Methodology for teaching Riddle Mastery in an Educational setting

My ranking system and whatnot may seem like a lot of categorizing, but trust me when I say that it is worth remembering. During my years working at summer camps, the campers fell utterly in love with my riddles and, in the way 3rd-5th graders will, took them and the systems/terminology I created for Riddle Mastery very seriously indeed. Indeed, these terms and systems were developed while I was working at camps, gradually taking shape over the course of countless conversations with eager, curious, and earnest campers. What did you expect? That I was bored and so just sat down one day and started doing this? The only way to determine a riddle's rank is to test it, and large summer camps provide a very fertile field for doing so. Do this enough and patterns will emerge as one notes which riddles are solved most easily by the most number of people in different age-groups, and which ones are more challenging. I even have a standard starter riddle which I give to determine the potential skill of a person or group. Believe me, I may have made up the riddles for fun before doing summer camps, but my classifications and ranks evolved on the job.
Again, do not underestimate the impact telling riddles can have. They are marvelous ice-breakers if nothing else, and before one starts thinking about unhealthy competitiveness among children that leads to bullying and rivalries, the whole affair was always utterly light and cheerful. Friendly competition personified that walked hand-in-hand with cooperation, the riddles were a topic of conversation – a collective puzzle set by an adult with the campers bonding over the shared challenge and experience, building friendships off of trying to solve them, while interest beyond that is itself quite real. There was always at least one camper a session who ended up, on their own volition and without my suggestion, bringing a journal and pencil to camp to record every riddle & answer I had told thus far, keeping the journal with them to catch all the new ones until the session's end. Others wanted to learn how to make riddles, and collectively I spent many hours over the course of weeks helping these 3rd-5th graders become Riddle-makers. One 3rd grader, a girl, created a Master ranked one that continues to torment people to this day. Truth be told, the only bad thing that ever came out of my riddles was that one particular group of kids one summer kept trying to steal my Riddle Sheet from my pocket.
Beyond that, there were other uses from a purely professional standpoint. Having an M.Ed myself, along with several friends and close relatives who teach upper elementary school, I can say with utter surety that every educator knows that that age-group tests their teachers, seeing how far they can push boundaries before their teachers reign them in. The interesting thing is that no camper ever tested me. Why? I assume it was because they were more interested in solving my riddles, and soon enough I was more than just another summer camp counselor – I was their friend whom they wanted to please. I know it sounds improbable, but there was one camper who was well-known enough in the camp that other counselors warned me before the session began that he was handful; and I saw why soon after meeting the lad. Yet he became so interested in the riddles that he never gave me more than token trouble and, in fact, spent much time trying to solve them with a group of boys. "When caught between the riddle and its answer there is no freedom," and that is how I taught: catching the campers between the two so that their own naturally inquisitive natures drove them not to push my boundaries but rather that which separates the riddles from the answer, the walls within their minds.
I gave some riddles earlier. Here are the answers.
What plays with words and logic, yet never tells a lie = a riddle
It can either be found by, or given to you, when found you understand it, when given you might not = the answer
Therein lies the key points and pillars of both kinds of Riddle Mastery, to teach others to look beyond the obvious and outside the box by expanding their minds. It may sound overly simple, but I have seen young minds visibly grow and become more confident over the course of a mere two week camp sessions. The growth owed to the riddles gradually stretching and strengthening mental muscles, the confidence born from the accomplishment of solving them. A true accomplishment as I never give any real hints as to the answers; I only say what type of riddle it is, what rank, and whether the answer is tangible or intangible. That, and a few hours for them to solve it (after which I reveal the answer as to never tell would be cruel). I love the glow of triumph on people's faces when they solve one. Especially since literally everyone always at the start tells me that they are bad or terrible at riddle-solving. Well, 99% of those who tell me that in the beginning end up solving a few Hard ones at least. And with that confidence comes pride. Due to my ranking system the kids knew exactly how hard each riddle was, and could of course observe how many of their counterparts had solved it or riddles of similar rank. Honestly, they were as intrigued by the system as by the riddles themselves since they saw in it potential for greater challenges ahead and the chance to earn the coveted title Riddle Master. I know this sounds rather…unlikely, but the method lent to and supported itself. I got the kids interested in riddles by giving them middle-ranking ones, the solving of which gave them confidence and pride in this hitherto unknown skill of theirs called riddle-solving. Both of which lead to interest; hence they learn my system and rules, which leads to greater skill, confidence, and pride as they learn to solve increasingly more difficult riddles. The result? Towards the end of the two-week session they eagerly await me telling them Master ranked riddles, often badgering me to tell one sooner than I deem wise. (This is a key point, as giving Hard and Master rank ones too early will result in a loss of confidence since it is unlikely that the children will be able to solve them. Mental muscles are like real ones, start with lifting smaller weights until you can handle the big ones.) The kids also learn more about themselves. I recall one group where a few realized they were notably better at Wordplay than Logic riddles, and vice versa for others. A fact that intrigued as opposed to upset them and prompted a healthy interest in the difference between the types of riddles (to say nothing of my Grandmaster Riddle that combines the two types).

