like trying to scratch your ear with your elbow

Extremely difficult; seemingly impossible. Keeping this business afloat in this economy is like trying to scratch your ear with your elbow. Working a full-time job while raising three young kids on your own is like trying to scratch your ear with your elbow—you're better off finding someone who can give you a hand.
See also: ear, elbow, like, scratch, to, trying
Farlex Dictionary of Idioms. © 2022 Farlex, Inc, all rights reserved.

like tryin' to scratch your ear with your elbow

Rur. impossible. Getting those kids to settle down is like tryin' to scratch your ear with your elbow. Fixing all the leaks in that old roof is like tryin' to scratch your ear with your elbow.
See also: ear, elbow, like, scratch, to
McGraw-Hill Dictionary of American Idioms and Phrasal Verbs. © 2002 by The McGraw-Hill Companies, Inc.
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References in classic literature ?
Now, if I sawght yehs tryin' work me fer drinks, wouldn' buy damn t'ing!
If yer don't know de guy, and he's tryin' to do de Johnny act, say de word, and I'll call a cop in t'ree minutes.
"De lady says dat she's on to de fact dat gals is dead easy when a feller comes spielin' ghost stories and tryin' to make up, and dat's why she won't listen to no soft-soap.
God knows I's ignorant an' poor; but," she added, "I knows what you an' Miss Davidson is tryin' to do.
"Well," at length spoke the tattered man, "there ain't no use in our stayin' here an' tryin' t' ask him anything."
Why, I see 'm tryin' to tell me sometimes so hard that he almost busts.
Yer hands don't shake, and yer eyes don't look as if ye was tryin' ter hold back the Angel o' Death himself, when you're jest doin' yer DUTY, Mr.
"He ain't tryin' his hardest, an' Red-head's just bustin' himself."
"The judges are tryin' to make him give the money back," Bert explained.
"It's jest no use tryin' to keep Miss Eva here," he said to Mammy, whom he met a moment after.
I've overheard enough to make me think he's tryin' to get her to run off with him." Hanson, to fit his own ends, hit nearer the truth than he knew.
"My father he run his packet, an' she was a kind o' pinkey, abaout fifty ton, I guess, - the Rupert, - he run her over to Greenland's icy mountains the year ha'af our fleet was tryin' after cod there.
"'I'm tryin' to tell you-all because I thought you-all ought to know,' says the tenderfoot.
My name's Dawson, Joe Dawson, an' I'm tryin' to scare up a laundryman."
"There's a whole lotta people tryin' to mess with your mind," she sings, in "Feel Good." "When you were just a little child they filled you in with every sin they could find/Tellin' you it's wrong to want my good lovin'/One way for you to know for sure/Does it feel good baby?