There’s a moment on almost every trip where you realize your instincts don’t apply. You walk into a market, a restaurant, an office, and the rhythm is different. People stand closer or farther away. Small talk lasts three minutes or twenty. The price on the tag is a starting point, or it’s final and asking is rude. Nobody hands you a rulebook. You either pay attention or you look foolish.
That moment is the most valuable part of travel, and it’s the part most people rush past on the way to the next photo. For Garrett O’Rourke, Miami Beach has been a useful place to notice it — because you don’t even have to leave to see it. South Florida runs on people from somewhere else. Walk a few blocks and you’ll hear three languages and see four completely different approaches to negotiating the same transaction. Living here is an ongoing lesson in how many reasonable ways there are to conduct business.
What years of sales work does to the way you travel
Over the years, I’ve spent most of my working life in sales, business development and call-center operations. That’s a career built on reading people fast — tone, hesitation, the pause before an objection, whether a question is real curiosity or a polite exit. When you’ve spent enough hours on the phone and in front of customers, you stop hearing only words and start hearing intent.
Travel does something strange to that skill. It takes away half your inputs. You can’t rely on cultural shorthand, familiar accents, or the assumption that a handshake means the same thing here as it does back home. Directness reads as confidence in one place and as rudeness in another. Enthusiasm closes a deal in one room and kills trust in the next. You’re forced back to fundamentals: watch, listen, don’t assume, and let the other person set the pace.
One thing I’ve learned is that discomfort is the tuition. The trips where everything went smoothly taught me almost nothing. The ones where I misread a room, misjudged how long something would take, or realized halfway through a conversation that I’d been pitching when I should have been listening — those stayed with me.
Why perspective is so hard to build at home
Businesses develop accents the same way people do. You spend a few years inside one company, one industry, one market, and you start believing that the way you do things is simply the way things are done. Your script is the script. Your sales cycle is the normal sales cycle. Your customer’s objections are the universal objections.
That’s not arrogance, usually. It’s just exposure. Nobody shows you a second option, so you don’t look for one. The problem shows up later, when the market changes or you expand into a new region or hire someone who came up in a different system. Suddenly the thing you thought was a law of nature turns out to have been a local custom.
Running a business teaches you how expensive that kind of blind spot is. I’ve watched good operators struggle not because they lacked discipline or work ethic, but because they only had one model in their heads. When you’ve only seen one way to sell, one way to structure a team, one way to handle a complaint, you can’t adapt — you can only push harder on what you already know.
Travel is one of the cheapest corrections available. Not as a luxury, and not as an escape from work. As a way to collect alternative models. A restaurant that runs a full dinner service with four people and no visible chaos is teaching you something about process. A vendor who never mentions price until the third conversation is teaching you something about trust and sequencing. A city where public transit actually works is teaching you something about maintenance and consistency over flash.
Practical lessons worth bringing home
Perspective is only useful if you do something with it. A few things I try to carry back from any trip, and a few habits that make the observations stick:
- Study the front line, not the brochure. Watch how the person at the counter handles a difficult customer. Watch how a server manages six tables during a rush. Front-line execution tells you more about how a place actually works than any marketing material.
- Notice pace before you judge it. Some cultures move slowly on purpose because relationships carry the risk that contracts carry elsewhere. If you read that as inefficiency, you’ll push, and pushing will cost you. Relationships matter, and in many places they are the infrastructure.
- Ask questions you already think you know the answer to. This is a sales habit that travels well. The answers you get are often different from the ones in your head, and the gap is where the learning is.
- Steal process, not aesthetics. It’s easy to come home wanting your office to look like something you saw. It’s more valuable to come home with a better way to handle handoffs, train new hires, or follow up.
- Write it down within a day. Observations fade fast. A few lines in your phone about what surprised you is worth more than a hundred photos.
- Assume you’re the one who’s unusual. Your normal isn’t the baseline. That single assumption prevents most of the mistakes people make abroad, and most of the mistakes they make expanding into a new market.
Miami Beach as a permanent case study
What makes Miami Beach interesting isn’t the postcard version. It’s that the whole place is a negotiation between people with different assumptions. A business here can’t succeed with one script, because the customer walking in next might have grown up 3,000 miles from the last one. You learn flexibility by necessity.
The architecture says something too. Buildings here were designed for heat, light and weather — practical constraints first, style second, and the style is better for it. That’s a reasonable model for a business. Solve the real constraint, and let the character come from how honestly you solved it.
As an investor, the same habit of looking for alternative models applies. Patience matters, and so does understanding that your read on a market is a read, not a fact. Different places price risk differently, value different assets, and define “safe” in different terms. Seeing that firsthand makes you slower to assume you’ve found an obvious opportunity, and slower is usually better. (That’s my personal perspective from experience, not individualized financial advice — everyone’s situation is different.)
The broader principle
Perspective isn’t a soft skill. It’s the thing that decides whether your experience compounds or just repeats. Two people can spend twenty years in the same job; one accumulates twenty years of judgment and the other accumulates one year twenty times. The difference is usually how much genuinely unfamiliar input they let in.
Travel is one of the most reliable ways to let it in. So is hiring people who don’t think like you, working in an unfamiliar market, or simply spending a week paying close attention in a neighborhood you never walk through. You don’t have to go far. You just have to be willing to be the least knowledgeable person in the room for a while — and to find that useful rather than embarrassing.
Experience matters, but only the kind you actually examine. The rest is just mileage.
Photo by Zoshua Colah on Unsplash