What I Use: Carry-On Bag

Heading to Seattle...
Heading to Seattle…

I’m semi-obsessed with traveling as lightly as possible. But it’s not always possible, as is the case this week as I head off to Redmond for what is increasingly thought to be an epic Windows 10 event. Because of a few work-related needs, I’m carrying a bit more than usual.

There’s inspiration to be had everywhere. And during the course of over 20 years of business travel, I’ve always observed what people are doing, technology-wise, in airports and train stations, and on-route. Obviously, that’s changed a lot over this time, given the rapid rise of ever more portable computers and digital devices. But I’ll sometimes spy a device or habit that I can appropriate. I am constantly reevaluating what I need to bring with me to stay productive on the road.

And believe me, I have rules. I’ll be writing a lot more about travel—technology and otherwise—as we move forward. But to give you an idea of where I’m coming from I fly non-stop only, on JetBlue only—thanks to the airline’s Boston hub—and then always in an “extra space” seat so I can actually work, at least domestically. No more cramming in the back of the chicken coop for me.

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And I carry on my bags, no exception. I bring two: One airplane bin-friendly piece of luggage and one small carry-on bag.

I do stress over the bags. Maybe “stress” is the wrong word, but this is one area where I sort of obsess. A few of the people I’ve travelled with for work-related reasons over the years believe I have a sort of bag fetish, and to be fair I have spent an inordinate amount of time and money looking into ever-more efficient bags. But the truth is, I’m done. I’ve found the perfect bags.

Both are sold by European travel guru Rick Steves, who has been an inspiration of sorts for many years. Steves’ company doesn’t make the bags, but they do help design them, and his decades of travel experience—Steves is a travel-light aficionado par excellence, go figure—have helped guide the evolution of his travel bag line.


For domestic travel, I use a Rick Steves Rolling Backpack for clothes and toiletries and, more important to this discussion, his Veloce Shoulder Bag for my laptop and other gear. It has a versatile combination of pockets and compartments for my needs, is lightweight yet super-durable, and comes in a variety of colors (though the red I prefer is long gone; not sure what I’m going to do when I do need to replace it).

On a typical work trip, I bring along the following:

Main compartent

Ultrabook. The last few trips this has been a MacBook Air running Windows 8.1 or Windows 10 or a Surface Pro 3, and both fit quite nicely—indeed, “hide” quite nicely—in the built-in laptop sleeve in the back of the bag. If your device is small enough—and the Air is—you can even hide it in the seat-back pocket on the plane, which is nice.


Small tablet. For consumption purposes—rented or download movies and Kindle-based e-books, mostly but also the occasional game (The Walking Dead and Valiant Hearts, recently; both are excellent). This has been an iPad mini Retina for a while now, though I’ve tested a few Android tablets (Nexus 9 most recently). I’d love to use a Windows tablet, of course, but the ecosystem just isn’t there.

Small blanket. Not quite the towel from “Hitchhiker’s Guide to the Galaxy,” but JetBlue sells a small blue blanket for $5 that you don’t notice in the bag at all. I use it to the make up for the tiny armrests on airplanes (and to prevent my arm from accidentally tapping one of the entertainment system buttons). Plus it can be used to divide/protect electronics if necessary.

Front pocket

The goal here is easy access to the things I need quickly or most frequently.

Boarding pass. There’s no JetBlue app on Windows Phone, so I need to use an iPhone or Android phone for electronic check-in, but I honestly prefer paper when I can get it. So I always do.

Phone. These days, it’s the Nokia Lumia 930 I recently wrote about, but also a second device that I use for media. On this trip it’s an iPhone 6 Plus, but it’s often a second Windows Phone. (And yes, I did put my JetBlue boarding pass in Passbook just in case. I didn’t use it on the flight to Seattle.)

Noise-cancelling headphones. If there is one piece of advice that is perhaps more important than others, it’s this one: when you travel via plane or train, you need to wear noise-cancelling headphones to protect your hearing. For many years I used and recommended a series of big and bulky over-the-ear Bose headphones, but about 15 months ago I switched to the in-ear Bose QuietComfort 20 acoustic noise cancelling headphones (Bose also makes a different version for Apple’s i-Devices). Yes, at $300 they are expensive, but they are also well worth the price. They’re tiny, and fit nicely in their little bag into the front of my carry-on bag. And they’re powered but work even when the battery is dead. This one is a no-brainer.

Other compartments

I have a kind of neat assortment of other things in the bag’s many other pockets and compartments. Thing worth mentioning include:

USB cables. I bring at least one normal USB cable for Windows Phones and other digital devices, and if I’m traveling with an i-Device I also bring an Apple-specific cable just in case.

Portable charger. A few months back I bought a 6000mAh Jackery Bar portable charger, replacing a smaller Nokia charger I had been using for a few years. I bring this sort of thing because I don’t ever want to arrive on the other side of the country and need my phone to actually work, only to discover that the battery is low or even dead. This one costs just $30, but you can get one with less of a charge for less too. High-quality.

So what about this trip?

I mentioned I had over-packed for this trip, though to be fair this was on purpose. Microsoft is set to announce the Windows 10 consumer preview on Wednesday and, I think, actually release it by the end of the week. So I wanted a few machines for testing. These are the MacBook Air running Windows 8.1 and the HP Envy x2 Detachable PC I’m currently reviewing. Together, these two laptops weigh down the bag a bit more than I’d like, but they both fit just fine.

The HP Envy x2 and MacBook Air both fit in the laptop sleeve.
The HP Envy x2 and MacBook Air both fit in the laptop sleeve.

I’m also bringing two extra phones, in this case the iPhone 6 Plus and a Google Nexus 5 that’s been updated to Android 5.0. I like to have these devices on hand in case Microsoft releases any new apps or app updates on those platforms, and while I’d have skipped on or both on a shorter trip, this time I’m gone for a full week, so they’re coming along.

I also have a gadget bag I toss in my main luggage. This can include a variety of things, but always extra USB cables with chargers (including a car adapter), laptop power cables, a power strip (for those hotel rooms without enough ports), an Ethernet adapter and so on. On this trip, I’m staying with Rafael, so I can dispense with a few items I won’t need, like an Ethernet cable, portable speaker and a portable router. But I need to bring my USB headset for the podcasts, which kind of balanced it out.

In the modern world, this kind of load-out amounts to me girding, or at least preparing, for war. The net result is a slightly heavier carry-on than I’d like. But I think I’m ready. Both for Windows 10. And for the week ahead.

Of course, my needs are kind of specific. Is there any advice from the real road warriors in the audience?

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