How does one become a Riddle-Maker

How does one become a Riddle-Maker? By making riddles, naturally, and I will do my best to impart the lessons I give my students here in written text. Unsurprisingly, the process begins with quote followed by two riddles of my own:

"Good riddles do, in general, provide us with satisfactory metaphors; for metaphors imply riddles, and therefore a good riddle can furnish a good metaphor." - Aristotle

What plays with words and logic, yet never tells a lie = ?

It can either be found by, or given to you, when found you understand it, when given you might not = ?

The answers are respectively "a riddle" and "the answer," the wording of each, plus the quote, describing how riddles work. Indeed, I use these riddles to teach prospective Makers and the point has never failed to get across. That said, I often tell my students that to make a riddle is to "describe something without really describing it, yet in such a way that it only perfectly fits a single answer." I will now walk you through the process.

1. The first step in riddle-making is thinking of the answer. Look around and pick some common thing everyone knows about, for the best riddles have obvious answers. As Patricia A. McKillip says, "A riddle is a tale so familiar you no longer recognize it." Let us settle with a chair.
2. Making the riddle involves describing it without being so obvious that a person will get it right away. For example "Something people sit in" is a bad chair riddle for two reasons: firstly, its is to obvious, and secondly it has several answers – such as a stool. So let us begin with "What has four legs yet never walks."
3. Not a bad riddle on the face of it, until you realize it could fit a table as well as a chair. A couch too, perhaps, but that is close enough as makes no matter, being honestly a very wide chair meant for several people and/or napping. Remember, a riddle can only have ONE answer. Thus we must change the riddle. So what does a chair have that a table does not? A back. Thus our chair riddle becomes: Four legs that don’t walk, a back with no spine, weight gives it strain, yet it feels no pain = a chair. A solid riddle, and one that rhymes no less.
4. Test the riddle. Give it to others (40+ people preferably) to make sure it is solvable and ascertain its difficulty ranking. The chair riddle here is not terribly difficult, yet is still a stolid Lower Middle-ranking riddle. 
• (I cannot stress the importance of testing enough. So often when my students make a good riddle their first question is "what rank do you think it is?" The first time they ask I answer, "the only way to know is to test," and every time after that, "As I always say, testing is the key." So I near-always brand new riddles as Middle-ranking simply because 90% of them turn out to be exactly that. While it is true that after 10+ years making and telling riddles that I can make a fairly good guess as to their more precise rank, I am wrong often enough to need test my own riddles no less diligently than my students. A Riddle Master must follow their own rules.)
  

However, we only got the chair riddle after changing it, and that is a critical part of riddle-making. I do not bold this idly. So many times have kids come to me with a riddle they created and love – one that even rhymes! – and are so proud of. Until I point out that the riddle has more than one possible answer. At this point they have one of two reactions: they either dig in, stubbornly trying to assert that there is only one perfect answer because they do not want the change the riddle they worked so hard on since if they change it then it will not sound as good. Or they, while disappointed, accept it and work to reword/adjust the riddle until it has only one perfect answer. The final reaction is the mark of a true Riddle Master. As I often tell my students, riddles do not have to rhyme. Yes rhymes are fun and can add a special flare to the riddle in question, which is why I try to make mine rhyme when possible, but they are not necessary. Indeed, many of my finest and favorite riddles (such as the Grandmaster) do not rhyme.

Sometimes you even have to start making the riddle all over again from scratch.“Kill your darlings” is a common piece of advice given by experienced writers, meaning that one must sometimes remove characters, sentences, or entire subplots one has worked hard to create yet that must be removed for the sake of your overall story. Well, the same applies to riddle-making. Better a non-rhyming riddle that may not even roll off the tongue that well yet works than a smooth rhyming one that does not. Believe me when I say that it pays to do the work, because if you do not then those you give the riddle to will point out the flaw by coming up with the other possible answer while trying to solve it and then explain why their other answer works when you say it is not the correct answer. Trust me, I learned this lesson the hard way and, besides from not being fun, it undermines your credibility as a Riddle Master. Today it is rare for my riddles to have flaws, but when one is pointed out, typically by someone trying to answer it and coming up with a workable answer I had not thought of, I thank them and vow to rework the riddle in question. This not only maintains your credibility, but shows the Solvers that Making is not easy and that even deeply experienced Masters do not always think of everything and can make mistakes.

Bottom line? Like a piece of writing, a riddle typically goes through multiple drafts (at least two) before it is ready. Remember that most if not all things are easier said than done and riddle-making is the opposite of the exception. Myself and the few Master Makers I have successfully trained can make solid riddles at will only after long practice. Even then most Masters are markedly better at making certain types of riddles. I excel at Logic and am decent at Wordplay, N and G are the reverse, R is purely Logic, L and E utterly Wordplay, B specializes in Logic-Wordplay Combination, and A – the only self-taught Maker I have ever met aside from myself – is equally skilled at both and even has mastery in Making Scenario riddles! Mark my words, he and Noam are going to be better than me someday. Anyway, like lifting weights or doing any sport or test of skill, Riddle-Making is challenging at first, but once you get the hang of it, again after months of practice, it becomes second nature. But just as being a skilled soccer player does not make one great at baseball or tennis, being a Master Logic Maker does not translate to equal skill in Wordplay or Scenario. (On that note, I recommend Logic mastery simply because it is the most popular type. Most Solvers just prefer them, though naturally there are plenty of exceptions.)

How do you know when you have achieved mastery? My general rule is you must have made at least twenty solid riddles of varying ranks (i.e. they cannot all be Easy-ranked and/or so obvious that everyone gets them right away).

Now we come to the final and key point. While training others to be Master Makers I have noticed this instant fascination with Hard, Master, and Sovereign-class riddles. Much as everyone always suddenly and desperately wants to solve my Grandmaster Riddle, so prospective Makers desire to create seriously and increasingly difficult riddles. Then, on doing so, count success when basically everyone fails to solve it. This is a trap. Two of the foremost principles of riddle mastery is to expand peoples minds and that riddles are supposed to be fun. Not solving a riddle expands nothing and is not fun. For full details read my Methodology for teaching Riddle Mastery in an Educational setting page if you have not already, but the overall point of riddles is for people to solve them. If you create mostly/only Hard through Master and above riddles, how many do you think will solve them? The answer: very few. What happens when very few people solve your riddles? The answer: very few will want to hear them. Remember that the Riddle-Solver is no less important than the Riddle-Maker, for neither can truly flourish without the other. That is why a good Riddle-Maker, one who desires to become a Riddle-Teacher and teach riddle mastery, will have mostly Middle-ranking riddles coupled with a healthy chunk of Easy ones. Again, the full details as to why this is critical is in the above linked Methodology page, but I can say directly that I saw several of my students learn this lesson the hard way. I reiterate, the overall point of riddles is for people to solve them and have fun doing it as their minds expand, because failing to solve a riddle expands nothing and is not fun. It is the Makers' task to train the Solvers in answering, and the Solvers' task to challenge the Makers in creating as well as test new riddles. Neither can truly flourish without the other.

Luck to you, and happy riddle-making!