So many people come to meditation seeking happiness. Often, it is a search for some vague notion of an idyllic and blissful future, where discomfort and uncertainty will cease. We can come to believe that if we focus on the positive for long enough, we simply won't ever need to experience the difficulties and challenges of life.
To me, happiness is just as much a feeling to be cultivated as it is the natural, effortless result of facing the obstacles that get in it's way. Mindfulness is about feeling resilient and safe enough to begin to face what we fear. To look at what hurts. To give up escaping difficulty, and in so doing, find peace even in the midst of it.
One of the largest obstacles people face in the modern, western world is insecure attachment. I don't mean "attachment" in the Buddhist sense of the word. Rather, "insecure attachment" is a psychological concept, referring to a set of foundational views of oneself and the world. An "insecurely attached" individual may see himself/herself as unworthy of happiness and meaningful connection, or the world as a place where these things cannot be found. These views tend to lie so deep in the structure of one's mind/personality that they aren't even recognized as views, much the same way as a colorblind person may not know that he/she is misperceiving certain aspects of the visual world until this is pointed out.
So the question is: how can we expect happiness if we're operating within a paradigm which we cannot see, in which happiness is undeserved or unavailable?
Even "happiness independent of conditions," which is talked about so often in meditation circles can remain fleeting if these insecure foundational views aren't addressed. Despite potentially finding deep peace in one's personal practice, relationships and life circumstances can continue to be draining, unsatisfying, or even threatening.
So many approaches, including most of the western mindfulness, leaves a person's attachment style untouched until decades into practice. That's how long it can take for this material to arise on it's own. I've adopted an approach which exposes the meditators attachment style early on, allowing it to be the doorway to deep insight. This way, a practitioner will feel the benefit of seeing through those self-defeating foundational views, while at the same time experiencing the related insights that traditional mindfulness practice reveals.