> My tentative theory is that the systems, incentives, and technologies in modern world have managed to slightly empower the individual, and massively empower large organizations, but at the significant expense of small organizations [...]
The large organization are turning to rent seeking, which adversely affects the liberty of the average individual.
Claiming that it has "slightly empowered the individual" is a reflection of where you are in the current social structure. If you've fallen below the line, then you're certainly not empowered at all, and more like you're enslaved. And that line keeps on going up.
The corrosiveness of increasing housing costs and health care costs are examples of this. The fact that individual transportation is both necessary and is likely to turn into a subscription-model is likely to be another example.
Regulatory capture is also a part of this. Large organizations enjoy the complexity of government regulations (while at the same time screaming about it) because they have the resources to navigate it, and they enjoy near monopolies which allow them to pass the costs down to their customers. And we've entirely forgotten how to break up monopolies, like we did with AT&T.
Also, most organizations these days exist to capture profits for the people who lead them. And this can even be seen in left-leaning political organizations that are more concerned with fund-raising than solving the problems that they're supposedly addressing (the DNC being the most massive example of this).
All of this corrodes individual liberties of the average person. It just may not have caught up with you yet, or you may have lucked into the resources to avoid it.
This is why I'm a left-libertarian anti-capitalist. The problem that we have today is too much power in the hands of large organizations (the fact that organizations are led by individuals, however, is not a logical contradiction -- the problem to solve here isn't a simple rule to limit the ability of individuals to work together, but an optimization problem to increase or maximize individual liberty, which necessarily results in a push-pull tradeoff at the interaction between individuals and groups that they might participate in). All large organized groups (Religion, Government, Corporations, Unions) needs to be restrained in their ability to exploit individuals. What we have now is that Unions have been destroyed and Government and Religion largely do the bidding of Corporations and their billionaire owners.
(Billionaires being individuals is also not a logical contradiction -- they have so many resources they may as well just be massive organizations -- employing hundreds of people and owning all kinds of property)