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checkered career

A history of employment characterized by many different kinds of jobs or by many alternating periods of success and failure. I had a checkered career after high school, taking any kind of work that I could find. I don't know if I would trust your finances to him, he's had a rather checkered career from what I've heard.
See also: career, checkered

zenith of (one's) career

The highest point of one's career. Now that I got a big promotion, I'm at the zenith of my career—it can't get any better than this!
See also: career, of, zenith
Farlex Dictionary of Idioms. © 2022 Farlex, Inc, all rights reserved.

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.
See also: career, checkered
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.
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