At first I thought maybe work didn't seem fulfilling, and he wanted to run his own business. Running a business can be extremely rewarding, so I thought this wa

At first I thought maybe work didn't seem fulfilling, and he wanted to run his own business. Running a business can be extremely rewarding, so I thought this was his plan. However, if he's only after money, then he might just be chasing a pipe dream. If he's making millions, he'll probably be buying exotic cars, and feel like a failure because he can't buy a yacht. Then he makes tens of millions, has his new toy yacht, but feels like a failure because he doesn't own a private jet. With his current income, he should be able to live quite well. You said, he wants to be financially free. If that's his goal, why is he racking up $8k in monthly expenses? It seems like he wants to live a lavish lifestyle, that's always above his means.