Perhaps the greatest victory of conservative politics in the West was convincing the working classes to vote against their own interests. The reasons for this vary significantly, but the point of mentioning in this is to contrast it with the left, in particular the educated left.
Universities have been a place for progressive thought for quite a long time, even if the political activity there waxes and wanes around it. The political views of students and staff wobble around in a (comparatively) tiny melting pot, and from there shape the political landscape a generation down the track. Economists tend to be fairly right-leaning, but are typically not as extreme as their political or pundit counter-parts. Engineers are apparently prone to extremism. No real thoughts on that last one.
The relationship between the powerful people in politics and the people that put them there is rather convoluted. Even in a representative democracy, there is almost always a political class that does not have much osmosis with the population at large (usually, is in bed with law and economics, which to be fair is what politicians spend most of their time legislating). Behaviours like pork-barreling and public relations seek to address this.
The Academic Left (if you'll forgive the rather broad brush) tends to want to be sincere. Even after their philosophising is successful, there will tend to be a split as the more politically minded groups are more comfortable with lying or black-bagging or whatever else.
Asking "What have labour unions ever done for you? Why are you paying that $2 per week?" isn't lying, per se, but the motivation is tremendously insincere, however effective it is. I won't defend every action of labour unions in the history of such unions, but they have had a fairly large hand in combating massive inequalities in power and wealth.
The Academic Left is a far cry from the people they claim to support. Assuming their claims are sincere, they are still from a much wealthier background and are much more educated than the working classes. Even today, with our relatively high social mobility, there is still a (metaphorical) wall there.
This is not new. A case study can be made from the Narodniks of the mid-19th century. Attempting to hold themselves to a higher moral code, the Narodniks made the mistake of romanticising the peasantry. The peasants were hardworking. Loyal. Rugged. Honest. Not machiavellian, but not stupid. The Narodnik strategies were based around these assumptions, and found themselves arguing with clannish, simple, illiterate people who didn't really understand the Narodnik philosophy, let alone find themselves agreeing with it.
The opposite case can be viewed at the moment, with a combination of the Academic Left and internet culture. Those on the left are condescending and act divisively towards reactionary conservative groups (say, MRAs, libertarians, whoever). This is done without the goal that such people might one day change such beliefs, or if it is fails to use tactics that would convert belligerents (e.g. "educate yourself" is satisfying to say, especially after having been asked the same question repeatedly, but on its own doesn't actually encourage anyone to educated themselves).
Both strategies alienate their target audience, namely people who the Academic Left want to change their beliefs. Perhaps this could be seen as an extreme group form of the idea that neither belligerence nor idealisation will make a person like you more. The opposite faction, the Academic Right (for what its worth) has taken public relations much more to heart.
I can definitely see some people refusing to cheapen their own values to promote their causes, but ultimately cultural changes are driven by such promotion. Be it yourself or someone else, someone has to do that "dirty work".
I don't know how to fix this. But it might resonate with some people. Haven't posted in a while. I have a pile of ideas but very little follow through at the moment.