Compare with something like unemployment benefits. The cost of benefits can be covered by taxes (which unlike the example above) can be progressively targeted and redistribute wealth to those most in need.
A social safety net is progressive, feasible (countries all around the world have them), and does not hinder technological or economic progress. What are the alternatives?
The expectation for everyone to retrain and do something else is not necessarily reasonable, especially in an environment that does not have much of a social support system for education, training, and extended periods away from the workforce.
And we all know that the market doesn't magically make replacement jobs better or the same as the previous ones.
The way I'd read this sentiment is that the arrangement of society is ultimately arbitrary and if we could only choose a different system we could by truly free. I'm not sure if I'm reading you correctly or not. That said, my impression is that people will not really be able to get away from something like that looks like traditional jobs. The core traits seem to be group dynamics, hierarchical competition, status-attainment -- all where resources are not infinite nor are opportunities for status.
We've already had sufficient technological advances such that people would not need to do much labor, but functionally speaking I just don't think people can organize themselves into _any_ possible arrangement. I think the potential arrangements that could exist are limited by nature.
We could have had (practically) limitless fusion energy if we had chosen to invest the money earlier. We could have had the fantastically cheap solar we have today decades ago. We could have had non-polluting electric public transit across the country instead of private cars.
The people with the power and hoarded resources to do so have consistently made decisions to preserve that status quo at any cost. Our leaders chose to abandon space, to continue burning fossil fuels, to dismantle and demonize public transit.
We could choose these things. It is absolutely within our capabilities as a species. Anyone who tells you otherwise is either trying to manipulate you or simply lack the imagination. We could moonshot our way to post-scarcity in a decade or two. It's just that those with the power to make those choices have vast incentive not to.
I posit that until this point in history there has never been a time where technology would allow us to grow and distribute food for free (in terms of both financial cost and labour of time). With the rise and convergence of AI, robotics, low-cost renewable energy, advances in optimal light-biomass conversion, diminishing costs on vertical farms, and self-driving vehicles, we have within our reach a way to produce food at essentially no cost.
Think through what would happen to society and our economy if food was free for anyone, anywhere. Think about the meaning of work.
If these ideas intrigue you, beta are readers wanted, see my profile for contact.
By wholly automating food distribution, from seed to delivery, we eliminate the costs of high-quality, nutritious food, relying on volunteers for infrequent system maintenance. (This requires bootstrapping capitalism; I won't dive into the details here, because it would take a book ...)
Aside, that diagram is in the novel and was drawn about ten years ago.
I have lost faith that other people who are not in my situation will do kind, high quality work for my benefit over long periods of time (my lifetime.)
I have a crazy dream of single families or neighborhoods owning land and owning lots of cheap open source robots that tend crops and maintain one another over time. And when I say cheap, I mean not worth the trouble to steal. Big backyards in urban settings will be coveted, community gardens everywhere. The software to run it would be open source and free, it would be designed to not deplete the land.
Maybe in my scheme no insecticides are needed because the robots can spot them as they enter the fields and kill them with pinching armatures or pew pew lasers.
My dream is probably stupid in a million ways and impossible unless I get lots of F-U money to do it myself. I imagine big ag interests would make it impossible to succeed and then I'd need 2x F-U money to out-lobby them. ;(
I promise you as an anarchist agitator that is unbelievably new just even in the last couple years and precisely what usually happens prior to actual direct action.
My fellow anarchists hate the fact that Donald Trump did more for anarchist-socialist praxis than every other socialist writer in history.