square peg in a round hole

plural square pegs in round holes

1. idiomaticSomeone 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.

   It is almost as if you have guidelines for putting a square peg into a square hole, but we are trying to apply those same guidelines to put a square peg into a round hole.

   [1985 July 9, Eugene Gressman, witness, “Statement of a Panel, including: Elliot H. Levitas, Esq., Kilpatrick & Cody, Washington, DC; Stuart E. Eizenstat, Esq., Powell, Goldstein, Frazer & Murphy, Washington, DC; Stan M. Brand, Esq., Brand & Lowell, Washington, DC; and Eugene Gressman, Professor of Constitutional Law, School of Law, University of North Carolina, Chapel Hill”, in Rulemaking Procedures Reform Act of 1985: Hearing before the Subcommittee on Administrative Practice and Procedure of the Committee on the Judiciary, United States Senate, Ninety-ninth Congress, First Session on S. 1145: A Bill to Increase the Accountability of, Policy Coordination by, and Management of Priorities by Agencies through an Improved Mechanism for Congressional Oversight of the Rules of Agencies […] (Serial J-99-38), Washington, D.C.: U.S. Government Printing Office, →OCLC, page 77

   3 more examples

   ["]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." / "I don't see why my son has any right to fancy himself a square peg," said the farmer, doggedly, "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.["]

   [1873, [Edward Bulwer-Lytton], chapter XXI, in Kenelm Chillingly: His Adventures and Opinions […], 2nd edition, volume I, Edinburgh; London: William Blackwood and Sons, →OCLC, book II, page 352

   To these people, native and European, he was a queer fish, but they were used to queer fish, and they took him for granted; […] In England and France he was the square peg in the round hole, but here the holes were any sort of shape, and no sort of peg was quite amiss.

   1919, W[illiam] Somerset Maugham, chapter LIV, in The Moon and Sixpence, [New York, N.Y.]: Grosset & Dunlap Publishers […], →OCLC, page 282

   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. If you can't do that, then look for that square hole where you will fit.

   [2005, Gini Graham Scott, “Dealing with Danger”, in A Survival Guide for Working with Bad Bosses: Dealing with Bullies, Idiots, Back-stabbers, and Other Managers from Hell, New York, N.Y.: AMACOM, American Management Association, →ISBN, part V (Ethical Challenges), page 153

   Synonyms: like a fish out of water