A square peg in a round hole is an idiomatic expression which describes the unusual
individualist who could not fit into a niche of his society.

English literature

The British novelist Edward Bulwer Lytton published the metaphor in a late 19th century book:

Kenelm Chillingly asks, "Does it not prove that no man, however wise, is a good judge of his own case? Now, your son's case is really your case —- you see it through the medium of your likings and dislikings, and insist upon forcing a square peg into a round hole, because in a round hole you, being a round peg, feel tight and comfortable. Now I call that irrational."

The farmer responded, "I don't see why my son has any right to fancy himself a square peg ... when his father, and his grandfather, and his great-grandfather, have been round pegs; and it is agin' nature for any creature not to take after its own kind."

-- Edward Bulwer Lynton in Kenelm Chillingly, His Adventures and Opinions (1873).

Business management

This idiomatic expression has proven to be quite durable into the 21st century. It is used in a range of contemporary business-related circumstances; and illustrative examples include:

"As they say, you can't fit a square peg in a round hole. If your boss is like that round hole and you are that square peg, you aren't going to fit in unless you re-shape your edges."

-- Gini Graham Scott in A Survival Guide for Working with Bad Bosses: Dealing with Bullies, Idiots, Back-stabbers, and Other Managers from Hell (2005).

Visual meaning

The idiomatic expression conjures a visual image, and this is evolving independently, e.g.,

• "We intend to show that Israel needs a security process as well as a peace process.... To continue with the old diplomatic approach would be like hammering square pegs into round holes." -- Dore Gold
  Dore Gold
  Dore Gold is an Israeli statesman who has served in various diplomatic positions under several Israeli governments. He is the current President of the Jerusalem Center for Public Affairs...
  
  
• "... relating back to the title of the panel session, square peg in a round hole; well, maybe, but sometimes you can force that peg in and make it stick. We seem to be somewhere between a feeling of cautious optimism and open-minded skepticism about the workability of disease management in fee-for-service Medicare. -- Bruce Steinwald, Director of Economics and Payment Issues in the Health Division at the U.S. General Accounting Office

See also

• Joseph Powell Williams
• Squaring the circle
  Squaring the circle
  Squaring the circle is a problem proposed by ancient geometers. It is the challenge of constructing a square with the same area as a given circle by using only a finite number of steps with compass and straightedge...