Writing Rules for Fun and Profit: The Agony and the Ecstasy

Written by Ross Guberman on February 24, 2021

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Ever since I created an editing app, my usual workshop feats, like engaging bleary-eyed associates and racing to the last flight to O’Hare, seem like child’s play. I still relish the challenge, but if I give you a peek behind the glossy interface, you’ll see what I mean.

Say you want to cut the adverb “wholly.” Talk about low-hanging fruit in the editing grove. And these days, you could get a high-school student in a coding class to write a rule that scans text for “wholly” and suggests cutting it.

Seems easy, right? Just imagine billions of devoted users replacing “We wholly reject your offer” with just “We reject your offer.”

Time to break out the champagne? Not so fast. That auto-edit might have impressed people around the turn of the century, but it won’t in 2021.

A Whole Lot of Sometimes

Here’s the problem: You can’t cut “wholly” wholly. Or at least you shouldn’t.


That company is a wholly owned subsidiary.

“Wholly” is doing work there. It’s not an “owned subsidiary” in the sense of “owning the libs.”

But that’s not the only problem with a hypersensitive “wholly” detector. English sentences are built on a house of cards. If an editing app removes “wholly” from “a wholly owned subsidiary,” guess what’s left? “A owned subsidiary.” Oops. That “a” should now be an “an.”

BriefCatch knows its “wholly owned” from its “wholly rejected,” and it knows its “a wholly” from its “an owned,” too.

The Whole Is As Great As the Parts

And our fun has just begun. Take this sentence:

The benefits are payable partly or wholly in merchandise.

What mischief would a Never “Wholly” app make here?

The benefits are payable partly or in merchandise.

I wouldn’t shop at that store, whatever it’s selling.

Embrace It Wholeheartedly

For my BriefCatch users and future users, this is why you want me up at 1 a.m. working on these nuances every night while other products focus mostly on marketing. As wholly tempting as it is to resort to simple Never Wholly rules, owning these exceptions is the holy grail of legal editing. BriefCatch and its owner aren’t ashamed to admit that we find this push-and-pull challenge fun.

Better us than you, as I’m sure you’d wholeheartedly agree.





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Ross Guberman

Ross Guberman

Ross Guberman is the president of Legal Writing Pro LLC and the founder of BriefCatch LLC. From Alaska and Hawaii to Paris and Hong Kong, Ross has conducted thousands of workshops on three continents for prominent law firms, judges, agencies, corporations, and associations. His workshops are among the highest rated in the world of professional legal education.

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