“You’ve reached the point now where business trips aren’t fun anymore.” A friend of mine told me that when I was 25, and he was correct. He was older than me and already worn out from the novelty. I was a junior ad exec just excited to have a job, much less one that was willing to send me places. I was like, “Can you believe they’ll PAY for my rental car? And my meals, too!”
After a few months on the job, I believed it all too well. I had to schlep from Manhattan to Hershey, Penn. with my boss every week—every goddamn week!—to show the client proofs of magazine ads for their candy. “Can’t we just send them the proofs on a Zip disk?” I asked her, because it was the year 2000 and that sort of thing was now possible. But no, she insisted. We had to unveil the proofs there, in person. That way, they’d see the ad better, and also they wouldn’t be able to tear it apart behind our backs. Sitting across the table from us, they’d feel compelled to like the ad more than if we weren’t there. Now, I had already sat across from clients and had them gleefully shit all over our work, without manners or hesitation. But my boss still thought this sociological element made a difference.
So we would meet at a shitty Budget rental office in midtown, drive deep into Pennsylvania until we smelled chocolate in the air, and then present sure-to-legendary proofs for a Classic Caramels ad to a humorless bald man. If I was lucky, we could secure a mid-morning meeting time that got us back to New York before rush hour, and I wouldn’t have to return to the office.
If I was unlucky, and I was unlucky fairly often, we had to stay overnight at one of the millions of comfy-but-unremarkable chain hotels that exist in this country. It was there in Hershey where the novelty of business travel first wore off for me, and it wore off fast. Later in my ad days I got to go to cooler cities, like LA and Vancouver. Sometimes I even got to get shitfaced on the company dime. And then sometimes I would have to block off an entire day driving a 50-year-old client from Vancouver to Whistler just so she could look at it, with no time to actually ski its slopes. So, more often than not, business travel was work: a gantlet of meetings and airport counters and sad breakfasts and extraordinarily painful small talk. I went from “I can’t believe I get to do this shit!” to “I can’t believe I have to do this shit” in less than a year.
It wasn’t until I had kids that I would appreciate business travel again, and it wasn’t until a pandemic ate its way across the world that I would CRAVE business travel. This is because my children are very loud, and need an occasional break from me as much as I need an occasional break from them. It’s also because my business trips became much more fun than those trips to Hershey ever were, free candy or no free candy.
Most important, it’s because I learned HOW to be a professional traveler. I got my system down, Up In The Air-style. I got my TSA clearance. I had a suitcase I trusted. I knew how and when to pack it. I knew when to arrive at the airport (always early). I knew which airports had rental lots at the terminal and which required a nine-hour shuttle ride into hell. I knew how to make time for myself to walk around any city I visited to get to know its layout from the ground. I knew where all the best food was at airports that were familiar to me. I knew to pack Advil PM to knock myself out on red eyes. And I always, without fail, treated myself to a milkshake on the road.
Sometimes I would block off time to see an old friend. But other times, I would be in an unfamiliar town with no familiar people in it. If you’ve ever been on the road, you know that it can get lonely. Scary, too. But I also learned how learned how to spend time with myself in those moments. I got better at it. And as I did, business travel became more of a getaway than a slog. There are obvious dad reasons for this, but it goes deeper than that, too. I could leave home, spend some time out in the world but inside myself, take a breath, and then come back to my wife and kids with more energy than I had before I left.
It’s easy to feel this way about business travel when that travel sometimes consists of you interviewing a famous person, or presiding over your own book signing. But I also came to appreciate the less finer aspects of the experience. I have not flown on an airplane in over a calendar year. The last time I did, I took a red eye to Europe just before the pandemic hit. No one was on my flight, so I could lie down across an entire row and, miraculously, slept through the entirety of cruising altitude. This was not a comfortable sleep, or even a long one. But it was the most clutch five hours of sleep I’ve ever gotten. Sometimes, when I can’t fall asleep at home, I daydream about that plane sleep, which is ENTIRELY backwards, but still works for me anyway.
I have a mental archive of my business trips now. I remember having to go emergency shopping in Austin because I forgot to bring underwear. I remember the shortest flight of my life—less than 20 minutes, wheels up to wheels down—from Charlotte to Asheville. I remember walking from my hotel in Miami to PortMiami to board Kid Rock’s theme cruise. I remember walking for MILES along Santa Monica Boulevard in LA from my hotel to a studio to profile Justin Bieber. When I told Bieber’s producer I walked there instead of taking a cab, he looked at me like I belonged in the fucking loony bin. I still remember that walk, though. Lotta Russian storefronts.
