You got my best wishes kid.
You are fretting about the job. I will offer you my read.
I am a Willie fan so I remember a bit. My read is you work in a sales setting. You like your job so it appears they like you and you are performing ok.
If the boss is a sales guy at heart, I offer the following. Sales guys (especially bosses) deal in favors, relationships & loyalty. They love granting favors and garnering the loyalty that they expect would result.
Most people react favorably to being trusted. Even sales weasels.
Employees who perform well are nearly always less cherished than those who are loyal to me.
If you approach this guy and tell your story and your plan and he supports you - this will go a long way toward your feeling good about life and dealing with your problem.
Give it some thought & decide if you want to play a hand with this guy to the river.