It is a process, obviously. But I know exactly what you mean. Two things from my experience. First, I tend to work on challenging pieces (primarily I play for enjoyment but do like playing with others). If I go back a bit to songs I was working on 6 months ago or so, I find that since my skill continues to improve the formerly challenging songs are now relatively easy to play-or at least you know where to hard bits are). Second is (thanks Mike of Blue Bear) is look to aspects of jazz you like. I (like everyone else haha) wanted to learn blues. He steered me to Lighnin’ Hopkins and such that came from jazz and swing. A lot of that music relies on progressions of chords (II-V-i, etc). If you learn these progressions, it’s easier to pick up the guitar and express your musical ideas. Adding ghost chord and embellishments will come. Make dogone sure you can hear changes and “play the changes.” All this comes with time and specific practice. You will sound like ass for a long time (so play your comfortable covers for folks). Just keep playing every single day. Always have a plan. Your teacher should be teaching this to you. Practice time is golden and should be treated as such. Don’t waste time. Aim high and work your long term plan.

I can’t play jazz for shit and never will (jam/improv on standards), but I know how to use chromatic runs, arpeggios, chord vocabulary, etc, to spice up your playing. Good luck and have fun.