Again, I know all this sounds absurdly simple and, from an educator's prospective, unorthodox, but it worked like a charm each and every time. I guess I am an unorthodox person to a degree, trying to find new yet no less effective while more fun ways to do things. Aldous Huxley once said that, "The secret of genius is to carry the spirit of the child into old age," while Albert Einstein noted that "If you want your children to be intelligent, read them fairy tales. If you want your children to be more intelligent, read them more fairy tales." I am not so arrogant as to name myself a genius, but I do try to live up to those quotes and employ them when educating. During lunchtime at camp I always chose to eat with the campers, even when I had the option to eat with other counselors. Part of it was because it is hard to hold a conversation when are campers running up to whisper a riddle-answer in your ear every few minutes, but mostly because I enjoyed it. Children have fascinating insights and by listening to them, by regularly talking to them on their level, I became their friend. (I also have some skill as a storyteller, so when riddles fail to quiet the crowd a tale succeeds. It got to the point where every lunchtime the campers wanted to hear a new story. Point of order, I was not reading to them; this was not story-time in the traditional sense. Like a Bard, I told them myths and legends I had more or less memorized and it enraptured them. On that note, I am well-aware that utilizing riddles in this way is not a good fit for many situations, but storytelling is much more flexible. I once worked at martial arts camp, and the parents knew me through their kids as the Instructor "who told amazing stories at lunch", their words not mine.)
However, like any education methodology – if I be so bold as to call my riddling such – it relies on the passion of the educator telling the riddles; they must put their heart into them and be firm. I spoke above about 3rd-5th graders pushing boundaries, saying that because of my riddles they did not push mine. This is true, except for one detail. They pushed my riddle boundaries: “Can you tell me the answer, I promise I won’t tell”, “We need another hint; what is the first letter of the answer?” ect ect. They pushed me, but I did not budge and that, I think, helped me overall as a camp counselor; the kids saw that I was firm and unyielding regarding my own self-imposed rules of Riddle Mastery, and so did not push me on actual camp rules. Interestingly, this is one of the reasons, I think, why they became so intrigued with the systems & terminology I developed. They saw how seriously I took my own rules and so took it seriously themselves. Whenever a camper solved a riddle they were supposed to whisper it in my ear so as not to spoil it for others and, if they were correct, I – after giving a hearty congratulatory cry of “Correct!” for all to hear – would instruct them to “give no hints and tell no one.” I know what you are thinking: Ian Adler, are you really na├»ve enough to think that not one 3rd-5th grader is not going to tell her or his best friend(s) or give out partial hints? Well, like I said, because I took the riddle rules seriously, so did they. Hence, in fact, not one camper ever disobeyed my “give no hints and tell no one” edict. Why? Not because they were afraid of my reaction, but rather because I had made clear that simply knowing the answer to a riddle means nothing. It is solving them that make the Riddle Master. In short, campers were not about to just give away the answer to a riddle that they had worked hard, often for over an hour, to solve. To use a different analogy, they took the riddle rules as seriously as the rules of a favorite sport or game and telling the answer amounted to cheating in their eyes. Not only that, they learned to use the rules like any good game players. Whenever I posed a riddle, the first thing the kids ask me is "is this Logic or Wordplay?" They recognize the key differences between the types, aware that knowing the type is absolutely necessary if they want to solve the current riddle since the thought process required of each is different.
