The one thing i think immediately helps, if time permits (often, what could be arguments in everyday conversation with my leftist-friends, typically fade away from conversation, and some things they say are unhelpfully but inadvertently un-addressed), is to show that you are not nearly as ignorant about their philosophy that they almost always think you are guilty of.
Additionally, you can hold their philosophy (if only momentarily, and for the sake of argument) as valid, but utilize this understanding to provide good counter-points, which means doing the hard thing & not just give one-line or one-phrase answers.
Those are perfectly fine when your arguing with or against the choir, but are usually not very successful when your arguing with people of a different faith (to carry the metaphor).
I think dissecting the back-history of the US to the point of when it was created (1776-ish), and showing that we started out with minimal government (minarchy), and showing them that Republicans lie about their free-market rhetoric (I had minor success yesterday, in showing how some are doing the similar “all-talk, no walk” nonsense when they talk about “Going Galt”), & that the free-market implicitly requires no state government at all to actually exist.
Draw similarities between how a free-market system could in-fact be established in a similar manner that the US was established, via some sort of self-imposed exodus of interested people to a certain area of land (or artificial land, seasteading, colonies in space, etc.).
Sympathize that state-capitalism itself seems to inevitably yield to either increasing Fascism, or increasing Socialism.
Points for drawing upon Schumpeter (even if only via his wikipedia page.) for this argument, as he was a supporter of capitalism (I’m unsure as to how radical of an advocate he was, as it seems he was more a old-classical economist rather than strictly free-market), but gave the diagnosis of capitalism (in a state society), as well as democracy, inevitably leading towards socialism.
Make a major point that voluntary socialism is a valid option in the free-market, and that other voluntary economic activity and/or systems can be easily validated as well, and shift the focus on the more fundamental question (that goes beyond simply political point & counter-point) of whether something is voluntary or involuntary.
State-socialism, State-capitalism, State-anything is implicitly involuntary, & involuntary action is aggression, and is therefore opposed by libertarians and/or the free-market via the Non-Aggression Principle.
Optionally, point out the importance of being against coercion, even coercion that does not or not immediately threaten one’s life (such as jailing of a victimless-crime), via the slippery slope & unintended consequences of coercion & involuntary action itself.
Ask why must everyone be a socialist?
Ask why must you force people with jailing, which, the leftist may not consider the same as killing, but both are aggressive, non-voluntary acts upon the “selfish” person who does not wish to “chip” in their life & wealth into the socialist pot?
Ask, if they agree the state (to a degree) must be abolished (it depends on how radical of a leftist you are talking to), why must it be through involuntary action? Why must be in the name of murder, starvation, theft of property, theft of wealth, life, rights, etc.?
Ask why don’t they equate economic liberty with personal liberty? Do they know any economics? If they do not, or do not wish to know economics, ask if they have a replacement for economics that doesn’t involve coercion?
I don’t mean to say you should ask every single question, but those are a few you could ask. At some point however, they will probably ignore you if you ask too much, but they might also go on the offensive (& hijack the conversation) if you do not ask too much.
If you can, however, I would try to sneak objections to (what could be considered) a mis-conception of libertarianism being inherently left or right or anything.
If they do not accept this, I would consider (at your discretion) of pandering to their views & showing how the free-market would accomplish one of the central goals of Socialism (equality for the masses) via purely capitalistic and/or economically voluntary actions, rather than involuntary, coercive State actions, which cannot possibly make everyone equal, as the State (and Socialism) implclity require the redistribution of wealth.
Show that while the stealing of wealth from the upper class (not necessarily the elite or the inevitable oligarchy that forms within democracy) may make for satisfying schadenfreude, at some point the effects of stealing wealth from those who have saved & invested & worked hard enough to earn it legitly, will interfere with the economy, as these people would be the very ones who would help re-invest their amassed savings & wealth to projects & products that require such capital to keep economies of scale developed*.
- Economic territory is not my strong point, so take with a grain of salt.
Provide a different political axis (like say, to take a simple example, the Nolan chart) and reason that you used to be left and/or right, but since taking the quiz for the chart, and reading up on different points of view (slide in an implication that the leftist is close-minded, and try to leverage that guilt a little bit, especially if they are not an academic in training, or have not been exposed to extensive indoctrination), that you cannot agree with either the leftist or rightist views of politics anymore. hgh
You could also reason that, despite many well-meaning rhetoric & good intentions on the part of leftists, their inevitable outcome of their political views lead to the same extreme of rightism (Fascism) that they detest, only with their own views taken to the extreme (Socialism).
Perhaps most importantly, show them a few bits & pieces of empirical proof that rational, democratic behavior elected Hitler into power (google: “swiss study Hitler voting” for the source), or for other points you have pursued or plan to pursue next time you argue.
You could also show how Hitler easily managed to co-opt Socialism itself for his own political gain, and that this clearly shows that this would not stop any other wannabe-dictator or the vanguard from doing the same.
Extend this as a foundation for the suspicion of Socialism not being egalitarian at all, in the sense that an Olgiarchy inevitably (if not immediately) forms, and that really, Socialism is just another variation on the Oligarchy-Statist form of government.
Possibly further extend this as a possible explanation as to why Socialism never seems to “work” in every country tried, as an Oligarchy or competing potential-Oligarchies vie for control of the State.
If an Oligarchy forms, Socialism will never be egalitarian, but egalitarian-lite will be the rhetoric they will utilize in order to continue to be “elected” (Comrade Chavez recently re-confirmed that you don’t really need to get elected to get the job).
Socialism is merely the Oligarchy privatizing gains, & socializing the losses, to the extent that the “people” can tolerate (scrape a living) without revolting.
The main point should honestly not be about winning (sometimes this helps, though), imo; the main point should be to try your best to at least make some doubt grow within your opponent, for that may make the next argument easier to argue.
Given enough doubt, you will not need to argue much at all, in some cases.
One at least hopes the persistence of free-market arguments at the very least cracks the self-indulgence of leftists & rightists thinking that their dialogue is more important than any other dialogue or other arguments.