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.

Most people don’t end up with bad financial plans because they were careless — they end up there because they followed advice that used to work. Here’s why smart decisions can still lead to incomplete results.