Since most self-cultivators’ life purpose is to achieve awakening state in this one life time. Usually only the cultivator himself can realize he has reached this goal. There is a story about a man who went out traveling searching the Tao (the way), he finally got back to the temple and saw his teacher still read all the books day and night but could not get it. It happened that a little fly was trying to go through the window covered with paper. He decided to convey a message to his teacher by saying: “ Oh, little fly, don't you see the door is wide open, why are you still trying so hard to pass through the old window paper?” His teacher then realized that his student had already obtained Tao.
Since the Tao is invisible and untouchable, we often follow a great teacher who has obtained Tao and manifested enlightenment in them. When cultivators ask what are the characteristics of a Taoist or Buddhist who have reached enlightenment?
Basically two things: no attachment to self and no attachment to certain ways, thus there is no suffering or agony as a consequence.
Attachment is not diligent practice, attachment will root more pain and discomforts; but a diligent practice leads non-attachment and fulfillment of cultivation.
So keep up with your practice to non-attachment following the natural flow and go to obtain your Tao/the Way. You will know once you are there/here.