What's the best way to respond to a sibling who continually makes poor choices with money and often asks to borrow money? I don't want to be heartless, but they're out of control asking for money anytime they want. I'm currently on Baby Step 2 of your plan, and I'm six months away from being debt-free. Do you have any suggestions?
I think you should just tell them the truth. You're trying to get out of debt, so you don't have extra money sitting around. Let this sibling know that you're working hard to change the way you handle your money. Let them know, too, that part of that is you’ve decided debt is dumb, so you don't borrow or loan money anymore.
Make sure you do this with a kind spirit, Jen. You could even let them know you might consider giving them some money as a gift if you had any extra lying around and you knew they were in control financially. But you're not really helping someone who's incompetent with money when you give them cash or even loan them money.
You've got to look at the big picture in situations like this. You're not helping someone if you participate in their misbehavior with them. Sometimes you have to love somebody enough to tell them the truth, and that can mean saying no and telling them to straighten up!