I have fallen in the trap before of assuming that soils someone is talking about where they are behave at all like anything I am used to. A draining soil with a clay topsoil is different from New England ledge and boulders with barely any topsoil, is different from Georgia or Texas red clay, is different from river valley blue silt clay, is different from coastal sand flats. Sometimes the best thing you can do is ignore the conventional wisdom and do what the neighbors have already shown works...but it doesn't hurt to ask why now and then, too.
Perhaps there is no bottom to the clay, it never drains, and if you want the water flow away from your roadway you actually need to build up more clay as a water barrier, rather than dig down as a place all the water will drain to. Maybe there is no rock worth buying in economical trucking distance. Maybe there is so much well draining rock just below the surface you only need to get the leaf litter out of the way. Sometimes a floating roadway is better than a well supported one. Sometimes one good ditch and culvert will do more than any amount of rock.
Is there frost? How deep? Is the property dead flat with nowhere for the water to go? Or is it sloping and well drained, except when the ground is frozen and snowbanks act like a dam? My lot is sand at least a yard deep, but I can still have standing water come spring if the snowpack, frozen ground, and snowbanks act just right...sometimes an afternoon chipping a drain channel will fix it, sometimes it won't.
So to me, it can vary so much with the local conditions that I would want to know more from OP, what their local soils are like, what the slope and groundwater of their lot is like, or what part of what state they are in. Then between the bunch of us on here, we might be able to zero in on it a little.