10/16/2014 12:13 pm ET Updated Dec 16, 2014

Overpacked and Under Pressure

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I'm a tall guy. I'm the man your eyes plead to when you finally drag your oversized, overstuffed suitcase onto the train after you've huffed and puffed through the station, dragging it on one faulty wheel. I'm the fella who will absolutely stand up to help you hoist that 60-pound beast into the overhead rack where it just might fit -- if we push hard enough.

If you travel, you've found yourself on one side or the other of that scenario. Or you've watched it play out as you sit (with deserved smugness) in your seat with your sensibly packed bag tucked under the seat in front of you.

Wrestling overpacked luggage is right up there with flight delays and unexpected rain when it comes to hassles that can ruin a traveler's day. At least, it's preventable. The trade-offs are small -- one or two fewer unique outfits vs. checked-bag fees and sweaty sprints through transportation hubs. I'm going to assume you have heard the usual warnings. Make a list, and stick to it. Lay out everything you want to take, then put half of it away. Choose the smallest possible bag so you're not tempted to overdo it. Worry more about comfort than fashion. That's all very disciplined and intellectual. But I believe more in the hands-on approach to understanding what you need to pack, how much you need to pack, and what you can live without if you don't pack it.

Monitor what you wear for one pre-vacation week.
Set aside a place in your closet and a laundry bag. Then for a week (or as long as you can maintain it), as you change clothes after work or get ready for bed, keep those clothes to the side. At the end, sort it out and count it out. Hmmm. You slip into the same pair of jeans whenever you're feeling casual. And what's this? In real life, you don't change socks three times a day? My point is that you don't need MORE on vacation than you wear at home. This inventory is better than any invented list at helping you realize what really belongs in your bag.

Pack early and take a little hike.
If you do nothing else I recommend, please do this. Packing early has several advantages. Making decisions before the eve of your departure means that you can spot anything that needs to get to the washing machine or the dry cleaner while there's still time. It means you won't make last-minute (and maybe regrettable) decisions if it won't all fit. Most of all, I want you to pack early so you can manhandle your bags while there's still time to cry "Uncle!" Load 'em up, and go for a walk. Carry your bag up and down a stairway. Take a spin around the block. Try lifting it above your head, as if to slide it into one of those overhead racks. No fair doing one bag at a time. If you will be taking a checked bag and a carryon, lug them all at once. Then, be honest with yourself and lighten up. I promise that you will thank me later.

Weigh your toiletries... and how much they really matter.
You already know that the TSA will only allow you to board a flight with small amounts of certain items in your carryon. But transferring them to your checked luggage isn't necessarily the best answer. Liquids, gels, pastes and creams are heavy. Oversized or half-empty bottles and tubes take up valuable space. If you weight it all separately, you'll be surprise at how it adds up. It's a rare hotel that doesn't provide everything you need. If you have essentials that simply have to go with you, buy travel-size amounts or transfer liquids to small squeeze bottles you can buy at pharmacies or stores that sell travel supplies.

Prepare for a stain and how to live with it.
Fear probably contributes to more over-packing than any other motive. "What if I spill Chianti on my slacks?" I understand. Your closet will be hundreds or even thousands of miles from where your vacation is happening. So you pack just-in-case clothing to be ready if the worst happens. Of course, the worst can happen. On the other hand, I'd ask you to think about how often you drastically stain clothing in your everyday life. For most of us, it's not that often that irretrievable splatters happen. So pack confidently. While you are planning your careful mix-and-match wardrobe, tend toward darker colors and patterns. (I know from the times I've traveled with my company Classic Journeys that a splatter of Vietnamese pho broth and stains from some stray Moroccan couscous are a lot harder to see on a plaid shirt.) Take along one of those stain sticks that can pretty effectively remove little accidents. And remember that -- though your mother always warned you that hotel laundry is too expensive -- it is possible to have an item cleaned if the worst happens. I say it's a small price to pay for a lighter bag.

Fantasize about souvenirs in advance.
If you -- or that chronic over-packer you travel with -- needs more convincing, take this final tip. Let's say you're willing to lug the heaviest, fullest bag possible. If you are a shopper or souvenir collector, just where are those new acquisitions going to go? Bags only get fuller as a trip progresses, and those neatly folded and rolled articles of clothing get packed and re-packed. If your bags are too stuffed and leaden to start with, how will it be roaming the cobbled streets and marathon-long airport concourses of the world with a few extra shopping bags? In the same way that you diet before a vacation so you can indulge while you're away, slim down your suitcase so you can enjoy some retail therapy without turning yourself into a pack animal.