How to become a Riddle-maker

Point of order, even Wizards of the Coast
acknowledged my skill once.

How does one become a Master Riddle-maker? By making riddles, naturally, and I will do my best to impart the lessons I give my students verbally 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 to make sure it is solvable and ascertain its level of difficulty. The chair riddle here is not terribly difficult, yet is still a stolid Lower Middle-ranking riddle.

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 role 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. 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. It, like lifting weights or doing any sport or test of skill, is challenging at first, but once you get the hang of it, after months of practice, it becomes second nature.

Luck to you, and happy riddle-making!