Why Not Indulge in the Luxury of Checking Your Bag?

Type-A people do not check bags when they fly. Ever. They brag about it, scheme around it, and sacrifice sartorial style on the road in the overriding interest of efficiency. They share tips about how to do it (one of our beloved Luminaries shared her tips on how to make it happen at my request). It’s one of the many justifications for taking a private jet. It’s a Thing if you are in the globe-trotting influencer elite.

For most of my life, I have been one of those people: I started my career right out of graduate school as a McKinsey management consultant living out of a suitcase, and I never broke the habit. For the past several years, I was working for a global bank and traveling consistently three weeks per month on business trips, and I never once checked a bag. It was a huge point of pride that while some of the men I traveled with had to line up at baggage claim to retrieve their over-sized suitcases, I was blithely free to move on, whisking my LV roller bag through the terminal with as much savior faire as I could muster after an overnight transatlantic flight.

I used to tease them that they should learn how to pack light, like a girl.

Sometimes this “never-check” mentality is unavoidable and not discretionary. For example, if you’re traveling with the boss, and the boss is not checking a bag, my advice to you is: don’t check your bag. Ditto if you have a big meeting, social engagement or other potentially life-changing event occurring on the day of your arrival. If you are traveling on an airline where you have no frequent flyer status and you’re not in first class; if you’re on a short trip and don’t care much about your wardrobe options; or if you’re traveling so frequently to one destination that you’ve got a whole second wardrobe on the other side of your journey, there’s no need to risk checking your bag. Because of course, it can end in tears.

But what would happen if the conditions were right, and you actually – gasp – decided to check your bag? Would the world as you know it cease to exist?

I decided to find out.

On three trips in the past six months, I have found myself in the ideal state to conduct this little experiment: once on a leisurely ski trip to Aspen, once on a multi-day trip to France, and most recently on a business trip to San Francisco. I flew on United, Lufthansa and American (I have high frequent flyer status on two of those three) and I checked the same bag each time. Not a rigorous statistical sample, I admit, but for our purposes, it will suffice.

The good news? I had no problems whatsoever with lost, delayed or damaged luggage (even in the two cases when I was not on a direct flight, and had to switch planes). The even better news? I really like traveling this way. It made me feel like a completely different person.

Why? For starters, it makes packing a lot less stressful. When you have a bigger bag to work with, it opens up all kinds of accessory options. You can bring two (or four!) pairs of shoes! You can bring the cute handbag that would be perfect for a particular occasion without stuffing it into a small carry-on, potentially ruining its shape forever. You can explore a wider range of color options (I still believe in having an anchor color scheme, but you can riff more broadly on it with more packing space). You can bring enough clothes to be able to change for dinner! You can bring an actual hardcover book with you. You can even go crazy and bring a framed picture of your family for your hotel room desk. Are you kidding me?

The second benefit? Once you’ve checked your bag, you can walk through the airport in a more carefree manner. You can even shop at the airport, because you’ve got capacity for another carry-on bag. I honestly used to wonder who could shop at all those airport retail stores, since I my carry-ons were already completely full when I arrived at the terminal – I could barely buy magazines without getting side-eyed looks from the gate attendant for having too many items in my possession as I boarded the plane. Geez.

But with only a Prada backpack as a carry-on, suddenly I was totally hands-free while maneuvering the airport terminal, and if I wanted to, I could even while away some time perusing cosmetics, scarves and handbags. Heck, I could even buy something! Cool.

The chill vibe continues throughout the boarding process. Your stress level will be materially lower if you are not fighting for overhead space for your bag. Heck, you can go nuts and board last, because why not? You got this. Your carry-on bag fits under your seat. Crazy.

A few years ago, I injured my shoulder and ended up needing surgery to repair it. My doctor was convinced that the injury was from repeatedly lifting my carry-on bags onto the TSA screening machine and then again into and out of countless overhead bins. It is a truly wonderful thing to not have to struggle and strain to get a bag over your head and into storage when you board the plane. Who knew that checking a bag is good for your health?

Now of course, there are some downsides. The primary one is those excruciating moments standing at the baggage claim carousel and praying that your bag is going to show up, undamaged.

Those are really long minutes.

A secondary concern is that so many bags look alike, or are identical (black Tumi, anyone?) that you need to be really careful that you don’t walk off with the wrong bag. A friend solves this problem by checking a purple Rimowa bag that no one ever mistakes as their own. I opt for a black bag, but tie an orange or yellow tag to it so that I know it’s mine (I used to have a red suitcase, but you’d be amazed how many red bags there are out there).

Your pace will be slower even after you leave the airport. Having a bigger bag means you’re more likely to need help with it when you arrive at your hotel, so if you’re one of those people (like me) who doesn’t like to surrender control of your bags at hotel check-in, just be ready to wave off the valets and deal with it yourself.

Sometimes these negatives are enough to make one forgo checking a bag, anytime, ever. But I learned that personally, on many trips I was overestimating the negatives, and under-appreciating the benefits.

Now, of course I could be jinxing myself just by telling this story — the next time I check a bag, it may end up in Greater Mongolia, or in a storage facility in New Jersey. For this reason, I remind you of another sacrosanct rule of travel for those who love their clothes: never, ever travel with anything that it would break your heart to lose. Carry-on or check-in, if it’s really precious, leave it at home.

I should also note that soon we may all be checking bags, thanks to new security regulations. The New York Times reported last week that all flights from Europe to the US may soon be subject to the same restrictions on having a laptop, tablet or other electronic device bigger than a cellphone in carry-on bags that currently apply to flights from 10 countries in the Gulf and Middle East. That’s going to force a lot of business travelers to start checking their bags.

So why not try this same experiment? The next time you have a business trip where you’re in control, you’re not rushing to something big immediately upon landing, and you’re with an air carrier you trust, give it try. Take a deep breath and check a bag. What have you got to lose?

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