This posting is referring specifically to philosophical Daoism. Religious Daoism is an entirely different subject and as such, not meant to be considered here. I will lead off by giving you two suggested books for reading:
Dao De Jing: A Philosophical Translation and Chuang-Tzu: The Inner Chapters
I own both of these books and highly recommend them for your own Daoism reference library.
There are many translations of the Tao Te Ching (pronounced Dao de jing, so often you will see it spelled multiple ways, even Daodejing). I would say reading multiple versions would help. The reason there are so many, is because the original Chinese texts cannot be simply translated by character. You need to fully understand the culture and time when it was written. This holds true for any language. For example: In the 1940s, I could say, “I’m feeling so gay today!” and people would think I’m talking about how happy I am. Of course, that sentence has an entirely different meaning in popular English today.
So if you were a translator from the future, say after English had developed 4,000 years from now (about the estimated age of the original Chinese texts), you would have to study Ancient English, and then try to pinpoint the time when the text was written and understand the social and political culture influencing the writer. Translating texts as old as these is a challenge for anyone, and the translations can vary, sometimes greatly.
The translation of the Dao De Jing I listed above is a very in-depth study, including not only the translated text, but also detailed explanations. It’s one of the most well researched versions I have personally read.
Next, as with any philosophy, different people take different things from it. Unlike more defined religious beliefs and practices, philosophy is by nature a venue for discussion and debate about ideas. There are very few absolutes which is why you will come across conflicting views such as “setting goals is good” vs. “do not be concerned with the future”.
My personal stance is somewhere in the middle. If I could live as a hermit, having no connections to society, I could certainly spend my days taking care of “now” and not be worried with the obligations of social living. But even then, I would still have to consider things such as storing up food for the winter.
Living with others however does need planning. We have to consider what we need to do to meet our needs. That is determined by the society in which we live. In many parts of the world,that commonly means developing useful skills, find employment (hopefully related to your chosen skills), and pay for the things you need. This requires planning and training. Both of these things require us to consider the future.
It is also worthwhile to know how to let go of certain worries. Being able to “go with the flow” is preferred to needing to “always be in control”. A Daoist in the 21st century will have to find a comfortable balance between the two ideas. I do not feel the desire to direct situations that are very far removed from my immediate influence. More often than not, I will see how things develop and adjust my own actions accordingly.
Some people call this “conforming” and are strongly opposed to it. In my perspective, moving to conform is the way of nature. Water flows down the hill, conforming to the contours of the land. Over time, the land conforms to the motion of the water.
Obviously, there are times when you are better off making the effort to stand against the current and resist the status quo. And therein lies the most important concept of Dao: balance. The universe’s most consistent observable truth is it strives for balance, equilibrium. It naturally seeks a state of rest between all other influences. The orbits of the planets around the sun are a balance between gravity and velocity.
When considering Daoism as a philosophy to live by, this is what I believe you should keep as your base. Are extreme activities ok? Certainly, but not all the time. Is it ok to eat that rich food? Alright, but not regularly. Oscar Wilde is quoted saying, “Everything in moderation, including moderation.” The concept was not new with him. I’m sure idea of “nothing in excess” has been attributed to great minds from all cultures throughout the ages.
Moderation calls for balance. The universe calls for balance. The most central theme for Daoism is balance.