They will feel how the people tell them to feel (ideally).
Now, the real problem, how to change people's minds?
I see that as a job well suited to HN frequenters: intelligent, imaginative, creative people need to take their responsibility as harbingers seriously and evangelize for a better future. Smack one molecule at a time and eventually the whole pot boils. Show people that the way things are done are not necessarily how they must be done. As a group, we've done a pretty good job in certain areas but I definitely see a lot of reluctance to tackle macro-social problems with the same zeal as attacking other historical accidents that impede progress like Uber taking on cab companies.
It's tricky, sure, but its all in our collective head.
I absolutely agree that we are in a great position to influence debate. If anything needs to be disrupted, it's the political system. I wish more folks with our skill sets were interested in tackling something like that.
Let's try the previous scenario, then. Is it "freedom" to do easily automated mindless manual drudgery?
And what people seem to miss is that every task - even the task of raw creation or idea generation - can be considered trivial once you sufficiently understand the process behind it. Any job or skill can be broken down into easily digestible bits, and once that's possible the system can be automated and scaled.
Hell, company generation is the same way. Look at Y Combinator. They've created a system that generates companies in a very automated, predictable fashion. They have an algorithm for making companies successful. It isn't 100% successful (yet) but any self-aware system will improve itself over time as the process is better and better understood.
So while I would obviously prefer to be running Y Combinator than assembling brooms in a factory, I'm not sure you can consider one more valuable or "worthy" based off of whether one is more "free" or not, especially if your definition of freedom is something that can't be automated - aka reduced to an algorithm.
And while I agree that economic systems can and should be changed as we shift towards a post-labor society, I'm worried about political obstacles to that. Even in the height of the worst recession in 70 years, we couldn't get Congress to approve food stamps for people out of work. How are those same politicians going to feel about cranking the work week back to 20 hours and tripling the minimum wage to make everything balance out? And if companies end up having to pay the same in labor costs to offset their automating, then what's the point in them automating? Will we actually see automation-enabling technology (3D printing, robotics, etc) hit their own peak and slide backwards in the face of higher fees/social unrest/political change/etc etc etc?
It's a trickier situation than you're giving credit.