Tailor your propaganda to your audience. When speaking to small business owners emphasise how the state is giving tax breaks to big corporations while putting a disproportionate burden on the middle class. If they have a strong aversion to the word socialism either avoid it using it altogether or try using that to your advantage: point out how the big "socialist" corporations like Amazon, Tesla, big pharma, big oil, etc. get subsidies and how the "socialist" banks are getting bailed out by the state at the expense of small business owners. Point out how these corporate monopolies are "socialist" because they are anti-competition and how they need to be broken up "for the sake of the free market". Use their frustration and redirect it against monopoly capital and the bourgeois state that props it up. Bonus points if you can get them to get angry at how much of their tax money the state spends on wars abroad for the profits of Raytheon and Lockheed and kickbacks for corrupt politicians instead of helping out small business owners.

At this stage of capitalist development it is impossible to turn back to free competition small proprietor capitalism. Attempting to do so would crash the whole system but those from the petty bourgeois strata who advocate for this often don't understand that. If they push for policies which undermine monopoly capital or the bourgeois state structures propping it up they will be inadvertently helping to usher in socialism faster. The petty bourgeois are not class allies but they might be useful if we can exploit the contradictions of capitalism such that they are persuaded for the sake of their own selfish, short sighted interests to turn against the pillars of the system: finance, insurance, big real estate, etc., and especially imperialism.

I've had conversations about socialism with people in my life who are well meaning. The thing I have found to work is to avoid using surface level words like "proletariat, socialism, etc." This is to avoid the thought terminating reaction they have to hearing red scare words.

Most people have hardships and struggles caused by capitalism, but they've been led to believe it's their fault or that the right flavor of capitalism isn't being used. My method is to talk about why those hardships may be happening due to capitalism, without saying the words "capitalism or ruling class". This allows them to listen and think over the concept that capitalism is destroying their livelihood, without recoiling and entrenching their position further.

In the case of shop owners, you can point out how corporations like Amazon can spend speculative money on undercutting smaller businesses like theirs through operations like the Gazelle Project and pay barely any taxes, being effectively subsidized by smaller businesses like theirs.

Despite being theoretically flawed, we can't deny the success Bernie Sanders's phrase "in this country we have socialism for the rich, rugged individualism for the poor" among the capitalistpilled Yankees.

Only with people who are genuinely interested in learning. Generally, they’re already close to me too. Strangers only want to yell their viewpoints at me. So, I either let them feel better about themselves or walk away.

Have any of you had luck with breaking down preconceived notions others may have?

I did, and I have many ideas for anyone wanting to better prepare themselves for these discussions.

I’d just like to be better prepared since apparently this is just something that happens to me.

Most people use [bourgeois] social media, ask them "out of curiosity", if they use any social media. This will give you two valuable insights:

• first, the main source of propaganda which instructs their worldview. We can easily identify propagandistic discourse by noticing how common it is, sometimes even word for word repeated by numerous people.
• second, the place where you will engage with content related to their grievances, and debate with people in the comments. The comment sections of Facebook and Instagram, for instance, are very lively and from there you can engage with multiple people with access to online research for you to back your own views

It was there that I was able to master my debate bro skills

I try to pick one thing with people.

Mainly because if you let people get a read on you they're always gonna be wrong, because many USians and Canadians are not intellectual, to put it mildly, and quite hostile.

But also because they can remember one point.