It is challenging to define freedom in a non political way in the current day and age. Most will point to political freedom as a true and just example of what the concept entails, however this is inaccurate at best.
Philosophical freedom is more complicated and, in my opinion, terrifying if realized. The concept of philosophical freedom, like so many things, comes from within.
The first realization is that true freedom (that is, the act or ability to be free) is not something that can be bought or sold. It is not something that can be thrust upon others and it cannot be declared for an individual or group. It is all in your mind.
The trick is not to apply this to everyday life. That is the misunderstanding we have when we consider the US to be free, and somewhere like the Republic of Rwanda to be not. This is political freedom and has very little to do with freedom itself and much more to do with liberty. Within Liberty you have greater choices, but none of them fall completely under the realm of freedom. One does, after all, have to pay taxes, earn a living and gain even a basic education.
With liberty you get rights which is important if you believe in social programs, health care, or education. True freedom guarantees none of these. True freedom, I think, means that you have the ability to do whatever you like. As far as I’m concerned this includes the choice to contribute to a society, or not. The choice to be employed, the choice to live with wolves instead of people, etc. It is the unyielding realization that the whole world is open to you if you want it.
Freedom realized, is very much like the concept of generating hypotheses outlined in Zen and the Art of Motorcycle Maintenance finding the first hypothesis is challenging. After that, it’s nearly impossible to not find something to test. It’s a multiplying effect. The staggering incapacitation comes only from the fact that we as people only have social obligations because we decided to. It’s easier to exist in a society that tells us what to do than to be faced with daily decisions about what to do, how to do it. We take orders and adhere to laws because it’s easier than making it on our own.
Freedom of expression is an interesting one though. Society as we know it allows for this freedom. We fight for it and call it art or individuality.
There is a concept out there though, that has something to do with self assuredness. It is one in which a person, an individual, is so comfortable with themselves that they don’t find any need to express it. They are not trying to prove anything to anyone. it has something to do with the shakiest opinions being defended by the loudest voices. You see the result of those people in the millionaires that won’t buy new shoes, or the IT personnel that won’t own a cell phone. They don’t have anything to prove to you or themselves. They don’t require that reassurance. They know where they stand.
Capitalism must hate these people. They have no reason to buy the latest of anything. Aside from replacing a broken piece of equipment, the only reason we need new things is because we’re told we do. We’re led to believe that we will no longer be accepted by our chosen peer group if we don’t get a new phone, car, laptop or set of clothes every year.
This is all our own fault. We cashed into a system by which we keep buying things to keep the economy moving. That’s the ball game. When people discover the inner freedom that says they don’t have to keep up with anything and stop desiring new things and thus buying new things, the economy gets mad. Prices go up on necessities, because you need to buy those. The value of a dollar goes down so you must keep working to buy those things and oddly enough, the price of luxury items goes down, because there is an excess, but mostly because they’re trying to restart the buying cycle. That coat you don’t need doesn’t cost nearly so much comparatively speaking. That's how they get you.
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