Early years

Jay's mother, Ye Hui Mei had already noticed Jay's sensitivity to music and sound from the time he was a toddler and as such, ensured he got the necessary musical training as early as possible, starting him out in Yamaha group classes and subsequently taking one-on-one lessons with a piano teacher.
Accounts by his Yamaha teachers describe him as a very quiet child who would not speak up to answer but would quietly compose a little song for a girl in the same class whom he liked...yes, even at that young age. :)

His piano teacher also recalls that Jay and his Mum were always punctual for his lessons and she would sit by the side, listening to what he said, taking notes so that she could revise with Jay on their own.
Now how many mothers you know would actually do something like that??
Certainly not me! *grimace*
I'm convinced she knew intuitively how far Jay could go and did her very best to make it happen.
As he was an only child, it was also probably much easier for her to focus so much attention on him.

Jay also loved to record sounds on a tape-recorder which he carried around with him everywhere and this formed the basis of his eventual signature rapping and song styles, in which he liked to incorporate different sound effects into his music.

However, Jay's training and grounding was in classical piano which he eventually majored in at high school, with a minor in cello. His favourite composer is Chopin, whom he pays tribute to in his album, November's Chopin and in his self-directed-and-acted movie, Secret.
He was a diligent student, even as a kid, thanks also to his Mum who was very strict and made sure he practised daily. At that time, he occasionally resented the fact that he could not go out to play like other kids but looking back now, he credits all that hard work for enabling him to go far in his musical career.
Jay was even contemplating a careeer as a performing pianist or piano teacher but sometime in his teens, he became interested in pop music, often mentioning Jacky Cheung as a strong influence with his hit song, Goodbye Kiss.  This would lead him away from the classical music path but his future compositions would show the impact of his early training as he frequently incorporated themes from the classics into his own songs.
He was also often called upon to provide piano accompaniment for concerts in school and displayed an uncanny knack for improvisation which he honed very well  and is evident up till now in his performances.
Give him three random notes and he'll knock out a tune for you...almost immediately.

Like so:

Jay was not the academic type though...he sat for the University entrance exams twice but did not do well enough make it through.
At the same time, he was also diagnosed with ankylosing spondylitis, an inflammatory joint disease which primarily affects the spine and was exempted from mandatory military duties.

So at age 18, with no University to look forward to and yet unable to enter the army, things were looking bleak for him. What else does a guy do but get a job, right?
He worked in restaurants as a server, not knowing that his former schoolmate had signed him up for a talent competition, Super New Talent King.
Taiwan has many such competitions, which is why their music industry is so vibrant,
Anyway, Jay refused to sing but agreed to be the acompanist for his friend.
Besides, he had also been keeping up with his music somewhat and writing songs.

Here's a news clip of that fateful show:

The duo did not win but Jacky Wu, the organiser and an influential personality in Taiwanese entertainment circles caught sight of Jay's music score and was impressed with its complexity. He sought out Jay and offered him a job, writing songs in his music production company, Alfa Music.
Jay took up his offer and started work the very next day. It was definitely preferable to waiting on tables and was also a good avenue for him to make use of his musical talent and composing abilities.