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Hi Jason,
In this culture, we’re taught to chase after our dreams, like you said. This gives us the false notion that happiness is something we have to seek out, beyond ourselves. But where is the happiness (contentment) really coming from? That’s right it’s coming from inside us. We have learned to allow ourselves moments of happiness when we have reached a goal. Well, why not just allow happiness to happen regardless? When we sit and recognize how amazing it is to be alive in the first place, having this experience, what more reason do we need? It really is that simple, on paper. In practice, that’s where it’s tricky, because we’ve been conditioned to believe that happiness MUST be pursued.
The brain is a muscle, a reflex organ, wanting to do what it’s used to doing. Getting yourself to unlearn that conditioning, and seeing the simple truth, and putting it into practice, well, takes practice. Though it’s a practice of not imagining things, not letting your mind wander. Meditation is simply that. Try sitting and see how long you can go without imagining anything at all. You’re only conscious of what your senses are picking up, that’s it. Just going 10 seconds is tough, right? They call this ‘calming the monkey mind’. I am no meditation master by any stretch but I’ve experienced enough to see the positive effects. Failure seems not as big of a deal anymore. I learn from it and move on. I still strive for things but it’s more about the kind of person I am becoming, how I treat others. There is still enjoyment and appreciation in material things, but it’s a not a ‘must have’. It’s a revelation of something I already knew about, yet kept overlooking (happiness comes from the inside and doesn’t need a reason to be experienced/shared).
Hope this helps!