10 Ways to Make Your Boring Work Trip, A Small Paid Vacation

September 19, 2019
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    Over my career I’ve been on several work trips. Most of them being quick run-n-gun video shoots or 3-day-long conference room bore-fests. But each of them had their own chunks of goodness in them. Each one I managed to make it the best trip I could. When I ask others about their work trips, they grumble and tell me how bad the hotel was or how crowded their airport was. It makes me a bit sad because even the smallest of trips can be overnight adventures. Here’s how to make even the most mundane work trip into a fun little vacation.   1. Book it yourself – Don’t let an office intern or even more so, your boss book your trip. Wait for tickets and hotel reservations to be placed in your hand and you’ll find yourself with 3 layovers and a room 10 feet from the airport. Look around at the local hotels. See how they are rated. Find ones with pools or social events. When it comes to your flight, look at every airline you can. See who flies direct or has layovers in better airports. Even better, pay for the trip yourself to earn credit card points and turn in a receipt. Enough of those and you’ll get a free trip on a real vacation.   2. Ask to Extend the Trip an Extra Day – Why fly back on a Wednesday night when you can fly out on a Thursday afternoon. Explaining how difficult it will be to organize a flight right after the conference has ended, and how easy it will be to fly out the next day makes a lot of sense with a little persuasiveness. Then it will give you time to do all the other goodness on this list.   3. Bring Tiny Bottles of Booze – You’re going to hear from people “you can’t bring booze on an airplane”. But, you can. I don’t need to tell you what to do with these. You’re a grown up.   4. Ask for a Car Upgrade – Honestly, to most of these car rental agencies, a car is a car. They enjoy making their customers happy and if giving you an upgrade will do that, they will. Generally, for the same price but sometimes for a very small extra charge. If you want to cruise Chicago in a Geo Metro, then keep your mouth shut. But… wouldn’t an Escalade be a little more grand?   5. Don’t Eat at Chain Restaurants – You can eat at a Chili’s any day of the week. Just because there’s one next to your hotel isn’t a reason to do it today. You’re in a whole new world with brand new opportunities. Ask the desk person where their favorite place is. Check out Yelp. Or just walk until you find that oddly named Thai restaurant in a strip mall that will end up being your favorite place of all time.   6. Drink Local Beers – Regional beers can be pretty amazing. A Wisconsin Lager will taste nothing like one made in New Mexico. Play around. Ask what that area is most proud of beer-wise and try them all. I mean… not ALL… you have meetings the next day.   7. Take a Billion Pics – You phone has a camera for a reason. Take as many pics as you can. Share a few on social media. Brag a bit that you’re out of town. Get a little instant gratification. It’s fun.   8. Reach Out to Local Friends – Writing on Facebook “Hey, anyone in St. Louis this Wednesday” will surprise you to the amount of old friends in the area. Catching up in a Hotel Bar is a great way to entertain yourself. It’s also gratifying to see how you age better than some of your friends.   9. Find all the Local Art – Every town has a bit of an art district. Maybe it’s a historical building or even a specific museum that’ll interest you. Sometimes it’s bit of a walk, but that’s the fun part. Exploring the area you’re in is easily one of the best parts of the trip.   10. Buy a Shirt – Buy a local shirt. Even if it’s ironic. Sure it might sit in a drawer for a few years but after a bit, when you pull it out and someone asks “Wait, you’ve been to Lakeland, Florida?”, you’ll have a fun little memory to share.

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