A man who wrote crossword puzzles for The New York Times and the Wall Street Journal explains what his job entails


  • Trip Payne is a professional puzzlemaker who has
    created puzzles for The New York Times, The New Yorker, and the
    Wall Street Journal.
  • Payne says puzzles typically begin with a “theme” and
    that for most people, puzzlemaking is a side job.
  • He says the most common question he gets is: “Do you
    know Will Shortz?”

Clue: Three-time champion of the American Crossword Tournament;
former puzzle writer for The New York Times, The New Yorker, and
the Wall Street Journal.

Answer: Trip Payne. Payne, who is currently co-editor for
Zynga’s Crosswords
With Friends
, has been a full-time puzzlemaker since 1990.

“When I was young, I was very interested in puzzles and games,”
says Payne, who was featured in the 2006 award-winning documentary
“Wordplay.” “I thought it would be interesting to try to make up my
own puzzles, and when I was 14 years old I had a crossword
published in Games Magazine. Over time, that hobby became my
career,” he tells Business Insider.

We recently spoke to Payne about what his job entails. Here’s
what he had to say:

‘Here’s how the puzzlemaking process works … ‘

“Puzzles typically begin with the ‘theme’ — the thing that
the longest answers in the puzzle have in common.

“The first thing that a puzzlemaker has to do is come up with
theme answers that will fit properly in the grid, since all
crossword grids have symmetrical patterns.

“After the puzzlemaker places the theme entries into a grid,
they then decide where the rest of the black squares should go.
This is not always easy — you want to make sure that you don’t
have too many places that will be tricky to fill in later, or where
you’d have to resort to hard words to fill it in.”

‘The next step is filling in the rest of the grid’

“The goal is to have every word in the grid be something that
the solver will recognize. Sometimes, as with the Daily Celebrity
Crossword, you want everything to be solvable even by someone who
has never solved a crossword before; other times you can have the
vocabulary be a little more difficult, but you never want it to be
truly obscure.

“Difficulty level should come from the cluing, not the words in
the puzzle. After the grid is done, then it’s time to clue. In an
easy puzzle, the goal is to make clues without multiple possible
answers (a 5-letter word for ‘Fast’ might be ‘RAPID or ‘QUICK’ or
‘HASTY’ or several other things). In a harder puzzle, you want
those ambiguities, and you also want to throw in some wordplay to
keep solvers a little bit off-balance.

“How long a puzzle takes to create depends on a lot of things
— the size, difficulty level, whether there are any particular
constraints, and so on. I’ve had puzzles take me mere hours to
create; I’ve had others take weeks. I can usually complete a simple
puzzle in a matter of hours, whereas a medium or hard puzzle could
take a day or two.”

‘Writer’s block could sometimes be an issue’

“Most of the time, I have a theme to begin with, or at least an
area. For example, Daily Celebrity Crossword has a different theme
each day, such as TV Tuesday and Sports Fan Friday, and that gives
me a starting place for brainstorming what the puzzle should be

“I have a great deal of respect for the constructors who have
assignments where they have to release puzzles every week with
fresh, original themes. I have rarely been in that position, but
when I was, it’s true that writer’s block could sometimes be an
issue. I would typically try to work ahead of schedule so that when
writer’s block did hit, it wouldn’t put me behind deadline.”

‘Without question, the best part of my job is the people’

“I work with great editors and constructors on a daily basis,
but aside from that, there is a puzzle community that I am
fortunate to be a part of, and many of my closest friends come from
that world.”

‘The job also has its challenges’

“It’s sometimes difficult to find ways to keep things fresh.
When you have to clue ‘ODE’ for the thousandth time, it can be a
drag to sit there and try to think of a new way to clue it.”

‘There is a stereotype of puzzle constructors, and puzzle
enthusiasts, of being ‘nerds”

“I don’t care for that word at all, and I don’t think it’s
accurate. Puzzlers generally have certain things in common — a
love of learning new things, an appreciation for wordplay, a nimble
mind, and so on — but we don’t typically look or behave like
characters from ‘The Big Bang Theory.'”

will shortz

‘The most common question I get is, ‘Do you know Will Shortz?”

“The answer is, yes; I’ve known Will, The New York Times
crossword puzzle editor, for about 30 years now.

“I’m also asked, ‘Which comes first, the words or the
clues?’ The words in the grid come first.”

‘For most people, puzzlemaking is a side job’

“I’m not sure of the exact number of puzzlemakers in the US, but
those who do it full-time (including editors) is a very small
number — probably not more than several dozen.”

‘Almost nobody makes a career solely constructing puzzles, and I
think it’s safe to say that nobody gets wealthy that way’

“Most people who want a career in puzzles also have to do
proofreading, editing, and so on. A lucky few get jobs editing the
puzzles for large newspapers or for publishing houses.

“If you get a normal-sized puzzle published in a newspaper, you
will probably earn somewhere from $150 to $300 for it; if you get
one published on a Sunday, it will be somewhere from $300 to $1000.
But you’ll be lucky to get more than a dozen or two puzzles
published in newspapers in a single year (and probably not more
than a small handful of those will be Sunday puzzles), so you can
see how grim the math is when it comes to earning a living that

‘My biggest piece of advice for a puzzlemaker is … ‘

” … never put an obscure word in the grid just because it’s
the only thing that will work. Re-do the puzzle instead, even if it
means going back to the beginning and putting the theme entries in
different positions.”

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A man who wrote crossword puzzles for The New York Times and the Wall Street Journal explains what his job entails