Why do we waste our lives as servants?

If self-employment is merely a "new boss," then why isn't self-sufficiency? Instead of relying upon the highly-developed apparatuses that society has created that enable one to achieve homeostasis and proceed through life, he is going to "indenture" himself to his bodily needs, creating far more work than in necessary. Is it better to be a "servant" to another than to be a "servant" to oneself? His point is incoherent.

Secondly, he presents this notion of a foundationally-flawed and perverse system, and asserts that he is going to leave it, without presenting an alternative. Suppose that one does reject society and become entirely self-sufficient. Then what? He appears to have no ultimate objective nor any motive other than disillusionment with the system. What occurs after he quits his job and builds a cabin in the woods? I'd rather be a servant to society where I know that I at least have nominal objectives and a context in which to live my life, than abandon everything and hope that a life of solitude (or whatever he intends to pursue, he was pretty ambiguous) is preferable to society.

His plan doesn't seem well-devised, and his explanation offers essentially nothing. Just because social arrangements in society are sub-optimal does not mean that abandoning everything is preferable, or even tenable.

Eh. If I had the means and the time to not be a servant, I'd go for it. However, I don't even have a business idea that I'm capable of executing on. So meh.

There is a third way, of being present in the world for your worldly obligations, and being able to pursue your personal/inner growth and experience as well.

Let's frame it in the "Autonomy, Mastery, Purpose" happiness rubric.

If you're smart, you level up to Mastery fairly quickly.

Once you're no longer an absolute novice, it's frustrating to spend your days without meaning or purpose. The novice finds meaning and purpose internally when learning. Once learning has plateaued, meaning and purpose come from integrating with society.

This is where the shackles of jobs start to erode your self: the masters at bad workplaces dole out meaning and purpose based on die rolls. They don't understand the connection between what people are good at, what they want to do, and how they should do it. You get told what to do. You have little leeway. When your choices are removed, the friction eats you alive.

Modern hippy startups try to get around the last part by letting people do whatever they want. Those companies can be pretty much counted on one hand though.

In short: companies exploit the Mastery of smart people while forcing you to look at Purpose through double slits and removing Autonomy resulting in your knobs of happiness being broken without you even realizing it.

Rent. Taxes. The very land your house is on.

Unless you become a master you are required to serve. If you don't find a middle-ground that is acceptable to you, the alternative is to live like a hobo.

Some people actually chose that.