You may ask how you know whether your life is evolving in desirable ways.  If you make such an inquiry, my guess is, you already know the answer.  Yet, will you choose to do anything about it?

Consider where you focus your attention. How you perceive your life shapes it more than your realize.  Your imagination is the canvas. You paint the canvas with visions and dreams and things you would like to happen.  You do this on a conscious and subconscious level. Your feelings can undermine any original ideas and goals.

For example, you may aspire to follow a life path yet, deep down, fear success.  If this is true, your choices may systematically make it very difficult to follow that chosen path.  In effect, you may not really desire to follow this path at all. 

At any time, you're surrounded by options.  You tell yourself if you really desire to do what people tell you and what you may think you tell yourself.  Your future person is talking to who you are now. This may seem hard to grasp, to be in two places at once.  Yet, the only way to get yourself to where you wish to be is to already be there, and look back to how to get to where you already are.

Turning points are like milestones.  You sense you're on the right track in life, making decisions that happen in what you perceive to be a logical sequence.  Changing who you are doesn't have to seem like you're losing anything.  In fact, the healthiest changes are those that enable you to overcome fear and see that what you're gaining is far better than what you ever had or how you previously felt. 

Ultimately, its not really a question of losing or gaining but rather, transforming. You forget who you were because you're so excited about who you are.  Being 'in place' is happiness.  Anything else you simply invented to cloud the real education.