Just a few months after I started solving crosswords regularly, I wondered if I could make one of my own. Upon learning that the New York Times accepted freelance submissions, I made it my goal to have one of my creations printed there before the age of sixteen. I set to work with graph paper, a pencil, a BIG eraser, and my old Franklin Crossword Puzzle Solver. It wasn't going to come easy; my first effort was really terrible. Not only did I unwittingly choose one of the most hackneyed themes out there (foods with nationalities in their names), but I had far too many black squares and the fill was plainly awful. I used obscure abbreviations and other stuff I could barely justify. I never submitted it anywhere. I'd put it here for a laugh, but I believe I removed all traces of it ever existing. Though I learned the ropes quickly thereafter, my first three Times submissions were met with rejections. I finally broke through in May 2000, when Will Shortz accepted a puzzle for publication on July 4 of that year. I'd reached my goal with four months to spare! The bug had bitten me, and I've been constructing puzzles ever since.
To the questions!
What do you think goes into a good puzzle?
If the puzzle has a theme, it should be consistently applied and use up most or all of the examples it affords. The fill should reflect the way people speak, using neologisms, lively phrases, and well-known vocabulary while avoiding crosswordese, seldom-seen abbreviations, obscurities, and other contrivances as much as possible. Clues should venture outside the dictionary, embracing wordplay and a wide variety of subjects to keep the experience interesting. The American crossword style has its exigencies, so concessions are occasionally necessary, but a good constructor strives to avoid these.
How long does it take you to make a crossword?
It depends on the size and the difficulty of what I'm trying to do. Most of the time, I make 15x15 grids, but a 21x21 puzzle will take longer. If there's a lot of thematic material, it might take a lot of fiddling with the black squares to get something that will work. If it's a wide-open themeless puzzle, it's harder to fill. You get the idea. I can't really put a figure on it because I pretty much never make an entire puzzle in one sitting.
Where have you been published?
Well, you know about the New York Times; check out XWord Info for all the grids I've had in there. I've also had puzzles in the Los Angeles Times, the Wall Street Journal, the Onion, the New York Sun, GAMES Magazine, and everywhere the CrosSynergy Syndicate gets published. Currently, I do most of my work for the independent American Values Club service; we're the same group that provided the crossword to The Onion's AV Club back when they had one.
How much do you get paid?
Not enough! But seriously, different places pay different amounts. Peter Gordon's Fireball Crosswords pays the most to freelance constructors, shelling out $301 for a 15x15 puzzle. For a Sunday-size (21x21) crossword, the New York Times tops the table with a hefty $1,000. But those are definitely outliers. For most constructors, it's just an enjoyable side gig.
Have you ever thought about putting out a book?
Do you write the clues or make the grid first?
This is left as an exercise for the reader.
Do you make other types of puzzles?
It's rare, but I like to spread my wings from time to time. I was the cryptograms editor for the National Puzzlers' League for five years, polishing seven member-contributed coded quips a month for everyone to enjoy. I like noticing little bits of wordplay such as those found in the flats of the NPL. I also aspire to challenge myself by making small Nikoli-style puzzles. If I get what I think is a good idea for any sort of puzzle, I'll try to carry it out!
You should put some sample puzzles on here.
That's not a question, but you're absolutely right. It's on my to-do list.