The Secret to Traveling for Business and Enjoying It

People travel hundreds of miles only to step off a plane, go to a meeting, and get back on another plane headed in the opposite direction. To any adventurer, traveling in this way without experiencing the local flavor qualifies as a misdemeanor. Recently, I’ve traveled to Germany, Mexico, Tennessee, and Oregon for work, and I’ve made it a point to maximize my travel experience whenever I could.

Here are my 3 top suggestions for maximizing your miles:

1. Work with your schedule.

If you’re traveling to a place you’re eager to explore, take an extra day or two of PTO before or after your work responsibilities. You can try strategically booking your meeting for a Friday or a Monday so you can spend the weekend exploring. Companies are accustomed to accommodating PTO tacked onto a business trip, and in many cases they will book travel for your partner if you’re turning the trip into a mini vacation.


If you only have a window of a few hours, research the area you’ll be in and pick one or two places to visit. As a general rule, I always ask my local contacts, hotel receptionists, or barista about their sightseeing recommendations when I’m on a time crunch, and I typically end up going with whatever they suggest. After you identify where you want to go, immerse yourself in your destination. If you travel to a museum, spring for the audio or guided tour. Your new wealth of knowledge will make you feel like you had a substantial experience. If you end up at a famous restaurant, get the local fare and ask the server about the history of the dish.

Tootsies is a historical Honky Tonk bar in Nashville and was a great suggestion from a college friend.

If you absolutely can’t free up time to explore, take a virtual tour and surf the web for the history of your location and visit websites of the attractions that interest you. This is a great idea when you’re in a new time zone and unable to sleep. You may have time on another trip to see everything in-person and you’ll be prepared with ideas about where you would like to visit.

Don’t forget takeout from a local joint.

2. Express interest in sightseeing and the local culture.

I used to believe it would be a huge imposition for coworkers to show me around after working hours. However, I now know that many people love to show outsiders their town and share the culture and its lore. If you’re excited about learning and new experiences, chances are that your coworkers will be excited to share it with you. Take your colleagues up on their offers to show you around, and return the favor when they’re in your town.

An impromptu Friday Night Tea Party in Guanajuato had my coworkers cracking up.


My favorite part of the trip to Mexico was the explanation of a local legend at Callejon del Beso – the Mexican version of Romeo and Juliet.

3. Ask questions.

This is a good rule of thumb for anything you do in life and definitely applies when you’re in a new locale. Ask your local contacts about the area, their interests, their families, etc. Half of the fun of traveling to a new location is getting to know people. It’s also a great way to conduct internal and external business development. There’s no better way to do this than asking someone a question about themselves or their city.

Benefits of Traveling for Work

Did I forget to mention the fluffy robes?

Connecting with coworkers outside of a 40+ hour per week holding cell creates deeper bonds. In the corporate world, words like “collaboration” and “culture” are mentioned frequently, but when billable hours are important and staffing issues abound, it can be a challenge to foster trust and open communication the way that casual interaction can. Being exposed to someone over a longer period of time will create a comfort level between the two of you. Sharing good stories over dinner will put a personal spin on your connection. It may even result in quicker email responses.

Being adventurous with your coworkers can mean gaining a greater understanding of them, and vice versa. You may learn that someone you previously disliked is enjoyable outside of the role they play each day. You may notice and admire traits about them, like how much they read about in order to gain insight into the industry, or how surprisingly adventurous they are with food. Likewise, coworkers will start noticing things about you. For example, I’m known for being a highly Type A, focused individual at work, but I’ve gotten the feedback that I morph into an awe-filled, wide-eyed adventurer when I’m outside of the office. I’m glad the colleagues I work with daily have come to know this other side of me.


Drawbacks of Traveling for Work

There will be disappointing times when you’re traveling for work and can’t see the sights because you need to power through the night in the business lounge. You’ll just have to try to explore the next city you go to. If your first impressions of a city make a huge impact, you can always try to take a vacation there.

Another drawback is that sometimes you may have a few not-so-shining moments in front of your coworkers. For the finale of this post, let me share a condensed list of mine:

Passing out in Tiananmen Square. Which was, of course, caught on tape. If it’s over 105 degrees, you better be pounding that water.

Singing Cher’s “Do You Believe in Life After Love?” to kick off what you hyped up all day to be an epic karaoke bar experience. This remains a Top 10 Most Embarrassing Moment of my adult life…and probably for the other six people who witnessed it. I’m still recovering and avoiding the witnesses six years later. If you find yourself in a similar situation, I suggest that you chose any other song – preferably one that is A) Happy, and B) Something your entourage can clap to.

Climbing a jungle gym after a few too many adult beverages. There is now a rule of not more than one such beverage at any given work function for me. Period. There is photographic evidence stored halfway across the country, which makes it worse (but I’ll see if I can track it down so you can wallow with me in my embarrassment).
Sleeping awkwardly on a plane beside one of my company’s Senior VPs. I mean deeply awkward sleeping. The kind where you start tipping forward and wake yourself up at least a dozen times in the span of half an hour. Cue extreme retroactive embarrassment as I’m typing this with the realization that I might have been snoring. If that doesn't connect two people and present my coworker with a very human side of me, I'm not really sure what would.

Don't be this guy!


If traveling for work is a goal of yours, consider expressing to your boss that you like to and want to travel. My entire department knows I'm a travel fanatic and that I have no major constraints tying me down, and I believe that is remembered when travel opportunities pop up.

Have you ever traveled for work? Email us or comment below with your favorite or most embarrassing moments!