I've known you for many years and I'm hoping my daughter will see this, recognize herself, and do something about her life. She hasn't worked in two years, her worthless husband hasn't had a job in over three years. Neither one of them is even trying to find work, nor do they have any marketable skills thanks to their decision to quit school and have babies. I've offered to hire them both to work at my business, but neither one of them even want to work. They'd rather live off unemployment and food stamps while mooching off my wife, who gives them money behind my back.
I know how hard it can be for young people, but to be perfectly honest, it isn't that frigging hard. I managed to make something of my life without a college education, and you have to admit I'm a pretty successful guy. There are places to work for those willing to knuckle down and to what it takes. I've told them both that if they want to keep receiving help from us, they are going to at least have to try to find a job, somewhere, anywhere, but it's killing me inside to cut them off because then what will happen to my grandchildren? I don't want to take custody of them because I've already raised my children. What can I do?
— At My Wit's End
This is going to piss you off, but here goes. You have zero idea what it's really like in the world. You see yourself as some kind of bootstrapping hero of capitalism, a self-made man who lifted himself up from nothing to become the successful businessman you are today. Don't get me wrong. You've done well. But the man you think you are is really your father.
You've only ever had one job in your life, when you went to work for your old man straight out of high school. He'd built a modestly successful business and you worked like a slave for him, but you did it knowing you were going to inherit the business one day. He was already on his second heart attack before you were 18, so you knew you wouldn't have long to wait. And you didn't, did you? So there you were, not even 30, and in charge of the business your father built, living in the paid-for house he left you in his will. You've never had to find a job on your own. You've never been without work or without means. You've never had to make a mortgage payment. You tell your daughter to find a job – any job, but just any old job won't even pay the daycare bills. You never had to pay for health insurance, either, much less go without it. Your biggest expense is taxes. Taxes are the least of your daughter's worries.
Now you're middle-aged, healthy as a horse with a good 20 or 25 years before you retire. That's 25 years before your daughter and her husband can even begin to hope to inherit the family business, years they'll have to slave for you, and slave for you they will, I have no doubt. I wouldn't work for you, either, pal.
There's no good solution here, but don't make it worse by cutting her off. The two of you are going to have to work together to find a way out. She's needs to do some growing up, but you need to open your eyes to the reality of her world. It's much, much harder than anything you've ever known. If you can see things from her point of view, she might surprise you by growing up right before your eyes. Keep treating her like a spoiled and ignorant child and that's all she will ever be.
Got a problem? Jack Waggon will set you straight: email@example.com