I construct crossword puzzles as a hobby, and to earn pin money ($50-100 per crossword). Here's how I do it.

The process usually happens in this order:

  • Find theme entries
  • Choose a grid
  • Fill the grid
  • Write clues

I'll discuss these steps and talk about how some specialized software and I work together to get this done.

Take a look at a puzzle such as you might find on uClick.com and you may notice a few things about it. First, the grid has symmetry; if you rotate it by 180 degrees, the pattern remains the same. You'll also notice that a few entries are longer than the rest. These almost always follow a theme involving wordplay of some sort. (In one puzzle I sold, the theme entries were CHARLOTTESWEB, ROSEMARYSBABY and SOPHIESCHOICE -- all movie titles of the form "{woman's name}'s {noun}".)

Since the theme entries are the least flexible part of the grid, a constructor typically begins by identifying these entries. You might, for example, try a puzzle using movies with "run" in the title. A search on IMDb provides a long list, from which I've chosen titles that are recognizable enough to be fair game. In order of their length, they are:

RUNSILENTRUNDEEP (16)
THERUNNINGMAN    (13)
CANNONBALLRUN    (13)
NUNSONTHERUN     (12)
RUNAWAYBRIDE     (12)
COOLRUNNINGS     (12)
NOWHERETORUN     (12)
MIDNIGHTRUN      (11)
BLADERUNNER      (11)
CHICKENRUN       (10)
SEESPOTRUN       (10)
RUNLOLARUN       (10)
RABBITRUN        (09)
LOGANSRUN        (09)

This is a pretty good field from which to choose theme entries. Because there are so many candidates, I have lots of choices for my grid.

Let's talk about choosing a grid. First, most puzzles produced for sale in the American market are 15x15, so the first entry is one letter too long. Second, because of symmetry, you can use entries of even length only in pairs. A 14-letter entry in a 15x15 grid must be padded with a black square at the beginning or the end, for example, and that black square must also appear in its symmetrically opposite location. This forces the matching entry to also be 14 letters long. Finally, a puzzle needs to have at least three theme entries, or four if they're particularly short entries. Usually, you can choose a grid with theme entries of the following lengths:

  • 15x3
  • 15x1 14x2
  • 13x3
  • 12x4
  • 11x4
  • 10x4
  • 9x4

Other combinations are possible, but these are the most common. When you begin making crosswords, a stock grid will suffice, but it is important to tweak the grids as necessary. If adding or removing a symmetric pair of black squares would result in cleaner fill (about which more below), do it.

Most constructors use software such as Crossword Compiler to aid in filling a grid, a task once done by hand. While it's more expensive than the average shareware purchase (with the options I chose, it cost about $150), a modestly successful constructor can cover that expense by selling two or three puzzles. The software includes plenty of stock grids, and these can be sorted by theme entry length.

In this example, I'll try to use four 12-letter entries: NUNSONTHERUN, RUNAWAYBRIDE, COOLRUNNINGS and NOWHERETORUN. There are several 12x4 grids from which to choose.

Next, I type the theme entries into their positions. There are, of course, 4x3x2x1 = 24 ways of doing this. I then ask the software to fill the grid. It tells me that it can't, because my theme entries leave a space that just doesn't match any known English word. So I swap theme entries around until I find a grid that can be filled.

This usually results in a technically legal grid full of awful words like ESNE, ERIE, WNW and ITO. There are only so many ways to clue ERIE, and the entertainment value of a puzzle is higher if the entries -- and clues -- are not cliches. On the other hand, no editor will buy a puzzle containing the word CUNT, even though it's a perfectly valid English word. People do crosswords at the breakfast table. Similarly, references to illness are often taboo. Some editors don't mind the entry AIDS if it's clued as "Lends assistance to", but most would rewrite a clue like "HIV-related disease" to something more innocuous.

To improve the fill, I identify words that I find unacceptable for various reasons. Then I ask the software to try again without using those words. Gradually, I end up with a grid that contains a minimum of crosswordese.

The other way of improving your fill is to add interesting words to your list. AOL, OGAKOR, SPAMMER, and so on keep your grid from being stuck in the 1920s. At the same time, you can remove words that you know you'll never use.

The final step in creating a crossword puzzle is to write an interesting clue for each entry. Synonyms are a common, but usually dull, way of cluing: for BET, you could use the clue "Wager". When necessary, you can use a fill-in-the-blank clue such as "'I'd ___ you anything'". The best clues often reinterpret the entry; the letters B-E-T can also refer to Black Entertainment Television, and a bit of research turns up a factoid that makes an interesting clue indeed: "First black-owned company on the New York Stock Exchange". That's not only a neat bit of trivia, but also much more original than "Wager". When you do research for a clue, be sure to cite your references; the editor needs to be sure that the clues are factual, and if you had to look it up, chances are they will too. In this case, the URL suffices: http://www.africana.com/Articles/tt_240.htm.

Now that you've got a complete puzzle, you can submit it to an editor. As with any other freelance work, it's extremely poor form to submit the same piece to multiple outlets when you know they only buy exclusive rights. You can find the spec sheets of various buyers on cruciverb.com; follow them to the letter. Some editors have a policy of responding within a few days, while others have a backlog of a few months. All outlets accept submissions from newbies, including the New York Times.

If you're crazy enough to shell out for the software and give it a try, good luck! If not, I hope you've enjoyed learning about the art behind a simple crossword puzzle.

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