Are these good questions to ask ourselves? No. They're questions with which to torture ourselves. When we face our lives honestly this kind of question about happiness is more likely to bring tears to our eyes than solace to our souls because, no matter how well our lives are going, none of us live perfectly fulfilled lives. Always there are unfulfilled dreams. Always there are areas of frustration. Always there are tensions. Always there are deeper hungers that are being stifled. And always, as Karl Rahner so poignantly puts it, we are suffering the torment of the insufficiency of everything attainable as we are learning that here in this life there is no finished symphony. Are lives are always lived in quiet desperation. A lot of times it is not easy to feel happy.
We tend to equate happiness with two things, pleasure and lack of tension. Hence we fantasize that for us to be happy we would need to be in a situation within which we would be free of all the tensions that normally flood into our lives from: pressure, tiredness, interpersonal friction, physical pain, financial worry, disappointment in our jobs, frustration with our churches, frustration with our favorite sports teams, and every other headache and heartache that can appear. Happiness, as it is superficially conceived of, means perfect health, perfectly fulfilled relationships, a perfect job, no anxiety or tension in life, no disappointments, and the time and money to enjoy the good life.
We more easily grasp this when we reflect back on various periods of our lives. Looking back, from the perspective of where we are today, we see that sometimes certain periods of our lives that were fraught with all kinds of struggles and within which had to make do with very little were indeed very happy times. We look back on them now with fondness and warmth. They were meaningful times and our present perspective washes back through time and purges the pain and highlights the joy. Conversely, we can also look back on certain periods of our lives when there may have been pleasure in our lives but that phase of our lives now appears clearly as an unhappy time. We look back at it with a certain heaviness and regret. What seemed like light then seems like a time of darkness now.
In his autobiography, Surprised by Joy, C. S. Lewis tells his readers that his journey to Christianity was not an easy one. By his own admission, he was "the most reluctant convert in the history of Christendom." But one of the things that ultimately brought him around to the Christianity was precisely the realization that meaning trumps our normal conception of happiness. He came to understand, he writes, that the harshness of God is kinder than the softness of man and God's compulsion is our liberation.
source: Fr. Ron Rolheiser