Also the ranking system alone kindled the interest of several, for telling stories of past kids who had attained the title Riddle Master made the current group want to emulate them and move up the ranks. My Grandmaster Riddle is a perfect example of this, for I always emphasize how hard it is by saying that less than twenty out of hundreds, both children and adult, have solved it, and that solving it grants one the title Riddle Master. Sounds grandiose, but the effect can be startling. I had one camp group who began with a lackluster interest in the riddles, so I told them about the Grandmaster, saying that I was breaking my own rules by telling them of its existence at such an early stage as well as how hard it was to solve. Point of order, I was telling the truth about breaking my own rules and, at that time, only one person had solved the Grandmaster. Anyway, it turned the trick and in the space of an hour they were both fascinated with and determined to solve the Grandmaster; I recall one boy getting picked up at the day's end and excitedly telling his mother as they departed about this riddle that "only one person in the entire world has solved," to use his words. Amazing how even friendly competition with others kids who they have never met and likely never will meet can drive children to improve. Which is honestly the prime educational function of the Grandmaster: a sort of riddle legend for lack of a better word, a way to generate excitement and interest that has yet to fail, particularly since I will not even tell people the Championmaster Riddle unless they solve the Grandmaster. This fact alone generates even greater interest, for all want to hear "Ian's hardest riddle" that is somehow more difficult than the Grandmaster and try to solve it. (This dynamic will change somewhat now that I have an Ultimatemaster, but the point is the same.)
As to the scheduling element of my methodology, at Day Camps I told one riddle in the morning shortly after the campers arrived and they had until lunchtime to solve it; a solid two-and-a-half hours or so during which those who thought they had the answer would come and whisper it in my ear. If correct they were answered with my “Correct! Give no hints and tell no one”, and if not they had to keep trying. Those who did solve it spent the rest of the time smiling in proud, contented accomplishment and often trying to solve my Grandmaster Riddle, which, given its difficulty, existed as a standing riddle the answer of which would be revealed at the end of the two-week session. At lunch I would reveal the answer to the morning's riddle before giving them the afternoon's one, the answer to which would be shared at pick-up. Hence it was two riddles a day, though if the majority of the group solved the riddle right away I would reveal the answer to the rest and give another. Two riddles a day, with 2-3 hours for each to individually solve it, dramatically increased the kids' mental dexterity and skill at riddle-solving, to say nothing of their personal pride and devotion to Riddle Mastery as, gradually, the daily riddles got harder and harder until, towards the session's end, I gave out Master-ranked ones. The Master-ranked riddles were always greeted with particular anticipation and excitement, for that I was giving them out at all was proof to the campers that they had the skill to solve them, yet they also knew that only a few of them likely would, meaning this was a chance to really earn their stripes and prove their smarts, all in a friendly and companionable social environment. And a few always did solve them, though they would have stood no chance of doing so had I given them at the session's start. When I said that I could see young minds visibly grow and become more confident over the course of a mere two weeks, I meant it utterly.
However, the above method does not work in every setting. Recently I had the honor of being an After-school teacher and found that my riddles are as beloved as ever. I had to make a few radical adjustments to my standard methodology since as an After-school program is hardly a Day Camp. Firstly, students cannot be given the leeway to leap from their seats to rush over and whisper an answer in my ear at will, and secondly an After-school is much shorter than a Day Camp. Hence I had no choice but to adopt a shout-it-out form of answering: I would give a riddle and the students called their answers aloud until someone solved it, the solver getting the solo credit for doing so and, since everybody had just heard the answer, forcing me to give another riddle. Meaning that I could go through 5+ riddles in a single day, the obvious downside to this system being that the students who would have solved it given more time had no opportunity to do so. Which is why I prefer the Day Camp method, as it allows for more minds to grow and does not make the slower solvers feel they lack riddle-solving ability. I hope any of my After-schoolers reading this are not offended, yet it is true, and I always wondered what my old campers would have said had they witnessed the shout-it-out form of answering. Well, actually no, I do not wonder at all. I am utterly convinced they would think I had weakened and semi-betrayed the "Give no hints and tell no one” principle I drilled into them. I am sure they would understand once I explained that a new setting requires new methods, but still.
