What made you weird before you learned how to hide it?
There are two types of people in this world:
The ones who’ve been ferally, irrationally obsessed with something.
The ones who are scared to want anything that much.
I’m not talking about “Oh yeah, I’m kinda into that.” I mean: forgot-to-eat, built-a-Google-Doc, ruined-your-social-life obsessed.
The kind of obsession that makes you bad at small talk and makes your eyes flicker when someone unknowingly mentions your Thing.
These are my favorite people.
If you’re one of them, I want to sit across from you at a booth, drinks sweating on the table, and ask: When did you first know this was your Thing? And how far off the deep end have you gone since?
Ideally, we’d have a big plate of fries between us.
Thanks for reading Side Quest! Subscribe for free to receive new posts and support my work.
For me, it started with dogs.
When I was eight, I became obsessed with the American Kennel Club list of dog breeds.
Not like “aww, puppies.”
I treated the AKC Complete Dog Book like it was a sacred text and I was prepping for a test no one else knew about.
Do you know the difference between a Cairn Terrier and a Norwich Terrier?
I do.
LEFT: Cairn Terrier // RIGHT: Norwich Terrier
I made flashcards. I built classification systems based on ear set, tail curl, coat texture, and country of origin. I could spot the difference between a Papillon and a Phalène just by looking at their ears.
I used to treat whoever sat next to me in school like an unwilling contestant on the world’s weirdest game show: “Would you rather own a Tibetan Spaniel or a Nova Scotia Duck Tolling Retriever?” They’d blink. I’d beam. I wasn’t doing it for them. This was for me.
Because when I fall in love with something, I want to know everything. I want to ruin dinner parties with unsolicited trivia. And I hope I never stop.
"I’ve always been obsessed with the idea of obsession—people who throw themselves over the cliff for something they believe in." — Philippe Petit, high-wire artist (famous for walking between the Twin Towers)
We live in a culture that worships detachment. We’re trained to think that caring is a PR liability.
But the people who try the hardest to seem ~so chill~?
They’re losers. Which, ironically, is probably their biggest fear.
Because trying is cringe.
But you know what else is cringe?
Making art. Starting a company. Telling someone that you actually give a shit.
Ask any artist, founder, or friend who made something unforgettable. They didn’t start with a five-year plan. They started with an obsession.
They spiraled. They got weird. They got rejected. They kept going.
Robin gives an eight-hour walking tour of Dealey Plaza, offering a second-by-second replay of November 22, 1963. This isn’t some sanitized History Channel version. This is his gospel, built from decades of reading, diagramming, and obsessing.
His opening line?
“I will not say ‘we suspect’ during this tour. I know what happened.”
Robin Brown and his daughter in Dallas, TX
At one point, we’re standing in the middle of Elm Street. Cars are honking. He’s explaining why Oswald couldn’t have had a clear shot from the Book Depository.
“The government said the trees were bare,” he tells me. “But Texas live oaks shed in the spring, not the winter.” Then he slaps both hands on his cheeks like Macaulay Culkin in Home Alone and yells: “Think about it!!”
(For the record, some say the trees were shorter back then. Robin doesn’t care. He’s not here to debate. He’s here to testify.)
He doesn’t do the tour for money; he runs a funeral home during the day. He doesn’t do it for attention; he wasn’t even trying to convince me.
He does it because he has to. Because real obsession is rarely a choice. It grabs you by the collar and says:
Sit down. We’re not done yet.
I’ve realized I’m drawn to people like that. Who are deeply, unapologetically stuck on something: a hobby, a niche, a lifestyle. The people who found their Thing a long time ago and never found their way out.
Captain Ahab chasing his whale. Don Quixote tilting at windmills. Carrie Bradshaw emotionally benched by Mr. Big for a literal decade. They’re not aimless. They’re pilgrims of obsession. And I respect the commitment.
He’d just had a breakout role in Killers of the Flower Moon, and Hollywood was suddenly very interested in him—this quiet guy from Texas with a face made for Marlboro ads and the energy of someone who has never sent a Snapchat.
The industry wanted to turn him into a thing. Ty said, "Yeah, no thanks."
Didn’t want the press. Didn’t want the parties. Didn’t want to talk about his “craft.” He just wanted to get back to his obsession: the ranch he runs with an octogenarian in West Texas.
Ty and I in Marfa, TX
When I asked if he planned to watch the Oscars, he looked at me like I’d asked if he wanted to fly to the moon.
“I don’t think I get that channel out here,” he said, rolling a cigarette. “If I ever win one? Mail me that SOB.”
These are not people of the algorithm. They’re not selling courses. They’re not optimizing for personal brand.
They are devoted. They’ve been building a private cathedral of meaning for years, brick by brick, even when no one else gave a shit.
(And if I’m being honest, one of my obsessions is writing about men in Texas who are obsessed with something.)
Obsession Is a Compass
When you’re obsessed, the world sharpens.
You see your Thing on a keychain in a museum gift shop, and it feels like finding the holy grail.
Colors are brighter. Details matter. You stop drifting.
Obsession is how people find their life’s work. Their person. Their purpose. It’s the seed of every great book, business, art movement, invention, and cult.
No one ever changed the world because they thought something was “kinda cool.”
Give me the girl who’s watched the same movie every year on her birthday since she was thirteen and still cries at the same part.
Give me the guy who learned everything about Soviet space dogs because he clicked one Wikipedia link at 2 a.m.
Give me the person who fell in love with a defunct band from the ‘90s and now owns three original tour shirts and a rare cassette they had to buy on eBay from someone in Finland.
That’s not a quirk. That’s a portal.
It’s proof that someone once felt the electric jolt of meaning and followed it all the way down.
Obsession is how you build a life that feels like it’s yours.
So go ahead: Start the archive. Buy the weird merch. Spiral like it’s a second job. Get cringe. Get culty. Get painfully specific.
Because the people who care too much are the ones who change the world. And at the very least, they make it a hell of a lot more interesting.
P.S. If you're currently obsessed with something strange, sacred, or beautifully specific, email me or comment below. I want to hear about it.
Thanks for reading Side Quest! Subscribe for free to receive new posts and support my work.
Thanks for writing this. I am obsessed with French Toast. It’s a problem.
I wonder if "commitment" would also work, obsession's sidekick.