What Does Checkered Career Mean?

Checkered Career Meaning

Definition: An employment history that includes many past changes.

Sometimes, people use this expression to refer to a person’s background in general, rather than specifically their past work experience. It often implies that the person has had a mixture of successes and failures.

Origin of a Checkered Career Meaning

This expression originated sometime in the 1800s. It relates to a checkers board because of the way that the red and black squares alter.

Examples of a Checkered Career Meaning

chequered careerIn the example below, two siblings are discussing a new teacher at their high school.

Jordan: Did you get the new teacher for your chemistry class?

James: Yeah. He seems great! Did you get him, too?

Jordan: Yeah. He was telling us a little bit about his background. It seems like he’s had a checkered career.

James: Why do you say that?

Jordan: Well, at first he was a really important chemist who had a lot of new inventions, and then he went to jail for some reason, and then he had a bunch of other random jobs, and now he’s teaching at our school.

what is a checkered careerIn the second dialogue, two coworkers are complaining about their boss.

Herman: I’m not even sure how our boss got promoted to his current position.

Allison: Why do you say that?

Herman: He doesn’t have any of the qualifications that he should. He’s also had a really checkered career.

Allison: What do you mean?

Herman: He’s had jobs in a whole bunch of different industries, some of which went bankrupt. Granted, a few of the companies made millions.

Allison: Maybe that’s why they hired him. It sounds like the variety could be helpful.

Herman: You’re probably right, but I still think it’s strange.

More Examples

This excerpt is from an article about a band that is reuniting after some time apart.

  • I think we owe it to our fans who have stuck with us during the many ups and downs of the band’s long and checkered career, says Lewis.  –OC Register

The second excerpt is about an actress who was very rude while traveling by airplane.

  • Marketing on school campuses has had a checkered career. Schools have taken money in the past to provide exclusive access to one soda company or another — thus encouraging the consumption of large amounts of sugar by students as well as loyalty to a particular brand. –LA Times


The phrase a checkered career describes a varied background with many changes both positive and negative.