Does having a job make you a phony? Well, it most always does, in various degrees, so let's take these three rules for now. Primo: never trust a man who earns a salary (or, more specifically, has a dependent source of income) – unless he is on minimum wage. People in bondage would do absolutely anything to "feed a family". Secondo: people who earn their living lying down (or standing up) are several times more trustworthy than those who do so sitting down. But don't just jump to all the wrong professions – I do most of my reading and some of my writing lying supine. Terzo: don't be fooled by money. These are just numbers. Being self-owned is a state of mind.
Some bank tellers are closer to self-ownership, given that they can easily switch to another job paying just minimum wage, while the chairman of the very same bank is, typically, a pure slave. The employees at the bottom cannot be easily forced to commit acts of desperation, or, say, fit their beliefs to accord with an action they have taken because they have to do so within their profession, rather than act according to preset beliefs. Such self-spinning justificatory strategy is commonly known as cognitive dissonance, as the person finds justification to resolve the mismatch between the initial set of mind and his subsequent actions. A banker, for example, can take crazy (but of course legal) actions loading the world with risk just to get a bonus, then subsequently find the justification that he is helping spur economic activity and that he is indispensable to society. Or people can indulge buying lottery tickets and claim – and believe – that they are doing it "for their children".
So unless they became ambitious and decided to upgrade their social rank, security guards, drivers of corporate cars, waiters, hotel cleaning staff, construction workers and similar employees are professionally free as their jobs are fungible. The distance between their current job and another one paying the same amount is very small, and there is a huge reservoir of jobs at the bottom of the pyramid – where reputation matters little beyond a clean criminal record and an official absence of psychiatric condition.
The chairman of the company, on the other hand, is scared of the security analyst who can give him a bad report, of the board of directors, of journalists who can say something unflattering, of his own vice-president looking to oust him (as he did his predecessor). Falling means a severe loss of status. He would be able to live a life materially acceptable to many, but would be losing his expensive car, his wine collection, his opera subscription, his country house, and, correspondingly, his second wife – which is not acceptable.
Actually, according to Seneca, fear of loss and actual loss are almost the same thing. Possessions are there to punish people unless they have a mechanism to handle it, hence his entire body of applied stoicism. Seneca, one of the wealthiest people in his day, wrote obsessively on one of the five hundred desks he owned about the poisonous aspect of possessions.
Self-ownership has little to do with externally-perceived status, but rather one's position on what is called the internal hedonic and social treadmill. Say you move into a new house, bigger and more opulent than your previous one. After about six months you will adjust to it, reverting to a happiness baseline. But if you lost the income to support the house, had to return to your initial endowment and move back to the old dwelling, you would be worse off than if you did not move at all. Add to this the external social dimension that should someone erect a palace next to your little house it will immediately shrink into a hut, leading to the same pains as if you did not start anywhere. This is the argument usually provided about the notion that money does not give happiness, which is not quite true. It should be rephrased that some people do not gain in happiness beyond a certain level of material comfort and safety, and strangely such a level is usually not too far beyond minimum wage.
To attain self-ownership you need to feel that you have no downside, which is why philosophers have traditionally been light of possessions – Socrates himself was rather poor. But this is not necessary: Seneca was rich yet knew how to avoid mental dependence on wealth. He managed to eliminate his dependence on external goods by writing them off daily, in order to boast that, should the event take place, nihil perditi, "I lost nothing".
The Greeks saw the world in three professions: artisanship, the craft of war, and farming. Only the last two were worthy of a gentleman – mainly on account that they were not self-serving and were free of conflicts of interest. A vendor of funereal goods could not be trusted to wish for the good health of his fellow citizens.