Looking back over my life, I think there have only been moments when I felt "happy," whatever "happy" is. This happiness may have sometimes had something to do with getting hold of some money, but the money itself never bought much happiness, although it bought comfort and security and a very few possessions that were satisfying to own. Schopenhauer, my favorite philosopher, says that happiness is an illusion, or "chimerical." He believed that what was of primary importance in life was the avoidance of pain. Bernie Madoff is a good example of a man who thought money could buy happiness. Instead it bought him a lot of unhappiness. Pip, the hero of Great Expectations, believed that money could buy him happiness by getting him into higher society and enabling him to marry Estella, a girl who had been specifically trained to make men unhappy. Miss Havisham in Dickens' great novel had a lot of money but it certainly didn't buy her happiness.
Here is a pertinent quote from Schopenhauer:
Accordingly, if the characteristic feature of the first half of life is an unsatisfied longing for happiness, that of the second is a dread of misfortune. For with it there has more or less clearly dawned on us the knowledge that all happiness is chimerical, whereas all suffering is real. Therefore we, or at any rate the more prudent among us, now aspire to mere painlessness and an undisturbed state rather than to pleasure. When in my young days there was a ring at the door, I was pleased, for I thought, “now it might come”; but in later years on the same occasion my feelings were rather akin to dread and I thought “here it comes”
Schopenhauer, “On the Different Periods of Life”
All suffering is certainly real. I am reminded of Buddha's Four Noble Truths, the first of which is: "All lives, from birth to death, are filled with suffering." The Second Noble Truth is: "This suffering is caused by a craving for worldly things.