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Simplification always sounds so... Simple, but for humans it seems to usually be the most difficult thing in the world. Especially within modern societies. More "primitive" societies seem to have a better understanding of simplification. This makes sense given all of these we know about have been given the opportunity to 'advance', Yet they choose not to.
Of course, that isn't to suggest they have no problems. Life is life. No one is always happy. A human being can find happiness or unhappiness in any place or time.
I think what is most important for you to find right now is what it is that is exactly your 'problem' and what it is exactly that you want.
If you wish to flow like the water then you must understand why your own waters are not flowing. Then make a decision for where you want them to flow. Or better yet, to understand why they stopped in the first place, to fix that problem, and to naturally allow them to move again wherever they choose.
Although, understand that the Way does not require you to flow anywhere precisely. A pond settled in to the world is just as valuable as a stream or river or an ocean. The waters in the pond itself still flow around the fish. They still flow into the ground and are still filled by the rains. The pond does not do any of this work on its own, the fish and the ground and the rains do this work, but the pond still moves. Action through inaction.
If you are 'over analyzing' your situation, then you already know what must be done. What then stops you from doing it? Sometimes we confuse over analyzing something with analyzing in the wrong way. If you believe a fish is a monkey, then you might constantly wonder how the monkey swims for so long.
In the Zhuangzi, there is a story of a farmer and a man. The farmer waters his fields by hand, from a stream nearby. He has to carry water in a pot from the stream to his fields, one pot at a time.
One day a man comes by and he tells the farmer there is an invention that can pump the water from the stream to his fields so that he does not have to carry the water anymore and will farm with little work. This man believed that doing less work for more gain is best.
The farmer then laughs at the man and tells him that to do this would not be the Way. He explains that by trying to uncomplicate the matter he is losing sight of the pure simplicity of it and in fact only complicating it instead.
This story is used to explain that the Tao doesn't need to be complicated, nor does it always make everything easier on humanity. That sometimes there are simply just ways of living that are understood and accepted by those living them. They are living in The Tao because they do not feel the need to make their lives 'easier'. They simply do what they know and love to do. And that sometimes our technologies and craftiness gets in the way of our understanding.
So, what is it that you love to do? Simplify your life by not just doing what is easiest or what you think will lead you to where you want to be the fastest. Pursue what seems to be the most natural route and you will arrive where you need to be. A river does not arrive faster by moving stones into its way. It arrives at its own pace and not a moment sooner.
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