Is her employer (Jami Gertz) just that chill? Has Kate already been fired? This Is Us has yet to tell us.
"I think the last time it was brought up the suggestion was that maybe he was some sort of ... writer? Like, for TV shows or movies, probably a comedy one, maybe he once wrote a really good one and lives off residuals and the support for this was that he seemed really used to or didn't think the Hollywood party Kevin had to go to was anything special and seemed to know how to deal with it? Maybe he just had an accident at a large store and is living off a really large settlement."
Maybe the last two episodes of season 1 will finally reveal what Toby does, and how he seems to have enough money to take off work for months at a time. I have my fingers crossed for "secretly a royal."