Good, go have coffee, and bond a little more. At the end of the day, though, somehow you need to do what’s best for you. I’d be wary of him feeding your ego, maybe by sending you to the classes. Sure, he wouldn’t if he thought you might somehow embarrass him. And yes, you might someday hit a winning streak and make good money. In the meantime you need to decide if it’s time to ignore you’re sunk costs and move on. It’s a very hard decision I know.

Perhaps when you have coffee, spell this all out frankly with him: what would he do and why? Maybe he’ll give you info and wisdom you don’t have. Or, you may find yourself not believing him. Or somewhere in between. All of that info will help you decide what to do.

Dear MichelleLea and Emma,

It takes time to ferret out others' INTENTIONS.  Ideally it would be great if everyone strived for a "win - win" situation.  

As for me, I would take every class offered to me to train and cross-train.  

Just watch to be sure he doesn't have a hidden agenda and that he treats you respectfully.

Your friend,

Monica