When my younger brother Darren lost his job, I didn’t hesitate. I wired him $3,000 to help with rent, groceries—just to buy some time while he got back on his feet.

That’s what you do for family, right?

But as I’ve learned the hard way, helpingsomeone and enabling them can look a lot alike—until it’s too late.

A Gut Feeling I Didn’t Want to Listen To

Two weeks after I sent Darren the money, I was scrolling through Instagram and saw something that made my stomach turn.

His girlfriend, Rita, was posing with high-end designer handbags—thousands of dollars in luxury—tagging herself at trendy restaurants and rooftop lounges like she was living the high life.