Staycation 3: Tiny Mobsters, Lovely Pelicans, and Air-Conditioned Shirts
Note: there’s a video podcast for this as well, and it’s below!
A few years ago, my wife and I started a new tradition for our anniversay.
We go on a vacation without leaving town.
We staycate.
We have to go there to stay. But we don’t go far, mostly we stay.
It’s not because we’re minimalists or anti-adventure. But because one year, our pet sitter said, “I can only do four days,” and mentioned some of her clients stay at a particular luxury hotel on the river wit
h two pools and an onsite restaurant and a huge boat dock.
We live in Charleston, South Carolina. It’s beautiful. People fly here from all over the world. There’s a lot to do, and tons of great restaurants.
So we just stayed and enjoyed it.
That first year? It was great!
Last year I actually said to my wife, “Look, pelicans! I love pelicans. I want to learn more about pelicans!”
You can tell my mind was on break.
So now we do it every summer.
(By the way, I just realized that no teacher is telling me to write an essay entitled My Summer Vacation - I just do it naturally. I can’t tell if that’s cute, or disturbing? Let’s go with cute.)
The Pool, the Mobsters, and the Man in the UV Shirt
This year, we checked into The Beach Club with some nice extra gifts from my Amex points like free breakfast and a $100 credit.
(I now think I was an idiot for taking so long to take advantage of credit card points. And thank you, David, for explaining it all to me!)
That first day, we found a couple—maybe 17 years old—who looked like they were cast from Jersey Shore: The Prequel. She was mad. He was squinting. His hair was slicked back like he’d been dipped in pomade. Every time he came out of the pool, he exhaled like an underworld boss on break from a turf war.
I was ready to write a movie around this kid. Not that anyone was asking.
Meanwhile, I was playing dermatologist-in-my-own-head. I’m half German, half Irish—basically the sunscreen-industrial complex’s target demo. I was obsessively applying SPF like I was frosting a human cake.
At one point I wore a UV-protective swim shirt—something I used to mock on sight. And I loved it.
It was like a personal air conditioner.
I finally understood those guys I used to see wading into the pool looking like elderly fly-fishing instructors who don’t know how to blend in the 64 ounces of sunscreen on their faces.
I became one of them. And it felt great.
What Made It a Real Vacation
We didn’t leave the state. We didn’t even leave our time zone. But we left everything else.
We unplugged—mostly. I didn’t bring my computer. I brought my phone, but it was so bright by the pool I could barely see the screen, which I now believe is nature’s way of saying, “PUT. DOWN. THE PHONE, BRIAN!!!”
We talked. We floated. We brainstormed my plans to dominate the world through Substack.
We didn’t rush. I didn’t check email. I didn’t try to cram in a dozen “relaxing” activities.
And somehow, that gave us space for bigger ideas to show up. Not on purpose. Just… organically.
I also realized: I’m the guy who used to want to stay home from school. I came up with 21 “I’m sick” excuses you’ve never heard. And my mom didn’t believe any of them.
Now I literally work from home. And I love it. I designed a life that works with who I actually am. This staycation reminded me why I did that.
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Why Staycations Actually Work
We think we need to “get away” to rest. But often we just need to step aside.
Here’s why our staycations work (and how to make yours not suck):
1. New Scenery, No Jet Lag
Reset your brain without changing your area code.
2. Real Rest, No Packing
There’s no logistical hangover. You don’t need a vacation from your vacation. Now the food and other over-imbibing? That’s a different story.
3. More Presence, Less Performance
You don’t have to impress anyone. You’re not posting daily reels from Venice. You’re just… where you are. Post some pelicans.
BETTER YET POST NOTHING.
4. Your City Becomes New Again
You notice little things. And you remember why you love this place so much.
Five Tips for a Killer Staycation
Leave your house. Even if it’s just a few miles away. If you stay home, the chores will call you. Your habits will take over. You won’t re-create.
Pick a vibe. Is this recovery? Romance? Reconnection? Make a theme.
Unplug the usual inputs. No doomscrolling. No “I’ll just finish this spreadsheet real quick.” Ok, so I still worked on spreadsheets but I’m weird - that’s relaxing for me.
Move slowly. That’s the point. Cars behind you won’t understand. Who cares.
Talk about anything but logistics. Dream. Ramble. Go deep. Have that conversation you never finish at home.
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The Surprise Payoff
Every time we do one of these, I get an idea. Not a forced idea. Not something I tried to extract from my brain like an espresso shot.
I get clarity.
Something that’s been noisy gets quiet. Something that felt tangled gets obvious. This time, it was about content—how I want to create and communicate going forward. It gave me the mental space to think clearly about the chaotic parts of what I do… without being overwhelmed by them.
It gave me and my wife time to converse about it. I took a lot of notes.
Also, I laughed a lot. Maybe that’s the best part.
Want to Try It?
You don’t have to wait for your pet sitter to cancel or your flight to be too expensive.
Book something local. Wear a ridiculous shirt. Bring someone you love. Stay long enough for your brain to breathe.
It’s not just a staycation.
It’s a reminder that **where you **are can be everything you need—if you let it.
Now just take a deep breath with me.
Let it out.
And repeat after me, “I love pelicans. I want to learn more about pelicans.”
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