How do our experiences change us and our philosophical outlooks? It is less "experience changing us" and much more "experience becoming us". — Bitter Crank
But we tend to be involved in situations which reinforce our pre-existing traits. Most people go through their lives enacting some variety of the Freudian "repetition compulsion," similar situations arise over and over to which we respond in similar ways. It is only with recognition of this that the notion dawns of wanting to experience life in a different way.
When I was quite young I mostly read Sartre. Eventually, contemplating his notion of "radical freedom," that we are so free that we can choose to do anything, even to the extent of doing something radically different from our normal predispositions, I had a clear intuition this was an essential truth. I began to consciously strive to enact this choice. Instead of choosing to avoid doing something I didn't really like doing, like going to a party with a bunch of people I didn't know, I chose to do the thing that I didn't like. Not only do it, but embrace it, be outgoing and gregarious. And the opposite, refraining from doing some things that I would otherwise spontaneously do.
After having done this a few times, it became obvious that this worked. People see us as we present ourselves. We are what we do. The more I did this, the easier it became to make choices, not based upon past habits, but upon a reflective/intuitive sense of the direction in which I wanted to go, who I wanted to be. The transformation took a long time, and is still on-going. But I do feel that now I have the power to take responsibility for the quality of my own experiences, maybe not always, but overall.