Never gamble in someone else’s game, as in Las Vegas. The house always wins long-term. Gamble in your own game.
Borrowing from business 101, the piece is substantial with good advices about being bold to take risks, but the sentence above seems to worth a different article of its own.
He uses the gambling analogy to argue his points on taking risks but he also uses them to exemplify how to take a winning photograph, which often is less about gambling, but rather smart choices.
My best photos were captured when I am being smart, when my impulses were at the lowest and my intuitions were high. His both examples seem to have represent this argument; he felt that something was up for grabs, and he went for it.
Anything I capture with high risks — that which usually involves sticking my upper body part out, unharnessed from a high point, or angry security dudes — produces impressive images, but never my best work. (via @pschiller.)