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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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