Between the Lines with Will deFries, founder of Sunday Scaries
A dispatch from Seoul—where fortunately, my Sunday Scaries are nonexistent.
Another Sunday, another issue of The Sunday Series written from a window seat. For fear of being too literal, as I sit here staring back at the wing, it just struck me how it’s been nearly two years since I shared my Seatmates responses with Tori Simokov, the writer behind Window Seat.
Reflecting back on all the life that’s happened since, it’s remarkable just how much of my Substack has been written from this very vantage point—from Scandinavia to St. Lucia to South Australia and now Seoul, I continue to churn out this newsletter week after week, no matter where I am in the world. And with another trip to Australia (this time, Western Australia!!!) on the docket next month, I suppose it comes as no surprise that, as overwhelming as it can be to produce content on the road, I’m equally fueled by the opportunity to keep my “desk” view forever in motion.
Today, we traveled from Osaka to Seoul on Korean Air’s gorgeous A321neo—a delightfully spacious aircraft that made for a smooth ride on our ninety-minute hop to the K-beauty capital. If you’re interested in getting the scoop on what we’ve been up to while here, be sure you’re subscribed to Stay Awhile with SmartFlyer where we’ll also recap how we traveled from New York on Japan Airlines’s stunningly outfitted A350.
Here on The Sunday Series, perhaps I’ll do a rundown of everything I bought in Japan and South Korea next Sunday…let’s just say, the fashion is FASHUN-ing here. Sick vintage bags (I’m still NOT over the gorgeous early 2000s embroidered Fendi baguette I scored in Tokyo). Plenty of tops from cool Japanese brands where notably, it’s all about layering. Sneakers made for long days of exploration—including the iconic yellow Onitsuka Tigers that felt very TSS-approved. Ceramics made with extra care in Kyoto. And naturally, snacks on snacks on snacks from 7-11. When I say we are acquiring some additional suitcases in South Korea for our K-beauty haul, I do not exaggerate.
But for now, back to the matter at hand. Today, I’m honored to be featuring Will deFries, founder of Sunday Scaries, as our “Between the Lines” guest. Yes, that Sunday Scaries! The one with a million followers on Instagram that crafts the cheeky slams laptop till Monday* carousels you’re always sharing to your IG story.
While it would be easy to assume that @sunday.scaries is a faceless entity, one of my favorite things to do when dissecting the internet is to get to know the actual people behind widely followed accounts. After all, they’re the tastemakers driving so much of the cultural conversation. So, I couldn’t think of a more aligned guest to do just that with in my own newsletter, which is also aptly named after the all-powerful Sunday.
For context, in the six (!!) years of writing this weekly letter, I think Will is only the second man I’ve ever done an interview with—and our first straight male guest on TSS at that. But after chatting with my friend Xan, who kindly introduced me to Will, I was eager to share more about the behind-the-scenes building of Sunday Scaries with readers. I hope our chat helps keep your own Sunday Scaries at bay!
Kayla Douglas: Will, you started Sunday Scaries back in 2013. What did the early days look like before you were sharing content with a million followers?
Will deFries: In 2013, I was living with my parents and operating it out of my bedroom. At that time, my life was living and breathing the concept of ‘Sunday Scaries’ — desperately single, struggling professionally to find my niche, going out two (or three) nights a weekend, and dreading my existence every Sunday night. Not that today’s content isn’t completely authentic, but that time of my life was the most representative of the ethos behind the brand.
And honestly, I do kind of miss it sometimes in a twisted way.
Kayla: A decade ago, did you know you were building a brand, or were you simply documenting a feeling?
Will: Somewhat, yes. I was also trying to create something that made people feel seen in their anxieties. Early on, it was somewhat established that the motto of the brand was something like, “We’re all less scared together than we are apart.” Driving that community through shared feelings and experiences is what really made me realize I could do it full-time. Even today, I try to operate with the same mindset.
Kayla: Can you point to a specific moment (a post, a reaction, or a piece of feedback) that made you realize Sunday Scaries had evolved from a clever phrase into something deeply embedded in our cultural lexicon?
Will: Though I didn’t come up with the term itself, I will take *some* credit for the rise of it. I think it would have been popularized regardless, but I was the first person to really do anything with it with an end goal.
