Editor’s Note: This interview first appeared in Path Finders, an email newsletter from the Daily Yonder. Each week, Path Finders features a Q&A with a rural thinker, creator, or doer. Like what you see here? You can join the mailing list at the bottom of this article and receive more conversations like this in your inbox each week.


Dorothy Rosby is a humor writer from South Dakota. Her new book, Tis the Season to Feel Inadequate, is out now and deals with “holidays, special occasions and other times our celebrations get out of hand.” Potentially useful for everyone this time of year. Enjoy our conversation about punching up, midwestern passive aggression, and the upside of shabby wrapping paper, below.


Olivia Weeks, The Daily Yonder: How’d you wind up as a humor columnist? The sheer volume of your output is quite impressive. Are you just constantly writing jokes in your head?

Dorothy Rosby: It was my experience as a humorous speaker that led me to writing humor. For many years, I’ve been a member of Toastmasters, an organization where members practice their public speaking skills. I love doing humorous speeches and I’ve won some humorous speech contests and am often invited  to do entertaining talks for local groups in my community. Eventually I decided to type up some of my speeches and submit them to my local newspaper, the Rapid City Journal in Rapid City, South Dakota. The editor agreed to take me on as a humor columnist. Shortly after that, I began marketing to other newspapers and now my column is self-syndicated in small community newspapers throughout the West and Midwest.

Dorothy Rosby is an author, speaker and syndicated humor columnist whose work appears in publications throughout the West and Midwest. (Photo submitted.)

I write mainly observational humor, which I’d describe as finding the absurd in everyday life. I also do a lot of self-deprecating humor, which I’d describe as finding the absurd in, well, me. Over the years, I’ve taught myself to observe and make note of things that other people who don’t have a looming deadline might miss. Ideas are everywhere. Every conversation, every experience, bad and good, everything that gets under my skin or makes me laugh is potential fodder. Unfortunately, the irritating things and the failures, faux pas and embarrassing moments make better humor. Let’s just say I’ve written about speeding tickets and wardrobe malfunctions more than once. Those sorts of things make good stories because readers relate to them.

When something like that happens, my initial reaction is to be annoyed or even angry. But very soon after that I realize it’s material and I write about it as soon as I can. Sometimes it’s just a quick note that goes in my rather elaborate filing system. Other times it’s a couple of paragraphs. But occasionally, it’s an entire essay, or rather a very rough draft of one. I’m very disciplined about getting things written down or typed up right away. And I don’t mind doing it. After all these years, observations about things that happen still feel like gifts, though the events that lead to them don’t necessarily feel that way. What it all means is that I never face a deadline with no idea what I’m going to write about.

DY: How much does your upbringing in rural South Dakota come up in your writing? Do you find that’s a good way to connect with the readers of small town newspapers you write for?

DR: I grew up in Buffalo, South Dakota, population of 350 and I worked at the local newspaper one summer while I was in college. After college I worked at a radio station in Emmetsburg, Iowa, population around 3600. I now live in Rapid City, the second largest city in South Dakota. But our entire state is home to just over 900,000 people so I still very much identify with rural and small town life.

All of that definitely affects my voice as a writer as well as the topics I write about and the way I see them. One good example is the way we experience community in rural areas. There are things that wouldn’t make sense to someone from a large city—the way we say hello to everyone we meet on the sidewalk; the way we can’t get out of the grocery store because we have to talk to everyone in it; the way we have to behave in public because our mother really could find out what we’ve done. And mean spirited or edgy humor wouldn’t work for my readers as well as it might work in a more urban area. That’s fine with me because I tend to go more for self-deprecating humor anyway. I seldom pick on an actual person. If I do, he or she really has it coming — and also most likely doesn’t read my column. For example, I’ve written about oligarchs and the CEOs of Equifax and big pharma.

But normally I avoid criticizing others. For the most part, I’m your basic stereotypical, mild-mannered Midwesterner — chronically nice, unfailingly polite and occasionally a wee bit passive aggressive. Maybe that’s a relief to a world that is increasingly divided. And it’s also suited to the small community audiences I write for. With the exception of my local paper, the Rapid City Journal, all of my subscribing papers have circulations of fewer than 10,000 readers and many fewer than 5,000. I regularly hear from my readers and have even become good friends with some of them.

DY: One of my favorite essays in your book was about your time as a professional gift wrapper. Can you share a little with the readers here about the moral of that piece – the benefits of mediocrity?

DR: For those who haven’t read the book, that essay is called “How to Wrap a Million Dollar Smartphone.” In it, I discuss recent studies that suggest attractive gift wrapping can backfire by leading the receiver to anticipate an equally attractive gift. So when they open your beautifully wrapped package and find an egg slicer or a hair removal device, they’re bound to be disappointed. I guess they might be disappointed anyway. If there’s a moral of the essay, it would be that the flashier the outward appearance, the more we’re let down when we find a lack of substance inside.

And I truly wish I had known that during my brief career as a professional gift wrapper. As I describe in the essay, I worked at a hardware store when I was a teenager. There were few options for shopping in my hometown and it was before the internet. So the hardware store carried a variety of housewares, toys and other items that were often purchased for gift giving. It also had a fabulous selection of wrapping paper and bows but only a few people on staff who could really do them justice. I wasn’t one of them.

The gifts I wrapped were always a little lumpy on the sides where the paper came together. Had I known the power of gift wrapping back then, I could have handed my customers their lumpy packages and said, “If your wife is disappointed that you bought mixing bowls for Christmas, don’t blame me.”

DY: The blurb for your book reads, “It’s the American way to create a celebration for everything, then turn it into a chore or worse, a nightmare.” Why is that? Do you have a unified theory of holiday-fueled feelings of inadequacy?

Rosby’s latest book, ‘Tis the Season to Feel Inadequate, was released by Unhinged Press in September. (Image: Unhinged Press.)

DR: I think a lot of us can’t help comparing ourselves to other people. And when we do that, it’s easy to come up short. Everyone we know got their Christmas letter out sooner than we did. Ours didn’t go out until February — if we sent one at all. Our mother liked our sister’s gift better than the one we gave her. Our friend’s peanut brittle is better because she remembered the peanuts. Another danger to our self-esteem is advertising. Don’t we all wish our family looked like the attractive, happy family sitting around the Christmas tree in the television commercials. No one is ever crying or fighting or pouting in those. And even though it’s Christmas morning, their hair is combed and their pajamas all match and don’t even look slept in.

I think for some of us, there’s also an effort to recreate holidays from yesteryear that may or may not have been as wonderful as we recall. After all, nostalgia is nothing more than the overwhelming sense that everything was better if it happened so long ago we can’t remember it accurately. Between our glowing but faulty memories and comparing ourselves to everyone else including the actors in television commercials, we’re bound to feel a little inadequate during the holiday season. It would be grand if we could all give ourselves a break and just enjoy it.


This interview first appeared in Path Finders, a weekly email newsletter from the Daily Yonder. Each Monday, Path Finders features a Q&A with a rural thinker, creator, or doer. Join the mailing list today, to have these illuminating conversations delivered straight to your inbox.


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