I find this passage to be a very challenging one. Not in a sense of understanding it: the message is clearly stated. The challenge is in the ideas, and trying to activate them in my life. 

The Master stays behind; 

That is why she is ahead. 

She is detached from all things; 

That is why she is one with them. 

Because she has let go of herself, 

She is perfectly fulfilled. 

Tao te Ching often uses contradictory statements to expose the truth. The message is revealed by pondering the way that seemingly opposite ideas work together.  

One way to look at the idea of staying behind is to think about work. The Master is not rushing to achieve and when she does, she does seek approval for these achievements. Accomplishing the task is the goal. Simply do the thing that needs to be done and move on. Then the idea of being ahead is clearer because it is not about racing from task to task, but about effort and completion of the task in the moment. 

It seems impossible to be detached and still connected.  But what if detachment doesn’t mean ignoring or pushing things away? Instead, it is not asking more than can be given naturally. Let’s use personal relationships as an example. Being detached means allowing a person to be themselves. By trusting like this, the Sage shows she understands a person’s true nature. How can you be more connected than that? 

Letting go is tough for me. I cannot let go of myself: I am still the stage of many plays, and I crave an audience for my performance. Fulfillment is impossible when you need it from others. 

I am trying to learn this lesson. And I think I know how to apply it. I feel a different way calling me, but it means letting go to reach it.  

The quote is taken from the wonderful Stephen Mitchell translation of Tao the Ching.

If you are interested in Taoism, you might enjoy my book Tao of Thoreau.