Sandy Weisz, Commissioner of The Mystery League

Sandy’s offices are right around the corner from Marbles. The area of Chicago where they are may become the Silicon Valley of the toy/game industry with the makers of Cards Against Humanity and Threes also in the space. Anna and I recently met with Sandy to discuss puzzle hunts for our November ChiTAG events and more. The possibilities are endless and fun. 


Who are you?

Sandy Weisz. I am the commissioner of The Mystery League (mysteryleague.com), which is a company of creative puzzlemakers. We’re located in Chicago, in the Bucktown neighborhood. (Which was given that name after all the goats that used to live here. Turns out the same is true for the original Gotham, in England.) We share offices with a number of game designers, including the makers of Cards Against Humanity and Threes. We’re around the corner from Marbles HQ.

What kind of puzzles do you make?

All kinds. Our staple is live-action puzzle hunts, which are 1- to 4-hour events, wherein teams romp around a building, park, neighborhood, or museum, hunting for clues, solving puzzles, and racing to be the first to finish. But we also like to build puzzle-based promotions; that is, marketing campaigns that have puzzles at their core.

Tell me more about puzzles you make — are they more like crosswords, jigsaws or something else?

Some are like crosswords (constrained to paper), some are like jigsaws (physical construction), but most are something different. We make a priority of designing puzzles that are integrated into the environment. So, for instance, for the hunt at the Art Institute, we built a puzzle that took the names of a bunch of paintings and anagrammed them. You were given the pictures and anagrammed names and had to match them up. And then also notice that each anagrammed name had an extra letter in it. Those extra letters formed the answer. But it’s not anything you could do at home — you had to walk around the space, find the artwork, find the titles, and go from there. We make as many puzzles in that vein as we can get away with.

Have you been into puzzles your whole life?

Quite! I got it from my dad, who loved puzzles, wrote puzzles, and put on a magnificent (and magnificently complicated) puzzle hunt for my 10th birthday. I was an avid reader of GAMES Magazine. I built puzzles and games at summer camp. On my first date with my wife, we bonded over a crossword. My kid’s name is an acronym.

What attracts you to puzzles?

Up until this recent change in career, I was a web designer and developer. I did that for twenty years. (I still do it, for personal projects, and I still like to teach it.) I went to college for computer science because I loved computers, but I spent all my free time designing for the newspaper. I carved out a career that straddles the line between creative and analytical. So it may seem like a strange jump from web design to puzzle design, but it covers a lot of the same ground: a mix between art and craft. A blend of storytelling and problem-solving.

As for the specific question of what attracted me: I dunno, my mind just happens to be hyper-tuned to notice patterns in the world. That’s a good trait for a puzzlemaker. Solving (and creating) puzzles are all about sussing out a pattern that cloaks for a deeper message.

What advice can you give to aspiring puzzlemakers?

Three things: Solve a lot of puzzles. Connect with other puzzle makers. And most importantly, just make puzzles. And put them out there. I can’t tell you how terrible my first puzzle hunt was. It was a hot, hot mess. But without it, I couldn’t have gotten better the second time, or the next, or the next, or the next. It’s hard to get started, especially if you’re a perfectionist and have a fear of failure, like I do. So start small: test your stuff on a few people. Then recognize the puzzle’s shortcomings and try for a bigger audience next time. I’m always happy to give feedback and advice if anyone wants to reach out to me with their work.

What would be your dream gig?

Construction of a permanent puzzle installation across the breadth of a city. Something that was baked into the infrastructure. From time to time, I’ve seen stories of people building puzzles into the architecture of a home or office. And sometimes they’re not found for years. I’d love to do the same thing on a city-wide level. Maybe I’ll Kickstart that.

Anything else?

Here at Mystery League HQ, we’re having a free puzzle hunt on Saturday March 21st for anyone who's curious about what we do. If you want to see first-hand how fun these puzzles and hunts can be, sign up at http://mysteryleague.com/mar21.

(… oh, and one more thing — there’s a mysterious creature hidden somewhere in this interview.)


Thanks, Sandy, for a great interview!