KO teachers wear many different hats as advisors, coaches, leaders, and educators. But it’s not every day that you meet someone on campus who is not only a KO teacher, but also a published author.
That someone is Upper School history teacher Rob Kyff. Mr. Kyff teaches AP U.S. History at KO, but what sets him apart is his work outside of the classroom: Mr. Kyff is a columnist and an author whose writings discussing words and word origins have spread nationwide.
For over 28 years, Mr. Kyff served as the Language Columnist for the Hartford Courant. He started the column in 1992 and was syndicated in 1996 by Tribune Media Services in Chicago. The staff at Tribune bestowed upon him the title of “The Word Guy,” which would come to define his career and passion for studying language. “I thought that [the title] was great,” Mr. Kyff commented, “It’s easy to understand, and it’s also kind of casual and familiar.”
In his columns and books, Mr. Kyff writes about all things words, such as grammar, punctuation, pronunciation, usage, regional English, and quirks of the English language. His favorite subjects to write about combine his teaching passions with his personal interests.
“I think the most interesting columns are the ones about the origin of words,” Mr. Kyff shared, “That’s partly because I’m a history teacher, and that’s where history and language intersect. I find it just fascinating to hear about where words originated, how they change over the years, and how some words are contradictory…It’s always interesting to find out these quirks of words and how they’ve changed.”
Mr. Kyff’s language column appeared in the Hartford Courant until April 2020 when the COVID-19 pandemic hit. Now, his column is distributed to an even larger audience through the Creators Syndicate in Los Angeles.
One of his favorite columns to write each year is “The Year in its Own Words.” Throughout each year, he keeps a running list of common words and phrases that defined the year, from “Building Back Better” to “Besties” to “Boosted.” At the end of each year, he compiles the words into a column written in a poetic, rhyming style.
“I really enjoy hearing new words and picking up on coinages and trendy words that people use,” Mr. Kyff said. This column is highly successful and has even caught the attention of one of the producers of NPR’s “All Things Considered” program who reached out to interview Mr. Kyff about the words of 2021.
In addition to his work as a language columnist, Mr. Kyff is also a published author. His first book, titled “Word Up!” was released in 2000 and is a self-published anthology of columns he had written over the eight years prior to the book’s release. “It covered every aspect of words, from pronunciation, to meaning, to origins, to grammar, usage, and punctuation,” Mr. Kyff explained. “Each chapter was really about one of those things.”
His second book is titled “Once Upon a Word: True Tales of Word Origins.” Released in 2003, this book focuses mainly on the origins of words and was his first book published by a real publisher, Tapestry Press.
This past year in June of 2021, Mr. Kyff’s third book, “Mark My Words,” was published as a collection of columns he wrote in 2019 and 2020.
Mr. Kyff’s writing presents the intricacies of the English language and a complex study of words in a format that is digestible and relatable for a variety of individuals. “I try to write for a middlebrow audience that is not for scholars or professors, but for people who have a reasonable knowledge of the language and a reasonable interest in language,” he said. Mr. Kyff creates a casual writing style through his use of humor and conversational diction. “I try to imagine I’m having a conversation with someone when I write,” he explained. “So I use short paragraphs, short sentences, and try not to get too detailed about explanations.”
Through his writing process, Mr. Kyff draws ideas from readers’ suggestions, his observations in daily life, and topics he is curious to learn more about. He does his own research and often gleans information from the books he owns. Mr. Kyff doesn’t outline his pieces; instead, he frames his writing around a central metaphor that makes the topic easy to understand. “I think the challenge is that words are a topic that is somewhat abstract, and if you can make it visual and have somebody imagining something, then it becomes more understandable,” he said.
Writing a column takes Mr. Kyff around five to six hours, and he always leaves extra time for peer review with his trusted mentors. While he was a full-time teacher at KO, Mr. Kyff followed quite the hectic schedule in order to balance his writing career with teaching, waking up at 5 a.m. to write for an hour and then heading off to teach at KO. Now that Mr. Kyff works at KO part-time, his schedule is more relaxed, allowing him ample time both to work on his writing pursuits and connect with his history students.
Mr. Kyff reflected on his writing career and how it has enhanced and impacted his teaching at KO. “It’s made me a clearer communicator as a teacher, because when you’re writing a column, it’s not that different from teaching a class,” he reflected. “You try to think, ‘what is the most effective, clear, and enjoyable way to convey information?’”
Mr. Kyff teaches effectively in the classroom and in his writing through the use of humor, analogies, and metaphors, and with an emphasis on making complicated topics clear and simple. “I think my teaching has helped my writing and my writing has helped my teaching,” he said.
KO has been a center point for Mr. Kyff to share his intellectual passions. “I have two loves,” Mr. Kyff shared. “I love teaching, and I love writing, and Kingswood Oxford has allowed me to do both of those… I really had an opportunity to indulge my passions in a productive way that was helpful to me. I’m really grateful for that, and there’s not many jobs where you can really do what you love to do.”
As both a teacher at KO and an acclaimed writer, Mr. Kyff has impacted the lives of many and has shared his love for words across many disciplines. As he put it, “It’s been the best of both worlds.”






