This is how I became a libertarian (aka anarcho-capitalist) basically. Long nights not being able to sleep because my head is running thru "How to run all of society" instead of resting for work the next morning. I realize now the vanity of even trying to sort out how society should be governed, but I was a Chavez loving leftist at the time.

Anyway, from a former leftist perspective, these questions aren't really that effective. Why? Because the left believes in self-sacrifice for the benefit of the collective. So in every example where you ask if you want such and such at a cost to your own liberty, the answer would yes. They don't have this double standard and are willing to risk a self-imposed tyranny if it serves the greater good.

So, for me, breaking through the notion of a greater good was what brought me around to anarchy (capitalism goes without saying in a free society). Anyway, here are some self-debating questions from a leftist angle:

1. Do the means justify the end? Does the end justify the means?

This is really the heart of the matter. If the end is the pentacle of human flourishing (as every ideology maintains), than the means are our only path to such a society. Brick by brick we have to work towards a better world.

1. If the means are immoral how can the ends ever become moral?

If our goal is a better world, how can immorality and injustice be the path forward? This is where the idea of taxation starts breaking down as a tool for good. If we build our society on a rotten foundation, no amount of redecorating is going help much.

1. Read up on the history of socialism. It you want the lesson of "the road to hell is paved with good intentions" hammered into your skull with resounding monotony , this is the way to do it. I got into socialist history as a fan of socialism but I came away completely disgusted.

As I said, I was a Hugo Chavez supporting socialist at one point. If I had live in Venezuela at the time, I'd have been 100% in support of the socialist revolution there. Fast forward a decade plus and people there are eating there family pets and zoo animals because they can't keep groceries on the shelves. It pains to me to know I supported these policies all because I wanted less people to suffer. But all the good intentions in the world are worthless when implemented via a system of coercion. They get corrupted from the outset.