The Riddler’s Way: Mastering Riddles

You’ll find here a simple list of practices to build your ability to create and solve riddles. However, the discipline of Riddling runs so far and so deep, this can only scratch the surface. Nevertheless, the more that learn even the little taste offered here, the more likely the tradition of Riddling will not fade into the whirling modern vortex of consumable entertainments.

I speak for myself, first and foremost, in all these things. Know this now. Yet what I have discovered may help you find your own heart-hidden-in-a-box.

The word Poet has always had far more easy fascination for me than an actual poem on a page. That poem stares a challenge: the Universe speaks plainly only to the Dead, or the soon-to-die. If you would live a life, cunning and richly, it behooves you to learn a subtler language than that of bluntness and injury. A knife cuts, yes. And? How did that knife come to cut you, of all people? Backtrack before it ever happens, read the future before it arrives, solve the Riddle before it comes to pass.


The Question

Everything in the world has a voice, and tells its stories over, and over, and over….everything. You must challenge yourself to open a vaccuum, a pulling space, in your mind, in your senses. You must become a constant wordless question. The great Riddlers of old would fade away to nothing more than a human ‘?’, invisible ghosts upon the land,. Stretched out to the horizon, they knew everything that happened the moment it occurred.

It all begins with a question. Nothing more.

Pick a single object, the more mundane the better. Once a day, for a week, ask 50 questions of this object. Pick a new object every day, if necessary.

Count off the questions with your fingers. When you reach ten, touch your head with that finger, as a marker. Starting with your fingers again, count until the next ten, touching your left shoulder to signal twenty. Then the right shoulder. Then the left hip. Then the right hip. You just marked off 50 questions.

Does 50 questions sound impossible? Good. Find them anyway. Cheat (and if you can, you’ve probably discovered some foolish limits anyway, that you’ve imposed upon yourself for no good reason).

You do not have to answer any of the questions, though you may find yourself curious about them. Do what you like with the answers. For now, just the questions.

The Web

Much like a spider’s web, you now weave a map of connections, everything leading back to the center, that object upon which you asked the 50 questions.

Once a day, find 50 links back to that object, 50 ways it connects to other things in the world. Count off the same as before. Links can consist of links-of-links, as far removed as you like, as long as they lead back to the center. You can consider the links in the web as metaphors, or associations, or poetic allusions, if it helps. Find those kinds of connections.

The Chronicles of the Dreamtime

Every night, when you go to bed, one part of you sleeps, while another wakes up. This one will teach you to master the riddling world, if you learn to speak its language.

When you wake up, you have two options. Immediately tell the story of your dreams, or what momentary snatches of them you remember, to the person next to you. Or, write them down. It amounts to the same thing. Some cultures honor the telling of dreams, and make space for it. In ours, you may find your best audience in the pages of a journal.

Write down all the details that you can remember, even the stupid, foolish, unpleasant, inconvenient, embarrassing ones. Especially those.

More layers exist for this, but essentially, take nothing for granted in the dream, and begin your mapping web on it. 10 links for every detail you can single out. Results don’t matter at this point, but the practice does. You don’t want to find out what anything ‘means’ – you want to see what connections you can make.

The ‘Aha!’

Having said results don’t matter, you may notice every once in a while, you get an ‘aha!’. Something clicks. Something makes sense. You accidentally decode a little piece of dream language. Good for you. Write it down. But don’t let it suck you in…this concerns the practice, not the results.

The Waking Dreamtime

If this next notion doesn’t turn your world upside-down, I don’t know what will. Because before you now lies the task of treating your waking world like a dream. Take one short interaction, between yourself and the world and treat it like the dream. Find the connections, 10 connections to every element you can single out. How short? Make it short it enough that it seems easy. Then make it a little longer every time you practice anew.

The Door Has Opened A Crack

You’ve just learned the most rudimentary practices of Riddling – rudimentary, but unspeakably powerful. Any single one of them could turn a life upside down, if practiced consistently. Consider that, if doing them all seems like too much. Start with one piece, one practice. Then add more practices, slowly, one at a time.

And the door will slowly open, inch by inch…you’ll hear the hinges complaining, but pay them no mind. Uncared for, abandoned, rusted with old grief, they have the right to complain, the Riddlers of Old (that took such care of them) having long ago disappeared into the maw of the machine that eats beauty and excretes despair. Make yourself indigestible to that machine. Keep the door opening, and oil the hinges with your Riddling mind.

Written by Willem