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

    Lady of the Decoration Frances Little
  • All I need to complete my checkered career is to keep a boarding-house!

    Lady of the Decoration Frances Little
  • The checkered career I have already exposed, has portrayed almost every phase of African life.

    Captain Canot Brantz Mayer
  • 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.

  • 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
  • I've been abroad more than once during my checkered career, the last time with a company that played the "Children of the Ghetto."


    George Niblo
  • During a long and checkered career, Constantine had experienced many ups and downs.

    The Story of Mankind Hendrik Van Loon
  • 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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