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Dec 30, 2025

A Line in the Sand

Celebrate Hilton Head Magazine

Photography By

M.Kat
Topic: What is Your Dream Side Hustle?

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Courtney’s Thoughts:

When I was young, I wanted to be Julie McCoy. Yes, that Julie McCoy, cruise director for the 1970s television series The Love Boat. I wore a little blue blazer with white piping (an Easter outfit leftover) and walked around the house with a clipboard. I wanted to plan the activities on the Lido deck, book the dinner entertainment, and taste-test Isaac’s signature drink. Once Julie was written off the show because of the actress’s drug addiction that led to delays on set, I switched my focus. 

I would instead pore over the wedding section of the JC Penney catalog and plan weddings for make believe clients, selecting their dress, veil, bridal party. I had a full-service operation, on my Fisher Price phone, in my 8×10 bedroom on Shawnee Drive. 

Ultimately, I wanted to plan everything (still do!), which my therapist will tell me was the early indication of my control-freak personality. I parlayed my need for control and my gift of considering every last detail into a 17-year marketing and events career at Palmetto Bluff. So, I guess I checked the box. 

In college, when questioning how a certain professor became a professor (and not because he was exceptional at his job), I thought maybe I could teach at the college level when I retired. And guess what, it turns out that all you really need to teach at the college level is a Master’s degree. So, I did that too, and my first side hustle was born. I decided not to wait until retirement and have been teaching college courses for the past 20-plus years. Full disclosure: I had zero idea what I was doing when I started and for that I apologize to the students at Northampton Community College circa 2002-2004. 

When I moved to Bluffton, I thought writing would be a fun side hustle. Heck, I’ve always preferred to write out my feelings over verbalizing them. I miss handwritten notes (but not the high school days that accompanied them). I wrote a research paper on the longevity of greeting cards in graduate school. So, my first published writing gig was a column for Bluffton Today, where I first met Barry (circa 2005) and penned a column about being a Jersey girl in the South. You can imagine how that went over. I’m told the Chief of Bluffton Fire District used to read my column out loud at the station and say, “Who does this girl (I was 32) think she is?”

And there was that time – 11 years ago – when I got hankering and took the firefighters agility test and wrote about it here. I dropped the 150-pound dummy and struggled to get him back up mere inches short of the finish line and missed the time cutoff by seven seconds. I met a cute firefighter though. A year later I said “yes” when he asked me out and now, I live vicariously through him. 

If fixing the healthcare system and/or the social service system could be a side hustle I would be all in. My pet peeve in life is things that become a “system,” because in my experience once it is a system it breaks.

If I could be paid for the one thing that comes easy to me, I would be making a fortune solving “Law and Order,” “NCIS,” and “Dateline” episodes within the first 10 minutes and ruining the suspense for everyone else. 

Alas, when I do finally retire and aim to fill my days with only side hustles, I want to do it with something that brings me joy. So, you will find me walking dogs around my neighborhood, where I already know all the dogs’ names (but not their owners). Sit. Stay. Repeat.

PS: When I describe Barry, as I am so often asked to do, I say, “He is a brilliant writer and editor.” So, while he pretends that writing is a side hustle, he is, in fact, one of those rare unicorns who has been able to make his passion his life’s work. Sorry to spoil it for you Barry, but you are a writer. And a damn good one. The second best one I know.  

Barry’s Thoughts:

I recently found myself, as one does, standing at the edge of the Bluffton Dog Park while two of my clients, adorned in inflatable wiener dog costumes, filmed themselves flinging plush poop emojis into the air. It should come as no surprise to regular readers of this magazine that the clients in question were Jevon Daly and Maggie Washo.

It’s not the first time that a client has asked me to partake in something far beyond my parameters as a writer. My freelancing career has brought with it extracurricular perks from staying the night in a haunted brewery to twisting through the air in a biplane. But few have encapsulated the weirdness of my job as perfectly as that day – watching my clients pretend to be a pair of defecating dachshunds.

Naturally, it was at that exact moment that Red Cedar Elementary School called me asking if I’d like to participate in their career day. Standing there watching two professionals discuss the funniest angle at which to shoot a plush poop emoji, knowing that that was my career that day, what else could I say but, “Can I assume everyone with real jobs said ‘no’?” 

I did end up accepting, even though I feel like I’ve been invited as more of a cautionary example than anything else. But it was fortuitous that Courtney reached out later that day with a potential topic for this month: What is your dream side hustle?

My response was, obviously, “Does ‘Batman’ count?” Courtney relented that it would count as a side hustle, but since it would require physical fitness and considerable financial resources, we quickly ruled it out for me.

The fact is, all I really have is side hustles. 

One day I might be chasing magazine publishers in inflatable canine costumes, but the next I could be sitting down and hearing someone’s life story. This issue of CH2 alone has me writing about Hilton Head Prep, Hilton Head Pharmacy, and Catherine Davies’ potentially psychotic love affair with running. And they’re not the only magazine I write for!

That’s to say nothing of the copy writing. One day might find me pitching copy for a luxury resort’s website before touring a multi-million-dollar home to complete a property write-up for a real estate client. The next might find me crafting prose for the packaging on a jewelry line. Writing for a living, it turns out, is not a monolith. It’s a million different things, all loosely tied together by my being better at writing than ChatGPT (for now). 

Oh, and I host trivia three nights a week (ironically enough, at Side Hustle Brewing at The Bank on Tuesdays). So that’s a side hustle to my side hustles. I hate to say it, but I’m kind of living my dream side hustle.

That might end up being my advice to those young Red Cedar Foxes come career day: Find what you enjoy doing and do it. If it’s a career, great. If it’s a side hustle, find other side hustles you also enjoy to occupy your time and keep the lights on. It won’t all be biplanes and poop emojis, but it’ll be enough.

And, young Foxes, if you have the means, be Batman. I know a couple of clients who more than likely have a costume for you.  

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