Can’t Win for Losing – Meaning, Origin and Usage

Are you going through a hard time in life where nothing seems to go right for you, no matter how hard you try? You could say, “I can’t win for losing,” to voice your despair at your run of bad luck. This post unpacks the meaning and origin of this expression.


The expression “can’t win for losing” means that you aren’t getting ahead in life, and nothing seems to work out for you, no matter how hard you try.

Typically, people will use this expression when feeling demotivated or depressed. It’s telling others that you think you will never get something right and you should just give up on trying.

Can’t win for losing” means that you’re on a run of bad luck and everything in your life seems like it’s falling apart. It’s a way of telling someone that you’re in a rut or feeling depressed because you’re not getting what you want out of life.

Example Usage

“I’ve got to stop playing online poker at that crypto casino. I can’t win for losing, and I’m deleting my savings.”

“I don’t know what is going wrong with my life right now, but I can’t win for losing. Everything I do keeps going wrong, and I’m ready to give up.”

“The Jets are going through a really bad patch in their season. They can’t win for losing right now, and it’s going to be tough for them to get out of this slump.”

“I don’t know why I can’t close any prospects. It’s like I can’t win for losing. Maybe this isn’t the right job for me.”

“I’ve been out here on the lake fishing all morning and not a single bite. I can’t win for losing. If I don’t hook something in the next 30-minutes, I’m going back to camp.”

“I can’t win for losing with this. Every time I try to convince her otherwise, she shuts down on me and tries to convince me otherwise.”

“It’s like I can’t win for losing, and it’s starting to make me feel depressed.”


The expression “can’t win for losing” originates from 1950s America. The original rendition of the phrase was “you can’t win” or “I can’t win, and it has the same meaning as “can’t win for losing.” According to language experts, the phrase changed to the current version of “can’t win for losing” sometime in the 1960s.

The change added a play on logic to the phrase, making it more popular with people describing a hard time in life or pointing it out in others. The term is still in use today, and you probably hear it from time to time when people describe their bad luck or other people experiencing a rough time in life.

Phrases Similar to Can’t Win for Losing

  • Bad juju.
  • Loser.
  • Things never go right.

Phrases Opposite to Can’t Win for Losing

  • Things always turn out okay.
  • Winning.

What is the Correct Saying?

  • Can’t win for losing.

Ways People May Say Can’t Win for Losing Incorrectly

Using the phrase “can’t win for losing” to describe other people holding you back in life is incorrect. The term describes something you’re doing wrong and that you need to reassess what you are doing to change the outcome.

Acceptable Ways to Phrase Can’t Win for Losing

You can use the expression “can’t win for losing” when you’re telling someone that nothing in your life is going right for you. No matter what you do, everything seems to end badly. The phrase suits professional and social use.

You could tell your friend that you’re having a hard time in life and can’t win for losing. Or you could say to your colleagues that you can’t close anyone and you can’t win for losing with your pitch. It’s a way of expressing that you’re in a bad spot in life, and nothing seems to work out for you, regardless of changing your approach.

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