Raise Your Business Travel Game
You're Seeing America Anyway, Might As We See It
Posted by Charlie Recksieck
on 2026-07-30
And we all say the same thing when somebody asks us about our work trip: "Business travel is boring."
There’s an old saying, "Only boring people get bored." Yes, on some work trips there really is no time to eke out any kind of local experience. But I'd bet that the majority of trips have a little bit of wiggle room for broadening your horizons.
Opportunity Costs
For most of my software career, at least the part where there was regular business travel, lots of my clients tended to be smaller utility companies. As a result, more of my travel opportunities were to mid-sized or smaller towns like Lincoln, NE, Gig Harbor, WA, Kissimmee, FL and the like. Every once in a while, I'd pull a Nashville or Las Vegas, but for the most part my work itineraries haven't been glamorous Brussels to Stockholm affairs.
But that doesn't mean that there's no fun to be had in Eastern Oregon or Midland, Texas. Seeing various regions, talking to people, sampling local favorites, it's all a great ancillary opportunity from even seemingly mundane business trips.
The Wisdom of Todd Barry
Comedian Todd Barry has a terrific book that I can't recommend more, Thank You for Coming to Hattiesburg. It's about what Barry does in cities during the day before the shows.
He discusses how he prefers to play in "secondary markets" (aka, smaller cities) and see the town. Most comedians turn the road into a grind of arrive in town, go to hotel, do show, sleep, do local morning radio or tv, back to the hotel to sleep or watch tv, then do another show and repeat.
This doesn't seem like the way it has to be; it's just one direction that some hacky road comics gravitate to. But Todd Barry embraces the experience, asking fans where he can get a good chicken sandwich or find a local cafe with personality in a certain town.
It sure seems like a better way to embrace being on the road. If you're gonna be seeing a little more of the world, you might as well see it.
My Business Travel Advice
Fulfill a Quest - If you're always on the hunt for the best local slice of pizza, or burger, that's easy to do in every city.
I'm a pizza slice sampling devotee, myself.
Or if you're a completist - use the opportunity of being in a city to see a game in a new major- or minor-league city/stadium to cross that off the list, or see a Presidential Library if there's one nearby.
Not to brag, but I've seen all of the California missions because of my mother's completism - and I can save you some time there: they're all one of two floor plans and all look the same. Skip it.
Avoid Chains - Yes, it's so tempting when there's an Applebee's in the same parking lot as your hotel. But wouldn't you prefer eating at the counter or bar in that town's downtown main boulevard and get to know the place even a little?
Extra Time - Yes, catching a local baseball game or playing a round of golf takes some time you might not have in the schedule. But even setting your alarm 40 minutes earlier to visit a cool coffee place on the way to the meeting gives you more of an excuse than the continental breakfast at your Holiday Inn Express.
Use Technology - Do a basic search and you'll find plenty of strong opinions on Reddit or other message boards; if best pizza slice shows up on 5 of the first 8 replies, you've got your place. AI agents are great with a very human prompt such as "I love alternative comedy and improv, is there a place with something tonight in the Minneapolis area?" And Google Maps curated lists you can find are a goldmine.
Do Some Research BEFORE Booking Hotel - If you Google ahead of time for your dates and find something cool in town, then book your hotel close to that event.
Two of us were gonna be in Boise for some kickoff meetings for a few days and both Robert and I wanted to take an extra day for an experience. We saw that Boise State had a home game so we rented bikes and hung out at tailgate parties all Saturday morning before looking for the "best hamburger in town" and ended up at Big Jud's. A spectacular burger joint, by the way, if you're in Boise.
In advance of the trip, we found a cool neighborhood with cafes, burrito place, ice cream store, bookstores and stayed near there. Our main technical contact at the client was a terrific conservative friend who teased me about the neighborhood, "Goddamnit Charlie, there's about seven liberals in the state of Idaho and I should have known you were gonna find them."
Secret Benefit of Being Local - The idea of conversation starters with clients is not nothing. This usually connects you to your clients or work colleagues a lot more than if you scurry back to your hotel room. They always say that a huge amount of business decisions are made at the bar, but that can also apply to talking with a client while watching a minor-league baseball game.
In one of the sneakiest-good movies about sales, The Big Kahuna, there's a great piece of advice about getting close to a potential customer, "If you wanna talk to somebody honestly, as a human being, ask him about his kids. Find out what his dreams are, just to find out, for no other reason."
Not to brag, but I've seen all of the California missions because of my mother's completism - and I can save you some time there: they're all one of two floor plans and all look the same. Skip it.
Avoid Chains - Yes, it's so tempting when there's an Applebee's in the same parking lot as your hotel. But wouldn't you prefer eating at the counter or bar in that town's downtown main boulevard and get to know the place even a little?
Extra Time - Yes, catching a local baseball game or playing a round of golf takes some time you might not have in the schedule. But even setting your alarm 40 minutes earlier to visit a cool coffee place on the way to the meeting gives you more of an excuse than the continental breakfast at your Holiday Inn Express.
Use Technology - Do a basic search and you'll find plenty of strong opinions on Reddit or other message boards; if best pizza slice shows up on 5 of the first 8 replies, you've got your place. AI agents are great with a very human prompt such as "I love alternative comedy and improv, is there a place with something tonight in the Minneapolis area?" And Google Maps curated lists you can find are a goldmine.
Do Some Research BEFORE Booking Hotel - If you Google ahead of time for your dates and find something cool in town, then book your hotel close to that event.
Two of us were gonna be in Boise for some kickoff meetings for a few days and both Robert and I wanted to take an extra day for an experience. We saw that Boise State had a home game so we rented bikes and hung out at tailgate parties all Saturday morning before looking for the "best hamburger in town" and ended up at Big Jud's. A spectacular burger joint, by the way, if you're in Boise.
In advance of the trip, we found a cool neighborhood with cafes, burrito place, ice cream store, bookstores and stayed near there. Our main technical contact at the client was a terrific conservative friend who teased me about the neighborhood, "Goddamnit Charlie, there's about seven liberals in the state of Idaho and I should have known you were gonna find them."
Secret Benefit of Being Local - The idea of conversation starters with clients is not nothing. This usually connects you to your clients or work colleagues a lot more than if you scurry back to your hotel room. They always say that a huge amount of business decisions are made at the bar, but that can also apply to talking with a client while watching a minor-league baseball game.
In one of the sneakiest-good movies about sales, The Big Kahuna, there's a great piece of advice about getting close to a potential customer, "If you wanna talk to somebody honestly, as a human being, ask him about his kids. Find out what his dreams are, just to find out, for no other reason."
Business travel is never going to feel like a vacation. But if you’re there anyway, you might as well come home with more than airline miles and a hotel receipt.