That said, After-school does have one enormous advantage over Day Camps: time. Let's face it, all day for two week is nothing compared to every afternoon for a whole school year. Hence, and despite the aforesaid disadvantages, the overall results were most pleasing. Pleasing and unexpected because, while all my previous campers were focused on riddle-solving, my After-school students were impassioned Riddle-makers. It is something of a personal plot twist really, having kids come up to me excited about a riddle they invented instead of wanting me to give them a riddle. The kids worked to solve each other’s riddles as much as mine, and looked to me for help in creating, testing, and perfecting the riddles they made, all wanting to earn the title Master Riddle-maker and/or Solver. A feat several achieved. Indeed, the 4th graders Noam and Giselle were better at making Wordplay riddles than me, creating more in months that I had in over a decade, and another boy, Ren, could make rhyming Logic riddles at will, while Jay had an aptitude for Scenario riddles I had never before seen, and they were all four excellent Solvers besides. I had many long conversations with them, for, returning to the use and importance of my ranking system, they wanted to know how I made Hard and Master ranked ones, even engaging in a friendly contest over who could create a Master one first (Giselle won), and began writing out their own Riddle Sheets which they guarded in much the same way I did.
I admit the making of personal Riddle Sheets caused issues now and again regarding exclusion as some wanted to work together to create riddles while others wanted to work alone or did not wish to expand their Riddle-making group since the more people who knew the answers the less fun they could have telling them to their classmates. A strange issue, since they took that protectiveness from me. However, the groups never wound up being more than three and most of the time they wanted to work solo or with me so they could then test their new riddles on their friends (I had drilled into them the importance of testing a riddle to determine its rank). No issue amounted to more than a brief argument nor caused any long-term problems. Indeed, they were so rare and small that I do not think my co-teacher even noticed them.
Bottom line? While I prefer the Day Camp method, the exponentially more time After-school allowed me to do riddles overcame most of its limitations. Most, and it invented a new one in that 5+ riddles a day for nine-ten months is a LOT of riddles. More than I had, so it was unutterably fortunate that so many of my students loved riddle-making as, towards the end, I relied almost solely on their riddles instead of my own. Which brings up another key point, that being that may be the most telling difference between the two styles of teaching Riddle Mastery: while the Day Camp method is ideal for teaching riddle-solving, the nine-ten months of After-school is perfect for teaching riddle-makers (as Making takes practice and two weeks of camp is not enough time to hone the skill).

 How might a ferryman leave his boat, yet leave the ferry operating = ?
Here is a hint, provided by Neil Gaiman:
only tell the ferryman the answer from a safe distance.
