Are you emotionally and physically capable of wearing pants, and other key questions to ask before your next business trip.

Pre-pandemic business travel was relatively painless, at least for me; after a year or two of flying around the US almost every week for work I’d become quite adept at packing lightly, maneuvering through airport security and finding my Uber to the next customer meeting.

Like every experienced business traveler, I fancied myself as slick as George Clooney in “Up in the Air.” But back on the road this week for my first business trip in almost 20 months, I feel less like Clooney and more like Kevin from “The Office” on his first-ever out-of-town trip to a paper convention. Super awkward.

I kept dropping things just out of reach onto the floor beneath my tiny little window-seat on the airplane – headphones, the caps to very full water bottles, my expensive airport-purchased snacks. My lockdown tummy kept getting in the way when I attempted to retrieve them, but I blamed the seatbelt.

Also, I was certain I’d lost my wallet at least three times in just 48 hours, leading to impressive displays of unnecessary panic-sweat. (It was right there in my faux-leather “European Carry All” every single time.) I’d clearly forgotten the “always put your wallet in the same place” rule that had previously served me so well on business trips. And I forgot how to quickly adapt to time zones, remaining firmly on East Coast time while trying to have dinner with customers on West Coast time. Yawning with a mouthful of shrimp is not a good look when you’re trying to build a relationship with an SVP from Company X.

All in all, then, a slightly rocky return to the road this week.

But that’s to be expected, I suppose, after nearly two years when a masked-up trip to the grocery store felt as adventurous as a weekend in Cancun. So, as I sit here at the airport gate waiting to board my plane ride home, I’d like to share some insights for all of you vaccinated business people about to return to your old “road warrior” personas (even though this pandemic is far from over).

Before you travel for business again, ask yourself these five important questions:

Am I emotionally and physically capable of wearing pants? I spent the last 20 months working from home, wearing proper collared-shirts for all my video conference calls while skillfully keeping my dad-bod-cargo-shorts just out of frame. Packing for this first business trip in what feels like forever, I rummaged through my closet and found pants after pants after pants that were beginning to fuse with their hangers from lack of use. Would any of these pants even fit anymore, and did I really want to know? I began hoping the 2021 definition of “business casual” had mutated to the point where a fashionable pair of boxer shorts is as acceptable as a pair of trusty Dockers. (I managed to squeeze into a pair of black jeans that worked with my jacket. I think.)

When was the last time I actually wore shoes? Me? I’m a sneaker kind of guy, but I’ve always had a special pair of shoes for business travel. Comfy, retro-stylish, polished pre-flight, and just right for walking to the customer meeting from my two-and-a-half star hotel. My special travel shoes served me so very well in 2019, before the pandemic. For this first-in-a-very-long-time business trip this week, though, I failed to consider that I hadn’t worn my comfy work shoes since February 2020. They hurt like hell this time around. I should have known to break them in again when I saw how dusty they were, there in the closet next to my dusty overnight bag and my dusty European Cary All.

Do I really need all these wires? My luggage seemed a lot lighter back in 2019. Did yours? Do you really need to squeeze three phone chargers, two double-socketed power bricks, a USB-to-VGA-to-HDMI-to-serial-port cord, two battery back-up power cells, a Kindle charger adapter, noise-cancelling headphones and a set of wireless earbuds into your European Cary All? Exactly how long is your flight?

*The look of concern when you start packing a travel bag.*

When was the last time I logged in to all my travel apps? Resetting your long-expired passwords the morning you need an Uber and a boarding pass is not the best way to regain your status as a savvy road warrior. Remember a few years ago when you knew your hotel loyalty program membership number by heart? After 20 months of lockdown, don’t underestimate just how out of practice you really are. Forget about remembering your Marriott User ID and password; did you remember to wear pants? (See #1.)

Could this upcoming 72 hour round-trip be a 30 minute video call instead? It’s a really good question. The dogs – who are nervously watching you pack that bag you haven’t touched in nearly 14 years (for them, two years for you) – would certainly like to know the answer.

So – safe travels, fellow road warriors! I’ll see you at the boarding gate (where, on my trip this week, they were showing a 9/11 documentary).