I'm nowhere near that level but extrapolating from my experience and that of people I know: such abrupt departures are never amiable and are the tip of quite complex political junctures. As a human being, someone like Sinofsky is no longer hurt by lost income, but that's a blessing in disguise because his motivations were for a long time not of financial nature, which means he is hurting in other dimensions. Feelings such as hurt pride, poetic justice/revenge (they're worse off without me), rejection, are not uncommon. Given the abrupt departure, a general loss of meaning and occupation is quite likely (from the mornings of a busy executive to the long silence of the mornings to follow).
(As an aside, the reciprocal "good job" messaging is irrelevant - quitting in style is professional courtesy, costs nothing, and leaves bridges in place and doors open.)
In particular at Microsoft (drawing from discussions with friends), one common theme I gathered is "complex". Life at Microsoft is complex, rich in context, structured, full of details that employees consider important but find it very difficult to explain to the uninitiated. Even the vocabulary has additions and some words have unusually stronger semantics. I have friends who have been enormously stressed, lost sleep, literally developed clinical cases of depression - on stakes that, when explained to an outsider, appear as immensely petty. This is twice as bizarre in an industry that has a high inflation of jobs, which makes it very easy to leave Microsoft. But that's difficult because the nature of these conflicts and challenges makes the employees who are part of them feel they're losing self worth if they quit.
So I could speculate that leaving Microsoft has Sinofsky experience the most complex of emotions. However, it's likely he'll rebound and be off to other conquests soon.
As an aside, I've noticed many of the factors and symptoms you note in members of any sufficiently large corporation. Perhaps in a microcosm of society, the frictions necessary to create psychological tension are amplified with respect to the size of the corporation and the degree of isolation.
In the case of Microsoft, this phenomena may be more pronounced. Software engineers/developers exist in a smaller subset of society than many other professions, and the compounded relative geographic isolation in Washington may make it difficult to see the forest through the trees during times of professional conflict. This is not to say that Seattle is by any means isolated, but the tech community there is indeed smaller than that of Silicon Valley, magnifying the overall degree of professional isolation.
The tech community in Redmond/Bellevue is limited, but in Seattle overall its actually quite rich; and the young kids can commute east on a connector right?
(As an aside, the reciprocal "good job" messaging is irrelevant - quitting in style is professional courtesy, costs nothing, and leaves bridges in place and doors open.)
In particular at Microsoft (drawing from discussions with friends), one common theme I gathered is "complex". Life at Microsoft is complex, rich in context, structured, full of details that employees consider important but find it very difficult to explain to the uninitiated. Even the vocabulary has additions and some words have unusually stronger semantics. I have friends who have been enormously stressed, lost sleep, literally developed clinical cases of depression - on stakes that, when explained to an outsider, appear as immensely petty. This is twice as bizarre in an industry that has a high inflation of jobs, which makes it very easy to leave Microsoft. But that's difficult because the nature of these conflicts and challenges makes the employees who are part of them feel they're losing self worth if they quit.
So I could speculate that leaving Microsoft has Sinofsky experience the most complex of emotions. However, it's likely he'll rebound and be off to other conquests soon.