3 Questions That Will Change How You Pack

I’m an over-packer at heart. I blame my mother, whose voice always echos in the back of my head when I’m trying to get ready to go somewhere.

“You never know what you’re going to need,” is her common refrain. “Just bring it! It’s better to be prepared.”

And that’s all it takes to convince me to pack that fourth pair of shoes for two nights away from my house. In my head, my mother’s voice encourages me: “You’ll want options.”

I used to think of this as a cute personality trait, until I went to Ireland for a month and brought basically enough clothes to wear for every day of the trip. I was dragging my huge suitcase all over Amsterdam, where we were stopping for two days, trying to find a place to stash it while we gallivanted, and somewhere on those cobblestone streets I started to re-evaluate why I brought all of that crap.

By the time I got back, I was no longer thinking about what was in my suitcase as my belongings that I needed, and instead thinking of everything as dead weight. When you start to think of your stuff in terms of pounds instead of sentimental or cosmetic value, it’s easier to make tough decisions.

So the big trick, in my opinion, isn’t about folding your clothes just so, or remembering to tuck small things inside your shoes. The trick is to downsize from step one, by preventing all of the excess from even going into your suitcase.

But how do you just “be reasonable” when packing? For everything going into your suitcase, ask yourself these three simple questions.

1. On a regular day, do I wear or use this?

When I’m packing, I find myself daydreaming about how cool and fun the trip is going to be and slipping things into my suitcase that are more in line with the ideal version of myself instead of the real one. For example, instead of remembering to pack my favorite jeans/sneakers/t-shirt combo, I’ll pack a button down I wore once, pants that are hard to move in and the strappy sandals I haven’t completely broken in yet.

Don’t do this! This makes no sense! Travel changes us, but it doesn't completely reverse our habits and inclinations. Same goes for toiletries and other items — if you don’t use six phone chargers regularly, don’t bring them. And why would you pack eye shadow when you haven’t worn it since 2008?  Be comfortable and be yourself. Maybe slip in one fancy dress or a pair of slacks you don't usually wear for a nice dinner. But remember to stay true to yourself.

2. Am I going to have time to wear or use this on my trip?

This is when you have to make the tough decisions. Instead of giving yourself options, think critically about how long you’ll be somewhere and what you’re going to be doing (at least generally). Then pick out what you’re going to wear on each day — write it down if you have to. Pack just those items, and stick with it. Of course you can throw in optional things like a light jacket, or an especially cute dress in case something pops up, but don’t go overboard. You know it doesn’t make sense to pack for a 10-day trip when you’re only going to be gone for four.

3. If I have to carry this every day of the trip, will I regret bringing it?

Finally, get ahead of the game by asking yourself this question before you’re dragging a boulder-sized suitcase around the bustling metropolis you’ve been dying to get to. If it’s something that you would be willing to toss into the trash in a foreign land instead of carry it with you, it’s not essential. Leave it home.

If you know you would regret packing a rain jacket when you're traveling to sunny Barcelona, leave it at home. But be carefully about leaving behind things you might regret not having too. If there's a chance of cool breezes or rain, spring for that extra sweater.