"I'd say that second-guessing yourself is a good thing, in moderation. If you always assume you're doing what's right and can't do wrong, you can end up in some big messes as a result. And this is a path with consequences for more than just yourself, so weighing the options is more important than ever." He wants Drake to know that what he's facing is not only normal, but expected, giving him the confidence he needs to face that uncertainty.