Point of order, namely to ram home the point that these riddles have real educational value, the After-school's Program Director complimented me on how my riddles were a continual communal bonding activity that sparked several strong friendships among students who had previously barely spoken to each other. I believe it improved the overall behavior of several of the, rambunctious ones as well, for I noted they were calmer upon developing an interest in the riddles, an interest augmented by pride in solving them and liking the feeling. Kids like to feel smart, humans are naturally fascinated by riddles, and solving a riddle is undeniable empirical evidence that you have more than fluff between your ears. Again, everyone begins by saying they are bad at riddles on first meeting me, yet I have never met anyone (the only and ironic exception being myself) who actually was bad. And this was before the riddles began to spread. The After-school's grade-range was Kindergarten to 6th grade, the groups barely interacted and I only taught the 4/5/6th group. Yet, like a tide or benevolent contagion,  the riddles spread. Some of my students told them at home, thus bringing their younger siblings into the mix, the impact of which I first became aware of when a first grade girl, the younger sister of one my 4th graders, brought a bunch of her friends over to me during outside time and demanded a riddle. Naturally I gave an Easy one which they solved with surprising quickness, and they ended up spending the rest of recess standing around me asking for and solving riddles. These were 1st graders. Yet was struck me even more than their surprising skill, as Easy rank riddles are not always easy for that age-group, was what the sister literally yelled when one of her counterparts gave up early and asked me for the answer: "No, you're supposed to solve it on their own!" she cried, covering her ears in fear I would give in. Imagine my reaction. If you guessed joyful astonishment, you got it. Here was a first grader whose only experience with Riddle Mastery was what her brother told her at home, and she already had a Riddle Master's mentality. Hence I answered her with a triumphant, "Yes! Spoken like a true Riddle Master!" And every recess following that the same thing happened, a group of first graders gathering around me begging for riddles and, to my amazement, swiftly answering Middle-ranking Wordplay ones as well as Logic. Seeing this, the lead teacher for the Kindergarten-1st grade group asked me for a riddle to use in a Riddles for Skittles (the candy) kind of game. In short, I gave her an Easy one and the the kids had to solve it to get the Skittles. Well, it worked like a charm and I nearly fell out of my chair when a Kindergartner came up to me with riddles she had invented. Then it spread to the 2nd and 3rd graders, though I remain unsure exactly how, and I ended up surrounded by them at the end of the day pick-up time communal free play telling riddles. One 2nd grader, Aidan, created his own hand-written Riddle Sheet with 60+ riddles, and when my 4th graders heard that a potential self-taught Riddle-maker was present they went to him at first opportunity and came back telling me in detail about how his riddles differed in style from my own. For context, they were so intrigued because I was the only other self-taught Maker they knew, so to meet one more or less their own age and just coming into his skill was for them sufficient cause for instant investigation. Oh, and one of them became close friends with this 2nd grader. Then there was a 3rd grade girl, Livia, who possessed one of if not the greatest natural talent for Solving I have ever seen given that she reached Master status in record time and I was not even her regular teacher (she solved more riddles in her first day of it then most do in a week)! I think you get the picture. With proper teaching, Riddle Mastery can become a short of self-sustaining and organic culture among Elementary schoolers. To be honest, even I was surprised by its success, and soon my fellows teachers, seeing the academic and cross-grade social-bonding potential of Riddle Mastery, deepened their involvement, with the Program Director again complimenting me on my success. It got to the point where children I had never met came up to me, sitting down in the middle of recess to ask for and ponder riddles.
Cold feet and two feet of snow
Now the question is, what else are riddles good for? I mentioned expanding young minds by forcing them to think creatively, metaphorically, and outside of the box, and doing this in a way they find fun adds to the benefit tenfold. A fun that invokes friendly competition in which everyone can win simply by solving the riddle. One my of After-school 4th graders said with great insight that knowledge is a huge commodity among his age group, because everyone wants to look smart and knowing something which others do not is a sign of smarts; the context of the conversation being how he was trying, with some success, to get his class interested in riddles. Now I am sure all you parents and teachers see the danger in this. If a kid does not solve one or several riddles does that make them dumb? Or rather, could not those skilled at solving create a sort of club, excluding those who are not? Not if you handle things correctly, and here is how. To start, I always begin by stressing that I am terrible at solving riddles, that I am purely a Master Maker (and Teller), and this eases the social pressure on the kids less skilled at solving to the point of it being nonexistent. If the guy teaching us Riddle Mastery is bad at solving then who cares if I am? Furthermore, I say point blank and repeatedly that there is no shame in not solving a riddle. Everyone's minds work differently, meaning some solve certain riddles instantly, in hours, or not at all; but I say this while encouraging them not to give up, expressing steady confidence in their abilities. "You can do it" and "I have faith in you" are my battle-cries as much as anything. This combination relieves all sense of shame at failing to solve it while lessening none of their jubilation if/when they do. In short, emphasize how many people have failed to solve to it while expressing confidence that they can be one of those who succeed. Also, nobody solves every riddle. I say "everyone's minds works differently, some riddles are easy to some but not for others" often enough, particularly when a veteran solver is struggling with an Easy-rank riddle and chagrined over the fact. So, could not those skilled at solving create a sort of club, excluding those who are not? Well, I have never seen it and always instantly promote inclusion when I see possible signs of such emerging. To date, no unfriendly exclusion insistent has occurred. Which leads us back to the question of what else are riddles good for? Teaching kids that everyone's minds works differently, of course! That poor Solvers can make great Makers, great Makers poor Solvers, and that failure in any of these brings no shame. Indeed, typically those unskilled kids just lose interest.
