Dear Amy: My brother has worked as a freelance artist (with side gigs, such as teaching) his whole life. He is capable of working hard, and is talented, but due to distractions (volunteer work) and poor choices (he doesn’t believe in agents, and refuses overly “commercial” work), he has never supported himself.

My parents have subsidized him, bailed him out and paid for a second college degree. Now he is 54, broke and living with my retired, elderly parents. He has again borrowed money from them for a new art-related venture, but it is nowhere near the kind of thing that would earn him a living.

When my folks are gone, no one else in the family will be willing to subsidize his failed and impractical dreams. My siblings and I think he should take any job, save what he can for retirement and be an artist on weekends. But he keeps using excuses.

How do you break it to someone that “do what you love and the money will follow” is not a retirement plan?


Amy says: You and your siblings needn’t continue to school your 54-year-old brother, who by your account is talented and competent. He has certainly figured out how to live his lifestyle while letting others support him.

He is who and what he is. You should focus on his impact on others. If he is manipulating your folks out of their retirement savings, then you should intervene. However, you should also consider that his presence in their household could be helpful and positive. If he is helping to take care of them, this has value to all of you.

Your statements to him should not revolve around directing him in his artistic career, but in letting him know that the buck stops at your doorstep. He may find himself being forced to take a low-wage job and public assistance down the road at a time when he could be retiring, but one advantage of having artistic talent is that he can continue to do what he loves, regardless of his lifestyle. Wish him luck, and keep one hand on your wallet.

Dreading family visit

Dear Amy: I have an upcoming long-weekend visit with my spouse, my two siblings and their spouses. We haven’t seen one another in years. I have gained a lot of weight, and I am very self-conscious. I have a long-term, binge-eating disorder they don’t know about.


Amy says: You might want to contact your siblings in advance to let them know that you have been wrestling with an eating disorder, and that you’ve gained weight.

Be transparent about this, and convey, very simply, “I’m pretty self-conscious about this, but I’m so excited about seeing all of you that I’m overriding my own worries. I’m giving you a heads up that I don’t look the way I used to, and I know I can count on you to handle it. Just try not to be too shocked (LOL).”

Ideally, they would respond to you with the obvious: “None of us looks the way we did. If you pretend not to notice my own weight gain and gray hair, then I won’t notice yours!”

If you have siblings who would be unkind, then this might explain why you haven’t seen them — or even shared photos with them — in such a long time. If you can deliberately adopt an attitude of gentleness and self-acceptance, it will help you to cope with this challenge.

I hope you’ll carry on with your plans. Don’t forget to bring some old photos to kick off some family storytelling.


Send Ask Amy questions to Amy Dickinson at P.O. Box 194, Freeville, NY 13068 or to Twitter: @askingamy Facebook: @ADickinsonDaily.