Two square things I wont be doing is avoiding drugs and pain. I am happy to be called square for avoiding these things.
Jazz is about musical expression. Words wont do it justice. But before you can express yourself well, you need to become competent at the mechanics required to express yourself. So you need to do all the learning of the basic stuff to do with your ukulele and the music. Following Glen Rose and the other teachers is a good way to learn the mechanics and become competent. Eventually you will need to stop following and just start doing and creating your own stuff.
Apart from following teachers like Glen Rose, read biographies and watch videos and listen to the records. A useful way to find a plan, if you don't have one, is to just follow the jazz timeline from early last century and study the players and the music in the historical sequence of development. Look up the players and bands, find recordings or sheet music of their work, listen to it and play it on your uke. Write out some notes so you don't forget the bits you like the most. When you catch up to 2018, just keep going using your own ideas.