I think your very first step Identify is the key to all this.

Is it rational to pursue an irrational goal rationally?

Our culture focuses on external validation, achievement and winning. My concern is that this is a form of manipulation focused on improving a societies economic measures of value over an individual's personal satisfaction.

In contrast, the science of happiness seems like a good start. This work seems to focus on developing techniques to come to feel satisfaction with ones current state. Perhaps a next step is to look at how communities and organisations can be structured to support this. Speaking for myself I naively assumed that making computer games would be an enjoyable career because I thought that making a game and playing a game would be similar, this is not the case. Does anyone have any suggestions for careers or lifestyles where one can feel a sustained sense of satisfaction? Or indeed a rational means to select/create one?