Matthew Stein '16 and the World of Interactive Puzzle Experiences

If Matthew Stein ’16 could select any job title in the world, it would be “wonder wizard.” The 30-year-old designs puzzles for a living, and although people often mistakenly think he creates jigsaws, his work falls more along the lines of creating magic.

“On the surface, puzzles revolve around keeping secrets, yet they’re more about how we guide players to discover those secrets and shift their perception of the world around them,” Stein explains. “So how that secret gets revealed, how that ‘aha!’ moment is set up and delivered, requires really thinking like a magician.”

Throughout his childhood in Pennsylvania, Stein’s mother, Diane Goldstein Stein ’81, P’16, ’21, designed scavenger hunts that kindled his interest in interactive puzzles. At 12, he discovered letterboxing, a hobby that combines treasure hunting and printmaking. It sparked a passion that has continued throughout his life and even inspired his Wesleyan application essay about learning perseverance through letterboxing.

“Puzzles are great at teaching you not what to think, but how to think. This natural alchemy of the computational and the creative is what really drew me to Wes in the first place,” he said. On campus, he found friends whose creativity and interdisciplinary thinking matched his own. Stein devoted himself to music and computer science. In his free time, he made crosswords for The Argus, led the Wesleyan klezmer band, and began crafting puzzle hunts. “Wes allowed me to add some depth and direction to that approach, which gave me the skill sets and the confidence to embark on such a non-traditional career path,” he said.

Working as a software engineer at Google after graduation, Stein found himself dreaming up puzzle projects late at night. A few years and many puzzles later, he decided to embrace his creative passions and shift his career toward puzzle design. Then the pandemic struck, limiting the capacity for in-person puzzle endeavors but leading to a thriving online community of both seasoned and novice puzzle enthusiasts.

“We all needed creative, stimulating ways to play and connect with each other from afar,” Stein said. “I was very lucky to—with some ongoing collaborators—have some projects that reached pretty broad audiences early on in the pandemic, which opened up new communities around my future work.”

One of his most notable creations (co-designed with Sandor Weisz) celebrated the 15th anniversary of Alinea, a three-star Michelin restaurant in Chicago, with a series of intricately crafted culinary-themed puzzles that led to a meta-puzzle pulling together elements of each previous puzzle. Pilcrow Bar, as the experience was titled, garnered participation from over 10,000 people across the internet.

Stein’s portfolio of projects also includes escape rooms, treasure hunts, and more. From creating an alternate-reality game teasing a secret album release for electropop producer Madeon to crafting an international treasure hunt hidden throughout Art of Play’s design journal, his projects require thinking outside the box and building experiences that get people to engage with each other and with the world around them.

“I don’t think I ever really lost the belief that we can—and should—interact with each other in a playful, wondrous, open-eyed way,” he said.

Stein embraced many independent projects before taking a job at Jane Street, a quantitative trading firm where he created escape rooms and puzzle events for university students and employees around the world. Recently, he returned to focusing on some long-term projects, including writing about puzzle design theory and pedagogy alongside his ongoing contributions on immersive gaming for the website Room Escape Artist.

From a young boy chasing treasure to a “wonder wizard” who lets his curiosity drive him in new creative directions, Stein wants others to view the world as he does—as a place rich with possibility and endless puzzles for solving.

“I’ve always seen myself as a wizard in some form,” he said. “I’m trying to guide people to experience magic in the world.”