In his book, The Hungry Spirit: Beyond Capitalism, A Quest for Purpose in the Modern World (1997), Charles Handy describes the problems he faced in determining his ideal self, in a passage that he calls ‘Proper Selfishness’:
“I spent the early part of my life trying hard to be someone else. At school I wanted to be a great athlete, at university an admired socialite, afterwards a businessman and, later, the head of a great institution. It did not take me long to discover that I was not destined to be successful in any of these guises, but that did not prevent me from trying, and being perpetually disappointed with myself. The problem was that in trying to be someone else I neglected to concentrate on the person I could be. That idea was too frightening to contemplate at the time. I was happier going along with the conventions of the time, measuring success in terms of money and position, climbing ladders which others placed in my way, collecting things and contacts rather than giving expression to my own beliefs and personality.”
In a section that he calls ‘Proper Selfishness’ Handy goes on to describe the importance of a strong sense of self and the challenges of remaining true to oneself as the world throws up all sorts of opportunities for us to be someone who we are not.
I highly recommend a read of Proper Selfishness (pdf)