To be troubled or perplexed; to be at one's wits' end—holding one's head in one's hands while worrying over a problem.
予算が足りず、プロジェクトマネージャーは頭をかかえている。
With the budget lacking, the project manager is at his wits' end.
子どもの進路について両親で頭をかかえた。
The parents were worried and at a loss about their child's future path.
複雑な問題に直面して、彼女は机に突っ伏して頭をかかえた。
Facing a complicated problem, she buried her head on the desk in despair.
新しい制度の対応に悩み、部署全体で頭をかかえている。
The whole department is struggling and at a loss over how to handle the new system.