Supposedly, going against the grain is really difficult.
It turns out, though, that it’s far more dangerous to cut with a rip saw, a blade that goes along the grain. It often leads to a botched project. When you’re cutting across the grain, you know exactly what to expect and won’t get surprised by a patch of resistance you didn’t expect.
The same thing goes for sailing. It’s way easier to sail diagonally across the wind than it is to run with it.
The story we tell ourselves about cutting across expectations is probably more difficult than the actual work.