square peg in a round hole
Someone or something that does not fit well or at all in a certain setting; a misfit; hence, someone or something that will not succeed in an endeavour, except possibly with much effort and force.
Meaning adapted from Wiktionary, available under CC BY-SA 4.0.
“He feels like a square peg in a round hole at his new job.”
“The creative artist felt like a square peg in a round hole while working in the strict, numbers-focused accounting firm.”
“Trying to use this old software on a modern computer is like putting a square peg in a round hole because the systems are simply not compatible.”
“Despite his best efforts to conform to the rigid expectations of the academy, he remained a square peg in a round hole, forever alienated by its narrow traditions.”
Commonly associated with a shape sorter, a baby toy that consists of (often wooden) pegs that need to be inserted through holes in a box, using the hole that has the same shape as the peg. While all the shapes are of roughly equal size, each peg will only fit in the hole that has the same shape. Inserting a peg in a different hole would require either modifying or breaking the toy.
- 01
ace in the hole
Synonym of ace up one's sleeve.
- 02
albatross round one's neck
Alternative form of albatross around one's neck.
- 03
ask round
To enquire of several people.
- 04
back to square one
Located back at the start, as after a dead end or failure.
- 05
beat someone round the ears
To beat (a person) with blows about the head.
- 06
blow a hole through
To destroy the integrity or cohesion of.
- 07
bring round
To resuscitate; to cause to regain consciousness.
- 08
burn a hole in someone's pocket
To cause someone to spend money or be tempted to spend money.
Last updated August 10, 2026