Pitchick hit the nail on the nead. You pretty much won't know until you try.
How old is he & what breed? That may help some

Also instead of leaving him out for a full day right away, try to leave him out only for an hour or 2, like while you run errands or something. If all goes well, eventually leave him out of his crate longer & longer each time, gradually working your way up to a full day.