Ideological Turing Test for Stuff I Used to Believe

I used to hold a different set of beliefs from what I believe today. I was once a fairly standard “progressive” lefty, perhaps with some libertarian leanings. Today I’m a pretty staunch libertarian. You’d think that having spent most of my life in a different sort of worldview would have granted me deep insight into progressive ideology. Actually, whenever I see weak leftist mantras pasted all over my Facebook feed, I get irritated that anyone could present such a silly argument. I still understand the superficial appeal of progressivism, but this appeal wilts under even a cursory analysis.

So what’s going on here? Why can I not muster a defense of a position that used to be my own? I can think of two competing explanations.

1) There is an intellectually sophisticated version of progressivism, and I just never learned it before I abandoned ship. Most progressives walk around with this sophisticated viewpoint in their heads. I just never got around to learning it.

2) Progressivism is intellectually shallow. It really does wilt under careful analysis, and even more careful analysis fails to exonerate it from the obvious criticisms.

I want this post to be about the general process of changing one's mind, not a troll-inducing smack-down of progressivism. If anyone is hung up on my poor choice of an example (of something I've changed my own mind about), replace it with something else. "I used to believe X, I've changed my mind and now believe Y. I changed my mind based on a deeper understanding and knowledge of the topic, not because of some personal/emotional appeal." I feel like in the case of progressivism I would fail an "ideological Turing test," where someone tries to fairly articulate a position they don't actually believe. I'd end up making a straw-man or somehow betraying my skepticism. 

I want to encourage the question, "What's going on here?" and perhaps discourage jumping to answer 2). If you've read deeply on a topic and it caused you to change your mind in a meaningful way, then you probably hold a sophisticated viewpoint. Possibly people who still believe X don't have your deep knowledge; if you could somehow impart your understanding to them they would change their mind to Y. But always entertain the notion that they will surprise you, perhaps even re-convert you.