Puzzles

In addition to my various “day jobs,” I am a semi-professional puzzle creator.

I specialize in enigmatic puzzles—puzzles in which a significant part of the challenge is figuring out what, precisely, you're meant to do in order to solve.

An enigmatic puzzle isn't just a single problem with a single trick. It's a trail: multiple steps, layered clues, and a satisfying end state in which earlier details (hopefully) click into place. It's something like an abstract escape room: you're presented with a set of information—and potentially, but not always, a specific objective—and from there you explore, interpret, and experiment your way to the answer.

Unlike a crossword, where the objective and process are standardized and clear from the outset, enigmatic puzzles are unfolding experiences. They blend logic, pattern recognition, narrative, and discovery.

These puzzles can take almost any form: a single image, a coded message, a cryptic-looking list of numbers, a strange diagram, a short story, or something more unexpected. What matters is not the format but the design. A well-constructed puzzle is fairly clued—no step should fundamentally require blind guesswork—and it allows the solver to have a sense of consistent forward progress on the margin.

That doesn't mean you won't get stuck. In fact, brief moments of being stuck are often essential, and help elevate the payoff to eventually finding the answer. But ideally, even those pauses feel like progress toward an eventual “a-ha!”. This means that well-designed enigmatic puzzles must contain what I think of as “invisible guardrails:” subtle structural features that help solvers build intuition about which paths are promising and which are not. (I discuss these design principles in more detail in a podcast conversation with Matthew Stein and Sonal Chokshi.)

Try a couple puzzles now 👀

I'll be adding guidance, links, and a few walkthroughs for first-time solvers soon.

In the meantime, here are a couple of puzzles you can try right now:

First: can you make sense of this cryptic message? (If it still looks puzzling after you've decoded it, that's not an accident—keep going!)

And next: this whimsical image. Believe it or not, it encodes a well-known English word.

And finally, here is a "playlist puzzle" that originally appeared in one of my Bloomberg Opinion Conundrums—can you sound out the answer?

As you attempt these, feel free to use any tools at your disposal—search engines, reference materials, even LLMs. In the world of enigmatic puzzles, any tools not explicitly forbidden are fair game.