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How Do You Make a Living, Puzzle Maker?

Francis Heaney talks to Noah Davis about the misconceptions and changing dynamics of the puzzling world.
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(Photo: yoohoojuju/Flickr)

(Photo: yoohoojuju/Flickr)

Francis Heaney has the type of job any crossword fiend would love. He spends his days as an editor at Puzzlewright Press and his free time creating crosswords and other types of puzzles for the New York Times, the American Values Club Crossword (formerly the Onion AV Club Crossword), and many other outlets. He talked to Pacific Standard about carving out a space in that world, the effect of the Internet on puzzling, and why the Times isn't the pinnacle for puzzlemakers.

How does one get to make a living in the puzzle world?

It was a very slow path to this being the thing I was making my living as. I was a puzzle fan from childhood. My grandmother got me a subscription to Games magazine when I was 10. I couldn't do all the crosswords in it at the time, although I was very possessive. When my grandfather did one of the crosswords, I was really ticked off. When I first moved to New York, I needed extra cash and had time on my hands between temp jobs. I thought I could write puzzles. I submitted some puzzles to Games. They got rejected, but they were just not-bad enough that they gave me some guidance. I took their advice, and they bought a few of those. I became a regular contributor there and at some other places.

I picked up some freelance work doing puzzle proofreading and testing, and editing at Games after they got bought. I wasn't a proper employee, but I was cobbling together a living between that and other assignments. I quit doing that because I got hired at Who Wants to Be a Millionaire?, writing for the books, computer games, and side projects. I was super dubious about whether it would work for me because I had gone so long without a day job that I wasn't sure if I would be able to wake up in the morning. My typical workdays for Games were blowing things off until 11 p.m., working until 5 a.m., then doing it all over again. I got the job, though, and it was fabulous.

When was that?

Around 2000. They cut loose our whole team at the point when they completely over-saturated media and public life with all the Who Wants to Be a Millionaire? stuff. The market for the things we were writing dried up. I spent a while coasting as a freelancer and eventually got hired as a copy editor at Cargo, which was like Lucky for boys. I loved that because no one was really strongly vested in the artistic content of writing about shaving cream or MP3 players. Writers didn't put up too much of a fight about changing their words. It was a very calm environment, and I got a lot of free ties.

At the same time, I was freelancing where I am now, at Sterling. For a long time, Peter Gordon, who is one of the top crossword editors around, was the entire puzzle department. He was constantly having more books to put out than one person should really be putting out. The Sudoku boom hit, and suddenly there was a whole new market of puzzle game book buyers. There was a budget to hire somebody, and he asked me. Did I want to make a living doing puzzles? Why yes, yes I did.

How has the Internet changed the industry?

Certainly, aspects of making a living have been tied to the Internet for years and years. When I was at Millionaire, one of my side gigs was writing for a couple of Web games. I've written for apps. One of my regular gigs is for what used to be the Onion's AV Club crossword. They canceled the feature. We liked writing a puzzle and not having to convince Will Shortz that some indie band I was into was one that people knew. We wanted to keep doing it so Ben Tausig, who is the editor/coordinator/most business-minded person we had, suggested we take it to Kickstarter. We kept it going as a subscription service. It kept the feature alive, paid us better than when we were doing it for the Onion, and gave us flexibility to mess around if we had a puzzle that wasn't 15x15. There are a lot of crossword writers who are making a really good side income or a main income from posting puzzles to blogs.

Back in 1999, a Las Vegas Sun story reported that "top dollar paid for a 15-square-by-15 square puzzle is about $80." How does that compare with today's rates?

I think the Times is paying $200 for a 15x15. Peter [Gordon] takes submissions for the Fireball, a subscription newsletter, and he pays $201. He's always tried to keep a competitive pricing with Will. When Peter was editing the New York Sun, he would raise his pricing to $1 more than the Times. He wanted to say that he was paying the highest price for a 15x15, which he was.

Is the Times the pinnacle?

"It was a very calm environment, and I got a lot of free ties."

The Times is definitely the most well-known. Getting published in the Times is a solid rite of passage for someone who wants to be a crossword writer. It's a milestone, and it's a thing you ought to do. It's a high-quality puzzle and it's very reliable, but do I think it's the best puzzle? No. Some days it is. But there is a lot more competition and a lot more styles of puzzles now than there were 15 or 20 years ago. If, like me, you have a snarky, indie bent to what you like in a puzzle, you're probably going to like the Fireball or the AV puzzle or something else in a given week. As a mainstream, softball lob, the Times is always going to meet a quality that a constructor should aspire to. But some days, it's like, “What are you doing? Why is this obscure thing getting into a Monday crossword?” But everyone fucks up. I've definitely put crap into grids before because I've spent 10 hours on a puzzle or something.

There are a lot of people, of which I am one, who will get together online and crab about a certain corner of a certain puzzle. That's just because we all have very strong opinions.

How did you get better? Are there common beginner mistakes?

My earliest puzzles were fine, but they didn't have a lot of personality. It was trying to make anything that worked at all. When you're trying to get something accepted to a specific market, you can get too focused on “What would the Times buy?”

I wrote a few crosswords for the Times in the '90s. By the time I was working at Games, I didn't have time to write on spec because I had enough to do. I took time off from writing standard crosswords for the hell of it. When I started working here, Peter was editing the New York Sun. Unlike the Times, Peter has what I would consider a much more sensible submission plan. The Times only accepts finished puzzles. If you have a crazy idea for a puzzle that's very difficult to construct and has a lot of constraints on it, you still have to finish that thing and send it in. If Will doesn't like it, sorry. Whereas Peter wants a theme submission. If he likes it, he'll tell you to make it. Before you construct it, you have guidance. Since I worked here, I could walk down the hall, tell him my idea, and see what he said. It was easier to go through with experimenting. Since then, the ease of publishing your own crosswords online and the number of places that are willing to work with you and give you feedback has grown. People have started to experiment more than they used to. That's how people get their own distinctive voice.

In terms of how did I get better, I wrote a ton of crosswords.

Is it easier now to make a living than it was in the past?

I don't know if there are more places that will pay something. Games is scaling back from two titles to one. Will Shortz's Wordplay is a good magazine, and it pays decently, but it's bimonthly. No one can make a living selling one or two puzzles a month to a bimonthly magazine. I'm very lucky because being an editor is pretty much one of the only reliable ways to continue making a living in puzzles. The people who are just doing it by writing puzzles are like the fast-talking 1930s reporters who had to sell articles to every paper in town.

It's a good environment for anyone who has a little bit of puzzle-writing talent and a bit of entrepreneurial skill. Anybody can go to Kickstarter and try to do a puzzle book. If you're just self-publishing and you don't have to split the cut with a publisher, that small audience is probably enough to put out that book if you're willing to deal with it. Or start a blog, post a puzzle every day, and try to make some money. A lot of people are doing really well that way.

How Do You Make a Living? is an ongoing Q&A series.