[southernplaces7]

If he's an entrepreneurial type with a circle of entrepreneurial connections, no legal boundary stops him from kicking off another venture when he leaves prison. Wouldn't be the first felon to do just that and pull it off with a bang either. For example, finance is full of former felons going right back to the top.

For more ordinary people with regular white collar formal employment, different story of course. Their scarlet letters are often indelible unless they really adapt in new ways and adopt new habits.