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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

take the chequered flag

To finish in first place in an auto racing competition. Primarily heard in UK. Neck and neck right up until the final moments of the race, photo analysis revealed that it was Steinman who took the chequered flag.
See also: chequer, flag, take
Farlex Dictionary of Idioms. © 2015 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.

take the chequered flag

finish first in a race.
In motor racing a chequered flag is used to signify that the winner has passed the finishing post.
See also: chequer, flag, take
Farlex Partner Idioms Dictionary © Farlex 2017