Let them fail. This one is very, very difficult for me.
I'm the woman with the 8 kids and the homeschool and the blog and the book. I'm kind of a "doer". Kind of.
When I see something that needs to be accomplished, my brain goes into ninja-administration mode, and I know exactly how to get from point A to point B (even if it's a curvy line).
But boys, especially older boys, need us to back off. They need to try things their own way and they need to be proven wrong by experience, not by our words. They need that exhilarating feeling that comes when you take a chance, dig in with both feet, and succeed.
Unless they ask for advice or help, let them get from point A to point B on their own. And if they never get to point B, tell them how amazing they are for trying. Resist every urge to shake your head and say, "I told you so." The world is already saying that to them, every day.