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90s Slang You Should Know

checkered career

A background that includes many changes, especially of employment. For example, Heather's had a checkered career, hopping from one city to another and one job to another. This expression, first recorded in 1881, uses checkered in the sense of “constantly alternating,” much like the squares on a checkerboard.
The American Heritage® Idioms Dictionary
Copyright © 2002, 2001, 1995 by Houghton Mifflin Company. Published by Houghton Mifflin Company.
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Examples from the Web for checkered career
Historical Examples
  • This rare faculty has stood him in good stead throughout all his checkered career.

  • It is one of the few things in my checkered career that I have hitherto escaped.

    Lady of the Decoration Frances Little
  • For the first time in his checkered career Mr. Gibney had a sane, sensible, and serious thought.

    Captain Scraggs Peter B. Kyne
  • Perk was feeling prime at that particular moment in his checkered career.

    Eagles of the Sky Ambrose Newcomb
  • A few years thereafter, the husband's checkered career was closed by a wound in the foot.

    Women of England, Volume 9 (of 10) Burleigh James Bartlett
  • The story of the checkered career of that remarkable woman is fairly accessible.

  • Few facts are more admirable in Rembrandt's checkered career than the noble struggle he maintained against misfortune and neglect.

  • Andrea Doria himself—“Il principe” as he was styled—had a long and in some respects a checkered career.

    The Mediterranean T. G. (Thomas Gray) Bonney, E. A. R. Ball, H. D. Traill, Grant Allen, and Arthur Griffiths
  • All I need to complete my checkered career is to keep a boarding-house!

    Lady of the Decoration Frances Little
  • With the recall of these incidents in his checkered career a new thought blazed up in his mind—rather a blinding thought.

    Felix O'Day F. Hopkinson Smith

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