The Machinery of Freedom: Guide to a Radical Capitalism by David D. Friedman
This book has a number of small chapters exploring an extreme libertarianism. The start focuses on changes that can be done to our society to get here. He observes that government has problems with prioritization and influence. Even policies as innocuous as social security end up taking from the poor to give to the rich. (The rich start work later and live longer than the poor.)
The book was originally written in 1969, with some minor notes and updates in this third edition. Some things have changed since then. Other ideas have been sort of implemented, but twisted so much to make them unrecognizable. He proposed a "ride sharing" system as a solution to urban mobility. A jitney service would pair people heading towards a destination with those that need rides. This would provide low cost mobility for riders and minimal-effort extra income for drivers, all while reducing congestion. This sounds just like the original vision of Uber and "ride-sharing" services. Alas, these services have morphed into unionized taxi services. Drivers have become quasi-employees that wait around explicitly to give rides to people. It makes traffic worse, and is more costly to all involved.
Government interference is a problem that continually grows. Parties may identify ways to benefit in the regulatory framework, resulting in new regulations to address those. Entrenched parties are reluctant to change. Teachers' unions are willing to advocate for increased education funding "in the name of the students". However, they are reluctant to advocate from an education system that eliminates their roles, even if that would really benefit students.
There are frequently mismatches is the number and degree of benefit. Industries are significantly impacted by the regulations and take an active role in writing them, often to the detriment of individuals. The American Medical Association is given as an example. It is in their interest to make it harder to become a doctor. They also benefit by limiting access to other types of medicine. They have helped encourage the current drug and licensure system. The system is geared to minimizing harm, rather than maximizing benefit. A drug may be delayed because 2 people were harmed - even if that delay caused 2000 people to be harmed due to the lack of the drug.
The end gets a little more modern. He ends the book with a discussion on schooling. He advocates unschooling - that way learning could be the focus rather than going through endless boredom and indoctrination. That also allows children to adopt more of culture from their parents instead of just from school.
He has arguments for just about any concern, from police force to military. There are also plenty of criticisms of government, regulation and democracy. Allowing everything to be bargained out would make things function ideally. However, the concern I see is that it would be a lot of work. For those that are motivated, anarchy can be great. For those that just want to sit back and let life happen, haven government, unions and all the institutions may be easier. It will not get you the best results, but does not require work. Alas, I feel that the world today is dominated by the lazy.
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