What other sayings are there like "you can't win by losing" and what does it mean?

I always heard it as “you can’t win for losing” (for instead of by).

And I have always understood it to mean “no matter what you do, as hard as you try, there are some things you don’t get”. It’s sort of a cry of despair and disgust.

@elbanditoroso Yes, I see that it’s for not by
So, is there another expression that’s not obvious as to what it means?

My old pappy had a bunch of them, like: That’s the way the cookie crumbles, you’re a chip off the old block, don’t throw rocks when you live in a glass house.

You can’t win if you don’t play .

Never up, never in.
Golf- meaning don’t leave it short

How about: He’d bitch if he were hanged with a new rope.

Another take on the no win situation

You can’t win for losing.

I always took it to mean there is no honor or a win in losing.
It’s like this last election. Many people thought the last two people standing was a poor choice. So to them there was no winning. if you lose no matter what.

I am the wisest man alive, for I know one thing, and that is that I know nothing.-Socrates
(If he knew nothing then he wouldn’t even gleam what it means to be wise, much less be able to talk.) I get what he was trying to say, but it was a bit of a reach because one could argue that a person who knows very little couldn’t possibly be wise. Usually they are just ignorant.

You can’t see for looking, as in…

You can’t see herds of wildebeest sweeping majestically across the plain outside of a Torquay hotel bedroom window

You can’t see the forest for the trees

Then there is the juxtaposition between:

A stitch in time saves nine and

He who hesitates is lost

They seems to be at cross-purposes.

“You can’t win for losing.”

One way to rephrase it: You can’t win, because you keep losing.

Another way to rephrase it: Since you’re losing, you can’t win.

As for what it means, I’ve always understood it the way @elbanditoroso suggested.

You can’t win if you don’t bet.
You can’t win if you don’t try.
You can’t win if you don’t buy a lottery ticket.

The rain in Spain falls mainly on the plains / The precipitation in Portugal pelts primarily on the plateaus

When you have your head up your @ss, everything looks like sh*t.

The laws of thermodynamics have been summarized as:
1. You can’t win
2. You can’g break even
3. You can’t quit the game

A nice explanation is given here

@rojo, that isn’t complicated at all. LMBO. I never heard of that one. I have to remember that.

Cutting off your nose to spite your face.

When my daughter was about 7 or 8 she said or did something, and I said, “You know what they say about people who live in glass houses…”
She said, “They shouldn’t haven’t sex?”

They’re not happy unless they’re unhappy. People like that drive me up the wall.

@ucme I specifically asked for a room with a view!

@Blueroses Saw you here & referenced Basil hoping you’d notice, you never disappoint :)