I'm sorry if this has been mentioned but I'm too lazy to go back and check.
After Annie's mother's funeral her and Jake sit down and have a talk what to do about the business. He first asks her if she wants to make lighting fixtures for the rest of her life? Here's the thing though, if you own the business you don't make the fixatures. You manage the company and have employees do that. What if he was speaking in a more metaphorical sense and meant "you don't want to be running a lighting fixture company for the rest of your life" even then, what kind of argument is that? Sure they can manage the company and increase their profits or maybe they can hire a manager to run it, take the profits and put it into the careers they want. If he wants to be a pilot he can still check in on the company and fly planes! CEOs of companies aren't constantly at their factories and warehouses. They can just use the profits from the place to fund their schooling and piloting and then sell it at a later date. Think of your future guys.
However, the more shocking thing we learn is Jake has only been working there for a year! We know him and his wife have been married for six years and of that he's only been working for her mom for one of them. On top of that Annie's mom was preparing Jake to take over for when she retires which sounds like it was soon. He's only been doing it one year! He went from entry level employee to future head of the company in a year? The mom is clearly looking out for them and he's just cutting work in the middle of the day for flight school? Who knows what other fuckery Jake has been up to. What was he doing those first five years? Why did he take the job if not for a secure future only to throw that all away the moment he gets it? I'm really siding with Annie's mom on this one, Jake is a a doughnut.