Most financial conversations about children revolve around college. But if there's only $100-$200 a month available, is age 18 really the most important problem to solve? A conversation about grandkids, Florida Prepaid, and long-term planning sent me down a rabbit hole I couldn't stop thinking about.

Why do we normalize financial fragility? A chance conversation at a networking event exposes the massive blind spots in mainstream financial planning, and why the traditional advice you've been given might be setting you up for failure.