We rented a house in an isolated hilltop town in southern Spain with a group of strangers from all over the world. For an entire month.

My husband, Brennan, is a scrupulous federal agent who can sometimes be a little suspicious of everyone. But don’t worry — the rest of the time, he’s a lot suspicious of everyone.

I’m definitely more of a risk-taker, but hugely private when it comes to my living space. In my youth, I’d rather sleep on a half-deflated air mattress in a 200 square-foot studio with no hot water than share a comfortable and well-equipped apartment with –hurl– roommates.

So we’re not the kind of people who say “f*ck it” and fly across an ocean to shack up with a bunch of unfamiliar people in an unfamiliar place.

What the hell got into us?

👉 If you mistake low-consequence decisions for a high-consequence decisions, you’re probably trapped in a comfort prison.

And now — the story behind why this advice matters. 👇

At the time, I was running the entrepreneurship publication and community arm of The Hustle (a pretty famous business and tech newsletter). My job was determining which stories got published, and which discussions were appropriate within our digital community of entrepreneurs.

One day I got a little “ping” from a member I didn’t know. His name was Nico. And Nico wanted to bend the rules a little bit — so he needed my blessing.

Our community discussion board had a strict “no solicitation” policy. No one shows up to an online community looking to get pitch-slapped, so we vehemently disallowed that shit. But Nico wasn’t selling anything. Instead, he wanted to recruit other members for a wild experiment.

Nico, his partner Anne, and their 4-month-old nugget, had found a bonkers deal on a stunning 5-bedroom villa in Spain — for the entire month of May. So before really thinking it through, they whipped out their credit card and booked it:

But they only needed one of those five bedrooms. So Nico set out to fill the rest of the house with an international collection of creatives and entrepreneurs.

And he wanted to invite our members to join the hive.

“Approved!”, I enthusiastically replied. “Best of luck finding some housemates! This sounds amazing.”

A few hours later, as Brennan and I were sharing the events of our day, I mentioned Nico’s experiment. “The villa looks absolutely heavenly,” I told him. And when I revealed the price, Brennan’s head shot up like Nvidia stock.       

“Maybe WE should go,” he remarked.

–blink–

We both just side-eyed each other for a minute. 

I was trying to figure out if he was joking or serious. He was also trying to figure out if he was joking or serious.

But we both knew that this was now an actual discussion — the outcome of which may result in us going to Spain to live with strangers in less than 60 days.

We decided that it wouldn't hurt to just express interest, speak with Nico and Anne, and get some more information. So I raced back to my computer and messaged Nico.

He responded instantly, and we all jumped on a video call.

We were met with warm smiles and affable energy on the other side of the camera. 

We learned Nico and Anne lived in Berlin, and were looking to spend the summer in Spain as Anne finished her maternity leave. 

Nico was an Argentinian entrepreneur who was developing a new mental health technology. And Anne was an esteemed filmmaker from Germany, whose latest documentary series would be premiering at the Cannes Series Festival.

Well… that was pretty damn cool.

But more importantly, these two fresh parents were undeniably sincere. We instantly liked them. And they seemed to like us, too.

We chatted for about 15 minutes, and then we all collectively decided — let’s do this crazy thing. Let’s go live in Spain together.

Holy moly.

And an escape plan.

If the place or the people turned out to be shit, we could respectfully skedaddle, allow them to keep our share of the rent for the month, and still have enough money to pull together a lovely (albeit shorter) European holiday.

But our lukewarm assumptions were blown to bits. 

The villa was spectacular. The little hilltop town was idyllic. The most delicious wine I’ve ever tasted was $4 a bottle at the local market.

And the people were the f*cking best.

Anne’s documentary series had just premiered to incredible acclaim, so despite still being on maternity leave, she was being bombarded with interview requests from major media outlets across Europe — which she took from our villa’s laundry room where the WiFi signal was the strongest.

Nico, myself, and a number of our other housemates spent our days gathered around a giant communal table, working on our various business projects, and collaborating on ideas. It was WeWork on goddamn steroids.

And in the evenings, we all assembled on the veranda to share a delicious meal, muchas copas, and soulful conversation. Nico would pull out a guitar, Anne and I would sing, and there was copious laughter and silliness.

On the weekends, we explored the surrounding coastal and hilltop towns together, from the Bohemian beaches of Tarifa, to the Moorish architecture of Vejer de la Frontera. One weekend, Brennan and I slipped away to Morocco — a short ferry ride across the Strait of Gibraltar. 

I’m not sharing all this to make you jealous (although you should absolutely be jealous).

I’m sharing this because it’s the outcome of a decision I never dreamed Brennan and I would make.

Three years later, and this whole thing still feels made up. It was a transformative life experience that I think about every day, but have never written about in this newsletter.

So why haven’t I written about it?

Because, frankly, there was no “why” in this story. I had no damn clue what possessed us to go completely against our nature and take a risk like this.

But last weekend, I devoured Simone Stolzoff’s second book, How to Not Know, and it challenged everything I thought I knew about decision-making. 

(I’m also a huge fan of Simone’s first book, The Good Enough Job, and have mentioned it in this newsletter before).

How to Not Know theorizes that uncertainty is a skill — not a weakness. And it made me realize that this seemingly insane decision was simply a way for us to exercise that uncertainty muscle with a pretty big safety net.

So what was the risk, exactly?

Honestly, all we were risking was a little discomfort. 

Maybe the villa wouldn’t be as clean and comfortable as it looked in the photos. Maybe the people wouldn’t be friendly and interesting. Or maybe they wouldn’t be tidy and courteous housemates.

Maybe, just maybe, we would have to trade one version of our European holiday for a different version of our European holiday.

Boo-f*cking-hoo.

On the surface, our decision to fly across an ocean and shack up with strangers seemed outrageous. We felt like it was outrageous. And I’m sure our family and friends thought we were nuts. 

But in reality, it was a fairly low-consequence decision that allowed us to step out of our comfort zone, practice spontaneity, and embrace uncertainty.

Now that I understand this, I’m realizing how often I mistake low-consequence decisions for high-consequence decisions when the consequence in question is just a little discomfort. And I’m embarrassed that, as someone who identifies as a risk-taker, I prioritize my comfort all the damn time.

I’m going to stop doing that.

So… does anyone want to share a house in Antarctica this summer? 😉

Cheers! 🍻

-Kristin :-)

P.S. — I don’t just write Drunk Business Advice — I bring it to life on stage. And I’d love to speak at your next event. Hit reply or click here to learn more.