At which stages in your life did you start questioning your own self?

Depends upon how you are asking this question. Are you talking about questioning yourself negatively, as someone who is failing in some aspect of life or are you asking this question more as an inquiry into yourself, as to who you actually are?

Well, most people do the first type of questioning, and it is fairly obvious that a person does this when he/she is not meeting with some success he/she has been desiring.

A more serious and more deeper form of questioning is when you start inquiring into oneself as to who you are, what are your motives in life, what is your purpose of life etc. This questioning happens when there is a sense of discontent that arises with everything in the world. Nothing in the world seems to give satisfaction. There is a sense of emptiness and loneliness, a sense that no one around you is understanding you. There is a vague feeling in oneself that there is something more to life than what one is currently seeing.

We are born into a world in which everything seems to be given. You don’t construct your world on your own. You don’t choose your education, you don’t choose the social structure or the economic or political structure of the world. Our schools, parents, organizations and religions rarely, or never help us in questioning life. Since childhood we are schooled into a particular way of living. Therefore our self is conditioned by all these forces. As we grow older, the conditioning gets more and more rigid. The society has it’s system of rewards and punishment which reinforces the conditioning in every individual at every stage.

What if you would like to know yourself without this conditioning? What if you would like to live life utterly newly, something beyond what all the traditions have established. One can see that even a possibility for such a question to arise is almost impossible. But if it does at any stage for any individual, it is the beginning of his awakening from a mechanical and conditioned life, to a life of freedom.

The conditioned life of society is built on fear and desire. The society trains your mind by rewarding if you follow it’s values and punishes you for not following it’s values. For example, the society rewards you with so many things if you have money and punishes you if you don’t. Your self worth is tied to the amount of money you earn. A person who wants to question oneself would see if there is anything of real value in earning money, or is it just a conditioning one has absorbed from society.

Likewise, there are many, many areas where one has just accepted things; like in religion, science, politics, sociology. A person who is questioning oneself to fit into society will continue being trapped in fear and desire. Whereas a person who is really asking these questions to himself as an inquiry, and who is not really interested in fitting into society, such a person has the possibility of finding a totally new dimension of living for humanity.