I remember having my connecting flight at O’Hare cancelled, and United putting me up at a nearby Westin for the evening. In true O’Hare fashion, the process of getting to that hotel, voucher in hand, took 97 hours. But I remember walking into that hotel and feeling ECSTATIC to have finally arrived there. It was a nice-ass hotel, and the older you get the more you cherish a nice hotel. They even gave us free drink tickets, which I immediately cashed in at the bar for an old fashioned or three. I was hardly the only person stranded in that lounge. Everyone else was decompressing from the O’Hare Experience and eager to drink as well. I didn’t strike up a conversation with any of those people, but I could still feel the collective relief in the air. It was a pleasant evening. I still think about it a lot. I don’t drink anymore but I still like hotel bars. I like the soft lighting. I like the ambient noise. I like the people watching. And I like staring up at the TVs behind the bar, watching shitty regular season baseball games. There’s a freedom to purgatory. I had a flight to catch out of Chicago the next morning. But that night, I was obligated to nothing and to no one. I could have been anyone to the people in that bar: a salesman, a scientist, a spy, a suave criminal. Anybody. You can try on any hat on those nights and they all fit.
I’ve been traveling since before I could form memories. My old man worked in the airline industry, and so we flew around all through my childhood, to places both exotic and dull. I remember Dad took me on a special father-son trip once but, on the way back, got an emergency business call and had to put me aboard a connecting flight from Denver to Chicago on my own. I couldn’t have been older than eight. The people sitting next to me on that flight gave me all of their cookies. I got home safely, if a touch fatter.
I remember aspects of my journeys that were NOT inconveniences, of course. I remember one Seattle hotel randomly giving me a suite that had its own goddamn dining room in it. I remember going to the beach in Santa Monica, realizing I wanted to jump into the ocean right there and then, and then taking an Uber back to my hotel for a suit so I could take an Uber BACK to the Pacific so I could go swimming in it. With my glasses on. With surfers scattered about the water and occasionally headed straight for me. I remember getting stuck with a trip to Columbus for a legal ad agency and staying in a hotel so nice that it made me forget that I was in Ohio.
I remember going to the rose test garden in Portland and scouting it out as a place to take my wife one day. In fact, I’ve made a mental note to return to every place I’ve been with her one day, Ohio excepted. I remember going to Hollywood and staying at a hotel that had its own private rooftop terrace. Guests only. Best hotel I’ve ever stayed in. One night there, after doing my assignment, I picked up a flask of Beam at a nearby liquor store and drank it all while lounging up on that roof. I talked to no one. That was a good night.
I’m leaving here tomorrow. I have not left home, on my own, since that under-the-wire sojourn to England and Spain back in February 2020. My wife spent all of 2019 nursing me back to health from a brain injury only to spend all of the NEXT year stuck with me in quarantine, so she’s just as eager for me to flee the premises as I am. I myself was so eager to get back on the road that I’m not even traveling for work, per se. I'll see some colleagues, but I paid for the goddamn hotel room myself. The tab won’t matter to me. All that will matter is that I’ll be back out in a world that’s been waiting for everyone. I haven't had that experience in a very long time. Given that the pandemic may render frequent business travel an anachronism (along with the working office itself, which would be a relief to commuters but not to the dickheads who give them marching orders), I'm gonna savor the few trips I do get down the line, including this one.
So when I check in tomorrow, I’m gonna go up to my room, tear my mask off, and do UNSPEAKABLE things with the complimentary body lotion (that last part is part of my business travel system). Then I’m gonna walk around Manhattan with my hands free. No ad proofs to carry. No clients to humor. If my trip ends up a failure, that’s okay. If my car runs out of gas on the way to New York and I can’t find any more of it, so be it. If the restaurant I’m going to tomorrow night fucks up my reservation, well then I’ll feel right at home. No matter what happens, I’ll still bring a piece of that trip back home with me. Every memory, good and bad, is a souvenir for my restless mind to gawk at. I’m ready for new places again.
And I’m ready for that milkshake.
