for meeting their own needs. But they provide us with the social conditions we need to carry out that responsibility: the freedom to act on the basis of our own judgment, in pursuit of our own ends; and the right to use and dispose of the material resources we have acquired by our efforts. These rights reflect the assumption that individuals are ends in themselves, who may not be used against their will for social purposes.
Let us consider what liberty rights mean in regard to medical care. If we implemented them fully, patients would be free to choose the type of care they want, and the particular health care providers they want to see, in accordance with their needs and resources. They would be free to choose whether they want health insurance, and if so, in what amounts. Doctors and other providers would be free to offer their services on whatever terms they choose. Prices would be governed not by government fiat, but by competition in a market. Since this is an imaginary state of affairs, no one can predict what mix of private practitioners, HMOs, and other sorts of health plans would emerge. But market forces would tend to ensure that patients have more choices than they do now, that they would act more responsibly than many do at present, and that they would pay actuarially fair prices for health insurance—prices that reflect the actual risks associated with their age, physical condition, and lifestyle. No one would be able to shift his costs onto someone else. In a truly free market, I might add, there would be no tax preference for obtaining health insurance through employers, so most people would probably buy health insurance the way they buy life insurance, auto insurance, or homeowners insurance—directly from insurance companies. They would not have to fear that losing their job, or changing the job, would mean losing their coverage.
So that is what liberty rights—the classical rights to life, liberty, and property—would mean in practice. The so-called "right" to medical care is quite different. It is not merely the right to act—i.e., to seek medical care, and engage in exchanges with providers, free from third party interference. It is a right to a good: actual care, regardless of whether one can pay for it. The alleged right to medical care is one instance of a broader category known as welfare rights. Welfare rights in general are rights to goods: for example, a right to food, shelter, education, a job, etc. This is one basic way in which they are quite different from liberty rights, which are rights to freedom of action, but don't guarantee that one will succeed in obtaining any particular good one may be seeking.
Another difference has to do with the obligations imposed on other people. Every right imposes some obligation on others. Liberty rights impose negative obligations: the obligation not to interfere with one's liberty. Such rights are secured by laws that prohibit murder, theft, rape, fraud, and other crimes. But welfare rights impose on others the positive obligation to provide the goods in question.
Health care does not grow on trees or fall from the sky. The assertion of a right to medical care does not guarantee that there is going to be any health care to distribute. The partisans of these rights demand, with air of moral righteousness, that everyone have access to this good. But a demand does not create anything. Health care has to be produced by someone, and paid for by someone."
http://www.objectivistcenter.org/showcontent.aspx?ct=14&h=53