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Difficulty - Difficult Challenges

Explore English idioms regarding difficult challenges with examples like "herculean task" and "like herding cats".

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English idioms related to Difficulty
like pulling teeth

used to refer to something that is inexplicably difficult

Ex: Getting him to answer one simple question was like pulling teeth. 
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teething (problems|troubles)

problems that a person encounters in the early stages of a project or activity

Ex: The app had a few teething problems, but it works smoothly now. 
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like Chinese arithmetic

said of something that is very complex or difficult for one understands or work with

Ex: The tax form looked like Chinese arithmetic to me. 
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to [be] murder
to be murder
[phrase]

(of a task) to be very difficult or almost impossible to do or complete

Ex: Getting all these boxes upstairs by myself was murder. 
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uphill battle

a difficult fight or challenge that requires a lot of effort and determination

Ex: Getting the school reopened will be an uphill battle. 
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herculean task

a task or challenge that requires an immense amount of effort, strength, or endurance to accomplish

Ex: Restoring the old hospital was a herculean task. 
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heavy going
heavy going
[phrase]

requiring significant effort to overcome or complete

Ex: The first chapter is heavy going unless you already know the theory. 
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a (tough|hard) row to hoe

a situation that causes difficulties for one

Ex: Taking over the team after three managers quit was a tough row to hoe. 
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to [bite] off more than {sb} (can|could) chew

to attempt to do something that is beyond one's capability

Ex: He bit off more than he could chew when he agreed to manage three projects at once. 
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(as|) red as a cherry

turning really red in the face because of doing a lot of physical activities

Ex: After running up the stairs, he was red as a cherry. 
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like herding cats

used to describe a job or task that is too difficult or challenging

Ex: Getting the committee to agree on a date was like herding cats. 
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draft-mule work

the hardest or most boring part of a task or job

Ex: Sorting all the receipts was the draft-mule work of the audit. 
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the deep end
the deep end
[phrase]

a situation that is very difficult because one is not prepared to deal with it

Ex: On my first day, they threw me in the deep end with three angry clients. 
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to [shoot] {one's} bolt

to utilize one's final and decisive efforts, often in a critical moment

Ex: The team shot its bolt in the final ten minutes, but the equalizer never came. 
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