There’s a particular kind of trip most business travelers know well. You land, you take a car to a hotel near the airport, you sit in a conference room that could be in any city on earth, you eat dinner somewhere convenient, and you fly home. Ask what the place was like and you have nothing to say. You were there for two days and you saw nothing. If you do that enough times, travel stops being an advantage and becomes a tax on your calendar.
I’ve thought about this a lot, partly because of where I live. Running a business out of Miami Beach means you’re already in a place people fly to. Clients and partners come here for reasons that have nothing to do with work, and then work happens anyway — better work, usually, than the kind that happens in a windowless room by an airport. That contrast taught me something about how to travel when I’m the one getting on the plane.
What Garrett O’Rourke Miami Beach Has Learned About Trips That Count
Over the years, running sales organizations and call-center operations, I’ve done a lot of travel with a single narrow purpose attached to it. Go see the client. Go see the site. Go sit with the team for two days and fix what’s broken. That kind of trip is efficient on paper and frequently wasteful in practice, because you’ve flown a long way to do something you could have half-done on a video call, and you’ve given up the part of travel that actually pays off.
The part that pays off is the unstructured time. It’s the dinner that runs an hour longer than planned. It’s walking a neighborhood near the office and noticing how people actually live and shop and spend. It’s the conversation in a car on the way to the airport where someone finally tells you the real reason a deal has stalled. None of that fits neatly into an agenda, and all of it is why you got on the plane instead of scheduling a call.
One thing I’ve learned is that the value of a trip is rarely in the meeting itself. The meeting is the reason you’re allowed to be there. What you get out of being there is context — how a market feels, how a team behaves when the boss isn’t in the room, how a partner treats the people who work for them. You can’t read that off a spreadsheet.
Why Business Travel Gets Wasted
I think the main reason is that travel gets planned by the same instinct that plans a workday: fill every slot, minimize dead time, get home fast. That instinct is usually correct at a desk and usually wrong on the road. When you compress a trip down to nothing but obligations, you eliminate the margin where the useful things happen.
There’s also a status problem around travel. Somewhere along the line, being exhausted became evidence of importance. Three cities in four days, red-eye home, straight into a Monday. I’ve watched people do this for years and I’ve never seen it produce better decisions. It produces tired people making decisions quickly, which is a different thing entirely.
And there’s the guilt factor. A lot of people feel that if they enjoyed any part of a business trip, they somehow cheated. So they book the trip tight enough that enjoyment is impossible, which is a strange way to protect your integrity. Running a business teaches you that you’re paid for outcomes, not for suffering. If you come back from a trip with a stronger relationship and a clearer read on a market, nobody should care that you also got a good walk in on Saturday morning.
Practical Ways to Make Trips Worth the Flight
- Give every trip one real objective, not five. If you can’t say in a sentence what the trip is for, you’ll fill it with meetings that justify the airfare rather than meetings that matter. One clear objective leaves room for everything else.
- Build in margin on purpose. Leave a half day open. Arrive the night before instead of the morning of. The cost is one hotel night; the benefit is that you arrive as a functioning human instead of someone who’s been awake since four.
- Eat where the locals eat and walk where they walk. This isn’t about food as a hobby. It’s the cheapest market research available. How busy is the place on a Tuesday? What are people spending? What’s under construction? You learn more about an economy from a neighborhood than from a market report about it.
- Stack the personal onto the professional deliberately. If you’re already flying somewhere, adding a day is close to free compared to making a separate trip later. The flight is the expensive part. Use it.
- Don’t schedule the flight home for two hours after the last meeting. That’s the window where the real conversation tends to happen, and you’ll miss it because you’re watching a clock.
- Write down what you noticed before you land. Not the meeting notes — the observations. The things that surprised you. Two weeks later they’re gone, and those were the part you couldn’t have gotten remotely.
What Living in South Florida Changed About How I Travel
Miami is a city where business and leisure were never neatly separated, and I don’t think that’s a flaw. Deals happen over long lunches. People do business with people they’ve spent unstructured time with. That’s not a local quirk; it’s just more visible here because the weather and the geography make it obvious. South Florida is a reminder that relationships are the infrastructure business runs on, and relationships need time that isn’t scheduled down to the minute.
Travel also does something for judgment that’s hard to quantify. Seeing how other cities handle density, transit, retail, construction and tourism gives you comparison points. As an investor, that matters more than it sounds — when you’ve walked a dozen downtowns you develop a feel for which ones are actually growing and which ones are just announcing things. That feel isn’t a substitute for the numbers, and it isn’t advice for anyone else; it’s personal perspective, and I still want to see the math before I’d act on any of it. But it sharpens the questions you ask.
The other thing travel does is slow you down, which most operators need and few will admit. When you’re responsible for a team, your default speed is fast, and fast is a bad setting for thinking. A long flight with no signal is one of the few remaining places where you can actually work through a problem without interruption. I’ve made better decisions at 35,000 feet than in most conference rooms.
The Broader Principle
Balancing business travel and leisure isn’t really about balance. It’s about refusing to treat a trip as pure logistics. You are spending real money and real days to be physically present somewhere — the least you can do is be present while you’re there.
The people I’ve learned the most from in business are not the ones with the tightest itineraries. They’re the ones who show up early, stay an extra day, ask questions about the place they’re in, and come home with something more than a signed document. Patience pays in investing and it pays in travel for the same reason: the returns show up in the time you didn’t rush.
Photo by Marko Pavlichenko on Unsplash