The Tao Te Ching speaks of a kind of aimlessness as appropriate. But I think it's a very particular kind of mindful aimlessness, much like the quality of wandering referenced in the famous Tolkien quote.
Yes, Taoism speaks of the natural aimless path and its journey.
(I have read, reread, contemplated, and discussed the Tao Te Ching.)
IMHO, western society is so far from natural (and so socialized) that natural begins to lose its meaning. Our minds are so unconsciously conditions that the let go of control initially would be like putting a heat seeking missile on target acquisition and firing it.
Perhaps we need to contemplate and transform that auto-pilot before we get out of the way and let it fly.
There is a big difference in the brain-dead gate-less aim-less path of ignorance and the mindful attention to the journey as a process adventure and discovery.
Thanks for reading and responding.