In a previous life, I had to travel a lot for work. While I hated being away from my dog for weeks at a time, it allowed me to see parts of the country I wouldn’t normally see. I got to fly fish Blue Ribbon trout waters in Montana and see our Nation’s Capitol in ways Forest Gump couldn’t while drinking 17 Dr. Peppers.
Avoid Chicago O’Hare At All Costs
I cannot emphasize this enough: do not fly out of or connect through ORD. Now, I fly Delta and it’s not a hub of theirs so this isn’t really much of a problem. But for the half dozen times someone else has booked my flights for me and I’ve had to connect at ORD, it’s been hell. Weather delays. Canceled flights. Sitting on the fucking tarmac for hours on end waiting to take off. It’s full of people and a total hassle to get around, both of which just exacerbate the hangover that comes from drinking every night with clients.
Editor’s Note: O’Hare is the fucking WORST. During a layover, I had to amend my “never sit down on public toilets” rule. After realizing there was no toilet paper in my stall, I proceeded to scour the next 18 stalls for toilet paper. None. Ended up MacGyver’ing it and wiped with my itinerary.
If you’re traveling for work, you’re working for corporate America. You can afford a nice carry on. It doesn’t have to be Tumi, but get something quality. I’d suggest Tumi. If you can’t pack for a week in a carry on and a briefcase, you’re carrying too much backage. I can pack a suit, three Vineyard Vines ties (BOUGIE!) and leave enough room for workout clothes if you’re a Cross Fit asshole (don’t workout and you don’t have this problem). I love Delta, but they lose bags all the time. Had a coworker make this mistake flying to Kansas and had no option but to expense dress clothes at a Wal-Mart for the week. Don’t be that guy. Roll your Brooks Brothers and steam it when you get to your final destination.
Location, Location, Location
If you’re traveling to a metro area, where you stay is extremely important to how much fun you can have. Ideally, you stay in a decent hotel within walking distance of multiple bars/restaurants. You want to give yourself options when the work day is done to experience what that area has to offer. “But OMB, I thought this was a work trip?” It is, but use it as an opportunity to scout out a new area. I had an option to move to Washington, DC, a year ago and I turned it down. Why? I’d been there for work 6-8 times and loved it, but the crushing cost of living wasn’t worth the move.
Yelp Is Your Best Friend
I fundamentally don’t understand people who write detailed reviews on Yelp. That’s valuable time I could be spending doing anything else. However, they’re great for finding the really great local places to eat on your company’s dime. If you’re eating at chain restaurants when you travel, get the fuck out of my face. I’ve done it, and there’s nothing more depressing than the cast of characters that eat at the Ruby Tuesday next to the Hampton Inn and Suites. Do a little research and you can find some really great places to eat and drink. My all time favorite: Okaloosa Island Oyster Bar in Fort Walton Beach. Sat there for two hours of pure bliss sucking down Miller Lites and oysters during March Madness.
Tinder Is Your New Best Friend
I’m a sales guy so I have no problem going out and meeting people. But don’t think for a minute I’m not on Tinder the second I check into my hotel room. You’re the new person, a complete mystery; use this to your advantage. You’re traveling corporate, you have a great job, that means you’re already head and shoulders above the local yokels. You don’t even have to try to get laid: use it to find fun. I’ve found some of my favorite good times by matching with girls on Tinder and meeting them out. If Tinder isn’t your game, find the local dive. If the bartender is worth their salt, they will draw a crowd and you instantly have group to go out with.
Where ever you’re going, you’re there for a week max and nobody will remember you (unless you’re me singing Michael Jackson karaoke in Bozeman in ’12.) Live it up, crush your work meetings, and enjoy a new part of the country. It’s what the Founding Fathers envisioned. .
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