grey-sky thinking
n. Negative or pessimistic thoughts, ideas, or solutions. Also: Grey sky thinking, grey-skies thinking.

Example Citations:
"Grey sky thinking" might be a better way of putting it. Officials at Glasgow City Council have been told to indulge in "blue sky thinking" in the quest for economies that could see its budget cut by 15% in three years and its workforce shrink by up to 3000.
—"Cutting to the quick," The Herald, September 24, 2009

Policy-makers, when they lift their heads from the immediate and try to look ahead, described the process as "blue-skies thinking". But what is needed now is "grey-skies thinking", the politics of gloom.
—Charles Moore, "Financial crisis: We will find our catharsis in the politics of gloom," The Daily Telegraph, September 20, 2008

Earliest Citation:
Roeder, declining to look back in terms of revenge, would not look forward to a safety points total either, preferring "each match as it comes", standard grey-sky thinking though their next, on Wednesday, is the FA Cup replay with Chelsea.
—Jeremy Alexander, "Souness lays blame with habitual offenders," The Guardian, February 4, 2002

Notes:
The more extreme version of this type of thinking — black-sky thinking — dates to about 2002. The use of blue-sky (or blue-skies) as an adjective meaning "overly optimistic, unrealistic," dates to 1895. Here's the earliest use I could find of the opposite adjective grey-sky:

In shopping centers, restaurants and lounges, you can see the changes wrought by newly-aware consumers living in an area where retailers are meeting fashion demands.

South Florida women, men and teenagers, unencumbered by the grey-sky mentality of the north, are strutting out with brightly colored, coordinated outfits.
—Carol Weber, "Fashion, with elan, has come to South Florida," The Miami Herald, September 25, 1983

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