Wayward is interesting because, like so many words with a faintly archaic cast, there is a potentially deeper layer of meaning connected to its historical roots that lies beneath the accepted modern usage of the word.
Wayward breaks conventionally into two easily and digestible pieces, way and –ward. First, way turns out to be aphetic, meaning that there was previously an unstressed vowel sound at the beginning of the word that has been dropped. Its original form was away.
The second element, -ward, is generally defined as something like ‘towards’ which is considered to be descended from the Old English word weard, and is related to the German word -wärts and the Latin term vertere, meaning ‘to turn’.
So, the original adjective ‘(a)wayward’ applies to someone who has ‘turned away’, with the implication that they have turned their back on something omnipresent and essentially “right”, such as family, religion, accepted morality, etc. As a shorthand, let’s call these things societal norms.
In general usage, in order to be described as wayward, one must turn one’s back on societal norms on an ongoing basis which, from the self-righteous perspective of society, implies a long and miserable process. This idea of the rejection of society as an ongoing journey activates a latent potential meaning in the truncated first element of the word in the sense that it brings to the fore the connotation of way as a ‘path’ or a ‘road’ down which one travels as one continually rejects society.
Ward also has another meaning besides the one listed above that can be derived from it’s Old English root, one that actually fits more closely with its general usage today: ‘to guard’ or ‘to protect’. A warden guards prisoners, a ward of the state is, in theory anyways, proteced by the state, one wards off an attack, etc.
Looked at in this manner, someone who is wayward could be one who is protective of their individual way, who keeps their path separate, segregated from that of the mainstream of society. I prefer this image, of the confident and dynamic person hacking their own path through the jungle, than that of a shamed dilletante who won’t conform to society’s rules out of pure dumb stubbornness.