The cultural assumption of a true free enterprise system would be: “Individuals are responsible for their own lives and labors. They trade as equals, but are beholdin' to nobody.”
Free enterprise isn't anything like big-corporate capitalism. We've been told the two are equivalent, but that's just another bit of cultural brainwashing.
Think about it. Job holders by definition aren't capitalists. Job holders, no matter how well paid they might be, function merely as the servants of capitalists, just as medieval serfs functioned as the servants of lords. They are beholdin'. They function in a climate of diminished responsibility, diminished risk, and diminished reward. A climate of institutional dependency.
The daily act of surrendering individual sovereignty – the act of becoming a mere interchangeable cog in a machine – an act we have been conditioned to accept and to call a part of “capitalism” and “free enterprise” when it is not – is the key reason why the present Job Culture is a disaster for freedom.
James Madison, the father of the Bill of Rights, wrote:
“The class of citizens who provide at once their own food and their own raiment, may be viewed as the most truly independent and happy. They are more: They are the best basis of public liberty, and the strongest bulwark of public safety. It follows, that the greater the proportion of this class to the whole society, the more free, the more independent, and the more happy must be the society itself.”
Madison was speaking specifically about independent farmers, but he was also a believer in the independent entrepreneur – and for the same reasons.
Madison (and his like-minded friend Jefferson) knew that people who are self-sufficient in life's basics, who make their own decisions, whose livelihood relies on their own choices rather than someone else's, are less likely to march in lockstep. Independent enterprisers are far more likely to think for themselves, and far more capable of independent action than those whose first aim is to appease institutional gods.
Living in the Job Culture, on the other hand, has conditioned us to take a “someone else will deal with it” mentality. “I'm just doing my job.” “The boss makes the decisions.” “I'm just following orders.” But if someone else is responsible for all the important choices in life, then we by definition, are not.
I reminds me of my favorite part of Paul Graham's essay on "Why to not not start a startup":
16. A job is the default
This leads us to the last and probably most powerful reason people get regular jobs: it's the default thing to do. Defaults are enormously powerful, precisely because they operate without any conscious choice.
To almost everyone except criminals, it seems an axiom that if you need money, you should get a job. Actually this tradition is not much more than a hundred years old. Before that, the default way to make a living was by farming. It's a bad plan to treat something only a hundred years old as an axiom. By historical standards, that's something that's changing pretty rapidly.
Now we look back on medieval peasants and wonder how they stood it. How grim it must have been to till the same fields your whole life with no hope of anything better, under the thumb of lords and priests you had to give all your surplus to and acknowledge as your masters. I wouldn't be surprised if one day people look back on what we consider a normal job in the same way. How grim it would be to commute every day to a cubicle in some soulless office complex, and be told what to do by someone you had to acknowledge as a boss—someone who could call you into their office and say "take a seat," and you'd sit! Imagine having to ask permission to release software to users. Imagine being sad on Sunday afternoons because the weekend was almost over, and tomorrow you'd have to get up and go to work. How did they stand it?
I have a plan to fix this, but it's a little difficult to describe because people have a hard time thinking outside of the surf mindset, the assumptions that underlie the "job culture". It will take some time.