There are pros and cons of experience. A con is that you can't look at the business with a fresh pair of eyes and as objectively as if you were a new CEO. Fire yourself on a Friday night and come in on Monday morning as if a search firm put you there as a turn-around leader. Can you be objective and make the bold change?
If you wait until your children are high school seniors to spring it on them that there's not a whole lot of money for school they won't have too many options.