- Republican conservatism (raised in a Republican household) to
- pseudo-communism (some crazy idea I had in high school without reading Marx) to
- Objectivism (a friend gave me The Fountainhead while in college, picked up Atlas Shrugged shortly after, then Capitalism: The Unknown Ideal and Peikoff's book on Objectivism) to
- utilitarian liberal (introduced to Mill in a course on political philosophy (along with Nozick, who is unconvincing), studied more utilitarianism in other courses)
Note that I'm a utilitarian first, and liberal by implication of (my) utilitarian logic. I'm also aware of the bevy of criticisms that have been leveled at utilitarianism, some of which are persuasive (the Greatest Happiness Principle does not adequately address the complexity of moral psychology), while others are simply demanding a precision of calculation that's not attainable. In practice, one can successfully apply utilitarian reasoning in a great many situations.
The problem that I have with libertarianism is that I don't buy the "negative rights only" stance (at all), and believe that social interventions backed by force of law are necessary to overcome historically and sociologically entrenched inequalities of opportunity (positive feedback loops of discrimination and decay). That we haven't done it as effectively or efficiently as we would like doesn't mean that it shouldn't be attempted at all. There's room for experimentation, and we're getting better at experimenting. Many of the recently developed entrepreneurial practices (fail early) can be fruitfully applied in this area.
I grew up a Socialist in a Socialist house hold. I spent much of my teenage years in all kinds of "important" positions in a socialist party in Denmark.
Then I became an entrepreneur and my whole world view changed. I didn't read Ayn Rand or any libertarian literature until 15 years later, but my world view changed completely during a year and I became what I later realized was a Libertarian. Most of my opinions are based on observation.
This also frustrates me sometimes with other libertarians (and in particular Republican's) is that they don't understand where socialists come from, so they often have difficulties communicating with them.
I understand all the arguments socialists make because I used to make them. But I also understand that their reasoning is based on absolutely flawed understandings of economics and human behavior.
I would recommend anyone reads Marx's Communist Manifesto http://en.wikipedia.org/wiki/Communist_Manifesto as it expresses the basic ideas behind not just Communism, but socialism as a whole and to a somewhat smaller extent the more left wing parts of the Democratic party in the US.
It would also be useful if Republicans, "liberals" and socialist had a quick read of Adam Smith's truly profound Wealth of Nations as this is kind of the libertarian equivalent of Marx's writings. So they would actually have a clue what we believe. PJ O'Rourke wrote a pretty good cliff notes edition of it:
http://www.npr.org/templates/story/story.php?storyId=6743689