I'd say it's definitely somewhere on the concerning scale, yes. [He's a bit worried now, actually.]

But, never fear, Fitzroy, I am certain we can figure something out. [He's just going to dive right into this little problem, hang on.] Maybe-- I wonder if you might be having trouble sleeping because you are thinking about how much trouble you are having sleeping? If we could distract you from these thoughts, then you should be able to sleep in no time!

[Or he could be completely off the mark, but hey, that's why he's brainstorming out loud in the first place.]