After 200 nights away from home in the last year and thousands of miles without a checked-bag, I’m bringing some levity to kick off the summer post-Memorial Day Weekend — enjoy.
For the modern business professional—or traveling clown—there’s never been a better time to embrace the suitcase as your permanent address. In fact, the Bureau of Occupational Irony recently released a report noting that clown-related job applicants have decreased more than any other field; this is despite the fact that these jobs are some of the most resistant to AI and openings are projected to skyrocket. I’m not sure what’s more disturbing: the clown labor shortage, or the fact that our best hope against automation has big shoes and a red nose.
Let’s begin with the fundamentals: efficient airport transit. If you’re not yet enrolled in TSA PreCheck, you are, technically speaking, living in the Middle Ages. Those of us in the PreCheck tribe (which hilariously can take less time than Clear) know the joy of waltzing through security with our shoes on and laptops nestled safely in our backpacks. Of course, it’s unclear whether PreCheck is a legitimate security innovation or just a government-issued participation trophy for those of us who fly a lot and manage to do so without descending into a toddler-inspired meltdown. Either way, the agents seem mostly nice, and I hear the benefits package is solid, so good for them.
Additional PreCheck perks include:
Beating the people in the regular security line, only to join an even longer line at Dunkin’, where the wait threatens your access to overhead bin space.
Playing roulette with what you can get away with leaving in your pockets: spare change, AirPods, your new bitcoin money clip from Temu (which is really just a paperclip with a sticker on it).
Once you’ve mastered TSA, it’s time to turn to the dark arts of packing. Here’s the first rule: never pack more than four pairs of underwear. Yes, this sounds like madness. But there’s a secret: plan a mid trip “visit” to a friend in whatever far flung city you’re visiting and mention that you forgot to pack all of your underwear — surely any good friend would understand your predicament and offer their laundry machine. While you’re at it, offer to fold theirs, too. Pretend it’s a gesture of goodwill, not an elaborate underwear laundering scheme. (Bonus tip: if you need extra socks, pick a friend with a dog — that way you can swipe a few pairs and use their dog as the scapegoat — sorry, Fido).
We’re off to a good start, so here are some other tricks of the trade:
Choose hotels that still provide those mini bottles of shampoo and conditioner. Avoid the ones where the bottles are welded to the tile like security cameras, ensuring that people like me won’t steal them.
Use these same shampoo bottles for everything: body wash, hand wash, shoe shine, laundry, or moral cleansing after that questionable supplier dinner.
Rotate the same outfit across multiple cities, and gaslight acquaintances who comment on your repetition. If they say, “You must really like that shirt,” just smile and reply, “How strange, I just borrowed it from the hotel lost-and-found.”
Bring one pair of shoes. They must be capable of supporting a hike, a boardroom presentation, and an unexpected dinner at a mid-tier sushi restaurant where everyone else is wearing loafers. Birkenstocks are a crowd-pleaser.
Your carry-on should have a designated pouch for “stuff I didn’t need but felt guilty leaving behind” (extra phone chargers, that novel you swore you’d read, a stress ball from an HR conference). Let this be your emotional support clutter.
You are now prepared for the mental challenge of facing all manner of unexpected obstacles as a seasoned road warrior. But what self-respecting travel essay would be complete without a packing checklist? Please, allow me to indulge:
Blazer that doubles as emotional armor.
7 hotel pens (various brands to account for situational differences in status-peacocking).
A single sock you keep forgetting to replace (yet somehow still does not have tenure).
Mini screwdriver to tighten the wheels of your dignity.
Sweatpants that can double as workout gear and loungewear. You will tell yourself you’ll use them for a morning gym session. They will, instead, bear witness to a different kind of personal record: number of M&Ms consumed in one sitting while rewatching The Office for the thousandth time.
A travel steamer. While technically designed for removing wrinkles, it can also be used to warm leftover spaghetti when you decide to skip lunch and work through emails instead.
At times, this lifestyle can feel like a high-functioning fugue state. You’ll know it’s gone too far when you find yourself referring to the Delta Sky Club as “home base,” or when a hotel front desk clerk greets you by name and hands you your usual room key with visible pity. And perhaps you’ve become a little too adept at batting away small talk from that person trying to convince you that adding an extended layover in Omaha is worth it purely for a trip to their “world-class” zoo.
But I’ve learned to appreciate the rhythm of it all. The same way a carny grows fond of the Ferris wheel or a clown finds joy in a suitcase full of rubber chickens, I’ve found comfort in the rituals: repacking with absurd precision, rationing clean socks, texting friends to see if I can swing by for a “chat” (which may or may not involve the mention of underwear).
And when it gets to be too much — the layovers stretch too long or the hotel oatmeal tastes like warm resignation — I think of the people who make it all feel okay. My fiancée. My friends. My dog, who greets me with joy regardless of how much I smell like a Marriott. Without them, I’d just be a guy in the TSA line trying to justify why he brought two pairs of noise-canceling headphones. (One’s for backup. The other’s for existential dread.)