It may have more to do with people having no desire to drag others into danger than Strange probably thinks it does. It's not as though Childermass can order him to the Wyldlands, seeing how it's clear the other magician will carry on refusing him as a supervisor. Of course, he can't explain that rationale if the question is left unasked.

Though his smile will falter some, he won't let it fade out entirely when Strange admits he suspects he'll disappoint again. Really, Childermass wouldn't be surprised by it. Just tired.

"I would very much like if you didn't, but... I'm not really your boss anymore, anyway," he says outright, though it's in a resigned way. He knows better. "I can only hope that I'll still be around to hold you to that in the future."