The Wine Experiment
A little over a year ago I was in Los Angeles at a bougie restaurant with coworkers who all claimed they were expert sommeliers (wine experts). Being a market researcher I thought I’d run a little experiment. I told them I’d order 4 glasses of wine and they would rank order them from least to most expensive. This restaurant had quite the range.
So I ordered the four wines and conspired with the waiter. He brought them out one at a time, and my coworkers aired the wine, sipped, and made notes. They each tasted notes of different grapes, compared the body of wine, and the finish (some had “soft” finishes while others had “hard” finishes). By the end each had their opinion on the ranking. And here’s what I had ordered:
#1 Wine = Most Expensive
#2 Wine = Least Expensive
#3 Wine = Least Expensive (yes, the same wine as #2)
#4 Wine = Least Expensive (yes, the same wine as #2 and #3)
The waiter and I did the grand reveal. In the first moment they were shocked and in denial, and then (perhaps because of all the wine) erupted in laughter. It was so funny. They were so sure. The other tables caught wind of the experiment. That whole section of the restaurant was ablaze in laughter. What a night.
My takeaway: business travel should be fun. If you’re not laughing and sharing an experience, then you’re doing it wrong. This guide will help ensure you can make business travel more fun.
Hire & Work with People You’d Like to be Stuck in an Airport With
While writing (and rewriting) this article, I decided I just had to make this point first. The people you work with are key here. Whenever I have hired someone or considered taking a job, one of the most critical questions I’ll ask myself is:
“Are these the type of people I could be stranded in an airport with?”
This means they are the kind of people that are interesting, engaging, and fun enough to want to spend a good portion of my time both in (and out) of worth with. It’s the ultimate gut check. Life is too short to be surrounded by boring people. And it’s a surprisingly high bar to clear.
Business travel is stressful, takes you away from your family/friends, and leads to work piling up afterwards. So you’ve got to make the most of it. Being with people you enjoy solves 99% of the worry of work travel. The last thing you want is to be somewhere far aware from your loved ones while simultaneously being trapped with co-workers you have zero desire to spend time with socially.
Don’t Just Work
Traveling for work has its requirements. Your company is spending money to send you to a conference, go to a critical meeting, etc. That comes with responsibilities and expectations. Duties that you absolutely should fulfill. But if your business trip consists solely of these tasks you’ll find yourself drained and unable to perform those key responsibilities well (which kind of defeats the purpose of sending you somewhere in the first place.
Here is what I have found to work best on business travel:
- Morning – wake up early and go on a run/walk around the city. It is so much fun exploring a new space. When I was in Germany I got to see so many things my coworkers missed by just getting outside. Ditto for trips throughout the United States.
- Afternoon – take an hour and recharge. If you’re at a conference, skip an afternoon session and call your spouse, talk with an interesting vendor, or just go walk outside. You’ll feel more recharged to finish your day strong.
- Evening – find an experience and coerce your coworkers to join you. This will be the most memorable part of your trip. I’ll try to find a really interesting restaurant (once I discovered this amazing dumpling restaurant in New York) or an experience (I recently visited a Native American museum that was fascinating). To do this, we recommend assigning a member of the team to research one really cool thing that you can all do in that city.
- Night – get to bed at a reasonable hour. Travel is tiring as is (the infamous “jet lag”). Don’t stay out too late so you can be sharp and alert for the key meetings, conferences, etc. You’ll enjoy your trip so much more if you’re not fighting exhaustion the whole time (full warning: it can be tempting to either (A) stay out extra late with colleagues or (B) spend the whole night working when you don’t have your normal routine to guide you, but if you stay disciplined here, you’ll actually have much more fun)
This all takes a little bit of extra research/planning, but is well worth it as it likely will be the only part you remember about your trip!
Pro tip: It’s sometimes fun to take food home from where you are visiting, but you need to think through how you are going to transport it. On a recent trip to New York I brought back Black Seed bagels in my backpack, only to have my backpack smell like Everything Bagels for the next month…
“Bring Your Family With You”
It’s easy to get sucked into “work mode” while you’re traveling. Or you may think that you don’t want your spouse to be jealous that they’re home with the kids while you’re out “having a great time”. This can lead us to having minimal communication with our loved ones while we’re gone traveling (I remember hearing very little from my Dad whenever he was out on business trips).
