The nature of happiness is much debated in philosophical literature. Some view happiness as an objective state of being. Hence, if one is living up to their human potential they are in a happy state even if they subjectively experience suffering. Others see happiness as a subjective experience related to things like an abiding positive interpretation of life events, an ability to be content with one's lot, having a sense of purpose in life, a steady flow of pleasant experiences to look forward to, etc.
Another fascinating discussion concerning happiness is whether it is characterized by passivity or activity. Those that perceive happiness as a sense of contentment link it to passivity. To be happy is to sit back and appreciate one's environment and to count one's blessings. In contrast, those that connect happiness with a sense of accomplishment, actualization of potential, and a sense that one is capable of boundless growth, identify it with activity.
In Kabbalah, happiness is viewed predominantly as a by-product of identifying with one's divine consciousness, while distress is caused by increased identification with one's ego/animal self. An oversimplified interpretation of this principle has led some people to deny their ego its needed share of stimulation, security, and 'happiness'. This may result in depression, an illness that tends to thwart progress, including spiritual progress.
In truth however, Kabbalah stresses that individuals should gauge their spiritual level and live in a style that's tailored to help them attain a sustainable connection to G-d. Hence, one who receives sufficient stimulation from their divine self - studying, praying, performing acts of kindness, etc - may well be ready to abstain from many of life's coarser ego pleasures. One lacking such refinement, however, is not. If he abstains from such basic pleasures - enjoyable food, sports, holidays, light reading, sense of accomplishment, friendship, music, etc - his ego will have little to look forward to and may become melancholy. Of course no one's suggesting anything immoral to keep one's ego happy, just basic kosher entertainment and recreation.
In my case I feel that my ego requires a more intense rush and excitement to feel happy and enthusiastic about life, something which skateboarding grants me. And, with a happier ego it's easier for me to perform my spiritual duties. I thus increase in happiness both subjectively and objectively...