How unfair of a question is that? Have you ever asked someone else that question? Have you ever asked yourself that question? In both cases, that question has danger written all over it for two reasons. One, asking that question implies, when coming from a place of insecurity, that you do not fit your own description of "enough". Two, your description of enough is probably describing someone you are trying to become.
Why do we want to know the answer to this question so much? Insecurity? Pride? Control? All of these things come to mind when I try to answer this question for myself. It certainly does come from a place of insecurity for many people. They want to know that they deserve what they have in life or that they were not at fault for any past losses. That is also what makes me think about control when this question crops up. We want to know that we are the reason for our life (also hinting at pride) and nothing we have or have achieved was out of our own control.
We, many times, have been told in our past to be content with what we have. Have you ever thought that should also apply to who we are? What if you were content with your faults? What if you were content with your emotions? What if you were content with your desires? Does this sound impossible or unreasonable? Those are all definitely easier said than done, but I believe you truly can be content with who you are as a person.
I do not believe contentment in ourselves comes from achieving or becoming something that makes us content, but taking our current circumstances and ourself out of our own hands and letting go of the drive to control them. You do not arrive at contentment, but, rather, you realize what you have is what you have and that you are blessed to even have the opportunity to struggle, the opportunity to feel pain, the opportunity to be happy, the opportunity to work hard, and the opportunity to let go. When your mentality on life changes from "I have to" to "I get to", everything else changes in turn. You take chances on things, you stop complaining so much, you actually start taking more initiative than ever before because you know this life is actually not a curse, but a conglomerate of blessings and gifts that started with one large, crazy gift called life.
Don't take your life for granted and don't ask if you are enough. Instead, ask "How am I to use this gift today?" and thank God for every moment you get to ask it.