One historical example: In the 1920’s when the United States began banning marijuana they did so by telling people that they needed a license to carry the plant, but in order to get the license, you had to have the plant on you. When people came in to get the license, they would be arrested for illegally carrying marijuana without a license.

A conundrum is just something puzzling. Or a riddle where there is a pun (play on words) as in “What’s black and white and read/red all over” – a newspaper. The pun is on the word “read/red”.

They really aren’t directly related. A catch 22 may result in a conundrum, but a catch 22 is more frustrating than confusing due to a lack of viable options for getting what you want. You know exactly what’s going on and aren’t confused by it. One may think that trying to find a way find a way past the catch 22 is a conundrum, but I wouldn’t call the catch 22 itself a conundrum.

A catch-22 is a specific type of difficult problem, where there’s no resolution that resolves all of the issues in the problem. An example would be if I’m out of work, I have plenty of time to go do fun stuff, but no money to do it; conversely, when I’m working, I have the money but not the time.

(If I don’t answer I will not earn the 2 points. If I do answer some trolls will come along and give me 2 thumbs down).

A conundrum is a riddle (What is black and white and read all over?).