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.

Most people were told $1 million was the retirement finish line. But that number doesn’t mean what it used to. The real issue isn’t just how much you save. It’s whether your money is structured to actually work when you need it.