I think he does not do a good job of analyzing the value proposition of "freedom" in this context. Freedom definitely is a value by itself, but he just posits a

I think he does not do a good job of analyzing the value proposition of "freedom" in this context. Freedom definitely is a value by itself, but he just posits and accepts that being a contractor gives you more freedom than being an employee. There are definitely counter examples, for example the cleaning personnel in many hotels is working on a contract basis. The more general observation is that being a contractor only gives you freedom if you have relative market power over your employer/contract giver. The same applies as a regular employee, but less so: there is value in retaining a skilled labor force, and employers are more reluctant to give that value up by firing people, as compared to contractors. (Also, many legislations restrict hire and fire of employees, but that might be a different topic.) Given a very acute risk of not finding any other contracts, contractors might find themselves having to live up to demands of your employer, ultimately ending up being less free than an employee in a comparable market.