Of course, it's possible to have both in your life at the same time. You can be perfectly happy with where you're at and still be willing to take risks. But usually it's a teeter-totter from one to the other. When you're content, you probably won't be in a hurry to change things. When you're constantly seizing new opportunities, it's harder to appreciate what you already have.
I don't have the secret formula for when contentment should override boldness, or vice versa. But I think this is one case where it's okay to flip-flop back and forth, depending on personal circumstances.
Bold living is rewarding, sure, but I think I'll focus on contentment in November.