Which brings up another key point, that being that this friendly atmosphere only works if you treat riddles like a game. Take it seriously as you might a game, but no further. Thus those kids who find they are not good players will drift away on their own without feeling excluded, knowing that they are welcome to join in at anytime and will be welcomed with open arms. And some kids might just start out as plain uninterested and remain so. Indeed, I have had several students whom I was utterly positive could be tremendous Riddle Masters, but they were indifferent and viewed the riddles as a game their peers loved but which they had no interest in learning. No harm done to any side. Riddles are 100% voluntary.
Opening of Aldhelm's riddles in the
late tenth- or early eleventh-century
manuscript London, British Library,
Royal MA 12 c xxiii, folio 84r

The riddle was a major, prestigious literary form
in early medieval England, and riddles were
written both in Latin and Old English verse.

Now many years have passed and my riddle-telling days at camps are generally over. Yet I look back and remember the joy I felt at expanding young minds with my unusual hobby, with my self-made riddles that force people to think outside the box; and I remember the enthusiasm of those minds. How they would recognize and greet me jubilantly, campers a year or two older running and calling me by name and begging for a riddle – even recalling a few they had heard the previous year(s). How when I came back to visit one of the camps many of campers from separate groups had by chance been placed together, and how they cried aloud at my unexpected arrival. How first in high school and then in college I joined creative writing clubs, and my riddles became a standard part of the meetings. How in the summer of 2018 one of my old C.I.T. friends who was then a full Counselor wrote me and explained how much his campers loves riddles – that he had been using what few of mine he remembered – and requested that I send him my full Master Riddle Sheet. How I then weeks later got the same request from my old supervisor at a different day-camp. Riddle Mastery may be an unorthodox educational tactic, but it is an effective one that left a lasting impact. As I told my one of my old associates, “indeed, whenever I cannot tell them myself, it eases my soul to know that they are still being used to stretch the minds of and strengthen the bonds between young adventurers.” Truth to tell, it is less unorthodox as opposed to simply a much older form of education. As aforesaid, Babylonian school texts employed it, and riddles were a respected literary form throughout the ancient world, even being one of the most important forms of oral art in Africa. In ancient Greece, riddle-competitions were popular as an intellectual entertainment at symposia and occur frequently in mythology and folklore. It is only in the modern world that Riddle Mastery has fallen into disuse, and I would like to rectify that. Why else did you think I wrote this page? It was not out boredom, I assure you. Rather, as an M.Ed I feel a certain obligation to path on my teaching tactics. Still not convinced of the importance of riddles in education? See these below links and consider the fact that all agree how puzzle-solving is good for children and that a riddle is but a mental puzzle.
I will end by reiterating the fact that for riddles to be a functional educational tool the teacher in question must become a Master Riddle-teller, as it were; an adept at teaching Riddle Mastery. Like anything, excitement and commitment is required if one desires one's students to respond as I have described, and sometimes in takes time. It was weeks before my whole After-school group truly embraced Riddle Mastery, but they never would have had I not persevered; and it can be a delicate balance showing such consistent enthusiasm without seeming single-minded or obsessive. Beyond excitement and commitment, all the teacher needs is a book of riddles (or personal Riddle Sheet if they are a Master Maker), and the willingness to always give a new riddle when circumstantially appropriate. (My hands nearly froze off per continually digging my Riddle Sheet out of my pocket and perusing it in beyond glove-worthy winter temperatures, but it was worth it.)

How would I teach Riddle Mastery as full-time classroom teacher? Seeing as I have never been one, I have no idea. But teachers are typically creative and innovative people adept at learning and adapting on the job, so I have no doubt that a solid way exists. What that way is is a riddle for you to solve.

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