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Crossword Makers Don’t Just Sell Their Time, They Enjoy It


Freelancers are usually passionate about their work but freelance crossword constructors have managed to turn their passion into their work.

Will Shortz has a unique degree. The editor of the New York Times crossword page is the only person in the United States with a bachelor’s degree in enigmatology — the study of puzzles. It was a course that he was able to put together himself using the Individualized Major Program at Indiana University where he wrote his thesis on “The History of American Word Puzzles Before 1860.” In addition to creating clues and editing submissions every day for the world’s most famous crossword puzzle, he has also been the editor of Games Magazine, and is now the founder and director of the American Crossword Puzzle Tournament. He’s one of the few people who have managed to build a career out of an activity usually done for fun.

But he’s not unique, and the ability to make money doing what you love, even from home, isn’t restricted to an editor at a national newspaper. Shortz himself doesn’t produce the puzzles published in the Times, relying instead on the 75-100 submissions that flow into the newspaper each week from crossword enthusiasts. He’ll pick crosswords from about 100 freelance contributors each year.

Those crossword creators are likely to be amateurs happy to earn an occasional $200 or so for a midweek crossword and as much as $1,000 for a Sunday edition. But a few crossword setters have been able to turn their love of puzzles into a reliable business that brings in money every day.

An Audience of Two Million

Myles Mellor, for example, sells crosswords to between 80 and 100 publications every month. His work has been published in magazines that range from airline glossies to art publications and from The History Channel Magazine to Homes Magazine Canada. He has published eight  books of crosswords through Books a Million bookstores, sells more crossword compendiums through Kindle, and in 2011, published seven crossword books that are sold in Barnes and Noble stores.

Although he’s been solving puzzles since he was a child, Mellor only started creating crosswords in 2001. When the death of his mother left his father in England lonely and depressed, Mellor made him some crosswords to help him pass the time.

“I was here in the US,” says Mellor. “I knew he loved puzzles as he taught me how to solve them when I was young. I started doing them for him and he loved them. After a few of them he said I should try to publish them.”

Today, Mellor’s crosswords are believed to reach as many as two million people.

Not all of the puzzles that Mellor creates are aimed at readers of mainstream newspapers and magazines. One of the most important factors that have contributed to the success of his freelance crossword business may be that Mellor has targeted a particular niche in the crossword market: the demand for themed crosswords used in corporate material and even in advertising. Clues and answers will be related to the product, the company or the subject of the magazine. One crossword for Wine Trails magazine, for example, used types of grape, flavors and other wine-related words. In addition to a host of magazines, his clients have included companies like McClaren McCann, Nascar and Pepsi whose completed puzzle revealed the phrase “Drink Diet Pepsi.” His puzzles appear in industry magazines in fields from fashion to finance, and he has even created a puzzle that was used as a wedding proposal.

Each puzzle is different, and the terms targeted in each industry will present a unique challenge, but the hardest kind of puzzles to create, says Mellor, are large custom puzzles that require real ingenuity to insert the words related to the product or the industry.

“I did some for MasterCard which had full newspaper page grids and were all custom,” Mellor recalls. “Six hundred and eighty clues. They were used for an ad campaign in major Canadian newspapers. That was the high end of the difficulty level.”

The crosswords will typically take between two hours and ten hours  to write, depending on the size and complexity of the puzzle. A newspaper style puzzle usually takes about two to five hours. Pricing varies, too, and depends on the client, as well as the size and type of crossword the client wants. Even the medium can affect the price with different models used for print, interactive and mobile crosswords. The cheapest may cost as little as $4 while the most expensive sell for as much as $1,000.

“There are many different models for different scenarios,” says Mellor.

Finding the work might require as much ingenuity as writing the clues. Clients reach Mellor in part through Google searches for crossword setters. (He says he has a “presence on Google” that enables clients to find him when they want theme or custom crosswords.) But he also pitches publications directly, following the submission guidelines laid down by the publisher.

The Cost is a Good Time

Costs, at least, are relatively low. Mellor uses Crossword Compiler, a software tool for crossword constructors that costs $169 for a professional bundle. The remaining costs will be a combination of online marketing, particularly search engine marketing to pull in clients, hours lost on unsolicited submissions that are rejected — and the time spent thinking up clues and testing the final puzzle.

But if time is the biggest expense it’s also a fee that most freelance crossword enthusiasts would be happy to pay.

Freelancers are generally a pretty happy lot. We consistently show greater job satisfaction and higher rates of optimism and happiness than salaried staff, helped in part by the ability to set our own schedules and manage our own time. But it can’t hurt that 87 percent of freelancers surveyed by Elance said that they were “following their passion.” Crossword enthusiasts though aren’t the only people who can turn their passion into a freelance business. Whether you spend your spare time gardening, gaming, filling crosswords or completing Sudoku puzzles, you should be able to find an opportunity to build that passion into a successful freelance business.


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