Policy maker, policy-maker, or policymaker? Pre-eminent or preeminent? First grader or first-grader? E-mail or email?

Hyphens can be tricky, but that’s no reason to tear your hair out.
According to Sturgis’s Law #5: “Hyphens are responsible for at least 90 percent of all trips to the dictionary. Commas are responsible for at least 90 percent of all trips to the style guide.”
The tricky thing here is that the dictionary will only tell you what to do if your word is in there. Often it isn’t. If it is, you’re in luck — as long as you don’t notice that (1) dictionaries are wildly inconsistent when it comes to hyphenation, and (2) dictionaries often disagree with each other.
Merriam-Webster Unabridged doesn’t list “policy-maker” or “policymaker.” This may be taken to mean that MW considers it two words: “policy maker.” The American Heritage Dictionary, however, lists “policymaker” as one word, no hyphen. And while we’re at it, MW thinks “policyholder” is one word. “Slaveholder” is one word, but “slave owner” is two.
For several editions now, the Chicago Manual of Style has been trying to impose method on the hyphenation madness. In section 7.85 of the 16th edition you’ll find a handy-dandy several-page chart. It sorts compounds by category, parts of speech, and specific words; gives examples of each subcategory; and then summarizes the “rule.”
It’s useful, it really is. I refer to it often. But it too will lead you into inconsistency, not least when you notice that British English uses hyphens more liberally than American English and the sky hasn’t fallen in yet. Chicago “prefers a spare hyphenation style.” So do the Merriam-Webster dictionaries. The operative word here is “style.” In matters of style, there’s generally a big gray area where choices have to be made.
What editors and teachers and style guides tend to forget is that hyphens serve a purpose — beyond driving editors crazy, that is. Hyphens are joiners: they link words into temporary compounds and attach prefixes and suffixes to root words. Over time temporary compounds may become permanent if they’re used enough. A few years ago “e-mail” was generally hyphenated, but these days it’s often one word: “email.”
“Policy maker” and “policy making” are in transition. That’s why one dictionary makes them two words and another closes them into one, and you’ll sometimes see “policy-maker” and “policy-making.” I suspect that the words are closing up fastest among people who write about public policy. They and their readers think of “policymaker” as one word, not two.
If you read books that were published a century, or even a few decades, ago, you’ll probably find hyphens where they’re seldom found today. “Rail road” was once two words, then it was hyphenated, then it fused into one: “railroad.” Other compounds have split into two distinct words: “no-one” is still out there, but “no one” is now standard. The hyphen is no longer needed to tell readers that “no” and “one” are a unit.
What if the potential for confusion still exists? That’s part of the gray area. A readership of educators and parents of young children will probably realize at first glance that a “first grader” is a kid in first grade. A more general audience might need a little help. I generally hyphenate “first-grader” myself, but when I’m editing, I’ll nearly always go with the author’s choice.
How about “high school student”? Yes, it is possible to read that to mean a school student on drugs, but this generally involves some contortion on the reader’s part or (more likely) an affection for puns. If your readers are familiar with the term “high school,” you can safely omit the hyphen.
Once in a while, though, the little hyphen is crucial. Chickens live in a coop; people buy food at a co-op. Newspaper columns are op-eds (an abridgment of “opposite the editorial page”), not opeds. Merriam-Webster’s hyphenates “co-ed” as both noun and adjective; American Heritage says it can go either way: “co-ed” or “coed.”
Which brings up another handy thing about hyphens: they can join, but they can also separate. In “co-op,” “op-ed,” and “co-ed,” the hyphen tells you to read or pronounce each word as two syllables, not one. This is why plenty of writers use a hyphen in words like “pre-eminent”: to signify that “pre-” is a prefix and that the first syllable of the word is not “preem.”
Merriam-Webster’s and Chicago don’t like such hyphens, so rule-following copyeditors routinely strike them out, whether they’re useful or not. I don’t know about you, but I can’t look at “reignite” without seeing “reign-ite” or “coworker” without seeing “cow-orker,” so I’m inclined to deal with hyphens on a case-by-case basis. Be wary of “one size fits all” rules when it comes to hyphens, or anything else for that matter.
A hyphen between prefix or suffix and root word can also subtly call attention to the root. The authors I edit often hyphenate “pro-,” “anti-,” and “non-” words. Whether they’re doing it instinctively or by choice, I suspect this is why they do it — because I do it myself. To me “pro-choice” is stronger than “prochoice,” “anti-liberal” than “antiliberal,” and so on.
The author of a current copyediting job hyphenates “desert-like.” Chicago says “-like” compounds should be closed if they’re closed in Webster’s, and sure enough, “desertlike” is given in the entry for “desert.” Is that a good reason to close up “desert-like”? I don’t think so. “Desert-like” calls a little more attention to “desert,” and the passage it’s part of is a little more vivid as a result. So I entered “desert-like” on my style sheet, so the proofreader will realize it’s intentional, and moved on.
Hyphens are handy, versatile little buggers. Sure, they can be overused, but so can anything else. Do learn whatever conventions prevail in your field or genre, but don’t worry about hyphens when you’re first-drafting. Even if the whole world will think you’re stupid because you put a hyphen in the wrong place, you don’t have to worry about it yet. Not until you’re ready for the whole world — or at least your writers’ group, or an editor — to have a look at your ms.
When you get to your second and subsequent drafts, that’s soon enough to think about whether this or that hyphen serves a purpose.
The WordPress spell check is a lover of hyphens. I surrender to it. Great post, thank you!
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Aha! Thanks for pointing that out. I’ve never used WP’s spell check (spellcheck? spell-check?).
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I note a commonality in the examples of combinations that tend not to be used to form a single compound. This is true for slave owner, re-ignite, co-op, no one, and many others. Merging them results in a mashup of two vowels that leaved pronunciation ambiguous. I leave it to you to find counter examples to a rule to avoid vowel mashups.
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I think that doubled or adjacent vowels are often easy to misread, but in general the prevailing U.S. style guides, notably the Chicago Manual of Style and Merriam-Webster’s Collegiate Dictionary, have been discouraging hyphens. Hyphens used to be more common in words like “re-emerge” and “pre-existing.” You’d sometimes see “cooperate” with a diaeresis over the second “o” to indicate that “op” was a second syllable: coöperate. Now the one instance where the style guides almost all want a hyphen is the double i: anti-intellectual, anti-inflammatory.
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