That is something I tend to reflect a lot too. How much liberty and individual identity we trade for some comfort and integration, when it comes to culture and tradition. We humans in society are like a bird that lives inside a cage with the door opened. Afraid of the world, predators and hunger, with fear and anxious about future, the bird chooses to live inside the cage, because he finds there food, water and a known world. I imagine conservatism and established culture/tradition as this scenario, where we, afraid of the world and the unknown, trade liberty for some comfort. The greater the social comfort, the greater is the liberty fee we pay these days.

Culture is sometimes also a trap, because it is fast food for the mind (it is easy to follow the same religion of our parents without questioning; the same ambition the society has regarding money and a good job playing the good employee game; the same social standards regarding a relationship and marry even if it is not for love, or having tons of kids because government says that economy needs a baby boom even if there is too much people in the world doing harm to nature and half lives in misery without care, etc...).

I fear becoming a trapped bird, so I despise the cage, try to question it when possible in the limits of my consciousness. Because of that I always felt like an outsider wherever I go, and someone with a mask, working, living in society, but just observing, not integrated. But in the other hand, in the extreme of living in the bird’s cage, wandering trough the woods of life alone, in hunger, thirsty and cold, outside the cage and against it, it is also not much liberty, since we can become prisoners of sadness and misery. Maybe there is a middle term somewhere, where we can be free of pre-determined ideas/norms/culture/society and happy, in harmony with the world at the same time. I think your way of life is an answer to that. You are not inside the cage, but at the same time you're also not in the rainy woods, in hunger and misery. I see great joy in your life. Your way of life is very inspirational for me, because I think you found a middle term I seek for and hope to find :)

I always loved Diogenes, I always thought of him as one of the greatest free man. Your text was a nice reflection. Thinking about Diogenes as one of the first liberals is a refreshing way of looking into this great free man  And I didn't know most of them lived in a different polis than where they were born, thanks. Maybe culture (meaning = as society norms and traditions) is like an Opium to the soul, and one must be careful with the doses to not be a prisoner of it.
Diogenes would be proud of you, you're a nice guy that turns Philosophy into something real trough your life, keep it up :)

PS: I confess - I’m a little lazy writing in English, since it is not my main language and it takes an extra effort to use >.< That’s why I take too much time between my answers sometimes :)