Resist that urge and “bring your family with you”. Let them share in your experience. Use texts, recorded videos, FaceTime, short calls (during breaks) to call your family and let them know what you’re doing / share the cool sights/sounds. My favorite thing to do on trips was to call my wife and kids and tell them all the things I’d seen and done that day. It made them feel like they were part of my business trip and gave us great things to talk about when I went back.
Most importantly it kept me connected to the ones that mattered most when I was far away.
Pro Tip: Find a designated time to call your spouse when you’re away. I often did this at the end of a workday (before we went to team dinner). It was a great chance to unwind (and get a break from my colleagues, as fun as they are, and chat with my wife). I always felt refreshed after these conversations.
Take an Extra Day
Too often are we overly efficient in our work travel. I have found that if my coworkers plan it, say for a 2-day conference, we’ll fly in the night before, stay for day 1 of the conference, and fly out at the end of day 2 of that conference. This is exhausting! And you don’t even get to see the city!
Instead, fly out the day after the conference.
Yes, that’s right. Just stay the extra day. This has some amazing benefits:
- You actually get to enjoy the whole conference. Sometimes the best connections I have made happen as a conference is wrapping up and you can have deep conversations with people.
- You’re not rushed. Having the evening of the second conference now open, plus the next day, is rejuvenating. It’s like your own little personal vacation. When I was in Europe for a work trip I took my last day to visit a beautiful cathedral and drive on the Autobahn, something I wouldn’t have been able to do had I left immediately.
- You can actually connect with your coworkers. Staying that extra day means some extra activities. I once had a coworker insist we ride electric bikes around a city on our extra day, something I had never done, and we had the times of our lives!
Pro Tip: hotels can hold your bags for you after you check out. So you can have a later flight out and not worry about carting your bags all around the city.
Make Travel Easy on Yourself
Learn to be a “pro” traveler. It’s a lot easier to enjoy a business trip when you’re not stressed about all the little details like showing up to the airport on time, packing, working your way through JFK Airport in NYC (a true nightmare if you haven’t ever lived it). Learn to travel like a “road warrior” and you’ll be able to focus on the more important things.
A few tips on doing this:
- Invest in a small, easy-to-transport airport bag. You want something that is easy to pack/unpack in a short amount of time, is super convenient to wheel around airports or bus stations, and is durable. Something like this works great. You want to be a “1 bag” traveler (it’s sooo much easier).
- Get a good pair of headphones (ideally with noise cancellation). They make flying so much better. Nothing takes the stress of standing in an airport line away like listening to an engaging audiobook or calming playlist.
- Get TSA pre-check. It’s worth every penny. We would also recommend getting Global Entry (if you travel internationally for work). There’s no joy in this world like skipping the airport line and not having to take off your shoes during security checks.
- Book your ride to/from the airport in advance. Both Uber and Lyft offer “schedule in advance” services.
- Get your company travel to credit towards your personal Frequent Flyer Program (ex: Delta Skymiles). Not only do you get more status (and the subsequent perks like preferred seating + lounge access), but it also “gamifies” travel and lets you get “paid” (in terms of future savings on travel) for traveling.
Write Letters to Your Family
One of the best pieces of advice I have received from a former boss was his airplane routine. He told me:
“Whenever I walk onto a plane, the first thing I do is sit down and write a letter to one of my children. I’ll type it up often before the plane takes off. It’s usually just a page of some recent memories and things I love about them. It makes me reflect deeply on who they are becoming and my relationship with them. When I get home I’ll print it off, sign my name at the bottom, and put it on their pillow.”
I have done this for the last four years and have written each of my four children and wife quite a few letters. It’s been eye opening to me how sitting and thinking deeply about that child or my wife makes me more endeared to them. I have also found these letters in their most treasured collections. My oldest children sometimes have them out on their bed stand at night and I can tell that they have re-read them.
What a legacy to leave. What child wouldn’t want a personal letter written to them from their dad? At the end of a work trip this is oftentimes the most meaningful part of the trip and better than any souvenir I could have brought home.
Conclusion
Work travel should be fun. I’ll even go as far to say it can be as much fun as a vacation with friends if you do it right. By choosing to work with the right people, not working the WHOLE day, bringing your family with you, taking an extra day, making travel easy on yourself, and writing letters to your family, you’ll come to enjoy work travel.
