The Monday Media Diet with Tori Simokov

On Flighty, Ling Ling Huang, and Long Island Compromise

I’ve been paying a lot of attention to the burgeoning travel Substacks. Tori Simokov (TS) writes a very good one. Happy to have her with us this week. -Colin (CJN)

Tell us about yourself.

I’m a travel writer and brand strategist based in Brooklyn, New York. I write Window Seat, a newsletter about the art of traveling well, and I also own V1 Projects, an independent creative studio that helps founders and creatives build brands through sharp strategy and striking design.

After a decade in creative strategy at major media and tech companies, I left the corporate world to go all-in on my own ventures. Now, I split my time between writing, designing, and finding the best way to redeem points for business class.

Describe your media diet.

Too many Substack newsletters to name plus industry media like Yolo Journal, Travel + Leisure, AFAR, and Skift are always in rotation. If I’m planning a trip, I’m probably deep in One Mile at a Time flight reviews trying to find the best business class cabin and seat combo. They’re the best. I subscribe to The New York Times, WSJ, and The Cut, and I’m constantly falling down TikTok rabbit holes on everything from aviation history to boutique hotel openings. I’m not much of a podcast person, but I’m a big reader, mostly fiction. I find reading novels helps tremendously with creativity and writing.

What’s the last great book you read?

Immaculate Conception by Ling Ling Huang. I read her debut and loved it, but this one really captivated me. It captured this feeling of being completely in awe of someone while also wanting, almost painfully, to be them. It dissects this kind of love that’s tangled up in comparison and identity that I found really interesting. I’ve never read a book like it.

What are you reading now?

Long Island Compromise by Taffy Brodesser-Akner. I really liked both the book and TV adaptation of Fleishman Is in Trouble, so I had high hopes for this book too. I’m only about halfway through, but I’m loving the way the characters are written so far.

What’s your reading strategy when you pick up a print copy of your favorite publication?

I’m a visual reader, so layout, typography, and design guide my eye as much as the headlines. I tend to flip through first, taking in the visuals and structure, before circling back to the stories that speak to me.

Who should everyone be reading that they’re not?

Mr & Mrs Smith is my favorite travel resource for hotels. I implicitly trust their curation (it’s spot-on every time) and the voice in each hotel write-up is something I aspire to in my own writing.

What is the best non-famous app you love on your phone?

Flighty. It’s not exactly obscure, but it’s essential. I love that you can aggregate all of your flights across multiple airlines into one sleek interface and track your flight info from years past. I’ve been using it since 2022 and can see how many times I’ve flown around the world (6.7x), my total flight time (18 days, 7 hours), and other cool info like that. Plus, it always notifies me my flight is delayed before the airline does.

Plane or train?

Plane, always. I’ll never get tired of seeing the way the world looks from above the clouds.

What is one place everyone should visit?

Anywhere in Japan. Being there was the only place I’ve been that felt both completely unfamiliar and instantly grounding. There’s something profound about stepping into a culture and language so different from your own; I think everyone should experience that kind of contrast at least once. I want that for everyone.

Tell us the story of a rabbit hole you fell deep into.

My best rabbit hole story is actually what spurred my love of travel.

The first time I flew alone, I was in college. I hadn’t flown in almost a decade, and somewhere along the way, I’d developed a debilitating fear of flying. I’m talking white-knuckled, heart-racing, convinced-we’re-going-down levels of fear.

I came home from that trip and, in a roundabout attempt to untangle my anxiety around flying, decided to watch Flight. Makes total sense, I know. In the film, Denzel Washington flies a malfunctioning plane upside down and lands it inverted. I was utterly mindblown. I simply could not rest without knowing if that was based on any kind of reality, so off to Wikipedia I went.

That rabbit hole led me to discover the TV show Mayday, also known as Air Crash Investigation, a long-running series that dramatizes real plane crashes, then walks you through how investigators solved them and, more importantly, how those findings led to safer skies. Morbid curiosity led me to watch one episode, then another. (Now you really think I have a problem.) But strangely, the more I watched, the safer I felt. I realized that even though each accident was a horrific tragedy, it was also a turning point that made flying more reliable for everyone.

Shortly after, I began a long-distance relationship that required frequent flying. I had to get on a plane at least once a month even though I was still afraid. But the more I learned, the less fearful I became. I understood the sounds and movements of a plane, and I knew what redundancies were in place. Years later, the fear gave way to something I never expected: an all-consuming joyful obsession.

Today, ten years later, I am a certifiable AV geek. I love airplanes more than most things in life. It still blows my mind that the thing I feared most became the thing I love most. That rabbit hole did more than calm my anxiety; it rerouted my entire life. Now I write about travel for a living, and nothing feels more natural to me than being in the sky. (TS)