Well, you should support your child being who they are. Woz is who he is, and trying to make him into Jobs would only make him unhappy.
However, Lil' Jobs would probably not be as happy if he didn't become Steve Jobs later in life. If his parents pushed him to be Woz-like, would he have been happy? I'm not sure he would have been.
For one thing, it is easy to be super chill when you are a naturally talented engineer who finds happiness in working on projects in your garage. Some people are built with a more driving ambition to affect larger systems (used in the more general sense). They want to be executives so they can bring a grand vision to life, be it a corporation, mass movement, or an empire. Anything less will be frustrating for them.
I agree that you should try and instill values of respect and a healthy sense of perspective vs. worldly ambition in your child, but the world needs leaders too.
That's true, but realistically no one decides as a child that they will be a world leader or a CEO. Parents who drive and "prep" their kids from an early age to do so are more likely to just burn their kids out before they even get to college. Just like you said, Jobs became Jobs "later in life". Push your children to do what they enjoy, and if they have the talent and the desire to be the next Jobs, they will have the opportunity to do so.