Diogenes walked backward across the Agora. He kept an indifferent, calm expression, despite the throngs of people surrounding him, who turned to look, snickering, and laughing. When he eventually gathered a large enough crowd, wondering what he was on about, he stopped, and yelled to them:

"You laugh at me for walking just a little distance backwards despite the fact that you all have lived your whole lives ass-backward. And what's more," he asked, "can you change your way of living as easily as this?" Whereupon he turned on his heel and walked off in a normal fashion.

A fool's game

Don't join, or aspire to join, the "middle class".

The more I think about this game, the less I think it makes any god damn sense.

The entirety of the middle class is based on a sensitive and fleeting position, that more or less requires you to be saddled with debt. Chain yourself to go to college. Chain yourself to get a house. It piles you with obligation and fealty to creditors and capitalists for years, so that you can enjoy a mildly more comfortable life today. In this century, being part of the middle class will be a loser's prospect; ultimately, your position will become the modern equivalent of the serf, except instead of working the lord's fields and giving him a share of the crops for your lifetime, you will work your own specialized means of production which you had to promise a share of a more abstract form of income, across your entire existence. And since the 70s the capabilities offered by this lifestyle have slowly shrunk and in some cases stagnated; what took one income now takes two, and so on. The middle class is it exists today is an aberration of history that will disappear into the lower classes from whence it came.

The middle class life as advocated by the general populace today is the life of what Aristotle called "natural slaves." People who do not think, but do, and allow the actions and suggestions of others to dictate their future. People who live but to be a tool for the owner that they have willingly and oftentimes happily selected. People who work to make other people rich. People who select safety and comfort in their chains at the expense of their freedoms. And in the end, with this sort of life, what will you have done?

You will be in a situation, where everything that ties you down in a psychological Celtic knot. You can't get rid of your expensive car because you have to drive 1 hour to work, which you need to do because it's the only place you can afford that's big enough to escape to after spending all your day doing things you don't want to do. Which you need to do now, because you have a car and house that's expensive and on loan, and so on. You've in essence entirely manufactured your own misery, pulling yourself into a natural state of slavery, which everyone else around you has perplexingly convinced you is the correct thing to do.

This loop of obligations and debts will stress you excessively and kill you as a person while you sink deeper and deeper into the creditor's intellectual traps. It also removes your flexibility; by taking on these obligations you are now for some unspecified duration committed to generally holding the life you currently have, even if circumstances change, and you are deeply unhappy. You then end up buying even more things to fill holes you think you have in your life, and you eat bottles of pills just to cope with the fact that you have built a life that is fundamentally contrary to human being. The additional stuff you have now becomes an additional thing that ties you down, because you now need to store this junk somewhere or maintain it, necessitating bigger habitation and more stressful, possibly less interesting and more time consuming positions, just to get by.

In this state, you've essentially lost your sense of self-worth and now define yourself purely by your vocational relationship with others and how many liabilities you can support. You only have other-worth. The loss of freedom that you experience is in fact, so internalized – so deep in its totality within your being – that like a cow in a pasture, you do not even consider the idea of leaving. The idea has faded away. Your dreams are dead. You have given up on yourself. Your best hope has become the possibility that your boss might increase your meager allowance and change the label you can refer to yourself as (while internally at the weekly manager meetings you are still a "resource" being quantitatively measured with all the glory of a sprocket).

And when wider economic conditions change – a great depression comes, or the next round of resource wars start, or like a newspaper typesetter your job is automated away, or like a milkman your job has been severed because the need it fulfilled is no longer there, or any myriad of other conditions – your life will go down the toilet, because you never really owned any of the things you said you owned; your masters just permitted you to have those things for as long as you produced for them.

What's the smart game?

It's actually very simple:

1. Don't ever get into debt unless you absolutely, positively have to. Build credit with a card, sure, and have a little available for the case that you actually do need an emergency loan, but generally never keep debt balances which roll over to your next due date. If you do have debts, endeavor to pay them off as soon as possible, or even trade down assets until you no longer need to hold debts.
2. Use what money you have to maximize your intellectual and physical assets and minimize your liabilities. Assets in this case refers to things and means that will allow you to produce for yourself or allow your money to produce money while you become capable of acquiring an asset. Liabilities in this case are things that will be a continuous cost burden. Everyone has and needs some set of liabilities no matter what. For instance, you can't change the fact that you need both food and shelter (but just because you need it doesn't mean you can't optimize it).

By doing this, you eventually will be able to avoid being beholden to anyone. Things will no longer hold power over you, and instead you can instead dedicate your time to building ways to exert your control over things. You are no longer stuck to the life of a mere villein. At first you might not have as much as the serf does, but you will also hold none of his burdens and in the end, you will have more than him in ways he may not appreciate nor understand. You will live below your means and maximize your capabilities, while he will live at his means and work mostly only to keep what he has borrowed (for when he has paid everything off today, he will borrow for something even bigger tomorrow).

While the serf is stuck walking backwards all his life, you will be able to turn on your heel.