In my life, I've observed occasional sleepless nights (one night per 1-3 month period) to coincide with positive moods, abundant activity, and a general sense of fulfillment. And when my mood and motivation drops, I reflect back and recall that it's been a while since I've enjoyed a sleep-free night.
I've always conceived of this as a consequence of being highly dynamic – my system is being stretched/pushed/twisted/strained by skipping sleep [1] – and a correlation to generally being enthusiastic about what's going on (I stayed up all night in the first place because I was obsessed with a fun problem). Of course, it is difficult to parse cause/effect/correlation, so I'm aware of the limits of these observations [2]. However, from the beginning I've felt confident that these sleepless nights were part of a broader pattern of good health.
[1] – As a general rule, I find "stress" to be healthy if it is acute (but survivable!) and unhealthy if it is chronic. This case (sleep) fits the rule... infrequent sleepless nights have a net positive effect, and prolonged sleep deprivation (even mild) is absolutely terrible for pretty much all aspects of health.
[2] – In observing my sense of happiness, I consider "seasons," or 3-6 months periods, so the previous analysis is actually quite feasible. Do I wake up motivated? Do I feel pleasure lying down to sleep? Am I being kind to the people in my life? Do I enjoy interacting with acquaintances? Do I feel capable? To me these questions offer clarity on some rough level of happiness, and makes possible an imperfect analysis of the effects of something like a sleepless night or other lifestyle change. It's not perfect – but it doesn't need to be perfect, as it is already a more effective analysis than the alternative (no analysis at all).