If you clear cut a big area, natural regeneration may not get you the forest you want. In a lot of areas out west you will get brush first. Left alone for a century or two, natural succession will turn it into forest but most people can't wait that long.
The front part of my property was pasture in the 1940 air photos we have found. You can tell they stopped grazing it in the '50s or so because the brush starts moving in. It's super thick brush now, except the parts I have cleared, with forest invading around the edges.