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TL;DR: How do I use "outside of the box" thinking well in puzzle making?

One of my friends came to school with a puzzle. It's a rather popular puzzle, but, us never having heard of it before, were unaware. This is sort of how the conversation went down.

Puzzle Friend: Hey guys! I have a puzzle I bet you can't solve.

Me: Lay it on us. (Friends agree)

Puzzle Friend: Okay, here it is. I have a hat. I give it to [friend 1]. Who has the hat?

Friend 1: I do.

Puzzle Friend: Correct! Now, if I take the hat from you, who has the hat?

Me: You do.

Puzzle Friend: No, you do.

Me: but... what?!

Puzzle Friend: Of course, now if I give the hat to [friend 2] who then gives it to [friend 1]. who has the hat? Me.

Friend 1: But...!

[etc.]

Now, our task was to find out the pattern. He said there was a simple pattern, and it was indeed simple, as I realized the solution was (solution below)

that the person to first talk after the question was asked had the hat (or something to that effect.)


Now, I realize that this puzzle is hard because it is unconventional and simply random, utilizing a "pattern" that was, as I believe, on a different level of thought, what can be described as "outside the box". I further believe that this "out of the box" aspect makes the puzzle hard. Is this a correct thought?

Furthermore, how can one use this "out of the box" perspective to make puzzles? I would qualify the aforementioned puzzle as mostly trolling, but can I use this sort of perspective to make a good puzzle? By good, I mean a puzzle that is engaging, interesting, and one that is not nigh impossible.

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    $\begingroup$ I don't understand how that makes sense with a physical object. $\endgroup$ – Ian MacDonald Mar 18 '16 at 2:00
  • $\begingroup$ @IanMacDonald It doesn't, which is the point: the "pattern" is some trolling as well. $\endgroup$ – Conor O'Brien Mar 18 '16 at 2:01
  • $\begingroup$ Totally depends on the type of puzzle, but outside the box thinking is what makes them fun and difficult. The idea is to make it in a specific way. And then follow the steps and make sure the answer is recoverable. A good way to test is to grab a friend or family member and show them the first step and say how to work through it. Then move onto the next until the puzzle is solved. If they say that a certain part is not possible to get past. Add another breadcrumb there. Good luck and I hope to see some good puzzles from you in the future. $\endgroup$ – Z. Dailey Mar 18 '16 at 3:48
  • $\begingroup$ @Z.Dailey Thank you for your insight! I believe that comment is worthy of an answer. $\endgroup$ – Conor O'Brien Mar 18 '16 at 3:58
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Totally depends on the type of puzzle, but outside the box thinking is what makes them fun and difficult. The idea is to make it in a specific way. And then follow the steps and make sure the answer is recoverable. A good way to test is to grab a friend or family member and show them the first step and say how to work through it. Then move onto the next until the puzzle is solved. If they say that a certain part is not possible to get past. Add another breadcrumb there. Good luck and I hope to see some good puzzles from you in the future.

Added note: can get some ideas from other people on the site. There's a few out there that make a wide variety of puzzles, just try to drastically change all aspects of the puzzle and merely gather ideas from them.

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