I Create Puzzles for The New York Times

I’ve always been a solver.

Since high school, I’ve solved crosswords and been a general games enthusiast. In my early 20s, I actually started making them. They were terrible at first, but after making 10 or 15 of them, I eventually got one accepted at The New York Times. I was still doing that while I was working in corporate communications — it was a fun distraction.

I got my MBA at Drexel in 2015, and one of my co-ops was at SAP, a big tech company headquartered in Newtown Square, Pennsylvania, which I turned into a full-time gig. I ended up staying there for almost eight years in a variety of different roles centered around corporate communications. 

When my current role at The New York Times opened up, it seemed like a great opportunity. I had worked in the business side of publishing and submitted puzzles before my MBA, and I had actually worked as an intern for The Times before that, so I knew most of the people in that ecosystem, and it seemed like it would be a great fit in something I was really passionate about.

Frankly, these roles didn’t really exist 10 or 15 years ago — there was one main crossword editor at The Times then. Now we have six games editors because of the explosion of new games that didn’t exist before. There are puzzle editors at The New Yorker, Bloomberg, Apple — all of these places — and it’s great to see the market expand.

That’s something I valued about my time at Drexel. I was technically a part of the marketing concentration, but there was a large entrepreneurial concentration, too, and I always appreciated those people forging their own paths.

At The New York Times, our newest release is a game called Pips. The goal is to place the available dominoes in a way that satisfies all the numerical conditions of the puzzle. We liked the idea that it would appeal to a non-Native English speaker, so we can bring in a new audience that was perhaps underserved before. With our word-based games, being a native English speaker is very helpful, not just for spelling but for things like understanding idioms and turns of phrase.

Pips is our first original logic puzzle. We felt like we already had a pretty good portfolio of word games — the crossword, Wordle, Spelling Bee, and even Strands and Connections. We had never really rolled out an original logic puzzle, and we saw a market for that.

The other part that’s different from most of our puzzles is that Pips has three levels of difficulty. You get three-for-one on a daily basis, and the three puzzles can appeal to different types of solvers, whereas if you want to do something like the main crossword, the difficulty does increase throughout the week, but if you’re a first-time solver and you stumble onto Saturday, it’s going to be really difficult. Here, having three levels of difficulty really does broaden the appeal.

The idea for Pips started at a bi-yearly Hackathon where anyone can pitch games. There’s an extended team of about 100 people working on all different stages of a puzzle. It moves through various stages of testing and approvals — market research determines if it’s something that might feel appropriate for our portfolio, and the tech side gets involved in design then our editorial team works to make the game distinct and fun.

Beta testing is the fifth phase. The process of going from a germ of an idea to when we released the beta version of Pips in April took nine or 10 months, and we rolled it out globally in August.

The editors here each have our own specialty, meaning we all focus on one or two games. Right now, for me, that’s Pips, and I also make a medium-sized crossword called the Midi that goes out to millions of people in our weekly gameplay newsletter.

On any given day, I’m working on Pips, which means I’m either creating boards for certain levels of the game, editing my own games, or editing games from another one of our puzzle makers.

Once I have the puzzle board and put in all the conditions, I solve it while thinking about all of the different ways it could be solved differently. I’ll write out the logical steps that a solver would take, and I find this to be extremely helpful because I’m putting myself in the shoes of the solver, trying to think about what they might notice, what domino they’re going to use from that step, and how they might move on from there.

When I’m designing an easy level, there are only four to six pieces, so sometimes there’s an obvious one: If there’s only one six tile and there’s a spot on the board that needs to be six, you know where it’s going. Other times, I spice it up a bit, where it’s still going to be easy and fun, but there’s a logical step you have to work out before you can get there. The more difficult the levels become, the more dominoes you have to work through logically to figure out the solution.

I also work daily on the main crossword puzzle. We publish one per day, but there are 200 submissions per week that come through from outside contributors hoping to have theirs published, so we’re going through submissions all the time at a relentless pace.

I also pre-edit two to three puzzles per week, which means we’ve accepted one and we have it slotted for an upcoming day in the next few months, but we have to match the clues to the day of the week and the difficulty it’s supposed to be.

Pips is made by hand, and I think that’s part of the appeal. It creates a stronger connection between the solver and the puzzle maker or the editor, because you know that the person has gone through the same steps that you’re going through right now. It speaks to the game itself and its design: It’s not supposed to be overly flashy or with a ton of ads, and people appreciate that. When everything feels like it’s AI-driven or will be soon, this feels refreshing, especially at this scale. 

Different games have different levels of what I would call editorial insight. With something like Connections, it feels like opening up the editor’s brain and seeing how she thinks with the tricks she puts in place. With something like Wordle, where we draw from a database of words, there’s still work that goes into there, but it’s less of a window into how she thinks. Pips would probably fall into that latter category, because we want to make it fun but there’s a limit to the numbers and types of boards that can appear; but people still appreciate the personal effort.

Puzzles are a solitary moment of escape. Whether you’re on the subway or unwinding at the end of the day or having your cup of coffee in the morning, whatever your daily routine is, they’re typically solved singularly by one person. That’s all well and good, and people love that, but the community aspect is a huge component of what we do.

We want people to feel like they’re part of some club or some larger group, even if you’re just sharing it with your family or competing with your friends on our leaderboard. It makes it exciting and it brings people together out of a solitary activity. That’s something we take very seriously and want to encourage — there’s something that’s triggered in the brain, a dopamine rush not only in solving it, but in solving it as fast as you can to beat your friends and family, and that’s something that we definitely tap into with all our games. DM