Early on, I had several people I looked up to compliment my writing to the point where it was completely motivating me. Once I had that approval, it kind of became a “Why can’t I do this?” moment for me.
Once COVID hit, however, people really started paying more attention. My guess is because every day felt like Sunday for an extended period, but I was simply glad to be there for everyone.
Kayla: Tell us about your background in podcasting and how you approach this medium of storytelling.
Will: I saw a few other companies launching podcasts in 2016, and it just made so much sense to me as someone who values independent media. With no actual experience with the medium, I walked into an office on Monday morning and simply said, “We need to start a podcast.” From there, things just kind of fell into place.
When I started The Sunday Scaries Podcast in 2019, I really wanted it to be a more digestible way to take in my writing — that’s probably where the storytelling took off for me.
Podcasts are a weird, congested, and difficult world. But the sense of community it can drive is unmatched.
Kayla: For Instagram, so much of what you do comes down to sourcing imagery that hits on the zeitgeist. What does your curation process look like?
Will: I honestly just save photos I like and hope that they resonate with others, too. If I’m watching a show, I’ll end up defaulting to that world. If a celebrity is being hilarious or bougie lately, they’ll probably get included in a *slams laptop* post. There’s really not much thought behind it other than, “Yeah, this feels Scaries.”
Kayla: The internet moves fast (and anxiety faster). How do you keep Sunday Scaries feeling current without chasing every trend?
Will: I’ve always just had my own idea of what the brand is and can be, and I’ve let that guide me more than trends. Of course, I clearly pay attention to trends but I think I’ve become somewhat savvy in understanding what is timeless and what is temporary.
I’ve been interested in graphic design since 2002, when I illegally downloaded Photoshop, so it’s always been easy for me to see through my ideas. Or change them for the future, too.
Kayla: You were an early adopter of Substack, getting on the platform back in 2022. In what ways has your long-form content evolved on Substack since launch?
Will: When I first launched on Substack, I simply wanted to have that old-school blogging feeling that sparked Sunday Scaries in the first place. I had always envisioned the brand having a regular Sunday “guide” for people feeling lackluster, and Substack felt like the perfect way to deliver this.
Obviously, Sunday Confessions has totally changed the trajectory of the Substack. People really seem to enjoy them despite it being user-submitted content versus my writing. The older I get, the less I want to force my writing, so it’s been a nice way to keep things fresh.
These days, I’ve actually been posting simultaneously on my old website, sunday-scaries.com, which I’ve been enjoying. I’m such a visual person that being able to manipulate everything from a design perspective is almost essential for me. I see myself diving far more into that this year than I did last year.
Kayla: Escapism is inherently woven into your brand as you create content that celebrates the art of running from our Sunday Scaries. How does travel play a part in the future of what you’re building?
Will: The first case of Sunday Scaries I ever had was leaving a Mexico spring break trip in 7th grade. I remember sitting on the airplane and thinking, “Why do I have to leave?” Ever since, it’s been ingrained in me that the worst Sundays are the ones where you say farewell to your vacation.
Additionally, however, travel just feels so in line with everything I want the brand to represent — exploration, leisure, relaxation, and that escapism you mentioned. If there’s one thing that can cure a case of the Sundays, it’s a plush embroidered robe and a freshly made hotel bed.
Kayla: If you wanted to outrun your Sunday Scaries tomorrow, where in the world would you go and what would you get up to?
Will: My number one bucket list place to visit right now is Forestis in the Dolomites. We considered pairing it with our Lake Como trip in 2023 but simply didn’t have the time.
From what I can tell, it’s a true Sunday sanctuary that I’d love to capture on film.
EDITOR’S NOTE: FORESTIS IS INDEED WORTH BEING AT THE TOP OF YOUR HOTEL WISHLIST! I’VE STAYED TWICE AND IT REMAINS ONE OF MY FAVORITE PROPERTIES IN THE WORLD.
Kayla: If we were with you in Austin on a Sunday, where would you take us to spend the afternoon?
Will: A light drink at June’s has never treated me wrong on a Sunday afternoon. And hopefully, I’m splitting their shaved jambon sandwich with my wife before we go home and sink into some Love Island.
Thanks for reading, friends. Looking forward to being back stateside and in your inbox next Sunday. xxKD
crazy that it's been two years!!
I love when my friends become friends! 🥰