Perhaps his definition of "success" doesn't involve him feeling embarassed about what he did to his family for a long shot, even if he made it. Note also that regardless of how you and your wife appear to feel about it now, your perspective may change 10 years from now. Mine has. I'm embarassed. Not a good feeling.
Fair enough, and I agree - nothing's for free. For me, the fear that 10 years from now I would regret not taking a chance is greater than the worry that I will feel as you do. It's a personal choice.
