If I really think about, how often am I content?

contentment (usually uncountable; plural contentments)
1.the state or degree of being contented  
2.happiness in one's situation; satisfaction
3.the neurophysiological experience of satisfaction and being at ease in one's situation, body, and/or mind.

I disagree with the first part of point 2, agree with the satisfaction. Happiness doesn't have anything to do with being content. Being satisfied doesn't go hand in hand with being happy. Being content is a choice, being happy is spontaneous.
One must learn how to be content, happiness just comes naturally. No learning curve needed for being happy.

You really never know where your next happy is coming from. It could be a song on the radio, an unexpected piece of mail,or an unsolicted comment. It could be a sunrise or sunset, or a chocolate chip cookie. Whatever it looks like, the smile that starts to come across one's face and heart, is unstoppable. The warm, fuzzies take you on a ride, you didn't see coming. There is euphoric in happy. There is none of that in being content. Learning to be content is an art form. To be happy, all you have to do is be human.

So back to the question, how often am I content? More often than I give myself credit for. The winds of life blow me around. I may bend and it may appear I am ready to snap but I pray my root system is strong enough to allow the fluidness of life to take me down to the ground and wait to spring back up. That is Something we all have to learn and to be content with that is just the way it is...