It's funny that we should have to learn the big-to-small lesson at all, but I think this is because as children we liked drawing detail. Of course, as children we were less hard on ourselves if our drawing didn't replicate the object.
But it does make things easier. And unlike many lessons, the drawing big-to-small lesson goes down just as easily if someone simply TELLS you to do it this way as if you learn it by accident.
So look: If you're interested in observational sketching, and you're hoping to more or less replicate what you see, start by placing the biggest shapes, then gradually go small. (Incidentally, working from the outside in has metaphoric value as well, but you can just sit and think on that one yourselves. All I'm saying is that there are usually life lessons in art lessons.)
Of course, if you don't care about replicating nature, but simply want to put down an impressionist rendering of what's before you, I say: Yes. Do it.