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What’s In Your Carry-On? 6 Things That Keep Me Comfortable and Productive on the Road

Nate wrote in to ask me about my travel packing strategy:

My burning question for you right now is what are your essential items that keep you comfortable and productive while you travel (virtual or real)? How has this list changed over time - or has it even changed since you published your first book?

My answer is that it’s changed a little over time, but not by much. When it comes to travel, I’m a creature of habit and routine. I take the same things with me everywhere I go, and everything fits in a single carry-on bag + my laptop bag (never check luggage!).

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Packing Essentials

It doesn’t take me long to pack for most trips. I typically bring the same clothes and “stuff” with me no matter my destination or purpose of travel. Sure, there’s some variance—a warmer scarf depending on season, or a nicer jacket depending on what kind of meetings I have on the other side.

On average, it takes me twenty minutes. No more, no less. If I’m doing laundry and sorting through the mail while packing, the whole process might take up to an hour, but that's the cost of multitasking.

The greatest challenge is indecision. Do I want two pairs of jeans? (Usually just one, but I waver.) Do I need to bring my bathing suit? (I don’t swim often, and when I do I can wear my running shorts.)

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Tips for Stress-Free Travel

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The title of this post is somewhat of a misnomer: I almost never experience travel that is truly stress-free. For starters, not all travel can or should be predictable. Sometimes the unexpected is better than the planned.

Secondly, not all stress is bad, because some of the most challenging times in our lives are the most stressful. No risk, no glory—that kind of thing.

Yet, when heading out into the world, it helps to control as many variables as you can. I'd rather experience travel stress related to something fun than something preventable that was my own fault. With that in mind, here's a primer on low-stress travel—and your contributions are welcome too.

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Packing List

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A number of people have asked what I take with me for long overseas trips, and how I travel with no backpack or checked baggage. I'm getting ready to head out on the road again in about 10 days, so this is a good opportunity to review how it works for me.

The biggest secret: packing light is actually easier than bringing a ton of stuff.

The overriding philosophy of my packing list is to keep it as simple as possible. That's basic, I know, but very important. At least for me, travel stress is directly proportionate to the amount of stuff I carry around. I don't own a backpack and haven't willingly checked a bag on one of my extended adventures.

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