In The Tao is Silent, Raymond Smullyan once summarized Daoism thusly:
The Sage falls asleep not
Because he ought to
Nor even because he wants to
But because he is sleepy.
“Trying not to try” is only a paradox until it isn’t. The Daoist philosopher Zhuangzi has it right. When we love something or enjoy something fully, there is no question of trying or of not trying. There is no question of passivity or of activity. There is just pure surrender to, and therefore energetic relationship with, whatever is happening.
Consequently, let’s not worry about trying or about not trying. Let’s just let whatever is happening happen. Nothing needs to be effortless during any contemplation or meditation. Likewise, nothing needs to be effortful. Think of bubbles rising to the surface of the water. The bubbles just arise and we are fascinated with them.
Daoism is simply one name we might give, if such is helpful, to the experience of just being energetically with whatever is happening. Without fight. Without struggle. Without resistance. Without agitation. And if fight, struggle, resistance, or agitation arise, then let us be with that! Being with struggle soon makes plain that one is precisely being with whatever is arising, here and now.
In the space of energetic being, there are just happenings. No problems and no doers.
Therefore, the sage falls asleep not even because he is sleepy. There is no because. There is no trying not to try nor is there not trying to try. The sage just falls asleep as sleep comes over him. That is all.